[invention Title]

ELECTROLUMINESCENT DEVICE USING THE ELECTROLUMINESCENT COMPOUNDS [Technical Field]

The present invention relates to an electroluminescent device in which an organic layer is interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1, and the dopant compound is a mixture of not less than 80% by weight and less than 100% by weight of the cis-form and more than 0% by weight and not more than 20% by weight of the trans-form:

wherein

^■ """ represents cis or trans configuration to the double bond. [Background Art]

Among display devices, electroluminescence (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. In 1987, Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as electroluminescent materials [Appl. Phys. Lett. 51, 913, 1987].

In an organic EL device, when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) , an electron and a hole are paired and emit light as the electron-hole pair is extinguished. The organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color. Since an organic EL device can exhibit green, blue and red colors, it is drawing a lot of attention as a full-color display device of the next generation. Aprocess of manufacturing an organic EL device is as follows: '

(1) First, an anode material is coated on a transparent substrate. Indium tin oxide (ITO) is frequently used as the anode material.

(2) Then, a hole injecting layer (HIL) is formed thereupon. The hole injecting layer is typically formed by coating copper phthalocyanine (CuPc) to a thickness of 10 to 30 nm.

(3) Then, a hole transport layer (HTL) is formed. The hole transport layer is formed by depositing 4,4' -bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) to a thickness of about 30 to 60 nm. (4) An organic emitting layer is formed thereupon. If required, a dopant is added thereto. In case of green electroluminescence, an organic emitting layer is formed frequently by depositing tris (8-hydroxyquinolato) aluminum (AIq ₃ ) to a thickness of about 30 toβOnm. For the dopant , N-methylquinacridone (MQD) is commonly used. (5) An electron transport layer (ETL) and an electron injection layer (EIL) are formed sequentially, or an electron injection/transport layer is formed thereupon. In case of green electroluminescence, the ETL and/or EIL may be unnecessary because AIq ₃ has good electron transport ability. (6) Then, a cathode is formed, and, finally, a protective layer is formed thereupon.

With such a structure, blue, green and red EL devices are obtained respectively depending on how the electroluminescent layer is formed. The existing green electroluminescent compounds used to create green EL devices do not have good life property or luminous efficiency.

In an organic EL device, the most important factor affecting such quality as luminous efficiency, property, etc. is the electroluminescent material. Several requirements of the electroluminescent material include high fluorescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform and thin film, and good stability.

Organic electroluminescent materials may be roughly classified into high-molecular-weight materials and low-molecular-weight materials . The low-molecular-weight materials may be classified into metal complexes and metal-free pure organic electroluminescent materials, depending on molecular structure. Chelate complexes such as tris (8-quinolato) aluminum, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, or the like are known. It is reported that electroluminescence from the blue to the red region can be obtained using these materials, and the realization of full-color display devices is being expected. [Disclosure]

80 [Technical Problem]

The present inventors have invented an electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, the organic layer comprising a combination of specific compounds, in order to realize an electroluminescent device having

85 high color purity, high luminous efficiency and long operation life.

An object of the present invention is to provide an electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising as dopant a

90 mixture of cis- and trans-form electroluminescent compounds with a specific proportion. Another object of the- present invention is to provide an electroluminescent device further comprising one or more host compound (s) in the electroluminescent layer in addition to the dopant. Another object of the present invention is to provide an

95 organic solar cell comprising a mixture of cis- and trans-form electroluminescent compounds with a specific proportion. [Technical Solution]

The present invention provides an electroluminescent device comprising an organic layer interposed between an anode and a cathode

100 on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1, and the dopant compound is a mixture of not less than 80% by weight and less than 100% by weight of the cis-form and more than 0% by weight and not more than 20% by weight 105 of the trans-form:

wherein

^w represents cis or trans configuration to the double bond; Ari and Ar ₂ independently represent (C6-C60) arylene or 110 (C5-C50) heteroarylene containing one or more heteroatom (s) selected from N, O and S;

Ri through R ₄ independently represent hydrogen, halogen,

(C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected fromN, O and S, morpholino, thiomorpholino,

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

120 (Cl-CβO)alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy,

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

(C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or each of Ri through

R ₄ 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

125 ring or a monocyclic or polycyclic aromatic ring; and the arylene or heteroarylene of Ari and Ar ₂ , and the aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkylamino,

130 arylamino, alkoxycarbonyl, alkylcarbonyl or arylcarbonyl of Ri through

R ₄ may be further substituted by one or more substituent (s) selected from a group consisting of deuterium, halogen, halo (C1-C60) alkyl,

(Cl-CβO)alkyl, (C6-C60) aryl, (C3-C60) heteroaryl with or without

(C6-C60)aryl substituent, morpholino, thiomorpholino, 5- or

135 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, carbazolyl, mono- or di (C1-C60) alkylamino, mono- or

140 di (C6-C60) arylamino, (C1-C60) alkyloxy, (C1-C60) alkylthio,

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

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

The electroluminescent layer may further comprise one or more 145 host compound (s) represented by Chemical Formulas 2 and 3:

(Ar ₁₁ J _a -X- (Ar ₁₂ ) _b (2)

(Ar ₁₃ ) _c -Y- (Ar ₁₄ ) _d (3) wherein

X represents (C6-C60) arylene or (C4-C60) heteroarylene; 150 Y represents anthracenylene;

Ar ₁₁ throughAr ₁₄ independently represent hydrogen, (Cl-C60) alkyl, (Cl-CβO)alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60)aryl; the alkyl, cycloalkyl, aryl or heteroaryl of Ar ₁ I through Ar _i4

155 may be further substituted by one or more substituent (s) selected from a group consisting of (Cβ-CβO)aryl or (C4-C60) heteroaryl with or without one or more substituent (s) selected from a group consisting of deuterium, (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano,

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

165 a, b, c and d independently represent an integer from 1 to 4.

In the present invention, "alkyl", "alkoxy" and other substituents including "alkyl" moietymaybe 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

170 include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but not limited thereto.

175 In the present invention, "heteroaryl" means aryl group containing 1 to 4 heteroatom(s) selected from N, 0 and S as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, 180 and may be partially saturated. The heteroaryl includes a divalent aryl group wherein the heteroatom (s) in the ring may be oxidized or quaternizedto form, for example, N-oxide or quaternary salt . Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl,

185 isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl,

190 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.

195 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, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.

And, in the present invention, the substituents including

200 " (Cl-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 " (C3-C60) heteroaryl" moiety may have 3 to 60 carbon atoms, 4 to 20

205 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, 2 to 20 carbon atoms, or 2 to 10 carbon atoms. The electroluminescent device according to the present invention exhibits an effective energy transfer mechanism between a host and a dopant and, therefore, may provide good, high-efficiency EL characteristics through improved electron density distribution. Further, it can overcome the problems associated with the existing materials, i.e., decrease of initial efficiency, short operation life, etc., and can provide high-performance EL characteristics with high efficiency and long operation life for individual colors.

The dopant compound represented by Chemical Formula 1 is mixture of cis-form and trans-form, comprising not less than 80% by weight and less than 100% by weight of the cis-form (80% by weight ≤ cis content < 100% by weight) and more than 0% by weight and not more than 20% by weight of the trans-form (0% by weight < trans content ≤ 20% by weight) .

In the dopant compound represented by Chemical Formula 1, Ari and Ar ₂ are independently selected from the following structures, but not limited thereto:

wherein

Rn through R ₁₇ independently represent hydrogen, deuterium,

230 halogen, halo (C1-C60) alkyl, (C1-C60) alkyl, (Cβ-CβO) aryl,

(C3-C60)heteroaryl with or without (C6-C60)aryl substituent, 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,

235 di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

(C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, carbazolyl, mono- or di (C1-C60) alkylamino, mono- or di (Cβ-CβO)arylamino, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60)aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,

240 (Cl-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy.

And, in the dopant compound represented by Chemical Formula 1, Ri through R ₄ independently represent hydrogen, halogen, (C1-C60) alkyl, halo (C1-C60) alkyl, 5- or 6-membered heterocycloalkyl containing one

245 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, cyano, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl,

250 (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or each of Ri through R ₄ 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. Ri through R ₄ are independently selected from the following structures, but not limited

255 thereto:

wherein

R ₂ i through R ₃₃ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, 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, carbazolyl, mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino, (Cl-CβO)alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy; 270 A represents CR ₃₄ R ₃₅ , NR ₃₅ , S or O;

R ₃₄ through R ₃₅ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S,

275 (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, (Cl-CβO)alkylamino, (C6-C60) arylamino, (C1-C60) alkyloxy, (Cl-CβO)alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio,

280 (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl,

(C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or R ₃₄ and R ₃₅ 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; and

285 e represents an integer from 1 to 5.

Specifically, in the dopant compound represented by Chemical Formula 1, Ari and Ar ₂ independently represent 1, 2-phenylene, 1, 3-phenylene, 1, 4-phenylene, 9, 9-dimethyl-l, 2-fluorenylene, 9, 9-dimethyl-l, 3-fluorenylene, 9, 9-dimethyl-l, 4-fluorenylene,

290 9, 9-dimethyl-l, 5-fluorenylene, 9, 9-dimethyl-l, 6-fluorenylene, 9, 9-dimethyl-l, 7-fluorenylene, 9, 9-dimethyl-l, 8-fluorenylene, 9, 9-dimethyl-2, 3-fluorenylene, 9, 9-dimethyl-2, 4-fluorenylene, 9, 9-dimethyl-2, 5-fluorenylene, 9, 9-dimethyl-2, β-fluorenylene, 9, 9-dimethyl-2, 7-fluorenylene, 9, 9-dimethyl-3, 4-fluorenylene,

295 9, 9-dimethyl-3, 5-fluorenylene, 9, 9-dimethyl-3, β-fluorenylene, 9, 9-dimethyl-4, 5-fluorenylene, 4, 2 ^Λ -biphenylene, 4, 3 '-biphenylene or 4 , 4 ^λ -biphenylene; and Ri through R ₄ independently represent hydrogen, deuterium, fluoro, chloro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl,

300 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, benzyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, morpholinyl, thiomorpholinyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, trimethylsilyl, triethylsilyl,

305 tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl, dimethylamino, diphenylamino, adamantyl, cyano, ethenyl, phenylethenyl, ethynyl, phenylethynyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, methylthio, phenyloxy,

310 phenylthio, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, methylcarbonyl, ethylcarbonyl, benzylcarbonyl, phenylcarbonyl, carboxyl, nitro or hydroxy, or they are selected from the following structures :

Specifically, the dopant compound represented by Chemical Formula 1 may be exemplified by the following compounds , but not limited thereto :

20

22





40

42

43

53

The host compound represented by Chemical Formula 2 or 3 maymplified by the compounds represented by Chemical Formulas 4

455 wherein

R ₄₁ and R ₄₂ independently represent (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S or (C3-C60) cycloalkyl, and the aryl or heteroaryl of R ₄₁ and R ₄₂ may be further substituted

460 by one or more substituent (s) selected from a group consisting of (Cl-CβO)alkyl, 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;

465 R ₄₃ through R ₄₆ independently represent hydrogen, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) aryl, and the heteroaryl, cycloalkyl or aryl of R ₄₃ through R ₄₆ may be further substituted by one or more substituent (s) selected from a group consisting of (C1-C60) alkyl with or without halogen

470 substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri(Cl-C60)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl;

Gi and G2 independently represent a chemical bond or (C6-C60) arylene with or without one or more substituent (s) selected

475 from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl and halogen;

Ar _2I and Ar ₂₂ independently represent (C4-C60) heteroaryl or aryl selected from the following structures:

480 wherein the aryl or heteroaryl of Ar _2I and Ar ₂₂ may be substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60)aryl and (C4-C60) heteroaryl;

Lu represents (C6-C60) arylene, (C4-C60) heteroarylene or a 485 compound represented by the following structural formula:

wherein the arylene or heteroarylene of Lu may be substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy,

490 (C6-C60)aryl, (C4-C60) heteroaryl and halogen;

R _5I through R ₅₄ independently represent hydrogen, (C1-C60) alkyl or (C6-C60) aryl, or each of themmaybe 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

495 ring;

R ₆ i through R ₆₄ independently represent hydrogen, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen, or each of them 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

500 ring or a monocyclic or polycyclic aromatic ring;

wherein

L ₂ I represents (C6-C60) arylene, (C3-C60) heteroarylene containing one or more heteroatom(s) selected from N, O and S or a 505 divalent group selected from the following structures:;

wherein L ₂ 2 and L ₂₃ independently represent a chemical bond, (C1-C60) alkyleneoxy, (C1-C60) alkylenethio, (C6-C60) aryleneoxy, 510 (C6-C60)arylenethio, (C6-C60) arylene or (C3-C60) heteroarylene containing one or more heteroatom (s) selected from N, 0 and S;

Ar _3I represents NR ₉₃ R ₉₄ , (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) 515 selected from N, 0 and S, (C3-C60) cycloalkyl, adamantyl, (C7-C60) bicycloalkyl or a substituent selected from the following structures :

wherein

520 R ₇₁ through R ₈₁ 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, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl,

525 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, (C1-C60) alkylamino, (C6-C60)arylamino, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyloxy, (Cl-C60)alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio,

530 (Cl-CβO)alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or each of Rn through R ₈₁ 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;

535 R ₈₂ through R ₉₂ 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, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl,

540 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, (C1-C60) alkylamino, (Cβ-C60)arylamino, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyloxy, (Cl-CβO)alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio,

545 (Cl-CβO)alkoxycarbonyl, (C1-C60 ) alkylcarbonyl,

(C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or each of Re ₂ through R ₉₂ 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;

550 R ₉₃ and Rg ₄ independently represent hydrogen, deuterium, halogen,

(C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing one or more heteroatom (s) selected fromN, O 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,

555 di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (Cl-CβO)alkylamino, (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl,

(Cl-C60)alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy,

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

560 (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or R93 and R94 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;

Rg ₅ through R ₁₀₆ independently represent hydrogen, deuterium,

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

570 tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl,

(C2-C60)alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino,

(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,

575 (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or each of R ₉₅ through

R ₁ 06 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;

E and F independently represent a chemical bond, - (CR107R102) g ^~ , 580 -N(Ri ₀₃ )-, -S-, -O-, -Si(R ₁₀₄ )(Ri ₀₅ )", -P(RiO ₆ )-, -C(=O)-, -B(Ri ₀₇ )-, -In(R ₁₀₈ )-, -Se-, -Ge(R ₁₀₉ ) (Ri _I0 )-, -Sn(Ri ₁₁ )(R ₁₁₂ )-, -Ga(R ₁₁₃ )- or Ri ₀₇ through Rn ₅ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl containing

585 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, tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl,

590 (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino, (C6-C60)arylamino, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyloxy, (Cl-CβO)alkylthio, (C6-C60 ) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl,

(C6-C60) arylcarbonyl, carboxyl, nitro or hydroxy, or Rioi and R ₁ 02/

595 R104 and R ₁ Os, R109 and Rno, Rm and R ₁₁₂ , and Rn ₄ and Ri ₁₅ 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; the arylene or heteroarylene of L ₂₁ through L ₂₃ , the aryl or

600 heteroaryl of Ar _3I , or the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, alkenyl, alkynyl, alkylamino or arylamino of R7 ₁ through Rs ₁ , Rs ₂ through R92, R ₉₃ , R _S4 , R ₉₅ through R ₁₀₆ or R ₁₀₇ through Rn ₅ may be independently further substituted by one or more substituent (s) selected from deuterium,

605 halogen, (C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl, (C3-C60 ) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S with or without (C6-C60)aryl substituent, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl,

610 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, (C1-C60) alkylamino,

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

(Cl-CδO)alkylthio, (C6-C60 ) aryloxy, (C6-C60) arylthio,

615 (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl,

( C6-C60 ) arylcarbonyl , carboxyl , nitro , hydroxy,

g represents an integer from 1 to 4; and f represents an integer from 1 to 4.

620 Specifically, the host compounds represented by Chemical Formulas 4 to 7 may be exemplified by the following compounds, but not limited thereto.

H-I H-2 H-3 H-4

H-5 H-6 H-7 H-f

630 H-13 H-14 H-15 H-16

H-17 H-18 H-19 H-20

H-21 H-22 H-23 H-24 H-25

H-26 H-27 H-28 H-29 H-30 H-31

H-32 H-33 H-34 H-35 H-36 H-37

640 H-38 H-39 H-40 H-41 H-42 H-43

H-44 H-45 H-46 H-47 H-48 H-49

H-50 H-51 H-52 H-53

H-54 H-55 H-56 H-57

H-58 H-59 H-60 H-61

650 H-62 H-63 H-64 H-65

H-66 H-67 H-68 H-69

H-70 H-71 H-72 H-73

H-74 H-75 H-76 H-77

H-78 H-79 H-80 H-81

660 H-82 H-83 H-84 H-85

H-86 H-87 H-88

H-89 H-90 H-91

H-92 H-93 H-94 H-95

H-96 H-97 H-98 H-99

670

H-100 H-IOl H-102 H-103

H-106 H-107

H-108 H-109

H-114 H-115

H-116 H-117

H-118 H-119

690 H-120 H-121

H-122 H-123

H-124 H-125

H-126 H-127 H-128 H-129

H-130 H-131 H-132 H-133

700 H-134 H-135 H-136

H-137 H-138 H-139

H-140 H-141 H-142 H-143

H-144 H-145 H-146 H-147 H-148 H-149

H-150 H-151 H-152 H-153 H-154 H-155

710 H-156 H-157 H-158

H-159 H-160 H-lβl H-162 H-163 H-164 H-165 H-166 H-167 H-168 H-169 H-170

H-171 H-172 H-173 H-174

H-175 H-176 H-177

720 H-178 H-179 H-180

H-181 H-182 H-183

H-187 H-188 H-189 H-190

H-191 H-192 H-193

730 H-194 H-195 H-196 H-197

H-198 H-199 H-200 H-201

H-202 H-203 H-204 H-205

H-206 H-207 H-208

H-209 H-210 H-211 H-212

H-217 H-218 H-219 H-220

H-221 H-222

745 The electroluminescent layer means a layer where electroluminescence occurs. It may be either a single layer or may comprise two or more layers. In case a dopant and a host are used together in accordance with the present invention, remarkable improvement in luminous efficiency may be attained by adjusting the

750 proportion of the cis-form and the trans-form of the dopant represented by Chemical Formula 1.

The electroluminescent device according to the present invention comprises the electroluminescent compound represented by Chemical Formula 1 and may further comprise one or more compound (s) selected

755 from a group consisting of arylamine compounds and styrylamine compounds at the same time. For example, the arylamine compound or the styrylarylamine compound may be a compound represented by Chemical Formula 8, but not limited thereto:

760 wherein

Ar _4I andAr ₄₂ independently represent (C1-C60) alkyl, (C6-C60) aryl,

(C4-C60)heteroaryl, (C6-C60) arylamino, (C1-C60) alkylamino, 5- or β-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S or (C3-C60) cycloalkyl, and Ar ₄₁ and Ar ₄₂ may

765 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 ₄₃ represents (C6-C60) aryl, (C4-C60) heteroaryl or a substituent selected from the following structures, when h is 1:

Ar ₄₃ represents (C6-C60) arylene, (C4-C60) heteroarylene or a substituent selected from the following structures, when h is 2:

Ar ₄₄ and Ar ₄₅ independently represent (C6-C60) arylene or 775 (C4-C60) heteroarylene;

Ri2i through R ₁₂₃ independently represent hydrogen, deuterium, (Cl-C60)alkyl or (C6-C60) aryl; i represents an integer from 1 to 4; j represents an integer 0 or 1; and

780 the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of Ar ₄ I and Ar ₄₂ , the aryl, heteroaryl, arylene or heteroarylene of Ar ₄₃ , the arylene or heteroarylene of Ar ₄₄ and Ar ₄₅ , or the alkyl or aryl of R ₁₂₁ through R ₁₂₃ may be further substituted by one or more substituent (s) selected from a group consisting of 785 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, 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, 790 (C1-C60) alkylamino, (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60) aryloxy, (C1-C60 ) alkyloxy, (C6-C60 ) arylthio, (Cl-C60)alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxy.

More specifically, the arylamine compound or the styrylarylamine 795 compound may be exemplified by the following compounds, but not limited thereto :

In the electroluminescent device according to the present

805 invention, the organic layer may further comprise, in addition to the 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

810 may comprise an electroluminescent layer and a charge generating layer at the same time.

An independent electroluminescence type electroluminescent device having a pixel structure in which the electroluminescent device according to the present invention comprising the electroluminescent 815 compound represented by 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 andAg is patterned in parallel may be manufactured.

The organic layer may further comprise, in addition to the

820 electroluminescent compound, one or more compound (s) selected from a compound having an electroluminescence peak with wavelength of 500 to 560 nm and a compound having an electroluminescence peak with wavelength of not less than 560 nm to form a white electroluminescent device. The compound having an electroluminescence peak with

825 wavelength of 500 to 560 nmor the compoundhaving an electroluminescence peak with wavelength of not less than 560 nm may be exemplified by the compounds represented by Chemical Formulas 9 to 15, but not limited thereto:

M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³ (9)

830 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; ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are independently selected from the 835 following structures:

wherein

R ₂₀₁ through R ₂₀₃ independently represent hydrogen, deuterium, (C1-C60) alkyl with or without halogen substituent, (C6-C60) aryl with or without (C1-C60) alkyl substituent or halogen;

845 R ₂₀₄ through R ₂₁₉ independently represent hydrogen, deuterium, (C1-C60) alkyl, (C1-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, tri (C6-C30) arylsilyl, cyano or

850 halogen, and the alkyl, cycloalkyl, alkenyl or aryl of R204 through R ₂₁₉ may be further substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl, (C6-C60)aryl and halogen; R ₂₂ o through R ₂₂₃ independently represent hydrogen, deuterium, (C1-C60) alkyl with or without halogen substituent or (C6-C60)aryl 855 with or without (C1-C60) alkyl substituent;

R ₂₂₄ and R ₂₂₅ independently represent hydrogen, deuterium, (C1-C60) alkyl, (C6-C60)aryl or halogen, or R ₂₂₄ and R ₂₂₅ may be linked via (C3-C12)alkylene or (C3-C12 ) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic 860 ring, and the alkyl or aryl of R ₂₂₄ and R ₂₂₅ or the alicyclic ring or the 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 from deuterium, (C1-C60) alkyl with or without halogen substituent, 865 (Cl-C30)alkoxy, halogen, tri (C1-C30) alkylsilyl, tri (C6-C30)arylsilyl and (C6-C60) aryl;

R226 represents (C1-C60) alkyl, (C6-C60) aryl, (C5-C60) heteroaryl containing one ormore heteroatom(s) selected fromN, 0 and S or halogen;

R ₂₂ 7 through R ₂₂₉ independently represent hydrogen, deuterium,

870 (C1-C60) alkyl, (C6-C60)aryl or halogen, and the alkyl or aryl of R ₂₂ 6 through R ₂₂ 9 may be further substituted by halogen or (C1-C60) alkyl;

^R 233 R234. ^R 237 ^R 238 ^R 241 R∑42

Q represents , ^R235R ₂ 36 _O r ^R 239 ^R240 _f wherein R _23I through R2 ₄₂ independently represent hydrogen, deuterium,

(C1-C60) alkyl with or without halogen substituent, (C1-C30) alkoxy,

875 halogen, (C6-C60) aryl, cyano or (C5-C60) cycloalkyl, or each of R ₂ 3 ₁ through R242 may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7)spiro ring or a (C5-C9) fused ring, or linked to R ₂ o7 or R ₂ o ₈ via alkylene or al kenylene to form a (C5-C7 ) fused ring ; ) wherein

R _3O i through R ₃₀₄ independently represent (C1-C60) alkyl or

(C6-C60) aryl, or each of them may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused

885 ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; the alkyl or aryl of R ₃₀₁ through R ₃₀₄ or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused 890 ring may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl with orwithout halogen substituent, (C1-C60) alkoxy, halogen, tri (C1-C60) alkylsilyl, tri (C6-C60) arylsilyl and (C6-C60)aryl;

L ²⁰¹ L ²⁰² M ² <T) _k : i3 ) wherein ligands L ²⁰¹ and L ²⁰² are independently selected from the following structures :

wherein

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

905 T represents (C6-C60) aryloxy or tri (C6-C60) arylsilyl, and the aryloxy or triarylsilyl of Tmaybe further substitutedby (C1-C60) alkyl or (C6-C60)aryl;

G represents O, S or Se; ring C represents oxazole, thiazole, imidazole, oxadiazole, 910 thiadiazole, benzoxazole, benzothiazole, benzoimidazole, pyridine or quinoline; ring D represents pyridine or quinoline, and the ring D may be further substituted by (C1-C60) alkyl, phenyl with or without (C1-C60) alkyl substituent or naphthyl;

915 R _40I through R ₄₀₄ independently represent hydrogen, deuterium, (C1-C60) alkyl, halogen, tri (C1-C60) alkylsilyl, tri (C6-C60) arylsilyl or (C6-C60) aryl, or each of themmay be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene to forma fused ring, and the pyridine or quinoline may be linked to R ₅₀₁ via a chemical bond 920 to form a fused ring; the aryl of ring C and R4 ₀₁ through R ₄₀₄ may be further substituted by (Cl-CβO)alkyl, halogen, (C1-C60) alkyl with halogen substituent, phenyl, naphthyl, tri (C1-C60) alkylsilyl, tri (C6-C60) arylsilyl or amino;

;

^R 501 ^503

N-Ar ₅₁ -N

R502 ^R 504 ( 15 )

wherein

Ar ₅ I represents (C6-C60) arylene with or without one or more substituent (s) selected from a group consisting of halogen,

930 (C1-C60) alkyl, (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, 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,

935 (Cl-CβO)alkoxy, cyano, (C1-C60 ) alkylartiino, (C6-C60) arylamino, (C6-C60)ar (C1-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60 ) alkoxycarbonyl, carboxyl, nitro and hydroxy, and the alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylsilyl, alkylsilyl, alkylamino or arylamino substituent of the arylene may

940 be further substituted by one or more substituent (s) selected from halogen, (C1-C60) alkyl, (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, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,

945 (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C1-C60) alkoxy, cyano, (C1-C60) alkylamino, (C6-C60) arylamino, (C6-C60) ar(Cl-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro and hydroxy;

R501 through R504 independently represent (C1-C60) alkyl,

950 (C6-C60)aryl, (C4-C60) heteroaryl, (C6-C60) arylamino,

(C1-C60) alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S or (C3-C60) cycloalkyl, or each of R _50I through R ₅₀₄ may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused

955 ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; and the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of R ₅₀ 1 through R ₅₀₄ may be further substituted by one or more substituent (s) selected from halogen, (C1-C60) alkyl,

960 (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,

965 (C1-C60) alkoxy, cyano, (C1-C60) alkylamino, (C6-C60) arylamino, (Cβ-C60)ar (C1-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, carboxyl, nitro and hydroxy.

The compound having an electroluminescence peak with wavelength of 500 to 560 nm or the compound having an electroluminescence peak 970 with wavelength of not less than 560 nm may be exemplified by the compounds represented by the following compounds, but not limited thereto:

103

104

105

107

109

In the electroluminescent device according to the present invention, it is preferred that a layer (hereinafter referred to as "surface layer") selected from a metal chalcogenide layer, a metal halide layer and a metal oxide layer is placed on the inner surface

1060 of one or both electrode (s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminummay be placed on the anode surface of the electroluminescent media layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent media layer.

1065 A driving stability may be 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.

1070 Further, in the 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,

1075 injection and transport of electrons from the mixed region to the electroluminescent media become easier, because the electron transport compound is reduced to an anion. Further, injection and transport of holes from the mixed region to the electroluminescent media become easier, because the hole transport compound is oxidized to a cation.

1080 Preferred examples of 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 present invention further provides an organic solar cell.

1085 The organic solar cell according to the present invention comprises one or more electroluminescent compound (s) represented by Chemical Formula 1, and the electroluminescent compound is a mixture of not less than 80% by weight and less than 100% by weight of the cis-form and more than 0% by weight and not more than 20% by weight of the

1090 trans-form.

The electroluminescent device according to the present invention, which comprises as a dopant a mixture of not less than 80% by weight and less than 100% by weight of an electroluminescent compound having cis configuration and more than 0% by weight and not more than 20%

1095 by weight of the electroluminescent compound having trans configuration, exhibits superior luminous efficiency, excellent color purity and very good operation life.

Ill [Description of Drawings]

The above and other aspects, features and advantages of the 1100 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> 1105 1: Glass

2: Transparent electrode

3: Hole injecting layer

4: Hole transport layer

5: Electroluminescent layer 1110 6: Electron transport layer

7: Electron injecting layer

8: Al cathode [Best Mode]

Hereinafter, electroluminescence characteristics of the devices

1115 according to the present invention will be described for the understanding of the present invention. However, the following examples are for illustrative purposes only and not intended to limit the scope of the present invention.

1120 [Preparation Examples]

[Preparation Example 1] Preparation of Compound 223

Preparation of Compound 1-1

1125 2, 7-Dibromofluorene (50.Og, 154.3mmol) and potassium hydroxide (69.2 g, 1.23 mol) were dissolved in DMSO (700 mL) under nitrogen atmosphere. After cooling to 0 ⁰ C, followed by slowly adding distilled water (113 mL) dropwise, the mixture was stirred for 1 hour. Then, after slowly adding iodomethane (CH ₃ I) (38.5mL, 0.617 mol), themixture

1130 was slowly heated to room temperature and then stirred for 15 hours. Distilled water (200 mL) was added to the reaction solution to terminate the reaction. After extraction with dichloromethane (300 mL) , the obtained organic layer was concentrated under reduced pressure. Compound 1-1 (53.0 g, 0.15 mol) was obtained by silica gel column

1135 chromatography (n-hexane/dichloromethane = 20/1) . Preparation of Compound 1-2

Compound 1-1 (53.Og, 0.15 mol) was dissolved in tetrahydrofuran (35OmL) and /3-BuLi (1.6 M in n-hexane) (63.2 mL, 158 mmol) was slowly added dropwise at -78 ⁰ C. After stirring for 30 minutes,

1140 i\7,W-dimethylformamide (16.3 mL, 211 mmol) was added. After slowly heating, followed by stirring for 2 hours, aqueous NH ₄ Cl solution (20 mL) and distilled water (20 mL) were added to terminate the reaction. The organic layer was separated and concentrated under reducedpressure . Compound 1-2 (20.9 g, 69.4 mmol) was obtained by recrystallization 1145 with methanol/n-hexane (1/1, v/v, 100 mL) . Preparation of Compound 1-3

Compound 1-2 (20.9 g, 69.4 mmol), diphenylamine (12.5 g, 104.1 mmol), cesium carbonate (24.1 g, 104.1 mmol) and palladium acetate

(Pd (OAc) ₂ ) (332 mg, 2.1 mmol) were suspended in toluene (800 mL) . After

1150 adding tri (t-butyl) phosphine (P ( t-Bu) ₃ ) (0.6Og, 4.2 mmol) , the mixture was stirred for 4 hours at 120 ⁰ C. After adding saturated aqueous ammonium chloride solution (10OmL), followed by extraction with ethyl acetate (150 mL) and filtration, Compound 1-3 (15.2 g, 39.0 mmol) was obtained by recrystallization with methanol/n-hexane (1/1, v/v,

1155 100 mL) .

Preparation of Compound 1-4

Compound 1-3 (15.2 g, 39.0 mmol) and NaBH ₄ (1.2 g, 42.9 mmol) were dissolved in tetrahydrofuran (150 mL) . After cooling to 0 ⁰ C, methanol (80 mL) was slowly added dropwise. After stirring for 30 1160 minutes, distilled water (10OmL) was added to terminate the reaction. After extraction with ethyl acetate (200 mL) and drying under reduced pressure, Compound 1-4 (13.2 g, 33.7 mmol) was obtained by column chromatography (dichloromethane/hexane = 1/1) .

Preparation of Compound 1-5

1165 Compound 1-4 (13.2 g, 33.7 mmol) was added to a reactor . Triethyl phosphite (7OmL) was added under nitrogen flowanddissolved. Triethyl phosphite (30 mL) was added to another reactor. After opening the lid, stirring was carried out for 30 minutes at 0 ⁰ C while slowly adding iodine (11.2 g, 33.7 mmol). The mixture of iodine and triethyl

1170 phosphite was added to the reactor containing Compound 1-4. After heating to 150 ⁰ C, the mixture was stirred for 4 hours . Upon completion of the reaction, triethyl phosphite was removed by distillation under reduced pressure. After washing with water (500 mL) , followed by extraction with ethyl acetate (500 mL) and drying under reducedpressure,

1175 Compound 1-5 (14.2 g, 28.7 mmol) was obtained by column chromatography (ethyl acetate/hexane = 1/1) .

Preparation of Compound 1-6

Triphenylamine (10.0 g, 40.7 mmol) was dissolved in iV,.A7-dimethylformamide (100 mL) and cooled to 0 ⁰ C.

1180 N,i\7-dimethylformamide (32 mL, 407.6 mmol) was added to another reactor and cooled to 0 ⁰ C, and POCl ₃ was slowly added. After stirring for 30 minutes, the mixture was slowly added dropwise at 0 ⁰ C to the reactor containing triphenylamine. After stirring further at 45 ⁰ C for 18 hours, the mixture was stirred after slowly adding saturated sodium

1185 hydroxide solution and adding excess water. The produced solid was filtered and washed twice with water and then twice with methanol. Compound 1-6 (10.0 g, 36.6 mmol) was obtained. Preparation of Compound 223 Compound 1-6 (7.8 g, 28.7 mmol) and Compound 1-5 (14.2 g, 28.7

1190 mmol) were added to a reactor and dried under reduced pressure. After adding tetrahydrofuran (50OmL) under nitrogen atmosphere, the mixture was dissolved and cooled to 0 °C. Potassium tert-butoxide (t-BuOK)

(8.6 g, 43.1 mmol) dissolved in tetrahydrofuran (100 mL) in another reactor was slowly added dropwise. After stirring for 2 hours at 0 1195 ⁰ C, distilled water (800 mL) was added and the mixture was stirred. The solid was produced by filtering under reduced pressure. The resultant solid was washed 3 times with methanol (600 mL) and then was washed with ethyl acetate (100 mL) . Compound 223 (11.2 g, 17.8 mmol, 64%) was obtained by recrystallization with tetrahydrofuran

1200 (80 mL) and methanol (500 mL) .

[Preparation Example 2] Preparation of Compound 383

Compound 1-3 (10.8 g, 28.7 mmol) and Compound 1-5 (14.2 g, 28.7

1205 mmol) were added to a reactor and dried under reduced pressure. After adding tetrahydrofuran (50OmL) under nitrogen atmosphere, the mixture was dissolved and cooled to 0 ⁰ C. Potassium tert-butoxide (t-BuOK)

(8.6 g, 43.1 mmol) dissolved in tetrahydrofuran (100 mL) in another reactor was slowly added dropwise. After stirring for 2 hours at 0

1210 ⁰ C, distilled water (800 mL) was added and the mixture was stirred.

The solid was produced by filtered under reduced pressure. The resultant solid was washed 3 times with methanol (600 mL) and then was washed with ethyl acetate (100 mL) . Compound 383 (12.9 g, 17.3 mmol, 62%) was obtained by recrystallization with tetrahydrofuran

1215 (80 mL) and methanol (500 mL) .

Electroluminescent compounds (Compounds 1 to 786) were prepared according to the method of Preparation Examples 1 and 2. Table 1 shows 1H NMR and MS/FAB data of the prepared electroluminescent compounds. 1220 [Table 1]

[Examples] Manufacture of electroluminescence device (comprising not less than 80 % by weight of dopant having cis configuration)

1225 First, a transparent electrode ITO thin 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, ethanol and distilled water, and stored in isopropanol for later use.

Next, the ITO substrate was mounted on a substrate holder of

1230 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 apparatus, the pressure inside the chamber was reduced to 10 ^'6 torr. Then, 2-TNATA was evaporated by applying electrical current to the

1235 cell. A hole injecting layer 3 having a thickness of 60 nm was formed on the ITO substrate.

Subsequently, after filling

7\7, W -bis (α-naphthyl) -N, W -diphenyl-4 , 4 ' -diamine (NPB) of the following structure in another cell of the vacuum deposition apparatus,

1240 NPB was evaporated by applying electrical current. A hole transport layer 4 having a thickness of 20 nm was formed on the hole injecting layer.

2-TNATA NPB After forming the hole injecting layer and the hole transport

1245 layer, an electroluminescent layer 5 was formed thereon as follows.

Compound H-33 of the following structure was filled in a cell of a vacuum deposition apparatus as a host, and Compound 223 (80 % by weight

≤ cis content < 100% by weight; 0 % by weight < trans content ≤≥ 20% by weight; cis content + trans content = 100% by weight) was filled

1250 in another cell as a dopant. The two materials were evaporated at different speed, 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.

H-33 Compound 223

Thereafter, tris (8-hydroxyquinoline) -aluminum (III) (AIq) of

1255 the following structure was deposited with a thickness of 20 nm as 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 injection layer 7. Then, an Al cathode 8 having a thickness of 150 nm was formed using another vacuum deposition apparatus to

1260 manufacture an OLED.

AIq ^ύ <*

Each OLED electroluminescent material was purified by vacuum sublimation at ICT ⁶ torr.

1265 [Comparative Examples] Manufacture of electroluminescence device (comprising less than 80 % by weight of dopant having cis configuration)

An OLED device was manufactured as in Examples, except that Compound 223 (0% by weight < cis content < 80% by weight; 20% by weight 1270 < trans content < 100% by weight; cis content + trans content = 100% by weight) was used as a dopant.

Luminous efficiency of the OLED devices manufactured in Example and Comparative Example, with different cis-trans proportion of the 1275 dopant compound, was measured at 1,000 cd/m ² . The result is given in Table 2.

[Table 2]

As seen in Table 2, the electroluminescent devices according

1280 to the present invention, which comprise a mixture of not less than

80% by weight and less than 100% by weight of a dopant compound having cis configuration and more than 0% by weight and not more than 20% by weight of the dopant compound having trans configuration, exhibited improved luminous efficiency and color purity as compared to the devices

1285 of Comparative Examples 1 to 3, which comprise less than 80% by weight of the dopant compound having cis configuration.

[Indus-trial Applicability1

The electroluminescent device according to the present invention, 1290 which comprises as a dopant a mixture of not less than 80% by weight and less than 100% by weight of an electroluminescent compound having cis configuration and more than 0% by weight and not more than 20% by weight of the electroluminescent compound having trans configuration, exhibits superior luminous efficiency, excellent color 1295 purity and 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 in form and details may be made thereto without departing from the

1300 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 that this disclosure not be limited to the particular exemplary

1305 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.