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Title:
ORGANIC ELECTROLUMINSCENT DEVICE USING ELECTROLUMINESCENT COMPOUNDS
Document Type and Number:
WIPO Patent Application WO/2010/062107
Kind Code:
A1
Abstract:
Provided is an electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more dopant compound(s) of formula (I) and one or more host compound(s) of formula (II), wherein at least one of Ar1to Ar4 in the arylamines of formula (I) is 1- or 2-naphthyl and the compounds of formula (II) are aromatic-substituted anthracene compounds. The disclosed electroluminescent device exhibits superior luminous efficiency, excellent color purity and very good operation life.

Inventors:
KIM CHI SIK (KR)
CHO YOUNG JUN (KR)
KWON HYUCK JOO (KR)
KIM BONG OK (KR)
KIM SUNG MIN (KR)
YOON SEUNG SOO (KR)
Application Number:
PCT/KR2009/006980
Publication Date:
June 03, 2010
Filing Date:
November 25, 2009
Export Citation:
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Assignee:
GRACEL DISPLAY INC (KR)
KIM CHI SIK (KR)
CHO YOUNG JUN (KR)
KWON HYUCK JOO (KR)
KIM BONG OK (KR)
KIM SUNG MIN (KR)
YOON SEUNG SOO (KR)
International Classes:
C09K11/06; C07C13/567; C07C15/28; C07C211/60; C07D209/82; C07D219/08; C07D223/22; C07D241/46; C07D279/14; C07D307/91; C07D333/76; C07D471/00; C07D471/02; C07F7/10; H01L51/50
Domestic Patent References:
WO2006033563A12006-03-30
WO2004078872A22004-09-16
WO2007102683A12007-09-13
WO2008031743A12008-03-20
WO2007021117A12007-02-22
Foreign References:
EP1541657A12005-06-15
US20060269781A12006-11-30
EP1437395A22004-07-14
EP1811585A12007-07-25
US20070048547A12007-03-01
EP2100940A22009-09-16
EP2103666A22009-09-23
EP2108690A12009-10-14
Other References:
SHEN J-Y ET AL.: "Ambipolar Conductive 2,7-Carbazole Derivatives for Electroluminescent devices", ADVANCED FUNCTIONAL MATERIALS, vol. 17, 2007, pages 983 - 996
Attorney, Agent or Firm:
KWON, Oh-Sig et al. (921Dunsan-dong, Seo-gu, Daejeon 302-120, KR)
Download PDF:
Claims:
[CLAIMS]

[Claim l]

An electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, wherein

785 the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1 and one or more host compound (s) represented by Chemical Formula 2:

wherein

790 Ari through Ar4 independently represent (C6-C30)aryl with or without substituent or (C5-C30) heteroaryl with or without substituent or each of them may be linked to an adjacent substituent via

(C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form a fused ring, with the proviso that at least one of Ari through

795 Ar4 is 1- or 2-naphthyl with or without substituent;

L represents (C3-C30) heteroarylene with or without substituent,

stilbenylene with or without substituent,

Ar11, Ari2 and R11 through R18 independently represent hydrogen,

800 (C6-C30)aryl with or without substituent or (C6-C30) heteroaryl with or without substituent, with the proviso that at least one of R11 through Ri8 is linked to an adjacent substituent via or to form a fused ring; the substituent substituted at the aryl or heteroaryl of Ar1

805 through Ar4, Aru, Ari2 and Rn through Ri8 and the heteroarylene or stilbenylene of L is one or more substituent (s) selected from a group consisting of deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl,

810 tri(Cl-C30)alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino, (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy and

815 (C6-C30)arylthio; ring A, ring B, ring C and ring D are independently an aromatic ring or a heteroaromatic ring, with the proviso that the ring C and the ring D are not benzene rings at the same time; X represents -Si(R31) (R32)- or -N(R33)-;

820 Y represents -(CR34R3S)1n-, -(R36)C=C(R37)-, -N(R38)-, -S- or -O- ;

R1 through R4, R21 through R24 and R3i through R38 independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, 5- to

7-membered heterocycloalkyl, (C3-C30) cycloalkyl,

825 tri(Cl-C30)alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, (C6-C30)ar(Cl-C30)alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio,

830 (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or hydroxyl or each of them may be linked to an adjacent substituent to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring;

835 the aromatic ring or heteroaromatic ring of the ring A, ring B, ring C and ring D and the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, alkylamino, arylamino, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkoxycarbonyl,

840 alkylcarbonyl or arylcarbonyl of Ri through R4, R21 through R24 and R31 through R38 may be further substituted by one or more substituent (s) selected from deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C4-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl,

845 di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (Cl-C30)alkoxy, cyano, (C1-C30) alkylamino, (C6-C30) arylamino, (C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl,

850 (C1-C30) alkylcarbonyl, carboxyl, nitro and hydroxyl; the heterocycloalkyl and heteroaryl includes one or more hetero atom(s) selected from B, N, O, S, P(=0), Si and P; and m represents an integer 1 or 2; )

855 wherein

An represents anthracenylene with or without one or more substituent (s) or -Z1-L100-Z2-;

Z1 and Z2 independently represent anthracenylene; Lioo represents (C6-C30) arylene or (C5-C30) heteroarylene with 860 or without one or more substituent (s) ;

Ario and Ar20 independently represent (C6-C30) aryl with or without substituent or (C5-C30) heteroaryl with or without substituent; the substituent substituted at An, Ario, Ar2o or Lioo is one or more selected from deuterium, halogen, (C1-C30) alkyl, 865 halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C30) cycloalkyl, tri(Cl-C30)alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, 870 (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro and hydroxyl; and 875 a represents an integer from 1 to 4. [Claim 2]

The electroluminescent device according to claim 1, wherein Ari through Ar4 are independently selected from the following structures: wherein

R41 through Reg independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl,

(C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-meitibered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di(Cl-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl,

(C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,

(Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy or (C6-C30)arylthio, andR52 and R53 may be linked via (C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring. [Claim 3]

The electroluminescent device according to claim 2, wherein at

least one of is selected from the following structures :

[Claim 4]

The electroluminescent device according to claim 1, wherein Ls selected from the following structures:

wherein

Arn, Ar12, Ri7 and Ris are the same as defined in Chemical Formula 905 1 ; and

R7i through R79 independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl,

(C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl,

(C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl,

910 di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl,

(C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,

(C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio,

(C6-C30)aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl,

915 (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or hydroxyl or each of them may be linked to an adjacent substituent to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring. [Claim 5]

920 The electroluminescent device according to claim 1, wherein the dopant is selected from the following compounds:





[Claim 6]

The electroluminescent device according to claim 1, wherein the ost is selected from the following compounds:

60

61

62

63

[Claim 7]

The electroluminescent device according to claim 1, wherein the 935 organic layer comprises one or more compound (s) selected fromarylamine compounds and styrylarylamine compounds. [Claim 8]

The electroluminescent device according to claim 1, wherein the organic layer further comprises one or more metal (s) selected from 940 a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements. [Claim 9]

The electroluminescent device according to claim 1, wherein the 945 organic layer further comprises a compound having an electroluminescence peak with red, green or blue wavelength. [Claim 10]

The electroluminescent device according to claim 1, wherein the organic layer comprises an electroluminescent layer and a charge 950 generating layer. [Claim 11]

The electroluminescent device according to claim 1, wherein one or more layer (s) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer is placed on the inner surface of one 955 or both electrode (s) among the pair of electrodes. [Claim 12]

The electroluminescent device according to claim 1, wherein a mixed region of a reductive dopant and an organic material or an oxidative dopant and an organic material is placed on the inner surface 960 of one or both electrode (s) among the pair of electrodes.

Description:
[DESCRIPTION] [invention Title]

ORGANIC ELECTROLUMINSCENT DEVICE USING 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 one or more host compound (s) represented by Chemical Formula 2:

wherein at least one of Ari through Ar 4 is 1- or 2-naphthyl with or without substituent; Ar 10 -(An) 3 -Ar 20 (2)

[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 injection layer (HIL) is formed thereupon. The hole injection 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 electroluminescent layer (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 to 60 nm. 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 Alq3 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, life 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 one or more

90 host compound (s) and one or more dopant compound (s) . Another object of the present invention is to provide an electroluminescent device having excellent luminous efficiency, superior color purity, low driving voltage and good operation life. [Technical Solution]

95 Exemplary embodiments now will be described more fully hereinafter with reference to the accompanying drawings, in which exemplary embodiments are shown. This disclosure may, however, be embodied in many different forms and should not be construed as limited to the exemplary embodiments set forth therein. Rather, these 100 exemplary embodiments are provided so that this disclosure will be thorough and complete, andwill fully convey the scope of this disclosure to those skilled in the art . In the description, details of well-known features and techniques maybe omitted to avoid unnecessarily obscuring the presented embodiments. 105 The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of this disclosure. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Furthermore, the use of the terms

110 a, an, etc. does not denote a limitation of quantity, but rather denotes the presence of at least one of the referenced item. The use of the terms "first", "second", and the like does not imply any particular order, but they are included to identify individual elements . Moreover, the use of the terms first, second, etc. does not denote any order

115 or importance, but rather the terms first, second, etc. are used to distinguish one element from another. It will be further understood that the terms "comprises" and/or "comprising", or "includes" and/or "including" when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements,

120 and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly

125 understood by one of ordinary skill in the art. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized

130 or overly formal sense unless expressly so defined herein.

The shape, size and regions, and the like, of the drawing may be exaggerated for clarity. The present invention relates to an electroluminescent device. More particularly, the electroluminescent device according to the 135 present invention comprises an organic layer 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 one or more host compound (s) represented by Chemical Formula 2:

wherein

Ar 1 through Ar 4 independently represent (C6-C30)aryl with or without substituent or (C3-C30) heteroaryl with or without substituent or each of them may be linked to an adjacent substituent via

) 145 (C3-C30)alkylene with or without substituent or (C3-C30) alkenylene with or without substituent to form a fused ring, with the proviso that at least one of Ar 1 through Ar 4 is 1- or 2-naphthyl with or without substituent;

L represents (C3-C30) heteroarylene with or without substituent,

150 stilbenylene with or without substituent,

Ar 11 , Ar 12 and R 1 I through R 1 S independently represent hydrogen, (C6-C30)aryl with or without substituent or (C3-C30) heteroaryl with or without substituent, with the proviso that at least one of Rn through

155 Ri 8 is linked to an adjacent substituent via or to form a fused ring; the substituent substituted at the aryl or heteroaryl of Ari through Ar 4 , Arn, Ar i2 and Rn through Ri 8 and the heteroarylene or stilbenylene of L is one or more substituent (s) selected from a group 160 consisting of deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30) bicycloalkyl, 165 (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino, (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy and (C6-C30)arylthio; ring A, ring B, ring C and ring D are independently an aromatic 170 ring or a heteroaromatic ring, with the proviso that the ring C and the ring D are not benzene rings at the same time; X represents -Si(R 31 ) (R 32 )- or -N(R 33 )-;

Y represents - (CR 34 R 3 5) m -, -(R 36 )C=C(R 37 )-, -N (R 3 B) -# -S- or -O-;

Ri through R 4 , R 21 through R 24 and R 3x through R 38 independently

175 represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, 5- to

7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl,

180 (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (Cl-C30)alkylamino, mono- or di (C6-C30) arylamino, (C6-C30)ar (C1-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30)aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or

185 hydroxyl or each of them may be linked to an adjacent substituent to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring; the aromatic ring or heteroaromatic ring of the ring A, ring B, ring C and ring D and the alkyl, aryl, heteroaryl, heterocycloalkyl,

190 cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, alkylamino, arylamino, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkoxycarbonyl, alkylcarbonyl or arylcarbonyl of R 1 through R4, R21 through R24 and R31 through R 38 may be further substituted by one or more substituent (s)

195 selected from deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C4-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl,

200 (Cl-C30)alkoxy, cyano, (C1-C30) alkylamino, (C6-C30) arylamino, (C6-C30)ar(Cl-C30)alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, carboxyl, nitro and hydroxyl; the heterocycloalkyl and heteroaryl includes one or more hetero

205 atom(s) selected from B, N, O r S, P(=0), Si and P; and m represents an integer 1 or 2.

Ario- (An) 3 -Ar 2 O ( 2 ) wherein

An represents anthracenylene with or without one or more 210 substituent (s) or -Zi-LiOo-Z 2 -;

Zi and Z 2 independently represent anthracenylene; L 10O represents (C6-C30) arylene or (C5-C30) heteroarylene with or without one or more substituent (s) ;

Ario and Ar 2O independently represent (C6-C30) aryl with or without 215 substituent or (C5-C30) heteroaryl with or without substituent; the substituent substituted at An, Ario, Ar2o or L100 is one or more selected from deuterium, halogen, (C1-C30) alkyl, halo(Cl-C30)alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or

220 more heteroatom(s) selected from N, O and S, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl,

(C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,

225 (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy,

(C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl,

(C6-C30) arylcarbonyl, carboxyl, nitro and hydroxyl; and a represents an integer from 1 to 4.

In the present invention, "alkyl", "alkoxy" and other

230 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, including a plurality of aryls linked by single

235 bond (S) . Specific examples include phenyl, naphthyl, 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

240 fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.

In the present invention, "heteroaryl" means aryl group containing 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s), other remaining aromatic

245 ring backbone atoms being carbon. It maybe 5- or 6-memberedmonocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with abenzene ring, andmaybe partially saturated. Further, theheteroaryl includes more than one heteroaryls linked by single bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s)

250 in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt. Specific examples include monocyclic heteroaryl suchasfuryl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl,

255 pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, 260 phenanthridinyl, benzodioxolyl, etc., N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), quaternary salt thereof, etc., but not limited thereto.

In the present invention, "arylene" includes those formed as identical or different arylenes are fused, and "heteroarylene" 265 includes those formed as identical or different heteroarylenes are fused.

In the present invention, the alkyl of " (C1-C30) alkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, 270 (Cl-C30)alkyloxycarbonyl r (C1-C30) alkylcarbonyl,

(Cl-C30)alkyloxycarbonyloxy, (C1-C30) alkylcarbonyloxy, etc." may have 1 to 20 carbon atoms, specifically 1 to 10 carbon atoms. The aryl of " (C6-C30) aryl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) aryloxy, 275 (C6-C30)arylthio, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, etc. " may have 6 to 20 carbon atoms, specifically 6 to 12 carbon atoms . The heteroaryl of " (C3-C30) heteroaryl" may have 4 to 20 carbon atoms, specifically 4 to 12 carbon atoms. The cycloalkyl of " (C3-C30) cycloalkyl" may have 280 3 to 20 carbon atoms, specifically 3 to 7 carbon atoms . And, the alkenyl or alkynyl of " (C2-C30) alkenyl or alkynyl" may have 2 to 20 carbon atoms, specifically 2 to 10 carbon atoms.

The electroluminescent device according to the present invention exhibits an effective energy transfer mechanism between a host and

285 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 290 efficiency and long operation life for individual colors.

In the dopant compound represented by Chemical Formula 1, Ari through Ar 4 are independently selected from the following structures, but not limited thereto:

295 wherein

R 41 through R 6 g independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from

300 N, O and S, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl,

(C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,

(Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy or

305 (C6-C30)arylthio, and R 42 and R 43 may be linked via (C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.

In the dopant compound represented by Chemical Formula 1, at

least one of is selected from the following

310 structures :

And, in the dopant compound represented by Chemical Formula 1, L is selected from the following structures, but not limited thereto: wherein

Ar u , Ar i2 , Ri ? and R i8 are the same as defined in Chemical Formula 1 ; and

R 7 i through R 79 independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl,

(C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano,

325 mono- or di (C1-C30) alkylamino r mono- or di (C6-C30) arylamino, (C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30)aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (Cl-C30)alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or hydroxyl or each of them may be linked to an adjacent substituent

330 to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring.

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

355

The host compound represented by Chemical Formula 2 may be exemplified by the compounds represented by Chemical Formulas 3 to 5:

wherein

Rβi and R 82 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,

365 and the aryl or heteroaryl of Rsi and R 82 may be further substituted by one or more substituent (s) selected from a group consisting of

(C1-C60) 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

370 tri (C6-C60) arylsilyl;

Rβ3 through R 8 6 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 83 through

R 86 may be further substituted by one or more substituent (s) selected 375 from a group consisting of (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;

G 1 and G 2 independently represent a chemical bond or 380 (C6-C6Q) arylene with or without one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl,

(C4-C60) heteroaryl and halogen;

Ar 30 and Ar 4 O independently represent (C4-C60) heteroaryl or aryl selected from the following structures:

the aryl or heteroaryl of Ar3 0 and Ar^ 0 may be substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60)aryl and (C4-C60) heteroaryl;

Lioi represents (C6-C60) arylene, (C4-C60) heteroarylene or a 390 compound of the following formula:

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

395 R 91 through R 94 independently represent hydrogen, (C1-C60) alkyl or (C6-C60) aryl, or each of themmay 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 mono- or polycyclic ring;

R 95 through R 9 e independently represent hydrogen, (C1-C60) alkyl,

400 (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen, or each of themmay 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 mono- or polycyclic ring;

405 wherein

Lio2 represents anthracenylene;

Lio3 and L104 independently represent a chemical bond, (Cl-CβO)alkyleneoxy, (C1-C60) alkylenethio, (C6-C60) aryleneoxy, (C6-C60)arylenethio, (C6-C60) arylene or (C3-C60) heteroarylene 410 containing one or more heteroatom(s) selected from N, O and S;

Ar 50 represents (C6-C60)aryl or (C5-C60) heteroaryl with or without one or more substituent (s) selected from deuterium, halogen,

(C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl 415 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, mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino,

420 (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxyl;

Rioi through Ri O6 independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl,

425 (C3-C60) heteroaryl, 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, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano,

430 mono- or di (C1-C60) alkylamino, mono- or 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 or hydroxyl; and b represents an integer from 1 to 4.

435 Specifically, the host compound represented by any of Chemical Formulas 3 to 5 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-8 H-9 H-IO

H-Il H-12 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 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 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 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

H-IOO H-IOl

H-102 H-103

H-104 H-105

H-106 H-107

The electroluminescent layer means a layer where electroluminescence occurs. It may be either a single layer or may

440 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.

The electroluminescent device according to the present invention comprises the electroluminescent compounds represented by Chemical

445 Formula 1 and Chemical Formula 2 and may further comprise one or more compound (s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time. Examples of the arylamine compound or the styrylarylamine compound are disclosed in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or

450 10-2008-0118428, but are not limited thereto. Further, in the electroluminescent device according to the present invention, the organic layer may further comprise, in addition to the electroluminescent compounds represented by Chemical Formulas 1 and 2, one or more metal (s) selected from a group consisting of organic

455 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 generating layer at the same time. The organic layer may further comprise, in addition to the electroluminescent compounds represented by Chemical Formulas

460 1 and 2, one or more organic compound layer (s) emitting blue, green and red light at the same time to form a white-emitting electroluminescent device. Examples of the compound emitting blue, green or red light are disclosed in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not

465 limited thereto. In the electroluminescent device according to the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode (s)

470 among the pair of electrodes. More specifically, a 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 attained

475 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, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.

480 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,

485 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

490 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. Further, a white-emitting electroluminescent device having two or more electroluminescent layer (s) maybe fabricated

495 by using a reductive dopant layer as a charge generating layer. [Best Mode]

Hereinafter, electroluminescence characteristics of the devices according to the present invention will be described for the understanding of the present invention. However, the following

500 examples are for illustrative purposes only and not intended to limit the scope of the present invention.

[Preparation Example 1] Preparation of Compound 8

505 Preparation of Compound 1-1

2-Bromo-9, 9-dimethylfluorene (20.Og, 102.9mmol) andAlCl 3 (27.5 g, 205.9mmol) were dissolved indichloromethane (50OmL) . Afteradding 5-bromoisobenzofuran-l, 3-dione (35.Og, 154.4 mmol), the mixture was stirred while heating at 40 0 C. 12 hours later, after terminating

510 the reaction by adding distilled water, followed by addition of 1 M HCl aqueous solution, the product was extracted with MC. Compound 1-1 (40.6 g, 96.4 mmol) was obtained by distillation under reduced pressure followed by column separation.

Preparation of Compound 1-2

515 Compound 1-1 (40.6 g, 96.4 mmol) was added to a mixture solvent of sulfuric acid (300 mL) and acetic acid (300 iuL) and stirred at 120 0 C. 10 hours later, when distilled water was added after cooling to room temperature, a solid was produced. The solid was filtered under reduced pressure and recrystallized with methanol and ethyl 520 acetate. Compound 1-2 (11.6 g, 29.0 mmol) was obtained.

Preparation of Compound 1-3

1-Bromonaphthalene (15.O g, 72.5 mmol) was dissolved in THF (100 mL) and n-BuLi (35 mL, 87.0 mmol, 2.5 M in hexane) was slowly added dropwise at -78 0 C. One hour later, after adding Compound 1-2 (10.6 525 g, 26.5 mmol), the mixture was stirred at room temperature for 12 hours. Upon completion of reaction, the product was extracted with ethyl acetate, dried with magnesium sulfate and filtered under reduced pressure. Compound 1-3 was obtained, which was used in the next reaction without purification. 530 Preparation of Compound 1-4

Unpurified Compound 1-3, KI (19.5 g, 117.6 mmol) and NaH 2 PO 3 H 2 O (23.8 g, 174.0 mmol) were dissolved in acetic acid (100 mL) and stirred at 120 0 C under reflux . 6 hours later, after cooling to roomtemperature, distilled water was added. The produced solid was filtered under 535 reduced pressure. Compound 1-4 (4.2 g, 6.1 mmol, 45%) was obtained by column separation.

Preparation of Compound 8

Compound 1-4 (4.Og, 6.79mmol), N-phenylnaphthalen-2-amine (3.3 g, 16.99 mmol) , Pd(OAc) 2 (0.07 q, 0.33 mmol) , P(t-Bu) 3 (50% in toluene, 540 0.3 mL f 0.67 iranol) and Cs 2 CO 3 (6.6 g, 20.38 iranol) were added to toluene

(50 inL) and stirred at 110 0 C for 5 hours. After adding methanol (50 inL) , the produced solid was filtered under reduced pressure and washed with distilled water, methanol and hexane. The solid was added to

EA (100 mL) and stirred for 2 hours under reflux. After filtration

545 under reduced pressure, followed by column separation, the obtained solid was dissolved in THF. After adding methanol, the produced solid was filtered under reduced pressure. Compound 8 (1.6 g, 1.95 mmol) was obtained.

[Preparation Example 2] Preparation of Compound 11

Preparation of Compound 2-1

Compound 2-1 (33.O g, 96.4 mmol) was obtained in the same manner as the preparation of Compound 1-1 in Preparation Example 1, except for using 9, 9-dimethylfluorene (20.0 g, 102.9 mmol) and 555 isobenzofuran-1, 3-dione as starting materials. Preparation of Compound 2-2

Compound 2-2 (9.4 g, 29.0 mmol) was obtained from Compound 2-1 in the same manner as the preparation of Compound 1-2 in Preparation Example 1. 560 Preparation of Compound 2-3 Compound 2-2 (50 g, 0.17 mol) was added to a flask and stirred for 10 minutes after adding AcOH (1 L). After adding H 3 PO 2 (380 g, 5.76 mol) and HI (781 g, 6.11 mol), the mixture was stirred at 150 0C for one day. Upon completion of reaction, after neutralization 565 with NaOH solution and HCl, the produced solid was filtered, added to ethyl acetate and recrystallized at 100 0 C under reflux. Compound 2-3 (40 g, 90%) was obtained.

Preparation of Compound 2-4

Compound 2-3 (4.4 g, 10.7 mmol) was dissolved in MC (100 mL)

570 and NBS (4.38 g, 24.64 mmol) was added. After stirring at room temperature for 12 hours, followed by distillation under reduced pressure and recrystallization with EA and methanol, Compound 2-4

(5.2 g, 9.14 mmol, 85.42%) was obtained.

Preparation of Compound 11

575 Compound 11 (1.6 g, 1.95 mmol) was obtained in the same manner as the preparation of Compound 8 in Preparation Example 1, except for using Compound 2-4 and dinaphthalen-2-ylamine.

[Preparation Example 3] Preparation of Compound 22

580 Preparation of Compound 3-1

2-Bromopyridine (12.4 mL, 127 mmol) was dissolved in ethyl ether (630 mL) and n-BuLi (51 mL, 127 mmol, 2.5 M in hexane) was slowly added at -78 0 C. One hour later, the mixture was added to a solution in which dimethyl phthalate (12.4 g, 127 mmol) was dissolved in ethyl 585 ether (1,270 mL) . After stirring for 5 hours, distilled water was added and the product was extracted with EA. After drying with magnesium sulfate followed by column separation, Compound 3-1 (16 g, 66.32 mmol, 52.22%) was obtained.

Preparation of Compound 3-2

590 Compound 3-1 (16g) was dissolved in THF (43OmL) andLTMP [prepared by dissolving TMP (36mL) in THF (290 mL) and slowly adding n-BuLi (78.3 mL, 2.5 M in hexane) at 0 0 C] was added at 0 0 C. After stirring for 8 hours, distilled water was added and the product was extracted with EA. After drying with magnesium sulfate followed by distillation 595 under reduced pressure and column separation, Compound 3-2 (10 g, 47.80 mmol, 72.09%) was obtained.

Preparation of Compound 3-3

Compound 3-3 (40 g, 90%) was obtained from Compound 3-2 in the same manner as the preparation of Compound 2-3 in Preparation Example 600 2.

Preparation of Compound 3-4

Compound 3-4 (5.2 g, 9.14 mmol, 85.42%) was obtained from Compound 3-3 in the same manner as the preparation of Compound 2-4 in Preparation Example 2. 605 Preparation of Compound 22

Compound 22 (1.6 g, 1.95 mmol) was obtained in the same manner as the preparation of Compound 11 in Preparation Example 2, except for using Compound 3-4 and N-phenylnaphthalen-2-amine.

[Preparation Example 4] Preparation of Compound 26

Preparation of Compound 4-1

Compound 3-2 (10 g, 47.80 mmol) was added to acetic acid (100 πiL) and sulfuric acid (12.7 mL, 239.0 mmol) and nitric acid (16.8 iiiL, 239.0 mmol) were added. After stirring at room temperature for 615 10 hours, distilled water was added. After neutralizing with NaOH aqueous solution, the product was extracted with EA and dried with magnesium sulfate. After distillation under reduced pressure followed by column separation, Compound 4-1 (4 g, 13.36mmol, 27.96%) was obtained. 620 Preparation of Compound 4-2

Compound 4-1 (4 g, 13.36 mmol) was added to TEA (28 mL) . After adding Pd/C (0.4 g) , formic acid (5.04 mL, 133.68 mmol) was slowly added. After stirring at 80 0 C for 4 hours, followed by cooling to room temperature, distilledwater was added. Theproduct was extracted 625 with EA and dried with magnesium sulfate. After distillation under reduced pressure followed by column separation, Compound 4-2 (2.6 g, 7.08 mmol, 53.02%) was obtained. Preparation of Compound 4-3

CuBr 2 (2.37 g, 10.62 mmol) and t-BuNO 2 (1.26 mL, 10.62 mmol) were 630 added to acetonitrile (100 mL) . After heating to 40 0 C, Compound 4-2 was added. After stirring at 80 °C for 12 hours, the mixture was cooled to room temperature. After adding distilled water, the product was extracted with EA. After drying with magnesium sulfate, followed by distillation under reduced pressure and column separation, Compound 635 4-3 (1.8 g, 4.90 mmol, 70.06%) was obtained.

Preparation of Compound 4-5

Compound 4-4 was obtained from Compound 4-3 in the same manner as the preparation of Compound 1-3 in Preparation Example 1, except for using 2-bromonaphthalene. Compound 4-4 was used in the next 640 reaction without purification. Compound 4-5 (2.1 g, 3.56 mmol) was obtained from Compound 4-4 in the same manner as the preparation of Compound 1-4 in Preparation Example 1.

Preparation of Compound 26

Compound 26 (1.2 g, 1.56 mmol, 44.08%) was obtained in the same 645 manner as the preparation of Compound 8 in Preparation Example 1, except for using Compound 4-5 and N-phenylnaphthalen-2-amine.

[Preparation Example 5] Preparation of Compound 43

Preparation of Compound 5-1

650 Compound 5-1 (16 g, 66.32 mmol, 52.22%) was obtained in the same manner as the preparation of Compound 3-1 in Preparation Example 3, except for using 3-bromopyridine as a starting material.

Preparation of Compound 5-2

Compound 5-2 (1Og, 47.80 mmol, 72.09%) was obtained from Compound 655 5-1 in the same manner as the preparation of Compound 3-2 in Preparation Example 3.

Preparation of Compound 5-3

Compound 5-3 (7.5 g, 25.06 mmol) was obtained from Compound 5-2 in the same manner as the preparation of Compound 4-1 in Preparation 660 Example 4.

Preparation of Compound 5-4

Compound 5-4 (6-9 g, 23.53 mmol) was obtained from Compound 5-3 in the same manner as the preparation of Compound 4-2 in Preparation Example 4. 665 Preparation of Compound 5-5

Compound 5-5 (7.2 g, 19.62 mmol) was obtained from Compound 5-4 in the same manner as the preparation of Compound 4-3 in Preparation Example 4.

Preparation of Compound 5-7

670 Compound 5-6 was obtained from Compound 5-5 in the same manner as the preparation of Compound 4-4 in Preparation Example 4. Compound 5-6 was used in the next reaction without purification. Compound 5-7 (6.4 g, 10.86 mmol) was obtained from Compound 5-6 in the same manner as the preparation of Compound 4-5 in Preparation Example 4.

675 Preparation of Compound 43 Compound 43 (5.3 g, 5.93 mmol) was obtained in the same manner as the preparation of Compound 26 in Preparation Example 4, except for using Compound 5-7 and N-p-tolylnaphthalen-2-amine.

[Preparation Example 6] Preparation of Compound 47

Preparation of Compound 6-1

Compound 6-1 (9.8 g, 37.37 mmol) was obtained in the same manner as the preparation of Compound 5-1 in Preparation Example 5, except for using 3-bromopyridine and dimethylpyridine-3, 4-dicarboxylate.

685 Preparation of Compound 6-2

Compound 6-2 (6.3 g, 29.97 mmol) was obtained from Compound 6-1 in the same manner as the preparation of Compound 5-2 in Preparation Example 5.

Preparation of Compound 6-3

690 Compound 6-3 (6.4 g, 21.32 mmol) was obtained from Compound 6-2 in the same manner as the preparation of Compound 5-3 in Preparation Example 5. Preparation of Compound 6-4

Compound 6-4 (3.5 g, 14.47 mmol) was obtained from Compound 6-3 695 in the same manner as the preparation of Compound 5-4 in Preparation Example 5.

Preparation of Compound 6-5

Compound 6-5 (4.1 g, 11.14 mmol) was obtained from Compound 6-4 in the same manner as the preparation of Compound 5-5 in Preparation 700 Example 5.

Preparation of Compound 6-7

Compound 6-6 was obtained from Compound 6-5 in the same manner as the preparation of Compound 5-6 in Preparation Example 5. Compound 6-6 was used in the next reaction without purification. Compound 6-7 705 (4.2 g, 7.11 mmol) was obtained from Compound 6-6 in the same manner as the preparation of Compound 5-7 in Preparation Example 5. Preparation of Compound 47

Compound 47 (3.5 g, 3.99 mmol) was obtained in the same manner as the preparation of Compound 43 in Preparation Example 5, except 710 for Compound 6-7 and N-D5-phenylnaphthalen-2-amine.

Electroluminescent compounds (Compounds 1 to 66) were prepared according to the method of Preparation Examples 1 to 6. Table 1 shows 1H NMR and MS/FAB data of the prepared electroluminescent compounds. Table 1

δ = 3.52 (8H , m) , 6.11 (2H m) , 6.54 (2H, m) , 6.63 (2H, hi) , 6.71 (2H, m) , (IH, , 6.95 (2H , m) , 7 .2-7.23

66 6. 81 m)

862.09 861.32

(4H, m) , 7.3 (2H , m) , 7 .36-7.38 (4H, m) , 7.45-7 .5 (bH, m) , 7.74-7.' 77 (4H, m) , 7 84-7 .88 (4H, m)

[Example 1] Manufacture of electroluminescent device

First, a transparent electrode ITO film (15 Ω/D) prepared from a glass substrate for an OLED (Samsung Corning) 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 a vacuum deposition apparatus. After filling

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

(2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to ICT 6 torr. Then, 2-TNATA was evaporatedbyapplying electrical current to the cell . Ahole injection layer having a thickness of 60 nm was formed on the ITO substrate. Subsequently, after filling

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

An electroluminescent layer was formed on the hole transport layer as follows. Compound H-I was filled in a cell of a vacuum deposition apparatus as a host, and Compound 2 was filled in another cell as a dopant . The two materials were evaporated at different speed, so that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.

740 H-I Compound 2

Thereafter, tris (8-hydroxyquinoline) -aluminum (III) (AIq) was deposited with a thickness of 20 nm as an electron transport layer. Then, lithium quinolate (Liq) was deposited with a thickness of 1 to 2 nm as an electron injection layer. Then, an Al cathode having 745 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 10 "6 torr.

750 [Comparative Example 1] Manufacture ofOLEX) device usingexisting electroluminescent material

OLED was manufactured in the same manner as Example 1, except for using dinaphthylanthracene (DNA) as a host and Compound A as a dopant in the electroluminescent layer.

DKfA Compound A Luminous efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 1,000 cd/m 2 . The result is given in Table. Table 2

[industrial Applicability]

The electroluminescent device according to the present invention, which comprises an electroluminescent compound with at least one arylamine group (s) substituted by 1- or 2-naphthyl, exhibits superior luminous efficiency, excellent color 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 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 775 departing from the essential scope thereof. Therefore, it is intended 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. 780