[DESCRIPTION]

[invention Title]

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME [Technical Field]

The present invention relates to novel organic electroluminescent compounds, and organic electroluminescent devices andorganic solar cells comprising the same . Specifically, the organic electroluminescent compounds according to the present invention are characterized in that they are represented by Chemical Formula 1:

Ar ₁ Ar ₂ R ₁ L R ₂ ^ - _jj

wherein

L is a substituent represented by the following structural formula :

wherein ring A represents a monocyclic or polycyclic (C6-C60) aromatic ring; and ring B represents anthracene. [Background Art]

In order to create a full-color organic light-emitting diode

(OLED) display, electroluminescent materials of red, green and blue

(RGB) colors are used. The development of RGB electroluminescent materials with high efficiency and long operation life is the most important task in improving the overall organic electroluminescence (EL) characteristics . Electroluminescent materials can be classified into host materials and dopant materials depending on their functions . In general, it is known that an electroluminescent layer created by doping a dopant into a host has the most superior EL characteristics. Recently, the development of organic EL devices having high efficiency and long operation life is emerging as an imminent task. Especially, considering the EL characteristics required by medium-to-large sized OLED panels, the development materials having much superior characteristics as compared to existing electroluminescent materials is highly required.

For green fluorescent materials, a system of doping a dopant such as a coumarin derivative (Compound a, C545T) , a quinacridone derivative (Compound b) , DPT (Compound c) , etc. to the AIq host to several to dozen % has been developed and is widely used. Although these existing electroluminescent materials exhibit high initial luminous efficiency as to be commercially applicable, the efficiency decreases markedly with time and operation life is severely problematic . As a result, they are limited in use for large-sized, high-performance panels .

Compound a Compound b

Compound c

For blue fluorescent materials, a lot of materials have been commercialized following Idemitsu Kosan' s DPVBi (Compound d) . IdemitsuKosan' s blue material systemand Kodak' s dinaphthylanthracene (Compound e) and tetra (t-butyl) perylene (Compound f) are known, but much more research and development are demanded. Until now, Idemitsu Kosan' s distyryl compound system is known to have the best efficiency. It exhibits a power efficiency of 6 lm/W and operation life of 30,000 hours or more. However, its color is sky-blue, which is inadequate for full-color displays. In general, blue electroluminescence is advantageous in luminous efficiency if the electroluminescence wavelength shifts a little toward the longer wavelength. But, it is not applicable to high-quality displays because pure blue color is not attained. Therefore, researches and developments to improve color purity, efficiency and thermal stability are highly required.

Compound d Compound f

Compound e

[Disclosure] [Technical Problem]

To solve the aforesaid problems, in one aspect, the present invention provides an organic electroluminescent compound having superior backbone structure, which has better luminous efficiency and operation life than existing materials and adequate color coordinates. In another aspect, the present invention provides an organic electroluminescent device having high efficiency and long operation life, which comprises the organic electroluminescent compound as an electroluminescent material. In another aspect, the present invention provides an organic solar cell comprising the organic electroluminescent compound. [Technical Solution]

The present invention relates to an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present invention has good luminous efficiency and excellent color purity and life property.

Therefore, OLEDs having very good operation life can be manufactured therefrom.

Ar ₁ Ar ₂

In Chemical Formula 1,

L is a substituent represented by the following structural formula :

wherein

Arepresents -N(R ₇ i)-, -S-, -0-, -Si (R ₇₂ ) (R ₇₃ )", -P(R ₇₄ )-, -C(=0)-, -B(R ₇₅ )-, -In(R ₇₆ )-, -Se-, -Ge(R ₇₇ ) (R ₇₈ )-, -Sn (R ₇₉ ) (R ₈₀ ) - or -Ga (R ₈ i) -; ring A represents a monocyclic or polycyclic (C6-C60) aromatic ring; ring B represents anthracene;

Ari and Ar ₂ independently represent a chemical bond,

(C6-C60 ) arylene, (C3-C60) heteroarylene containing one or more heteroatom(s) selected from N, 0 and S, 5- or 6-membered 95 heterocycloalkylene containing one or more heteroatom (s) selected from N, O and S, (C3-C60) cycloalkylene, (C2-C60) alkenylene, (C2-C60) alkynylene, (C1-C60) alkylenoxy, (C6-C60) arylenoxy or (C6-C60) arylenethio;

Ri and R ₂ independently represent hydrogen, deuterium, halogen,

100 (Cl-C60)alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, O and S, morpholmo, thiomorpholmo,

5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

105 (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, ammo, mono- or di-(Cl -C 60) alkylammo, mono- ordi- (C6-C60) arylamino,

(C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio,

(C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

(C1-C60) alkylcarbonyl, (C6-C60 ) arylcarbonyl, carboxyl, nitro or

110 hydroxyl, or a substituent selected from the following structures:

wherein

X and Y independently represent a chemical bond, - (CR5iR52)m~, -N (R ₅₃ ) -, -S-, -O-, -Si (R ₅₄ ) (R55) -, -P (R ₅₆ ) -, -C (=0) -, -B (R ₅₇ ) -, -In (R ₅₈ ) -,

115 -Se-, -Ge(R ₅₉ ) (R ₆₀ )-, -Sn(R ₆₁ ) (R ₆₂ )-, -Ga(R ₆₃ )- or -(R ₆₄ )C=C(R ₆₅ )-, excluding the case where both X and Y are chemical bonds at the same time ;

R ₃ , R ₄ and R _3x through R ₄ a independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl

120 containing one ormore heteroatom (s) selected fromN, OandS, morpholmo, thiomorpholmo, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C60) cycloalkyl, tri (Cl-C60)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl,

125 (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, amino, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylammo, (C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or

130 hydroxyl, or each of R ₃ i through R ₄₃ may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;

R5 ₁ through R ₆₅ and R ₇₁ through R ₈₁ independently represent hydrogen,

135 deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom(s) selected fromN, OandS, morpholmo, thiomorpholmo, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, tπ(Cl-C60)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl,

140 tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, ammo, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylammo, (C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (Cl-CβO) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

145 (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy1, or R _5i and R ₅₂ , R5 ₄ and R ₅₅ , R59 and R ₆ cw Rβi and ^R 62? ^R 64 and R ₆₅ , R ₇₂ andR ₇₃ , R ₇₇ and R ₇₈ and R ₇₉ and R ₈ o may be linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring/

150 thearylene, heteroarylene, heterocycloalkylene, cycloalkylene or alkenylene of Ari and Ar ₂ or the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, alkenyl, alkynyl, amino, alkylamino or arylamino of Ri, R ₂ , R ₃ , R ₄ , R ₃₁ through R ₄₈ , R ₅₁ through Res and R _7i through

155 Rei may be further substituted by one or more substituent (s) selected from deuterium, halogen, halo (C1-C60) alkyl, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from

160 N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

(C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60 ) alkynyl, cyano, amino, mono- or di- (Cl-CβO ) alkylamino, mono- or di- (C6-C60 ) arylamino,

(C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio,

165 (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxy1; and m represents an integer from 1 to 4.

In the present invention, "alkyl", "alkoxy" and other 170 substituents including "alkyl" moietymay be either linear or branched.

In the present invention, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring. Specific examples include phenyl, naphthyl,

175 biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes all of 1-fluorenyl, 2-fluorenyl,

180 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.

In the present invention, "heteroaryl" means aryl group containing 1 to 4 heteroatom (s) selected from N, 0, S and Si as aromatic ring backbone atom(s) , remaining aromatic ring backbone atoms being carbon . It may be 5- or 6-membered monocyclic heteroaryl or polycyclic

185 heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt. Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl,

190 imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl,

195 benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), quaternary salt thereof, etc., but not limited thereto.

200 And, in the present invention, the substituents including " (C1-C60) alkyl" moiety may have 1 to 60 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms. The substituents including " (C6-C60) aryl" moiety may have 6 to 60 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. The substituents including

205 " (C3-C60) heteroaryl" moiety may have 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms. The substituents including " (C3-C60) cycloalkyl" moiety may have 3 to 60 carbon atoms, 3 to 20 carbon atoms, or 3 to 7 carbon atoms. The substituents including " (C2-C60) alkenyl or alkynyl" moiety may have 2 to 60 carbon atoms,

210 2 to 20 carbon atoms, or 2 to 10 carbon atoms.

In Chemical Formula 1, L may be selected from the following structures, but not limited thereto:

215 wherein

A is the same as defined in Chemical Formula 1; Rn through R ₂₄ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino,

220 thiornorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (Cl-CβO)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60)arylsilyl, adamantyl, (C7-C60) bicycloalkyl,

(C2-C60)alkenyl, (C2-C60) alkynyl, cyano, ammo, mono- or

225 di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxyl; and

230 the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, alkenyl, alkynyl, amino, alkylamino or arylamino of R ₁₁ through R ₂₄ may be further substituted by one or more substituent (s) selected from deuterium, halogen, halo (C1-C60) alkyl, (C1-C60) alkyl, (C6-C60) aryl,

235 (C3-C60) heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino, thiomorpholmo, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

240 (C7-C60) bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, ammo, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio,

(C6-C60) aryloxy, (C6-C60 ) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and

245 hydroxyl .

In Chemical Formula 1, L may be selected from the following structures, but not limited thereto:

wherein

Rn through R ₂₄ independently represent hydrogen, deuterium, 265 halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl,

270 tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, amino, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar(Cl-C60)alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

275 (C1-C60 ) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy1;

R _7I through R ₇₄ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60 ) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S, morpholino,

280 thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl, adamantyl, (C7-C60) bicycloalkyl, cyano, amino,

(C6-C60) ar (C1-C60) alkyl, (C1-C60) alkoxycarbonyl,

(C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl or hydroxyl;

285 and the alkyl, aryl heteroaryl, heterocycloalkyl, cycloalkyl or adamantyl of Rn through R ₂₄ and R _7i through R ₇₄ may be further substituted by one or more substituent (s) selected from deuterium, halogen, halo (C1-C60) alkyl, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl

290 containing one ormoreheteroatom(s) selected fromN, OandS, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60)arylsilyl, adamantyl, (C7-C60) bicycloalkyl,

295 (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, amino, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino,

(C6-C60)ar(Cl-C60)alkyl, (Cl-CβO) alkyloxy, (C1-C60) alkylthio,

(C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

(C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and

300 hydroxyl. and independently may be selected from the following structure, but not limited thereto:

305 wherein

R ₉₁ and Rg ₂ independently represent hydrogen, (C1-C60) alkyl,

(C3-C60)cycloalkyl, (C6-C60)aryl or (C3-C60 ) heteroaryl, or may be linked to an adjacent substituent via (C3-C60) alkylene or

(C3-C60) alkenylene with or without a fused ring to form an alicyclic

310 ring or a monocyclic or polycyclic aromatic ring;

R ₉₃ through Rg ₅ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, O and S, morpholmo, thiomorpholmo, carbazolyl, 5- or 6-membered heterocycloalkyl

315 containing one or more heteroatom(s) selected from N, 0 and S,

(C3-C60)cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60 ) arylsilyl, adamantyl,

(C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, ammo, mono- ordi-(Cl-C60) alkylamino, mono- or di- (C6-C60) arylamino,

320 (C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio,

(C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

(C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxyl;

R ₉₆ and Rg7 independently represent hydrogen, deuterium, halogen,

325 (C1-C60) alkyl, (C6-C60) aryl , (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, OandS, morpholino, thioinorpholino,

5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, OandS, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

330 (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, amino, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or 335 hydroxy1;

Lu and Li ₂ independently represent a chemical bond, (Cl-C60)alkylene, (C6-C60) arylene, (C3-C60) heteroarylene, 5- or 6-membered heterocycloalkylene containing one or more heteroatom (s) selected from N, 0, S and Si, (C3-C60) cycloalkylene, adamantylene, 340 (C7-C60)bicycloalkylene, (C2-C60) alkenylene, (C2-C60) alkynylene, (C6-C60) ar (C1-C60) alkylene, (C1-C60) alkylenethio,

(Cl-CβO)alkylenoxy, (C6-C60) arylenoxy or (C6-C60) arylenethio; the arylene, heteroarylene, heterocycloalkylene, cycloalkylene, adamantylene, bicycloalkylene, alkenylene, alkynylene, arylenoxy or

345 arylenethio of Ln and Li ₂ may be further substituted by one or more substituent (s) selected from deuterium, halogen, (C1-C60) alkyl, halo (Cl-C60)alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or

350 more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (Cl-C60)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60)arylsilyl, adamantyl, (C7-C60) bicycloalkyl,

(C2-C60) alkenyl, (C2-C60) alkynyl, cyano, amino, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino,

355 (C6-C60)ar (C1-C60 ) alkyl, (Cl-CβO) alkyloxy, (C1-C60 ) alkylthio,

(C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

(C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxyl; X and Y independently represent -C (R ₅ I ) (R ₅₂ )-, -N(R ₅ 3) ^~ , -S-, -O-, 360 -Si(R ₅₄ ) (R ₅₅ )", -P(R ₅₅ )-, -C(=O)-, -B(R ₅₇ )-, -In(R ₅₈ )-, -Se-, -Ge(R ₅₉ ) (R ₆₀ )-, -Sn(R ₆ i) (R ₆₂ )-, -Ga (R ₆₃ ) - or - (R ₆₄ ) C=C (R ₆₅ ) -;

R ₅₁ through R ₆₅ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60 ) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, O and S, morpholmo,

365 thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl,

(C2-C60 ) alkenyl, (C2-C60) alkynyl, cyano, amino, mono- or

370 di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino,

(C6-C60)ar (C1-C60) alkyl, (C1-C60 ) alkyloxy, (C1-C60 ) alkylthio,

(C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

(C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxyl, or R ₅₁ and R ₅₂ , R ₅₄ and R ₅₅ , R ₅₉ and R ₆₀ , R ₆ i and R ₆₂ and R ₆₄

375 and R ₆₅ may be linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;

Z represents O, S or NRgβ;

R98 represents hydrogen, deuterium, halogen, (C1-C60) alkyl, 380 (C3-C60) cycloalkyl or (C6-C60) aryl; the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, alkenyl, alkynyl, amino, alkylamino or arylamino of R ₅₁ through R _δ5 and Rg ₁ through R ₉₈ may be further substituted by one or more substituent (s) selected

385 from deuterium, halogen, halo (C1-C60) alkyl, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, tri (C1-C60) alkylsilyl,

390 di(Cl-C60)alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, amino, mono- or di-(Cl-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar(Cl-C60)alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

395 (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxy1; a represents an integer form 1 to 5; and b represents an integer form 1 to 4.

More specifically, and may be independently 400 selected from the following structures, but not limited thereto:

20

405 More specifically, the organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but not limited thereto:

22





450

33



42

50

The organic electroluminescent compound according to the present invention may be prepared in accordance with Schemes 1 to 7 : [Scheme 1]

530 [Scheme 2]

[Scheme 3]

[Scheme 4]

[Scheme 5]

[Scheme 6]

540 [Scheme 7] wherein A, Ar ₁ , Ar ₂ , Ri and R ₂ are the same as defined in Chemical Formula 1.

Further, as shown in Schemes 8 to 10, Rn and/or Ri ₂ substituent (s) 545 may bind to the substituent L of the organic electroluminescent compound according to the present invention: [Scheme 8]

[Scheme 9]

[Scheme 10]

where in

A, Rr ₁ , Ar ₂ , Ri, R _∑ , Rn and R ₁₂ are the same as defined m Chemical 555 Formula 1.

The present invention further provides an organic solar cell. The organic solar cell according to the present invention comprises one or more organic electroluminescent compound (s) represented by Chemical Formula 1.

560 The present invention further provides an organic electroluminescent device. The organic electroluminescent device according to the present invention comprises a first electrode; a second electrode; and at least one organic layer (s) interposed between the first electrode and the second electrode, wherein the organic 565 layer comprises one or more organic electroluminescent compound (s) represented by Chemical Formula 1.

The organic layer comprises an electroluminescent layer In addition to one or more organic electroluminescent compound (s) represented by Chemical Formula 1, the electroluminescent layer 570 comprises further comprises one or more dopant(s) or host(s) . The dopant or host used in the organic electroluminescent device according to the present invention is not particularly limited.

The dopant used in the organic electroluminescent device according to the present invention may be selected from the compounds 575 represented by Chemical Formulas 2 to 4:

wherein

Arii and Ari ₂ independently represent hydrogen, deuterium,

580 halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, mono- or di- (C6-C60) arylamino, mono- or di- (C1-C60) alkylammo, 5- or

6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S or (C3-C60) cycloalkyl, or Arn and Ar _i2 may be linked via (C3-C60 ) alkylene or (C3-C60) alkenylene with or without

585 a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;

Ar _i3 represents (C6-C60) aryl, (C4-C60) heteroaryl or aryl having one of the following structures, when c is 1:

590 Ar _i3 represents (C6-C60) arylene, (C4-C60) heteroarylene or arylene having one of the following structures, when c is 2 :

wherein

Ar ₁₄ and Ar _i5 independently represent (C6-C60) arylene or 595 (C4-C60) heteroarylene;

Rioi through R ₁₀ 3 independently represent hydrogen, deuterium, (C1-C60) alkyl or (C6-C60) aryl; d represents an integer from 1 to 4; e represents an integer 0 or 1;

600 the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of Arn and Ar ₁₂ , the aryl, heteroaryl, arylene or heteroarylene of Ar ₁₃ , the arylene or heteroarylene of Ari4 and Aris, or the alkyl or aryl of Rioi through Ri ₀₃ may be further substituted by one or more substituent (s) selected from halogen, deuterium,

605 (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri {C6-C60} arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano,

610 mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60) aryloxy, (C1-C60) alkyloxy, (C6-C60) arylthio, (C1-C60) alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxyl;

615 [Chemical Formula 4]

wherein

Rm through R _1J4 independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl containing

620 one or more heteroatom(s) selected from N, O and S, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from

N, O and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl,

625 (C1-C60) alkoxy, cyano, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro or hydroxyl, or each of R ₁₁₁ through Rn ₄ may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without

630 a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylsilyl, alkylsilyl, alkylamino or arylamino of Rm through R ₁₁₄ , or the alicyclic ring or monocyclic or polycyclic aromatic

635 ring formed as they are linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from deuterium, halogen, (C1-C60) alkyl, (C6-C60 ) aryl, (C4-C60) heteroaryl containing one or more heteroatom (s) selected from

640 N, 0 and S, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C60) cycloalkyl, tri (Cl -C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri(C6-C60)arylsilyl _r adamantyl, (C7-C60) bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C1-C60) alkoxy, cyano, mono- or

645 di- (C1-C60 ) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar (C1-C60J alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro and hydroxyl.

The dopant compound represented by Chemical Formulas 2 to 4 may be exemplified by the compounds having the following structures, but

650 not limited thereto:



64

65

The host used in the organic electroluminescent device according to the present invention may be selected from the compounds represented by Chemical Formulas 5 and 6:

(Ar ₂₁ IrL ₂ I-(Ar ₂₂ I ₉ (5) 670 (Ar ₂₃ J n-L ₂₂ - (Ar ₂₄ ) _! ( 6 ) where in

L ₂ i represents (C6-C60) arylene or (C4-C60) heteroarylene; L22 represents anthracenylene;

Ar _2I through Ar ₂₄ independently represent hydrogen, (C1-C60) alkyl,

675 (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or

(C6-C60) aryl, and the cycloalkyl, aryl or heteroaryl of Ar ₂ I through

Ar ₂₄ may be further substituted by one or more substituent (s) selected from a group consisting of (C6-C60)aryl or (C4-C60) heteroaryl with or without one or more substituent Cs) selected from a group consisting

680 of deuterium, (C1-C60) alkyl with or without halogen substituent (s) ,

(C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tπ(Cl-C60)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl, (C1-C60 ) alkyl with or without halogen substituent (s) , (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano,

685 tπ(Cl-C60)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tπ(C6-C60) arylsilyl; and f, g, h and 1 independently represent an integer from 0 to 4. The compound represented by Chemical Formula 5 or 6 may be exemplified by the anthracene derivatives or benz [a] anthracene 690 derivatives represented by Chemical Formulas 7 to 10:

wherein

695 R ₁₂ I and Ri ₂₂ independently represent (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S or (C3-C60) cycloalkyl, and the aryl or heteroaryl of R ₁₂₁ and R ₁₂₂ may be further substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl,

700 halo (C1-C60) alkyl, (C1-C60 ) alkoxy, (C3-C60) cycloalkyl, (C6-C60) aryl, (C4-C60) heteroaryl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl;

R123 through R ₁₂ 6 independently represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl,

705 (C5-C60) cycloalkyl or (C6-C60) aryl, and the heteroaryl, cycloalkyl or aryl of R123 through Ri ₂₆ may be further substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl with or without halogen substituent (s) , (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and

710 tri (C6-C60) arylsilyl;

Gi and G ₂ independently represent a chemical bond or (C6-C60) arylene with or without one or more substituent (s) selected from (Cl-CδO)alkyl, (C1-C60) alkoxy, (C6-C60 ) aryl, (C4-C60) heteroaryl and halogen;

715 Ar3i and Ar ₃₂ independently represent (C4-C60 ) heteroaryl or aryl selected from the following structures:

wherein the aryl or heteroaryl of Ar ₃₁ and Ar ₃₂ may be substituted by 720 one or more substituent (s) selected from deuterium, (C1-C60) alkyl, (Cl-CβO)alkoxy, (C6-C60)aryl and (C4-C60) heteroaryl;

L _3I represents (C6-C60) arylene, (C4-C60) heteroarylene or a compound having the following structure:

725 wherein the arylene or heteroarylene of L _3i may be substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl, (Cl-C60)alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl and halogen;

Ri3i through Ri ₃₄ independently represent hydrogen, deuterium,

730 halogen, (C1-C60) alkyl or (C6-C60) aryl, or they may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; and

Ri ₄ i through Ri ₄₄ independently represent hydrogen, deuterium,

735 (Cl-CβO)alkyl, (C1-C60 ) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen, or they may be linked to an adjacent substituent via

(C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;

740 wherein

L ₄ i and L ₄₂ independently represent a chemical bond, (C6-C60) arylene or (C3-C60) heteroarylene, and the arylene or heteroarylene of L ₄₁ and L ₄₂ may be further substituted by one or more substituent (s) selected from deuterium, (C1-C60 ) alkyl, halogen, cyano, 745 (C1-C60) alkoxy, (C3-C60 ) cycloalkyl, (C6-C60) aryl, (C3-C60) heteroaryl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl and tri (C6-C30 ) arylsilyl;

Ri _5I through R ₁₆₉ independently represent hydrogen, halogen, deuterium, (C1-C60) alkyl, (C6-C60 ) aryl, (C4-C60 ) heteroaryl, 5- or 750 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri(C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl,

(C1-C60) alkoxy, cyano, mono- or di- (C1-C60) alkylamino, mono- or 755 di- (C6-C60)arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro or hydroxyl, or each of Ri _5x through Ri ₆₉ may be linked to an adjacent substituent via (C3-C60) alkyleneor (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic

760 aromatic ring;

Ar _4I represents (C6-C60) aryl, (C4-C60 ) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, adamantyl, (C7-C60) bicycloalkyl or a substituent selected from the following

765 structures:

wherein

Ri70 through R ₁₈₂ independently represent hydrogen, halogen, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or

770 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C60] cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

(C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl,

(C1-C60) alkoxy, cyano, mono- or dα- (C1-C60) alkylamino, mono- or

775 di-(C6-C60)arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60) aryloxy,

(C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro or hydroxyl;

E ₁ and E ₂ independently represent a chemical bond, -(CR ₁₈₃ R ₁₈ ^) _n - _? -N (Ri ₈₅ ) -, -S-, -O-, -Si (Ri ₈₆ ) (Ri ₃₇ ) -, -P (Riββ) - _/ -C (=O) -, -B (R ₁₈₉ ) -,

780 -In (Ri ₉₀ ) -, -Se-, -Ge (R ₁₉ i) (Ri ₉₂ ) -, -Sn(R ₁₉₃ ) (Ri ₉₄ ) -, -Ga (R ₁₉₅ ) - or - (Ri ₉₆ ) C=C (R ₁₉₇ ) -;

Ri83 through Ri ₉₇ independently represent hydrogen, halogen, deuterium, (C1-C60) alkyl, (C6-C60 ) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s)

785 selected from N, O and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (Cl-CβO)alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C1-C60) alkoxy, cyano, mono- or di- (C1-C60) alkylamino, mono- or di-(C6-C60)arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60) aryloxy,

790 (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro or hydroxyl, or each of R _i83 through Ri ₉₇ may be linked to an adjacent substituent via (C3-C60) alkyleneor (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;

795 the aryl, heteroaryl, heterocycloalkyl, adamantyl or bicycloalkyl of Ar ₄₁ , or the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylsilyl, alkylsilyl, alkylamino or arylamino of R _15I through Ri ₈₂ may be further substituted by one or more substituent (s) selected from deuterium, halogen,

800 (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl,

805 (C1-C60) alkoxy, cyano, mono- or di- (C1-C60) alkylamino, mono- or di-(C6-C60)arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60 ) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro and hydroxyl; j represents an integer from 1 to 4; and m represents an integer 0 to 4.

The host compound represented by Chemical Formulas 7 to 10 may be exemplified by the compounds having the following structures, but not limited thereto:

75

77





80

The organic electroluminescent device according to the present invention comprises the organic electroluminescent compound represented by Chemical Formula 1, and, at the same time, may comprise 825 one or more compound (s) selected from a group consisting of arylamme compounds and styrylarylamme compounds. The arylamine compounds or the styrylarylamine compounds may be exemplified by the compound represented by Chemical Formula 11, but not limited thereto:

830 wherein

Ar ₅ I and Ar ₅₂ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60 ) heteroaryl, mono- or di- (C6-C60) arylamino, mono- or di- (C1-C60 ) alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) 835 selected from N, O and S or (C3-C60) cycloalkyl, and Ar _5I and Ar ₅₂ may be linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;

Ar ₅ 3 represents (C6-C60 ) aryl, (C4-C60 ) heteroaryl or a 840 substituent selected from the following structures, when o is 1:

Ar ₅ 3 represents (C6-C60) arylene, (C4-C60 ) heteroarylene or a substituent selected from the following structures, when 0 is 2:

845 Ar54 and Ar ₅₅ independently represent (C6-C60) arylene or (C4-C60) heteroarylene;

R ₂ 01 through R203 independently represent hydrogen, halogen, deuterium, (C1-C60) alkyl or (C6-C60) aryl; p represents an integer from 1 to 4;

850 q represents an integer 0 or 1; and the alkyl, aryl, heteroaryl, arylamino, alkylammo, cycloalkyl or heterocycloalkyl of Ar _5I and Ar ₅₂ , the aryl, heteroaryl, arylene or heteroarylene of Ar ₅₃ , the arylene or heteroarylene of Ar ₅₄ and Ar ₅₅ , or the alkyl or aryl of R ₂ oi through R ₂ 03 may be further substituted

855 by one or more substituent (s) selected from deuterium, halogen,

(C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from

N, O and S, (C3-C60 ) cycloalkyl, tri (C1-C60) alkylsilyl, di(Cl-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

860 (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, mono- or di- (C1-C60) alkylamino, mono- or di- (C6-C60) arylamino, (C6-C60)ar (C1-C60) alkyl, (C6-C60) aryloxy, (C1-C60) alkyloxy, (C6-C60)arylthio, (C1-C60) alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and 865 hydroxyl.

Specifically, the arylainine compound or styrylarylamine compound may be exemplified by the following compounds, but not limited thereto :

In the organic electroluminescent device according to the present invention, the organic layer may further comprise, m addition to

875 the organic electroluminescent compound represented by Chemical Formula 1, one or more metal (s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements. Also, the organic layer may comprise an electroluminescent layer and a charge

880 generating layer.

An independent electroluminescence type organic electroluminescent device having a pixel structure in which the organic electroluminescent device according to the present invention comprising the organic electroluminescent compound represented by

885 Chemical Formula 1 is used as a subpixel and one or more subpixel(s) comprising one or more metal compound (s) selected from a group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag is patterned in parallel may be manufactured.

The organic layer may further comprise, in addition to the organic

890 electroluminescent compound, one or more compound (s) having an electroluminescence peak with wavelength of not less than 560 ran. The compound having an electroluminescence peak with wavelength of not less than 560 nm may be exemplified by the compounds represented by Chemical Formulas 12 to 16, but not limited thereto:

895 M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³ ( 12 ) wherein

M ¹ is a metal selected from a group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals;

900 ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are independently selected from the following structures:

wherein

R301 through R303 independently represent hydrogen, (C1-C60 ) alkyl with or without halogen substituent (s) , (C6-C60) aryl with or without 910 (C1-C60) alkyl substituent (s) or halogen;

R304 through R ₃ I ₉ independently represent hydrogen, (C1-C60 ) alkyl, (Cl-C30)alkoxy, (C3-C60) cycloalkyl, (C2-C30) alkenyl, (C6-C60) aryl, mono- or di- (C1-C30) alkylamino, mono- or di- (C6-C30) arylamino, SF ₅ , tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, 915 tri (C6-C30) arylsilyl, cyano or halogen, and the alkyl, cycloalkyl, alkenyl or aryl of R ₃₀₄ through R ₃₁₉ may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C6-C60) aryl and halogen;

R ₃₂ O through R ₃₂₃ independently represent hydrogen, (Cl -C 60 ) alkyl 920 with or without halogen substituent (s) or (C6-C60 ) aryl with or without (C1-C60) alkyl substituent (s) ;

R ₃₂ 4 and R ₃₂₅ independently represent hydrogen, (C1-C60) alkyl, (C6-C60)aryl or halogen, or R ₃₂₄ and R ₃₂₅ may be linked via (C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring 925 to form an alicyclic ring or a monocyclic or polycyclic aromatic ring, and the alkyl or aryl of R ₃₂₄ and R ₃₂ or the alicyclic ring or monocyclic or polycyclic aromatic ring formed as they are linked via

(C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected

930 from (C1-C60) alkyl with or without halogen substituent (s) , (Cl-C30)alkoxy, halogen, tri (C1-C30) alkylsilyl, tri (C6-C30)arylsilyl and (C6-C60) aryl/

R ₃₂₅ represents (C1-C60) alkyl, (C6-C60) aryl, (C5-C60) heteroaryl containing one or more heteroatom(s) selected from N, O and S or halogen;

935 R ₃₂₇ through R ₃₂₉ independently represent hydrogen, (Cl-CβO) alkyl, (C6-C60)aryl or halogen, and the alkyl or aryl of R ₃₂₆ through R3 ₂ 9 may be further substituted by halogen or (C1-C60) alkyl;

R333 R ₃₃₄ R337 R338 ^R 3411 R342

Q represents ^- ? , ^R 335R _{336 or} R339 ^R 340 _f wherein R _33i through R ₃₄₂ independently represent hydrogen, (C1-C60) alkyl with or 940 without halogen substituent ( s) , (C1-C30 ) alkoxy, halogen, (C6-C60) aryl, cyano or (C5-C60) cycloalkyl, or each of R ₃₃₁ through R ₃ 42 may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7)spiro ring or (C5-C9) fused ring, or may be linked to R ₃₀ 7 or R ₃₀₈ via alkylene or alkenylene to form a (C5-C7) fused ring; ) wherein

R ₃ 5i through R ₃₅₄ independently represent (C1-C60) alkyl or (C6-C60) aryl, or they are linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring 950 to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; the alkyl or aryl of R ₃₅₁ through R ₃₅₄ , or the alicyclic ring or monocyclic or polycyclic aromatic ring formed as they are linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected 955 from (C1-C60) alkyl with or without halogen substituent (s) , (Cl-CβO)alkoxy, halogen, tri (C1-C60) alkylsilyl, tri (C6-C60)arylsilyl and (C6-C60) aryl;

960 L ²⁰¹ L ²⁰² M ² (T ) _r ( 16 ) wherein ligands L ²⁰¹ and L ²⁰² are independently selected from the fol lowing st ructures :

965 wherein

M represents a divalent or trivalent metal; r is 0 when M ² is a divalent metal, and r is 1 when M ² is a trivalent metal ;

T represents (C6-C60) aryloxy or tri (C6-C60) arylsilyl, and the 970 aryloxy or tπarylsilyl of T may be further substituted by (C1-C60) alkyl* or (Cβ-CδO)aryl;

G represents O, S or Se; ring C represents oxazole, thiazole, imidazole, oxadiazole, thiadiazole, benzoxazole, benzothiazole, benzoimidazole, pyridine 975 or quinolme; ring D represents pyridine or quinolme, and the ring D may be further substituted by (C1-C60) alkyl, phenyl with or without (C1-C60) alkyl substituent (s) or naphthyl;

R ₄ Oi through R ₄₀₄ independently represent hydrogen, (C1-C60 ) alkyl, 980 halogen, tri (C1-C60) alkylsilyl, tri (C6-C60) arylsilyl or (C6-C60) aryl, or they may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene to form a fused ring, and the pyridine or quinoline may be linked to R _40I via a chemical bond to form a fused ring; and

985 the aryl of ring C and R _40I through R ₄₀₄ may be further substituted by (C1-C60) alkyl, halogen, (C1-C60) alkyl with halogen substituent (s) , phenyl, naphthyl, tri (C1-C60) alkylsilyl, tri (C6-C60) arylsilyl or ammo.

The compound having an electroluminescence peak with wavelength

990 of not less than 560 nm included in the electroluminescent layer may be exemplified by the following compounds, but not limited thereto:

In the organic electroluminescent device according to thepresent invention, a layer (hereinafter referred to as "surface layer") selected from a metal chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both

1050 electrode (s) among the pair of electrodes . More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent layer. A driving stability may be

1055 attained therefrom.

The chalcogenide may be, for example, SiO _x (1 ≤ x ≤ 2) , AlO _x (1 ≤ x ≤ 1.5) , SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF ₂ , CaF _2/ a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, etc.

1060 Further, in the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be placed on the inner surface of one or both electrode (s) among the pair of electrodes. In that case, 1065 transport of electrons from the mixed region to the electroluminescent layer becomes easier, because the electron transport compound is reduced to an anion. Further, transport of holes from the mixed region to the electroluminescent layer becomes easier, because the hole transport compound is oxidized to a cation. Preferred examples of 1070 the oxidative dopant include various Lewis acids and acceptor compounds . Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.

The organic electroluminescent compound according to the present

1075 invention has superior luminous efficiency, excellent color purity of the material and very good life property. Therefore, it may be used to manufacture OLED devices having very good operation life.

[Description of Drawings]

The above and other aspects, features and advantages of the 1080 present invention will become apparent from the following description of preferred embodiments given in conjunction with the accompanying drawing, in which:

FIG. 1 is a cross-sectional view of an OLED device. <Description of symbols of significant parts of the drawing> 1085 1: Glass

2: Transparent electrode 3: Hole injecting layer 4 : Hole transport layer 5: Electroluminescent layer

1090 6: Electron transport layer 7: Electron injecting layer 8: Al cathode [Best Mode]

Hereinafter, organic electroluminescent compounds according to 1095 the present invention, preparation method thereof and electroluminescence characteristics thereof will be described referring to representative exemplary compounds. However, the following examples are for illustrative purposes only and not intended to limit the scope of the present invention.

1100

Preparation Examples

Preparation Example 1: Preparation of Compound 6

1105 Preparation of Compound 1-1

Magnesium (Mg) (1.1 g, 44.9 mmol) and iodine (I ₂ ) (1.7 g, 6.9 πunol) were mixed with THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature, 3-bromo-5, 5-dimethyl-5H-dibenzo [b, d] silole (10.0 g, 34.6 mmol)

1110 dissolved in THF (500 mL) were added to the mixture solution of Mg and I ₂ . After stirring for an hour under reflux, the solution was cooled to room temperature. After adding phthalic anhydride (5.1 g,

34.6 rtimol) , followed by stirring for 5 hours at 50 ⁰ C, distilled water was added at room temperature. After extracting with MC, followed

1115 by drying with MgSO ₄ , Compound 1-1 (10.0 g, 27.9 mmol, 82.05 %) was obtained by distillation under reduced pressure and column separation.

Preparation of Compound 1-2

Compound 1-1 (10.0 g, 27.9 mmol) was mixed with methanesulfonic acid (70 mL) and stirred for 2 hours at 100 ⁰ C. After cooling to room 1120 temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution. Compound 1-2 (4.0 g, 11.7 mmol, 43.51 %) was obtained by column separation.

Preparation of Compound 1-3

1125 2-Bromonaphthalene (7.2 g, 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added at -78 ⁰ C. After stirring for an hour, Compound 1-2 (4.O g, 11.7 mmol) was added at -78 ⁰ C. After stirring for 6 hours at room temperature, distilledwaterwas added. After extracting withMC, followedby drying 1130 with MgSO ₄ , Compound 1-3 (6.7 g, 11.7 mmol, 100 %) was obtained by distillation under reduced pressure. Preparation of Compound 6

Compound 1-3 (6.7 g, 11.7 mmol) , KI (5.5g, 33.5 mmol) andNaH ₂ PO ₂ H ₂ O

(7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred

1135 under reflux. 6 hours later, the mixture was cooled to room temperature and distilled water was added to filter the produced solid under reduced pressure. The solid was neutralized by washing with aqueous NaOH solution. Compound 6 (3.O g, 63.7 %, 5.3mmol) was obtained by column separation.

1140

Preparation Example 2: Preparation of Compound 180

Preparation of Compound 2-1

Mg (1.1 g, 44.9 mmol) and I ₂ (1.7 g, 6.9 mmol) were mixed with

1145 THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature, 3-bromo-5, 5-dimethyl-5H-dibenzo [b, d] silole (10.0 g, 34.6 mmol) dissolved in THF (50O mL) was added to the mixture solution of Mg and I ₂ . The mixture was stirred under reflux for an hour and cooled to room temperature . 5-Bromoisobenzofuran-l, 3-dione

1150 (5.12 g, 34.57 mmol) was added. After stirring at 50 ⁰ C for 5 hours, distilled water was added at room temperature. After extracting with MC, followed by drying with MgSO ₄ , Compound 2-1 (10 g, 27.89 mmol, 82.05 % ) was obtained by distillation under reduced pressure and column separation.

1155 Preparation of Compound 2-2

Compound 2-1 (10.0 g, 27.9 mmol) was mixed with methanesulfonic acid (70 mL) and stirred for two hours at 100 ⁰ C. After cooling to room temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution. 1160 Compound 2-2 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column separation.

Preparation of Compound 2-3

Compound 2-2 (2.O g, 4.1 mmol), phenylboronic acid (1.3 g, 10.3 mmol) and tetrakis palladium (0) tπphenylphosphine (Pd(PPh ₃ ) ₄ ) (0.6

1165 g, 0.4 mmol) were dissolved in toluene (100 mL) and ethanol (50 mL) .

After adding 2 M aqueous sodium carbonate solution (50 mL) , the mixture was stirred at 120 ⁰ C for 4 hours under reflux. After cooling to 25

⁰ C, distilled water (200 mL) was added to terminate the reaction, followed by extraction with ethyl acetate (150 mL) and drying under

1170 reduced pressure. Compound2-3 (1.6g, 3.3mmol) was obtainedby column chromatography .

Preparation of Compound 2-4

2-Bromonaphthalene (7.2 g, 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added 1175 at -78 ⁰ C. After stirring for an hour, Compound 2-3 (4.0 g, 11.7 mmol) was added at -78 ⁰ C. After stirring for 6 hours at room temperature, distilledwater was added. After extracting with MC, followedby drying with MgSO ₄ , Compound 2-4 (7.9g, 11.7 mmol) was obtained by distillation under reduced pressure. 1180 Preparation of Compound 180

Compound 2-4 (7.9g, 11.7 mmol) , KI (5.5g, 33.5 mmol) andNaH ₂ PO ₂ H ₂ O

(7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the produced solid was filtered under

1185 reduced pressure. The solid was neutralized by washing with aqueous NaOH solution. Compound 180 (3 g, 5.3πunol, 63.9%) was obtained by column separation.

Preparation Example 3: Preparation of Compound 444

Preparation of Compound 3-1

3, 7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole (2.0 g, 4.1 πunol) , 1-naphthylboronic acid (1.3 g, 10.3 mmol) and tetrakis palladium (0) triphenylphosphine (Pd (PPh ₃ ) ₄ ) (0.6 g, 0.4 mmol) were

1195 dissolved in toluene (100 mL) and ethanol (50 mL) . After adding 2

M aqueous sodium carbonate solution (50 mL) , the mixture was stirred at 120 ⁰ C for 4 hours under reflux. After cooling to 25 ⁰ C, distilled water (200 mL) was added to terminate the reaction, followed by extraction with ethyl acetate (15OmL) and drying under reduced pressure .

1200 Compound 3-1 (1.6 g, 3.3 mmol) was obtained by column chromatography.

Preparation of Compound 3-2

Mg (1.1 q, 44.9 mmol) and I ₂ (1.7 g, 6.9 mmol) were mixed with THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature, Compound 3-1 (10.0 g, 24.1 mmol) dissolved in 1205 THF (500 mL) was added to the mixture solution of Mg and I ₂ . After stirring for an hour under reflux, the mixture was cooled to room temperature. 5-Bromoisobenzofuran-1, 3-dione (5.1 g, 34.8 mmol) was added. After stirring at 50 ⁰ C for 5 hours, distilled water was added at room temperature. After extracting with MC, followed by drying

1210 with MgSO ₄ , Compound 3-2 (10.0 g, 27.9 mmol, 82.1 %) was obtained by distillation under reduced pressure and column separation. Preparation of Compound 3-3

Compound 3-2 (10.0 g, 27.9 mmol) was mixed with methanesulfonic acid (70 mL) and stirred for two hours at 100 ⁰ C. After cooling to

1215 room temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution . Compound 3-3 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column separation.

Preparation of Compound 3-4

1220 Compound 3-3 (2.0 g, 4.1 mmol), 1-naphthylboronic acid (1.3 g,

10.3 mmol) and tetrakis palladium ( 0) triphenylphosphine (Pd(PPh ₃ J ₄ )

(0.6 g, 0.4 mmol) were dissolved in toluene (100 mL) and ethanol (50 mL) . 2 M aqueous sodium carbonate solution (50 mL) was added and the mixture was stirred at 120 ⁰ C for 4 hours under reflux. After cooling

1225 to 25 ⁰ C, distilled water (200 mL) was added to terminate the reaction, followed by extraction with ethyl acetate (150 mL) and drying under reduced pressure. Compound 3-4 (1.6g, 3.3mmol) was obtained by column chromatography.

Preparation of Compound 3-5

1230 Bromobenzene (7.2 g, 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added at -78 ⁰ C. After stirring for an hour, Compound 3-4 (4.O g, 11.7 rranol) was added at -78 °C. After stirring for 6 hours at room temperature, distilledwater was added. After extracting withMC, followedby drying

1235 withMgSO ₄ , Compound3-5 (8.8 g, 11.7 mmol) was obtained by distillation under reduced pressure.

Preparation of Compound 444

Compound 3-5 (8.8g, 11.7 mmol) , KI (5.5g, 33.5 mmol) and NaH ₂ PO ₂ H ₂ O (7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred

1240 under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the produced solid was filtered under reduced pressure. The solid was neutralized by washing with aqueous NaOH solution. Compound 444 (3.O g, 5.3 mmol, 63.9 %) was obtained by column separation.

1245

Preparation Example 4: Preparation of Compound 502

Preparation of Compound 4-1

Mg (1.1 g, 44.9 mmol) and I ₂ (1.7 g, 6.9 mmol) were mixed with 1250 THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature, l-bromo-5, 5-dimethyl-5H-dibenzo [b, d] silole (10.0 g, 34.6iranol) dissolved in THF (50O mL) was added to the mixture solution of Mg and I ₂ . After stirring for an hour under reflux, the mixture was cooled to room temperature. Phthalic anhydride (5.1 g,

1255 34.6 mmol) was added. After stirring at 50 °C for 5 hours, distilled waterwasaddedat roomtemperature. After extracting withMC, followed by drying with MgSO ₄ , Compound 4-1 (10.0 g, 27.9 mmol, 82.0 %) was obtained by distillation under reduced pressure and column separation.

Preparation of Compound 4-2

1260 Compound 4-1 (10.0 g, 27.9mmol) was mixed with methanesulfonic acid (70 mL) and stirred for two hours at 100 ⁰ C. After cooling to room temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution. Compound 4-2 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column

1265 separation.

Preparation of Compound 4-3

2-Bromonaphthalene (7.2 g, 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added at -78 ⁰ C. After stirring for an hour, Compound 4-2 (4 g, 11.7 mmol)

1270 was added at -78 ⁰ C. After stirring for 6 hours at room temperature, distilledwater was added. After extracting withMC, followedby drying with MgSO ₄ , Compound 4-3 (7.O g, 11.7 mmol, 100 %) was obtained by distillation under reduced pressure. Preparation of Compound 502

1275 Compound 4-3 (7.Og, 11.7 mmol) , KI (5.5g, 33.5 mmol) and NaH ₂ PO ₂ H ₂ O (7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the produced solid was filtered under reduced pressure. The solid was neutralized by washing with aqueous 1280 NaOH solution. Compound 502 (3.O g, 5.3 mmol, 63.9 %) was obtained by column separation.

Preparation Example 5: Preparation of Compound 517

1285 Preparation of Compound 5-1

Mg (1.1 g, 44.9 mmol) and I ₂ (1.7 g, 6.9 mmol) were mixed with

THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature,

9-bromo-7, 7-dimethyl-7H-benzo [d] naphtho [2, l-b]silole (10.0 g, 29.5

1290 rwnol) dissolved in THF (500 mL) was added to the mixture solution of Mg and I ₂ . After stirring for an hour under reflux, the mixture was cooled to room temperature. Phthalic anhydride (5.1g, 34.8 mmol) was added. After stirring at 50 ⁰ C for 5 hours, distilled water was added at room temperature. After extractingwithMC, followedby drying

1295 with MgSO ₄ , Compound 5-1 (10.0 g, 27.9 mmol, 82.1 %) was obtained by distillation under reduced pressure and column separation.

Preparation of Compound 5-2

Compound 5-1 (10.0 g, 27.9 mmol) was mixed with methanesulfonic acid (70 inL) and stirred for two hours at 100 °C. After cooling to

1300 room temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution. Compound 5-2 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column separation.

Preparation of Compound 5-3

1305 2-Bromonaphthalene (7.2 g, 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added at 78 ⁰ C. After stirring for an hour, Compound 5-2 (4.O g, 11.7 mmol) was added at -78 ⁰ C. After stirring for 6 hours at room temperature, distilledwater was added. After extracting withMC, followedby drying

1310 with MgSO ₄ , Compound 5-3 (7.6 g, 11.7 mmol, 100 %) was obtained by distillation under reduced pressure. Preparation of Compound 517

Compound 5-3 (7.6g, 11.7 mmol) , KI (5.5g, 33.5 mmol) and NaH ₂ PO ₂ H ₂ O (7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred

1315 under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the produced solid was filtered under reduced pressure. The solid was neutralized by washing with aqueous NaOH solution. Compound 517 (3.O g, 5.3 mmol, 63.9 %) was obtained by column separation.

1320

Preparation Example 6: Preparation of Compound 534

Preparation of Compound 6-1

Mg (1.1 g, 44.9 iranol) and I ₂ (1.7 g, 6.9 iratiol) were mixed with

1325 THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature,

9-bromo-ll, 11-dimethyl-llH-benzo [d] naphtho [ 1, 2-b] silole (10.0 g, 29.5 mmol) dissolved in THF (50OmL) was added to the mixture solution of Mg and I ₂ . After stirring for an hour under reflux, the mixture

1330 was cooled to room temperature. Phthalic anhydride (5.1g, 34.6mmol) was added. After stirring at 50 ⁰ C for 5 hours, distilled water was added at room temperature. After extractingwithMC, followedby drying with MgSO ₄ , Compound 6-1 (10.0 g, 27.9 mmol, 82.1 %) was obtained by distillation under reduced pressure and column separation.

1335 Preparation of Compound 6-2

Compound 6-1 (10.0 g, 27.9 mmol) was mixed with methanesulfonic acid (70 mL) and stirred for two hours at 100 ^C C. After cooling to room temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution.

1340 Compound 6-3 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column separation .

Preparation of Compound 6-3 2-Bromonaphthalene (7.2 g, 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added

1345 at -78 ⁰ C. After stirring for an hour, Compound 6-2 (4.O g, 11.7 mmol) was added at -78 ⁰ C. After stirring for 6 hours at room temperature, distilled water was added. After extracting with MC, followed by drying with MgSO ₄ , Compound 6-3 (7.6 g, 11.7 mmol, 100 %) was obtained by distillation under reduced pressure.

1350 Preparation of Compound 534

Compound 6-4 (7.6g, 11.7 mmol) , KI (5.5g, 33.5 mmol) and NaH ₂ PO ₂ H ₂ O (7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the produced solid was filtered under

1355 reduced pressure. The solid was neutralized by washing with aqueous NaOH solution. Compound 534 (3.O g, 5.3 mmol, 63.9 %) was obtained by column separation.

Preparation Example 7: Preparation of Compound 538

Preparation of Compound 7-1

Mg (1.1 g, 44.9 mmol) and I ₂ (1.7 g, 6.9 mmol) were mixed with THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature,

1365 3-bromo-5,5-dimethyl-5H-benzo[d]naphtho[2,3-b]silole (10.0 g, 29.5 itmol) dissolved in THF (500 itiL) was the mixture solution of Mg and

I ₂ . After stirring for an hour under reflux, the mixture was cooled to room temperature. Phthalic anhydride (5.1g, 34.6mmol) was added.

After stirring at 50 ⁰ C for 5 hours, distilled water was added at

1370 room temperature. After extracting with MC, followed by drying with

MgSO ₄ ,. Compound 7-1 (10.0 g, 27.9 mmol, 82.1 %) was obtained by distillation under reduced pressure and column separation.

Preparation of Compound 7-2

Compound 7-1 (10.0 g, 27.9 mmol) was mixed with methanesulfonic 1375 acid (70 mL) and stirred for two hours at 100 ⁰ C. After cooling to room temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution. Compound 7-2 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column separation. 1380 Preparation of Compound 7-3

2-Bromonaphthalene (7.2 g _r 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added at -78 ⁰ C. After stirring for an hour, Compound 7-2 (4.O g, 11.7 mmol) was added at -78 ⁰ C. After stirring for 6 hours at room temperature, 1385 distilled water was added. After extracting with MC, followed by drying with MgSO ₄ , Compound 7-3 (7.6 g, 11.7 mmol, 100 %) was obtained by distillation under reduced pressure. Preparation of Compound 538

Compound7-3 (7.6g, 11.7 mmol) , KI (5.5g, 33.5mmol) andNaH ₂ PO ₂ H ₂ O 1390 (7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the produced solid was filtered under reduced pressure. The solid was neutralized by washing with aqueous NaOH solution. Compound 538 (3.O g, 5.3 mmol, 63.9 %) was obtained 1395 by column separation.

Preparation Example 8: Preparation of Compound 545

Preparation of Compound 8-1

1400 Mg (1.1 g, 44.9 mmol) and I ₂ (1.7 g, 6.9 mmol) were mixed with

THF (70 mL) and stirred under reflux. One hour later, after cooling to room temperature,

4-bromo-5,5-dimethyl-5H-benzo[d]naphtho[2,3-b]silole (10.0 g, 29.5 mmol) dissolved in THF (500 mL) was the mixture solution of Mg and

1405 I ₂ . After stirring for an hour under reflux, the mixture was cooled to room temperature. Phthalic anhydride (5.1 g, 34.8 mmol) was added.

After stirring at 50 ⁰ C for 5 hours, distilled water was added at room temperature. After extracting with MC, followed by drying with

MgSO ₄ , Compound 8-1 (10.0 g, 27.9 mmol, 82.1 %) was obtained by

1410 distillation under reduced pressure and column separation.

Preparation of Compound 8-2 Compound 8-1 (10.0 g, 27.9 mmol) was mixed with methanesulfonic acid (70 mL) and stirred for two hours at 100 ⁰ C. After cooling to room temperature, distilled water was added. The produced solid was 1415 filtered under reduced pressure and washed with aqueous NaOH solution. Compound 8-2 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column separation.

Preparation of Compound 8-3

2-Bromonaphthalene (7.2 g, 35.2 mmol) was dissolved in THF (100 1420 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added at -78 ⁰ C. After stirring for an hour, Compound 8-2 (4.O g, 11.7 mmol) was added at -78 °C. After stirring for 6 hours at room temperature, distilled water was added. After extracting with MC, followed by drying with MgSO ₄ , Compound 8-3 (7.6 g, 11.7 mmol, 100 %) was obtained by 1425 distillation under reduced pressure. Preparation of Compound 545

Compound 8-3 (7.6g, 11.7 mmol) , KI (5.5g, 33.5 mmol) andNaH ₂ PO ₂ H ₂ O

(7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred under reflux. 6 hours later, after cooling to room temperature,

1430 distilled water was added and the produced solid was filtered under reduced pressure. The solid was neutralized by washing with aqueous

NaOH solution. Compound 545 (3.O g, 5.3 mmol, 63.9 %) was obtained by column separation.

1435 Preparation Example 9: Preparation of Compound 582

Preparation of Compound 9-1

Mg (1.1 q, 44.9 mmol) and I ₂ (1.7 g, 6.9 mmol) were mixed with

THF (70 inL) and stirred under reflux. One hour later, after cooling

1440 to room temperature. Compound 3-1 (10.0 g, 24.1 mmol) dissolved in

THF (500 mL) was added to the mixture solution of Mg and I ₂ . After stirring for an hour under reflux, the mixture was cooled to room temperature. Phthalic anhydride (5.1g, 34.8 mmol) was added. After stirring at 50 ⁰ C for 5 hours, distilled water was added at room

1445 temperature. After extracting with MC, followed by drying with MgSO ₄ ,

Compound 9-1 (10.0 g, 27.9 mmol, 82.1%) was obtained by distillation under reduced pressure and column separation.

Preparation of Compound 9-2

Compound 9-1 (10.0 g, 27.9 mmol) was mixed with methanesulfonic 1450 acid (70 mL) and stirred for two hours at 100 ⁰ C. After cooling to room temperature, distilled water was added. The produced solid was filtered under reduced pressure and washed with aqueous NaOH solution. Compound 9-2 (4.0 g, 11.7 mmol, 43.5 %) was obtained by column separation. 1455 Preparation of Compound 9-3

Bromobenzene (7.2 g, 35.2 mmol) was dissolved in THF (100 mL) and n-butyllithium (14.6 mmol, 2.5M in hexane) was slowly added at -78 ^C C. After stirring for an hour, Compound 9-2 (4.O g, 11.7 mraol) was added at -78 ⁰ C. After stirring for 6 hours at room temperature,

1460 distilled water was added. After extracting with MC, followed by drying with MgSO ₄ , Compound 9-3 (7.3 g, 11.7 mmol, 100 %) was obtained by distillation under reduced pressure. Preparation of Compound 582 Compound 9-3 (7.3g, 11.7 mmol) , KI (5.5g, 33.5 mmol) and NaH ₂ PO ₂ H ₂ O

1465 (7.1 g, 69.0 mmol) were mixed with acetic acid (100 mL) and stirred under reflux. 6 hours later, after cooling to room temperature, distilled water was added and the produced solid was filtered under reduced pressure. The solid was neutralized by washing with aqueous NaOH solution. Compound 582 (3.O g, 5.3 mmol, 63.9 %) was obtained

1470 by column separation.

Organic electroluminescent compounds (Compounds 1 to 665) were prepared according to the method of Preparation Examples 1 to 9. Table 1 shows ¹ H NMR and MS/FAB data of the prepared organic electroluminescent 1475 compounds .

[Table 1]

Example 1: Manufacture of OLED device using the organic electroluminescent compound according to the present invention 1480 An OLED device was manufactured using the organic electroluminescent compound ^' according to the present invention.

First, a transparent electrode ITO film (15 Ω/D) 2 prepared from a glass substrate for an OLED (Samsung Corning) 1 was subjected to ultrasonic washing sequentially using trichloroethylene, acetone,

1485 ethanol and distilled water, and stored in isopropanol for later use.

Next, the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. After filling

4, 4 ' , 4"-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine

(2-TNATA) of the following structure in a cell of the vacuum deposition

1490 apparatus, the pressure inside the chamber was reduced to ICT ⁶ torr. Then, 2-TNATA was evaporated by applying electrical current to the cell. A hole injection layer 3 having a thickness of 60 nm was formed on the ITO substrate.

Subsequently, after filling

1495 N, W-bis(α-naphthyl) -W, AT -diphenyl-4, 4 ' -diamine (NPB) of the following structure in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current. A hole transport layer 4 having a thickness of 20 nm was formed on the hole injection layer .

1500 2-TNATA NPB After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. Compound 6 was filled in a cell of a vacuum deposition apparatus as a host, and Compound E was filled in another cell as a dopant. The 1505 two materials were evaporated at different speeds, so that an electroluminescent layer 5 having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.

Compound 6 Compound E

Thereafter, tris (8-hydroxyguinoline) -aluminum (III) (AIq) of the following structure was deposited with a thickness of 20 nm as 1510 an electron transport layer 6. Then, lithium quinolate (Liq) of the following structure was deposited with a thickness of 1 to 2 nm as an electron inj ection layer 7. Then, an Al cathode 8 having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.

Each OLED electroluminescent material was purified by vacuum sublimation at ICT ⁶ torr. Comparative Example 1 : Manufacture of OLED device using existing

1520 electroluminescent material

A hole injection layer 3 and a hole transport layer 4 were formed as in Example 1. Tris (8-hydroxyquinoline) -aluminum (III) (AIq) was filled in a cell of a vacuum deposition apparatus as an electroluminescent host material, and Coumarin 545T (C545T) of the

1525 following structure was filled in another cell. The two materials were doped by evaporating at different speeds. An electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer. Preferred doping concentration is 1 to 3 wt% based on AIq.

C545T

1530 Then, an electron transport layer 6 and an electron injection layer 7 were formed as in Example 1, and an Al cathode 8 having a thickness of 150 nmwas formed us ing another vacuum deposition apparatus to manufacture an OLED.

1535 Luminous efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1, which comprise the organic electroluminescent compounds according to the present invention and the existing electroluminescent compound respectively, was measured at 5,000 cd/m ² . The result is given in Table 2.

1540 [Table 2]

As seen in Table 2, when the compounds according to the present invention were used to manufacture green electroluminescent devices, luminous efficiency was significantly improved as compared to Comparative Example 1 , while the color purity was maintained comparable or better. Example 2: Manufacture of OLED device using the organic electroluminescent compound according to the present invention

1550 A hole injection layer 3 and a hole transport layer 4 were formed as in Example 1, and an electroluminescent layer was formed thereupon as follows. Dinaphthylanthracene (DNA) of the following formula was filled in a cell of a vacuum deposition apparatus as a host, and Compound 43 was filled in another cell as a dopant. The two materials were

1555 doped by evaporating at different speed, at 2 to 5 wt% based on the host. An electroluminescent layer 5 having a thickness of 30 ran was formed on the hole transport layer.

DNA Compound 43

Subsequently, an electron transport layer and an electron infection layer were formed as in Example 1, and an Al cathode having 1560 a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.

Comparative Example 2: Electroluminescence characteristics of

OLED device manufactured using existing electroluminescent material

1565 A hole injection layer and a hole transport layer were formed as in Example 1. Dinaphthylanthracene (DNA) was filled in a cell of a vacuum deposition apparatus as an electroluminescent host material, and Compound A, a blue electroluminescent material having the following structure, was filled in another ell. An electroluminescent layer 1570 having a thickness of 30 nm was formed on the hole transport layer at a deposition rate of 100:1.

Compound A

Subsequently, an electron transport layer and an electron 1575 injection layer were formed as in Example 1, and an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.

Luminous efficiency of the OLED devices manufactured in Example 1580 2 and Comparative Example 2, which comprise the organic electroluminescent compounds according to the present invention and the existing electroluminescent compound respectively, was measured at 1,000 cd/m ² . The result is given in Table 3. [Table 3]

1585

As seen in Table 3, when the compounds according to the present invention were used to manufacture blue electroluminescent devices, color purity was significantly improved as light blue to blue, as compared to jade green, and luminous efficiency was maintained

1590 comparable to or better than Comparative Example 2.

Example 3: Manufacture of OLED device using the organic electroluminescent compound according to the present invention

A hole injection layer 3 and a hole transport layer 4 were formed

1595 as m Example 1.

9, 10-Di (biphenyl-4-yl) -2- (naphthalen-2-yl) anthracene (DBNA) was filled inacellofa vacuum deposition apparatus as a host, and Compound 636 was filled m another cell as a dopant. The two materials were doped 2 to 5 wt% based on the host, by evaporating at different speed.

1600 An electroluminescent layer 5 having a thickness of 30 nm was formed on the hole transport layer.

DBNA Compound 636

Subsequently, an electron transport layer 6 and an electron injection layer 7 were formed as in Example 1, and an Al cathode having a thickness of 150 nm was formed using another vacuum deposition 1605 apparatus to manufacture an OLED.

Luminous efficiency of the OLED devices manufactured in Example 3 and Comparative Example 1, which comprise the organic electroluminescent compounds according to the present invention and 1610 the existing electroluminescent compound respectively, was measured at 5,000 cd/m ² . The result is given in Table 4. [Table 4]

As seen in Table 4, when the compounds according to the present invention were used to manufacture green electroluminescent devices, 1615 luminous efficiency was significantly improved, and color purity was maintained comparable to or better than Comparative Example 1. [industrial Applicability]

The organic electroluminescent compound according to the present invention has superior luminous efficiency, excellent color purity

1620 of the material and very good life property. Therefore, it may be used to manufacture OLED devices having very good operation life. While the exemplary embodiments have been shown and described, it will be understood by those skilled in the art that various changes

1625 in form and details may be made thereto without departing from the spirit and scope of this disclosure as defined by the appended claims.

In addition, many modifications can be made to adapt a particular situation or material to the teachings of this disclosure without departing from the essential scope thereof . Therefore, it is intended

1630 that this disclosure not be limited to the particular exemplary embodiments disclosed as the best mode contemplated for carrying out this disclosure, but that this disclosure will include all embodiments falling within the scope of the appended claims.

1635