WO2010050781A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

Info

Publication number
WO2010050781A1
WO2010050781A1 PCT/KR2009/006353 KR2009006353W WO2010050781A1 WO 2010050781 A1 WO2010050781 A1 WO 2010050781A1 KR 2009006353 W KR2009006353 W KR 2009006353W WO 2010050781 A1 WO2010050781 A1 WO 2010050781A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
heteroatom
aryl
tri
halogen
Prior art date
Application number
PCT/KR2009/006353
Other languages
French (fr)
Inventor
Young Jun Cho
Chi Sik Kim
Sung Jin Eum
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
Original Assignee
Gracel Display Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gracel Display Inc. filed Critical Gracel Display Inc.
Priority to CN200980143444.8A priority Critical patent/CN102203076B/en
Priority to JP2011534396A priority patent/JP2012507508A/en
Publication of WO2010050781A1 publication Critical patent/WO2010050781A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

Disclosed Provided are a novel organic electroluminescent compound and an organic electroluminescent device using the same as an electroluminescent material. The disclosed organic electroluminescent compound is represented by Chemical Formula 1: (Formula I should be inserted here) wherein Ar1 represents (C6-C60)arylene, (C3~C60)heteroarylene containing one or more heteroatom(s) selected from N, O and S, 5- or 6-membered heterocycloalkylene containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkylene, adamantylene, (C7-C60)bicycloalkylene, (C2-C60)alkenylene, (C2-C60)alkynylene, (Cl-C60)alkylenethio, (Cl-C60)alkyleneoxy, (C6-C60)aryleneoxy, (C6-C60)arylenethio or; (Formula II should be inserted here) and ring A and ring B independently represent a 5- to 7-membered heterocyclic amino group or a ring selected from the following structures: (Formula III should be inserted here) wherein the 5- to 7-membered heterocyclic amino group may further contain NR2I or one or more heteroatom(s) selected from O and S. The organic electroluminescent compound provides superior luminous efficiency and excellent life property. Therefore, it may be used to manufacture OLED devices having very good operation life.

Description

[DESCRIPTION] [Invention Tit Ie]
Novel organic electroluminescent compounds and organic electroluminescent device using the same [Technical Field] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the same in an electroluminescent layer. More specifically, it relates to a novel organic electroluminescent compound used as a blue-emitting electroluminescent material and an organic electroluminescent device using the same as a dopant. [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, 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.
For blue-emitting materials, a lot of materials have been commercialized following Idemitsu Kosan's DPVBi (Compound a). Along with Idemitsu Kosan's blue-emitting material system, Kodak's dinaphthyl anthracene (Compound b) and tetra(t-butyl)perylene (Compound c) are known, but much more research and development are necessary. Until now, Idemitsu Kosan's distyryl compound system is known to have the best efficiency. It exhibits a power efficiency of 6 lm/W and operation life of 30,000 hours or more. However, its color purity is degraded with time, and operation life when applied to a full-color display is only thousands of hours. In general, blue electroluminescence is advantageous in luminous efficiency if the electroluminescence wavelength shifts a little toward the longer wavelength. But, it is not applicable to high-quality displays because pure blue color is not attained. Therefore, researches and developments to improve color purity, efficiency and thermal stability are highly required.
Figure imgf000004_0001
[Disclosure]
[Technical Problem]
The present inventors have invented a novel electroluminescent compound to realize an electroluminescent device having superior luminous efficiency and remarkably improved operation life.
To solve the aforesaid problems, in one aspect, the present invention provides an organic electroluminescent compound having superior backbone structure, which has better luminous efficiency and operation life than existing dopant materials and adequate color coordinates. In another aspect, the present invention provides an organic electroluminescent device having high efficiency and long operation life, which comprises the organic electroluminescent compound as an electroluminescent material. In another aspect, the present invention provides an organic solar cell comprising the organic electroluminescent compound. [Technical Solution] 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 exemplary embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of this disclosure to those skilled in the art. In the description, details of well-known features and techniques may be omitted to avoid unnecessarily obscuring the presented embodiments. 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 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 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, 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 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 or overly formal sense unless expressly so defined herein. The present invention relates to an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present invention has good luminous efficiency and excellent color purity and life property. Therefore, it can be used to manufacture OLED devices having very superior operation life.
Figure imgf000006_0001
In Chemical Formula 1, R1 and R2 independently represent hydrogen, deuterium, halogen, (Cl-
C60)alkyl, (C6-C60)aryl , (C3-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino, thiomorphol ino, 5- or 6- membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , tri(Cl-C60)alkyl.silyl, di(Cl-C60)alkyl(C6- C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl , (C7-C60)bicycloalkyl , (C2- C60)alkenyl, (C2-C60)alkynyl , cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (Cl-C60)alkyloxy, (Cl-C60)alkylthio, (C6- C60)aryloxy, (C6-C60)arylthio, (Cl-C60)alkoxycarbonyl , (Cl-C60)alkylcarbonyl , (C6-C60)arylcarbonyl , carboxyl , nitro or hydroxy1 , or Ri and Rg may be linked via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; Ar1 represents (C6-C60)arylene, (C3-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S, 5- or 6-membered heterocycloalkylene containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkylene, adamantylene, (C7-C60)bicycloalkylene, (C2- C60)alkenylene, (C2-C60)alkynylene, (Cl-C60)alkylenethio, (Cl- C60)alkyleneoxy, (C6-C60)aryleneoxy, (C6-C60)arylenethio or
Figure imgf000007_0001
ring A and ring B independently represent a 5- to 7-membered heterocyclic amino group or a ring selected from the following structures:
Figure imgf000007_0002
the 5- to 7-membered heterocyclic amino group may further contain one or more heteroatom(s) selected from NR21, 0 and S; Rn through R18 independently represent hydrogen, deuterium, halogen,
(Cl-CΘO)alkyl, (Cβ-CβO)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) selected from N, 0 and S, (C3- C60)cycloalkyl, tr i (Cl-CΘO)alkylsi IyI , di(Cl-C60)alkyl(C6-C60)arylsi IyI , tri(C6-C60)arylsilyl, adamantyl , (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, cyano, (Cl-CΘO)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl- C60)alkyl, (Cl-CβO)alkyloxy, (Cl-CβO)alkylthio, (C6-C60)aryloxy, (C6- C60)arylthio, (Cl-C60)alkylcarbonyl , (Cl-CβO)alkoxycarbonyl , (C6- C60)arylcarbonyl , carboxy1 , nitro or hydroxyl , or each of Rn through Ri8 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 mono- or polycyclic aromatic ring; R21 represents hydrogen, deuterium, (Cl-CβO)alkyl , (C6-C60)aryl , (C3-
C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl, adamantyl , (C7-C60)bicycloalkyl or (C6-C60)ar(Cl- C60)alkyl; X and Y independently represent a chemical bond, -(CR3IR32)H,-, -N(R33)-,
-S-, -0-, -Si(R34 )(R35 )-, "P(R36)-, -(X=CO-, -B(R37)-, -In(R38)-, -Se-, -Ge(R39)(R40)", -Sn(R41)(R42)-, -Ga(R4S)-Or -(R44)C=C(R45)-; R31 through R45 independently represent hydrogen, deuterium, halogen,
(Cl-C60)alkyl , (C6-C60)aryl , (C3-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino, thiomorphol ino, 5- or 6- membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , tri(Cl-C60)alkylsi IyI , di(Cl-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(Cl-C60)alkyl, (Cl-C60)alkyloxy, (Cl-C60)alkylthio, (C6- C60)aryloxy, (C6-C60)arylthio, (Cl-CδO)alkoxycarbonyl , (Cl-CΘO)alkylcarbonyl , (C6-C60)arylcarbonyl , carboxyl, nitro or hydroxyl, or R31 and R32, R34 and R35,
R39 and R4O, R4I and R42, and R44 and R4S may be linked via (C3-C60)alkylene or
(C3-C60)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; the arylene, heteroarylene, heterocycloalkylene, cycloalkylene, adamantylene, bicycloalkylene, alkenylene, alkylenethio, alkyleneoxy, aryleneoxy or arylenethio of Ar1 and the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialky1si IyI , dialkylarylsi IyI , triarylsi IyI , adamantyl, bicycloalkyl , alkenyl , alkylamino, arylamino, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkoxycarbonyl , alkylcarbonyl or arylcarbonyl of R1, R2, Rn through Ri8, R21 and R31 through R45 may be further substituted by one or more substituent(s) selected from a group consisting of halogen, (Cl- C60)alkyl with or without halogen substituent(s), (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(s), morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , tri(Cl-C60)alkylsilyl , di(Cl- C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl , (C7- C60)bicycloalkyl, (C2-C60)alkenyl , (C2-C60)alkynyl , cyano, carbazolyl, (Cl- C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl , (Cl-CβO)alkyl (C6- C60)aryl, (Cl-C60)alkyloxy, (Cl-C60)alkylthio, (C6-C60)aryloxy, (C6- C60)arylthio, (Cl-CβO)alkoxycarbonyl , (Cl-CβO)alkylcarbonyl , (C6- C60)arylcarbonyl , carboxyl, nitro and hydroxyl; and m represents an integer from 1 to 4. In the present invention, alkyl , alkoxy and other substituents including alkyl moiety may be either linear or branched. In the present invention, aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring. Specific examples include phenyl, naphthyl , biphenyl , anthryl , indenyl , fluorenyl, phenanthryl , triphenylenyl , pyrenyl , perylenyl, chrysenyl , naphthacenyl , f luoranthenyl , etc., but not limited thereto. 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, and may be partially saturated. The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt. Specific examples include monocyclic heteroaryl such as furyl , thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl , isothiazolyl , isoxazolyl, oxazolyl , oxadiazolyl, triazinyl, tetrazinyl , triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl , pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl , benzothiophenyl , isobenzofuranyl , benzoimidazolyl , benzothiazolyl , benzoisothiazolyl , benzoisoxazolyl , benzoxazolyl , isoindolyl, indolyl, indazolyl, benzothiadiazolyl , quinolyl, isoquinolyl, cinnolinyl, quinazol inyl , quinoxal inyl , carbazolyl , 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, heterocyclic amino means a 5- to 7-membered cyclic amino group. It may contain one or more heteroatom(s) selected from N, 0 and S, and the heterocyclic amino group may include only single bonds or include one or more carbon-carbon double bond(s). In the present invention, the substituents including (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 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. R1 and R2 independently represent methyl, ethyl, n-propyl , i-propyl , n- butyl , i-butyl, t-butyl , n-pentyl, i-pentyl, n-hexyl , n-heptyl , n-octyl , 2- ethylhexyl , n-nonyl, decyl , dodecyl , hexadecyl, benzyl, trifluoromethyl , perf luoroethyl , trif luoroethyl , perf luoropropyl , perf luorobutyl , methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i- pentoxy, n-hexyloxy, n-heptoxy, trimethylsi IyI , triethylsi IyI , tripropylsilyl , tr i (t-butyl )si IyI , t-butyldimethylsi IyI , dimethylphenylsi IyI , triphenylsilyl , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, morpholino, thiomorpholino, adamantyl, bicyclo[2.2. l]heptyl , bicyclo[2.2.2]octyl , bicyclo[3.2.1]octyl , bicyclo[5.2.0]nonyl, bicyclo[4.2.2]decyl , bicyclo[2.2.2]octyl , 4- pentylbicyclo[2.2.2]octyl , ethenyl , phenylethenyl , ethynyl , phenylethynyl , cyano, dimethylamino, diphenylamino, monomethylamino, monophenylamino, phenyloxy, phenylthio, methoxycarbonyl , ethoxycarbonyl , t-butoxycarbony1 , carboxyl , nitro, chloro, fluoro or hydroxyl. The alicyclic ring or the mono- or polycyclic aromatic ring formed as R1 and R2 are linked via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring may be exemplified by the following structures, but not limited thereto:
Figure imgf000011_0001
Ari is selected from the following structures, but not limited thereto:
Figure imgf000012_0001
wherein
R51 through Rβ7 independently represent hydrogen, deuterium, halogen,
(Cl-CβO)alkyl , halo(Cl-C60)alkyl , (C6-C60)aryl , (C3-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , tri (Cl- C60)alkylsilyl , di(Cl-C60)alkyl(C6-C60)arylsi IyI , tri(C6-C60)arylsi IyI , adamantyl, (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2-C60)alkynyl , cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl , (Cl- C60)alkyloxy, (Cl-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , (Cl-C60)alkylcarbonyl , (C6-C60)arylcarbonyl , carboxyl , nitro or hydroxyl, or R51 and R52, R53 and R54, R55 and R56, R6o and R61, R63 and R64, and R65 and R66 may be linked via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; and the alkyl , aryl, heteroaryl , heterocycloalkyl, cycloalkyl, trialkylsilyl , dialkylarylsilyl , triarylsilyl , adamantyl, bicycloalkyl , alkenyl, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkylamino, arylamino, alkoxycarbonyl , alkylcarbonyl or arylcarbonyl of Rs1 through R67 may be further substituted by one or more subst ituent (s) selected from a group consisting of halogen, (Cl-CβO)alkyl with or without halogen substituent(s), (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(s), morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , tri (Cl- C60)alkylsilyl, dϊ (Cl-CΘO)alkyl (C6-C60)arylsi IyI , tri(C6-C60)arylsi IyI , adamantyl, (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2-C60)alkynyl , cyano, carbazolyl, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl , (Cl-C60)alkyl(C6-C60)aryl, (Cl-C60)alkyloxy, (Cl-C60)alkylthio, (C6- C60)aryloxy, (C6-C60)arylthio, (Cl-C60)alkoxycarbonyl , (Cl-CΘO)alkylcarbonyl , (C6-C60)arylcarbonyl , carboxyl, nitro and hydroxyl. More specifically, Ar1 may be exemplified by the following structures, but not limited thereto:
Figure imgf000014_0001
wherein R51 through R67 independently represent hydrogen, deuterium, methyl, ethyl, n-propyl , i-propyl, n-butyl, i-butyl, t-butyl , n-pentyl , i-pentyl, n- hexyl , n-heptyl , n-octyl , 2-ethylhexyl , n-nonyl , decyl , dodecyl , hexadecyl , benzyl, trif luoromethyl , perf luoroethyl , trifluoroethyl , perf luoropropyl , perfluorobutyl , methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t- butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, trimethylsi IyI , triethylsilyl, tripropylsilyl , tr i (t-butyl )si IyI , t-butyldimethylsi IyI , dimethylphenylsi IyI , triphenylsilyl , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, phenyl, naphthyl , biphenyl, 9,9-dimethyl f luorenyl , 9,9-diphenylf luorenyl , phenanthryl , anthryl , fluoranthenyl , triphenylenyl , pyrenyl , chrysenyl , naphthacenyl , perylenyl, morpholino, thiomorpholino, adamantyl , bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl , bicyclo[3.2.1]octyl, bicyclo[5.2.0]noπyl, bicyclo[4.2.2]decyl , bicyclo[2.2.2]octyl , 4- pentylbicyclo[2.2.2]octyl , ethenyl , phenylethenyl , ethynyl , phenylethynyl , cyano, dimethylamino, diphenylamino, monomethylamino, monophenylamino, phenyloxy, phenylthio, methoxycarbonyl , ethoxycarbonyl , t-butoxycarbonyl , carboxyl , nitro, chloro, fluoro or hydroxyl. The ring A and the ring B may independently be selected from the following structures, but not limited thereto:
Figure imgf000016_0001
More specifically, the organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but not limited thereto:
Figure imgf000017_0001
Figure imgf000018_0001
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
Figure imgf000074_0001
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000082_0001
Figure imgf000083_0001
Figure imgf000084_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
For example, the organic electroluminescent compound according to the present invention may be prepared according to Scheme 1, but not limited thereto: [Scheme1]
Figure imgf000088_0001
wherein ring A, ring B, Ari, Ri and R2 are the same as defined in Chemical
Formula 1.
The present invention also provides an organic solar cell. The organic solar cell according to the present invention comprises one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
The present invention further provides an organic electroluminescent device. The organic electroluminescent device according to the present invention comprises a first electrode! a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
In the organic electroluminescent device according to the present invention, the organic layer comprises an electroluminescent layer. The electroluminescent layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula 1 as an electroluminescent dopant and one or more host(s). The host used in the organic electroluminescent device according to the present invention is not particularly limited, but may be selected from the compounds Chemical Formulas 2 and 3: (Arn)a-Li-(Ar12)b (2) (Ar13)C-L2-(ArI4),! (3) wherein Li represents (C6-C60)arylene or (C4-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S; L2 represents anthracenylene; Arn through Arw independently represent hydrogen, deuterium, (Cl-
C60)alkyl, (Cl-C60)alkoxy, halogen, (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C5-C60)cycloalkyl or (C6-C60)aryl , and the arylene, heteroarylene or anthracenylene of Li and L?, and the cycloalkyl, aryl or heteroaryl of Arn through Arw may be further substituted by one or more substituent(s) selected from a group consisting of (C6- C60)aryl with or without one or more subst ituent(s) selected from a group consisting of (Cl-CΘO)alkyl with or without halogen subst ituent(s), (Cl- C60)alkoxy, (C3-C60)cycloalkyl , halogen, cyano, tri(Cl-C60)alkylsilyl , di (Cl- C60)alkyl(C6-C60)arylsilyl and tri(C6-C60)arylsi IyI , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (Cl-CβO)alkyl with or without halogen subst ituent(s) , (Cl-CΘO)alkoxy, (C3-C60)cycloalkyl , halogen, cyano, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl and tri(C6-C60)arylsilyl ; and a, b, c and d independently represent an integer from 0 to 4. The host represented by Chemical Formula 2 or 3 may be exemplified by the anthracene derivatives or benz[a]anthracene derivatives represented by Chemical Formulas 4 to 7:
Figure imgf000090_0001
wherein
Rioi and R102 independently represent hydrogen, deuterium, (Cl-C60)alkyl , halogen, (C6-C60)aryl , (C4-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) selected from N, 0 and S or (C3- C60)cycloalkyl , and the aryl or heteroaryl of R1O1 and R102 may be further substituted by one or more substituent(s) selected from a group consisting of (Cl-C60)alkyl , halo(Cl-C60)alkyl , (Cl-C60)alkoxy, (C3-C60)cycloalkyl , (C6- C60)aryl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, halogen, cyano, tri(Cl-C60)alkylsilyl , di(Cl-C60)alkyl(C6- C60)arylsilyl and tri(C6-C60)arylsilyl ;
Rio3 through R106 independently represent hydrogen, deuterium, (Cl-
C60)alkyl, (Cl-C60)alkoxy, halogen, (C4~C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C5-C60)cycloalkyl or (C6-C60)aryl , and the heteroaryl , cycloalkyl or aryl of R103 through Rioβ may be further substituted by one or more substituent(s) selected from a group consisting of (Cl-C60)alkyl with or without halogen subst ituent(s) , (Cl-C60)alkoxy, (C3- C60)cycloalkyl, halogen, cyano, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6- C60)arylsilyl and tri(C6-C60)arylsi IyI ;
Pi and P2 independently represent a chemical bond or (C6-C60)arylene with or without one or more subst ituent(s) selected from (Cl-C60)alkyl , (Cl- C60)alkoxy, (C6-C60)aryl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S and halogen;
Ar2I and Ar22 are independently selected from the following structures:
Figure imgf000091_0001
Ln represents (C6-C60)arylene, (C4-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S or a compound the following formula:
Figure imgf000092_0002
the arylene or heteroarylene of Ln may be substituted by one or more substituent(s) selected from (Cl-C60)alkyl , (Cl-C60)alkoxy, (C6-C60)aryl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S and halogen;
Rm, Rii2, Rii3 and Rm independently represent hydrogen, deuterium, (Cl-
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 ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
Rm, Ri22, Ri23 and Rm independently represent hydrogen, deuterium, (Cl-
C60)alkyl, (Cl-CδO)alkoxy, (Cβ-CβO)aryl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S 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 ring or a mono- or polycyclic aromatic ring;
Figure imgf000092_0001
wherein L2I and L22 independently represent a chemical bond, (C6-C60)arylene or
(C3-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S, and the arylene or heteroarylene of L21 and L22 may be further substituted by one or more substituent(s) selected from (Cl-CβO)alkyl , halogen, cyano, (Cl-CβO)alkoxy, (C3-C60)cycloalkyl , (C6-C60)aryl , (C3- C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl and tri(C6- C30)arylsilyl; R201 through R219 independently represent hydrogen, deuterium, halogen,
(Cl-C60)alkyl, (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsi IyI , tri(C6-C60)arylsilyl, adamantyl , (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, (Cl-C60)alkoxy, cyano, (Cl-CΘO)alkyl amino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl, nitro or hydroxyl , or each of R201 through R219 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 mono- or polycyclic aromatic ring; Ar3i represents (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl , adamantyl, (C7-C60)bicycloalkyl or a substituent selected from the following structures :
Figure imgf000094_0001
wherein
R220 through R232 independently represent hydrogen, halogen, (Cl-
C60)alkyl, (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri(Cl-C60)alkylsi IyI , di(Cl-C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl, adamantyl , (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, (Cl-CβO)alkoxy, cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl-
C60)alkoxycarbonyl , carboxyl , nitro or hydroxy1 ;
Ei and E2 independently represent a chemical bond, -(CR233R234)q-, -N(R23s)-
, -(S)-, -(0)-, -Si(R236)(R237)-, -P(R38)", -C(=0)-, -B(R239)-, -In(R240)-, -Se-, -Ge(R24I)(R242)", -Sn(R243)(R244)", -Ga(R245)- or -(R246)C=C(R247)-;
R233 through R247 independently represent hydrogen, deuterium, halogen,
(Cl-CΘO)alkyl , (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl , tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, (Cl-C60)alkoxy, cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl, nitro or hydroxyl , or each of R233 through R247 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 mono- or polycyclic aromatic ring; the aryl , heteroaryl, heterocycloalkyl , adamantyl or bicycloalkyl of Ar3I, or the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylsilyl, alkylsilyl, alkylamino or arylamino of R2oi through R232 may be further substituted by one or more subst ituent(s) selected from halogen, (Cl-C60)alkyl, (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3-C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6- C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl, (C7-C60)bicycloalkyl , (C2- C60)alkenyl, (C2-C60)alkynyl , (Cl-C60)alkoxy, cyano, (Cl-C60)alkylamino, (C6- C60)aryl amino, (C6-C60)ar(C1-C60)alkyl , (C6-C60)aryloxy, (C6-C60)arylthio, (Cl-CΘO)alkoxycarbonyl , carboxyl , nitro and hydroxyl; p represents an integer from 1 to 4; and q represents an integer from 0 to 4. 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 combination of a dopant and a host is used in accordance with the present invention, remarkable improvement in luminous efficiency may be attained. The doping concentration may be from 0.5 to 10% by weight. When compared with other existing host materials, the host provides excellent electron and hole conductivity, superior stability, good luminous efficiency, and significantly improved life property. Therefore, when the compounds represented by Chemical Formulas 4 to 7 are used as an electroluminescent host, they may substantially compensate for the electrical drawbacks of the organic electroluminescent compound represented by Chemical Formula 1. The host compounds represented by Chemical Formulas 4 to 7 may be exemplified by the following compounds, but not limited thereto:
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
Figure imgf000105_0001
Figure imgf000106_0001
Figure imgf000107_0001
Figure imgf000108_0001
The electroluminescent device according to the present invention comprises the organic electroluminescent compound represented by Chemical Formula 1 and may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine 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:
Figure imgf000108_0002
wherein Ar4I and Ar42 independently represent (Cl-C60)alkyl , (C6-C60)aryl , (C4-
C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C6~C60)aryl amino, (Cl-C60)alkylamino, morpholino, thiomorphol ino, 5- or 6- membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S or (C3-C60)cycloalkyl , or Ar4I and Ar42 may be linked via (C3-
C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring, and the aryl , heteroaryl , arylamino or heterocycloalkyl of Ar4i and Ar42 may be further substituted by one or more substituent(s) selected from halogen, (Cl- C60)alkyl, (C2-C60)alkenyl , (C2-C60)alkynyl , (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3-C60)cycloalkyl , tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6- C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl, (C7-C60)bicycloalkyl , (Cl- C60)alkoxy, cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl- C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl-C60)alkoxycarbonyl , carboxyl , nitro and hydroxyl ;
Ar43 represents (C6-C60)aryl , (C5-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C6-C60)arylamino or a substituent selected from the following structures, when g is l:
Figure imgf000109_0001
Ar43 represents (C6-C60)arylene, (C4-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S or a substituent selected from the following structures, when g is 2:
Figure imgf000110_0001
Ar44 represents (C6-C60)arylene or (C4-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S;
R251, R252 and R253 independently represent hydrogen, deuterium, (Cl-
C60)alkyl or (C6-C60)aryl ; the aryl , heteroaryl , arylamino, arylene or heteroarylene of Ar43, the arylene or heteroarylene of R44, or the alkyl or aryl of R251 through R253may be further substituted by one or more subst ituent(s) selected from halogen, (Cl- C60)alkyl, (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsi IyI , tri(C6-C60)arylsilyl, adamantyl , (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, (Cl-C60)alkoxy, cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl , nitro and hydroxyl ', e represents an integer from 1 to 4; and f represents an integer 0 or 1.
More specifically, the arylamine compound or the styrylarylamine compound may be exemplified by the following compounds, but not limited thereto:
Figure imgf000111_0001
In the electroluminescent device according to the present 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 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 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 and Ag is patterned in parallel may be manufactured. The organic layer may comprise a compound having an electroluminescence peak with wavelength of 480 to 560 nm and a compound having an electroluminescence peak with wavelength of not less than 560 nm at the same time. The compound having an electroluminescence peak with wavelength of 480 to 560 nm or the compound having 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:
1 101 102 103 ML L L (9) wherein M 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;
101 102 103 ligands L , L and L are independently selected from the following structures:
Figure imgf000113_0001
wherein R301 through R303 independently represent hydrogen, deuterium, (Cl-
C60)alkyl with or without halogen subst ituent(s) , (C6-C60)aryl with or without (Cl-CΘO)alkyl subst ituent(s) or halogen; R304 through R3I9 independently represent hydrogen, deuteriiun, (Cl-
C60)alkyl, (Cl-C30)alkoxy, (C3-C60)cycloalkyl , (C2-C30)alkenyl , (C6-C60)aryl , mono- or di(Cl-C30)alkylamino, mono- or di(C6-C30)arylamino, SF5, tr i (Cl-
C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl , tri(C6-C30)arylsilyl , cyano or halogen, and the alkyl, cycloalkyl, alkenyl or aryl of R304 through R3I9 may be further substituted by one or more subst ituent(s) selected from (Cl- C60)alkyl, (C6-C60)aryl and halogen; R320 through R323 independently represent hydrogen, deuterium, (Cl-
C60)alkyl with or without halogen subst ituent(s) or (C6-C60)aryl with or without (Cl-CβO)alkyl subst ituent(s); R324 and R325 independently represent hydrogen, deuterium, (Cl-CβO)alkyl ,
(C6-C60)aryl or halogen, or R324 and R325 may be linked via (C3-C12)alkylene or
(C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring, and the alkyl or aryl of R324 and R325, or the alicyclic ring or the mono- 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 subst ituent(s) selected from (Cl-CβO)alkyl with or without halogen subst ituent (s) , (Cl-C30)alkoxy, halogen, tri(Cl-C30)alkylsilyl, tri(C6-C30)arylsilyl and (C6-C60)aryl ; R326 represents (Cl-CΘO)alkyl , (C6-C60)aryl , (C5-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S or halogen; R327 through R329 independently represent hydrogen, deuterium, (Cl-
C60)alkyl, (C6-C60)aryl or halogen, and the alkyl or aryl of R326 through R329 may be further substituted by halogen or (Cl-CβO)alkyl ;
Figure imgf000115_0001
or
Figure imgf000115_0002
; wherein R331 through R342 independently represent hydrogen, deuterium, (Cl-CΘO)alkyl with or without halogen substituent(s) , (Cl-C30)alkoxy, halogen, (C6-C60)aryl , cyano or (C5-C60)cycloalkyl , or each of R331 through R342 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 may be linked to R307 or R30S via alkylene or alkenylene to form a (C5-C7)fused ring;
Figure imgf000115_0003
wherein R401 through R404 independently represent (Cl-CΘO)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 ring to form an alicyclic ring or a mono- or polycyclic aromatic ring! the alkyl or aryl of R401 through R404, or the alicyclic ring or the mono- or polycyclic aromatic ring formed as they are linked via (C3- C60)alkylene or (C3-C60)alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from (Cl-CΘO)alkyl with or without halogen subst ituent(s), (Cl-C60)alkoxy, halogen, tr i CCl- C60)alkylsilyl, tri(C6-C60)arylsilyl and (C6-C60)aryl ;
Figure imgf000116_0001
wherein
201 202 igands L and L are independently selected from the following structures:
Figure imgf000116_0002
represents a divalent or trivalent metal; h is 0 when M is a divalent metal, and h is 1 when M is a trivalent metal ; T represents (C6-C60)aryloxy or tri(C6-C60)arylsilyl , and the aryloxy or triarylsilyl of T may be further substituted by (Cl-CΘO)alkyl or (C6-
C60)aryl ; G represents 0, S or Se; ring C represents oxazole, thiazole, imidazole, oxadiazole, thiadiazole, benzoxazole, benzothiazole, benzimidazole, pyridine or quino1 ine ! ring D represents pyridine or quinoline, and the ring D may be further substituted by (Cl-C60)alkyl , phenyl with or without (Cl-CΘO)alkyl subst ituent(s) or naphthyl ; R50I through R504 independently represent hydrogen, deuterium, (Cl-
C60)alkyl, halogen, tri(Cl-C60)alkylsilyl, tri(C6-C60)arylsi IyI or (C6- C60)aryl , or each of them may be linked to an adjacent substituent via (C3- C60)alkylene, or (C3-C60)alkenylene to form a fused ring, and the pyridine or quinoline may be linked to R501 via a chemical bond to form a fused ring; the aryl of ring C and R40I through R404 may be further substituted by
(Cl-CβO)alkyl , halogen, (Cl-CΘO)alkyl with halogen subst ituent (s) , phenyl, naphthyl, tri(Cl-C60)alkylsilyl , tri(C6-C60)arylsi IyI or amino;
Figure imgf000117_0001
Figure imgf000118_0001
wherein Ar5I represents (C6-C60)arylene with or without one or more substituent(s) selected from a group consisting of halogen, (Cl-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(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl , tri(C6-C60)arylsilyl, adamantyl , (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, (Cl-CβO)alkoxy, cyano, (Cl-CΘO)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl , nitro and hydroxy1 , and the alkyl, cycloalkyl, heterocycloalkyl, aryl , heteroaryl, arylsilyl, alkylsilyl, alkylamino or arylamino substituent substituted at the arylene may be further substituted by one or more substituent(s) selected from halogen, (Cl-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(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsi IyI , tri(C6- C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl , (Cl-CΘO)alkoxy, cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl, nitro and hydroxy1 ; R60I through R6o4 independently represent (Cl-C60)alkyl , (C6-C60)aryl ,
(C4-C60)heteroaryl , (C6-C60)arylamino, (Cl-C60)alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S or (C3-C60)cycloalkyl , or R601 through Rδ04 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 mono- or polycyclic aromatic ring; and the alkyl, aryl , heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of RΘOI through R604 may be further substituted by one or more substituent(s) selected from halogen, (Cl-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 , tr i (Cl- C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl , tri(C6-C60)arylsilyl , adamantyl, (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2-C60)alkynyl , (Cl- C60)alkoxy, cyano, (Cl-CβO)alkyl amino, (C6-C60)arylamino, (C6-C60)ar(Cl- C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl-C60)alkoxycarbonyl , carboxyl , nitro and hydroxy1. The compound having an electroluminescence peak with wavelength of 480 to 560 nm or the compound having an electroluminescence peak with wavelength of not less than 560 nm may be exemplified by the compounds represented by the following compounds, but not limited thereto:
Figure imgf000120_0001
Figure imgf000121_0001
Figure imgf000122_0001
Figure imgf000123_0001
Figure imgf000124_0001
Figure imgf000125_0001
Figure imgf000126_0001
Figure imgf000127_0001
Figure imgf000128_0001
Figure imgf000129_0001
Figure imgf000130_0001
Figure imgf000131_0001
Figure imgf000132_0001
Figure imgf000133_0001
Figure imgf000134_0001
Figure imgf000135_0001
Figure imgf000136_0001
Figure imgf000136_0002
Figure imgf000137_0001
Figure imgf000137_0002
Figure imgf000137_0003
Figure imgf000137_0004
Figure imgf000138_0001
Figure imgf000139_0001
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) 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 therefrom. The chalcogenide may be, for example, SiOx (1 = x = 2), AlOx (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, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc. 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, 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 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. Since the organic electroluminescent compound according to the present invention has superior luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very good operation life.
[Description of Drawings] The above and other aspects, features and advantages of the disclosed exemplary embodiments will be more apparent from the following detailed description taken in conjunction with the accompanying drawings in which: FIG. 1 is a cross-sectional view of an OLED device. [Best Mode] Hereinafter, the organic electroluminescent compounds according to the present invention, preparation methods thereof, and electroluminescence characteristics of devices 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.
[Preparation Example]s [Preparation Example 1] Preparation of 1
Figure imgf000141_0001
Preparation of Compound A 1,4-Dibromobenzene (20.0 g, 84.78 mmol), 1,2,3,4-tetrahydroquinoline
(16.9 g, 127.17 mmol), Pd(OAc)2 (0.07g, 4.24 mmol), PCt-Bu)3 (50% in toluene, 3.4 mL, 8.48 mmol), Cs2CO3 (82.9 g, 254.34mmo1 ) and toluene (300 mL) were mixed and stirred at 110 °C for 5 hours. Upon completion of reaction, the mixture was cooled at room temperature, extracted with ethyl acetate/water (1/1), and dried under reduced pressure. Compound A (13.7 g, 47.54 mmol) was obtained by column separation. Preparation of Compound B Compound A (13.7 g, 47.54 mmol) was dissolved in tetrahydrofuran (250 mL). After lowering temperature to -78°C , 1.6 M /rBuLi (44.6 mL, 71.31 mmol) was slowly added dropwise. After stirring for 30 minutes, N,N- dimethylformamide (7.3 mL, 95.08 mmol) was added. After slowly heating, followed by stirring for 2 hours, aqueous NH4Cl solution (150 mL) and distilled water (150 mL) was added to terminate the reaction. The organic layer was separated and the solvent was removed under reduced pressure. Compound B (9.9 g, 41.83 mmol) was obtained by column separation. Preparation of Compound C Compound B (9.9 g, 41.83 mmol) and NaBH4 (2.4 g, 62.75 mmol) were added to a reactor. After removing air under reduced pressure, nitrogen gas was filled therein. After adding tetrahydrofuran (300 mL), methanol (200 mL) was slowly added dropwise while stirring the mixture. Upon completion of reaction, the product was washed with water (500 mL) and extracted with ethyl acetate. Compound C (8.2 g, 32.63 mmol) was obtained by column chromatography using dichloromethane and hexane. Preparation of Compound D Compound C (8.2 g, 32.63 mmol) was added to a reactor. After removing air under reduced pressure, nitrogen gas was filled therein, Compound B was dissolved by adding triethyl phosphite (50 mL). In another reactor, triethyl phosphite (20 mL) was added. While slowly adding iodine (I2) (8.3 g, 32.63 mmol) with the lid open, the mixture was stirred at 0°C for 30 minutes. The mixture of iodine and triethyl phosphite was added to the reactor containing Compound C. After heating to 150°C, the mixture was stirred for 4 hours. Upon completion of reaction, triethyl phosphite was removed by distillation under reduced pressure. The product was washed with water (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was dried under reduced pressure and Compound D (10.0 g, 27.82 mmol) was obtained by column separation. Preparation of Compound E 2,7-Dibromof luorene (50 g, 154.26 mmol) and potassium hydroxide (KOH) (69.2 g, 1234 mmol) were dissolved in DMSO (700 mL) under nitrogen atmosphere. After cooling to 0°C, followed by slowly adding distilled water (113 mL) dropwise, the mixture was stirred for an hour. Then, after slowly adding iodomethane (CH3I) (38.49 mL, 617.04 mmol) dropwise, followed by slowly heating to room temperature, the mixture was stirred for 15 hours. Excess water was added to terminate the reaction and extraction was carried out using dichloromethane. The resultant organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure. Compound E (53.0 g, 150.50 mmol) was obtained by column separation. Preparation of Compound F Compound E (53.0 g, 150.50 mmol) was dissolved in tetrahydrofuran (350 mL). After lowering temperature to -78°C , 1.6 M /rBuLi (63.2 mL, 158.04 mmol) was slowly added dropwise. After stirring for 30 minutes, yV,/V-dimethyl formamide (16.32 mL, 210.7 mmol) was added. After stirring for 2 hours while slowly heating, aqueous NH4Cl solution (80 mL) and distilled water (80 mL) were added to terminate the reaction. The organic layer was separated and the solvent was removed under reduced pressure. Compound F (20.9 g, 69.40 mmol) was obtained by column separation. Preparation of Compound G Compound F (20.9 g, 69.40 mmol), 1,2,3,4-tetrahydroquinoline (12.5 g,
104.10 mmol), cesium carbonate (24.1 g, 104.10 mmol) and Pd(OAc)2 (332 mg,
2.08 mmol) were suspended in toluene (800 mL). P(H3u)3 (599 mg, 4.16 mmol) was added and the mixture was stirred at 120°C for 4 hours. After adding saturated aqueous NH4Cl solution (500 mL), followed by extraction with ethyl acetate (500 mL), drying, filtration and concentration under reduced pressure, Compound G (15.2 g, 39.00 mmol) was obtained by recrystal 1 izat ion using methanol/tf-hexane (300 mL, v/v = 1/1). Preparation of Compound 1 Compound D (3.5 g, 9.72 mmol) and Compound G (7.8 g, 21.37 mmol) were added to a reactor and dried under reduced pressure. Tetrahydrofuran (150 mL) was added thereto under nitrogen atmosphere and the mixture was stirred. Potassium tert-butoxiάe (t-BuOK) (4.14 g, 37.17 mmol) dissolved in tetrahydrofuran (30 mL) was slowly added dropwise at 0°C, and the mixture was slowly heated to room temperature. After stirring for 4 hours, water (300 mL) was poured upon completion of reaction. The produced solid was filtered and washed with methanol (500 mL). This procedure was repeated 3 times. Compound 1 (3.6 g, 6.44 mmol) was obtained by recrystal 1 izat ion using tetrahydrofuran and methanol, followed by washing with hexane.
[Preparation Example 2] Preparation of Compound 5
Figure imgf000144_0001
Preparation of Compound H Compound G (10.0 g, 28.29 mmol) and NaBH4 (1.4 g, 36.78 mmol) were added to a reactor. After removing air under reduced pressure, nitrogen gas was filled therein. After adding tetrahydrofuran (300 mL), methanol (200 mL) was slowly added dropwise while stirring the mixture. Upon completion of reaction, the product was washed with water (500 mL) and extracted with ethyl acetate. Compound H (8.45 g, 23.84 mmol) was obtained by column chromatography using dichloromethane and hexane. Preparation of Compound I Compound H (8.45 g, 23.84 mmol) was added to a reactor. After removing air under reduced pressure, nitrogen gas was filled therein, and Compound B was dissolved by adding triethyl phosphite (50 mL) . In another reactor, triethyl phosphite (50 mL) was added. While slowly I2 (6.1 g, 23.84 mmol) with the lid open, the mixture was stirred at 0°C for 30 minutes. The mixture of I2 and triethyl phosphite was added to the reactor containing
Compound H. After heating to 150°C , the mixture was stirred for 4 hours. Upon completion of reaction, triethyl phosphite was removed by distillation under reduced pressure. The product was washed with water (300 mL) and extracted with ethyl acetate (300 mL). The organic layer was dried under reduced pressure and Compound I (12.4 g, 20.58 mmol) was obtained by column separation. Preparation of Compound 5 Compound G (6.2 g, 9.9 mmol) and Compound I (5.8 g, 9.9 mmol) were added to a reactor and dried under reduced pressure. Tetrahydrofuran (200 mL) was added thereto under nitrogen atmosphere to dissolve the compounds. After cooling to 0°C , t-BuOK (1.7 g, 14.8 mmol) dissolved in tetrahydrofuran (20 mL) in another reactor was slowly added dropwise. After stirring at 0°C for 2 hours, distilled water (300 mL) was added and the mixture was stirred. The produced solid was filtered under reduced pressure. The resultant solid was washed with methanol (200 mL). This procedure was repeated 3 times. Compound 5 (4.2 g, 6.22 mmol) was obtained by washing with ethyl acetate (50 mL), followed by recrystal 1 ization using tetrahydrofuran (50 mL) and methanol (300 mL).
Electroluminescent compounds (Compounds 1 to 1252) were prepared according to the method of Preparation Examples 1 and 2. Table 1 shows H NMR and MS/FAB data of the prepared electroluminescent compounds.
Figure imgf000146_0001
Figure imgf000147_0001
Figure imgf000148_0001
Figure imgf000149_0001
Figure imgf000150_0001
Figure imgf000151_0001
Figure imgf000152_0001
Figure imgf000153_0001
Figure imgf000154_0001
Figure imgf000155_0001
Figure imgf000156_0001
Figure imgf000157_0001
Figure imgf000158_0001
Figure imgf000159_0001
Figure imgf000160_0001
[Example 1] Manufacture of OLED device using organic electroluminescent compound according to the present invention
An OLED device was manufactured using the organic electroluminescent compound according to the present invention.
First, a transparent electrode ITO film (15 Ω/D) 2 prepared from a glass substrate for an OLED (Samsung Corning) 1 was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, 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)- pheny1amino)triphenylamine (2-TNATA) of the following structure in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10 torr. Then, 2-TNATA was evaporated by applying electrical current to the cell. A hole injection layer 3 having a thickness of 60 nm was formed on the ITO substrate.
Figure imgf000161_0001
Subsequently, after filling N,N -bis(-naphthyl )-yV,yV-diphenyl-4,4'- diamine (NPB) of the following structure in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current. A hole transport layer 4 having a thickness of 20 nm was formed on the hole injection layer.
After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. Compound H-32 of the following structure was filled in a cell of a vacuum deposition apparatus as a host, and Compound 7 was filled 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.
Figure imgf000162_0001
Thereafter, tris(8-hydroxyquinol ine)-aluminum(III) (AIq) of 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 manufacture an OLED.
Figure imgf000162_0002
Each OLED electroluminescent material was purified by vacuum
-6 subl imation at 10 torr . [Comparative Example 1] Manufacture of OLED device using existing electroluminescent material A hole injection layer and a hole transport layer were formed as in Example 1. Dinaphthylanthracene (DNA) was filled in a cell of a vacuum deposition apparatus as an electroluminescent host material, and Compound A of the following structure was filled in another cell as a blue-emitting electroluminescent material. An electroluminescent layer having a thickness of 30 run was formed on the hole transport layer by setting the deposition speed at 100: 1.
Figure imgf000163_0001
Then, an electron transport layer and an electron injection layer were formed as in Example 1, and an Al cathode having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
[Example 2] Electroluminescence characteristics of manufactured OLED devices Luminous efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1, which comprise the organic electroluminescent compounds according to the present invention and the existing
2 electroluminescent compound respectively, was measured at 1,000 cd/m . The result is given in Table 2. [Table 2]
Figure imgf000165_0001
As seen in Table 2, when the compounds according to the present invention were used to manufacture blue-emitting electroluminescent devices, color coordinate was significantly improved as compared to Comparative Example 1.
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 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.

Claims

[CLAIMS]
[Claim 1]
An organic electroluminescent compound represented by Chemical Formula l:
Figure imgf000167_0001
In Chemical Formula 1,
Ri and R9 independently represent hydrogen, deuterium, halogen, (Cl-
C60)alkyl, (C6-C60)aryl , (C3-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino, thiomorphol ino, 5- or 6- membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , tri(Cl-C60)alkylsilyl , di(Cl-C60)alkyl(C6- C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl , (C7-C60)bicycloalkyl , (C2- C60)alkenyl, (C2-C60)alkynyl , cyano, (Cl-C60)alkylamino, (C6-C60)aryl amino, (C6-C60)ar(Cl-C60)alkyl, (Cl-CβO)alkyloxy, (Cl-C60)alkylthio, (C6- C60)aryloxy, (C6-C60)arylthio, (Cl-C60)alkoxycarbonyl , (Cl-CβO)alkylcarbonyl , (Cβ-CβO)arylcarbonyl , carboxyl, nitro or hydroxy1 , or Ri and R2 may be linked via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring!
Ari represents (C6-C60)arylene, (C3-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S, 5- or 6-membered heterocycloalkylene containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkylene, adamantylene, (C7-C60)bicycloalkylene, (C2- C60)alkenylene, (C2-C60)alkynylene, (Cl-C60)alkylenethio, (Cl- C60)alkyleneoxy, (C6-C60)aryleneoxy, (C6-C60)arylenethio or
Figure imgf000168_0001
Y ring A and ring B independently represent a 5- to 7-membered heterocyclic amino group or a ring selected from the following structures:
Figure imgf000168_0002
the 5- to 7-membered heterocyclic amino group may further contain one or more heteroatom(s) selected from NR21, 0 and S; Rn through R18 independently represent hydrogen, deuterium, halogen,
(Cl-C60)alkyl , (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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri (Cl-CΘO)alkyl si IyI , di(Cl-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(Cl~ C60)alkyl, (Cl-C60)alkyloxy, (Cl-C60)alkylthio, (C6-C60)aryloxy, (C6- C60)arylthio, (Cl-CδO)alkylcarbonyl , (Cl-CβO)alkoxycarbonyl , (C6- C60)arylcarbonyl , carboxyl , nitro or hydroxyl , or each of Rn through Ri8 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 mono- or polycyclic aromatic ring; R21 represents hydrogen, deuterium, (Cl-CβO)alkyl , (C6-C60)aryl , (C3-
C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl, adamantyl, (C7-C60)bicycloalkyl or (C6-C60)ar(Cl- C60)alkyl; X and Y independently represent a chemical bond, -(CR3^)-T, -N(R33)-, -S-, -0-, -Si(R34)(R35)", -P(R36)-, -CC=O)- , -B(R37 )-, -In(R38)-, -Se-, -Ge(R39)(R40)", -Sn(R4O(R42)-, -Ga(R4S)-Or -(R44)C=C(R45 )-; R31 through R45 independently represent hydrogen, deuterium, halogen,
(Cl-CβO)alkyl, (C6-C60)aryl , (C3-C60)heteroaryl containing one or more heteroatom(s) selected from N, O 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(Cl-C60)alkylsi IyI , di(Cl-C60)alkyl(C6- C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl, (C7-C60)bicycloalkyl , (C2- C60)alkenyl, (C2-C60)alkynyl , cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (Cl-CβO)alkyloxy, (Cl-C60)alkylthio, (C6- C60)aryloxy, (C6-C60)arylthio, (Cl-C60)alkoxycarbonyl , (Cl-C60)alkylcarbonyl , (C6-C60)arylcarbony1 , carboxyl , nitro or hydroxy1 , or R31 and R32, R34 and R35,
R39 and R40, R4I and R42, and R44 and R45 may be linked via (C3-C60)alkylene or
(C3-C60)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; the arylene, heteroarylene, heterocycloalkylene, cycloalkylene, adamantylene, bicycloalkylene, alkenylene, alkylenethio, alkyleneoxy, aryleneoxy or arylenethio of Ar1 and the alkyl, aryl , heteroaryl, heterocycloalkyl, cycloalkyl , trialkylsi IyI , dialkylarylsi IyI , tr iarylsi IyI , adamantyl, bicycloalkyl , alkenyl, alkylamino, arylamino, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkoxycarbonyl , alkylcarbonyl or arylcarbonyl of R1, R2, Rn through R1S, R21 and R31 through R45 may be further substituted by one or more substituent(s) selected from a group consisting of halogen, (Cl- C60)alkyl with or without halogen substituent(s) , (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(s) , morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , triCCl-C60)alkylsilyl , diCCl- C60)alkyl(C6-C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl, CC7- C60)bicycloalkyl, (C2-C60)alkenyl , (C2-C60)alkynyl , cyano, carbazolyl, (Cl- C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl , (Cl-C60)alkyl(C6- C60)aryl, (Cl-C60)alkyloxy, (Cl-C60)alkylthio, (C6-C60)aryloxy, (C6- C60)arylthio, (Cl-C60)alkoxycarbonyl , (Cl-CδO)alkylcarbonyl , (C6- C60)arylcarbonyl , carboxyl , nitro and hydroxyl; and m represents an integer from 1 to 4.
[Claim 2]
The organic electroluminescent compound according to claim 1, wherein the ring A and the ring B are independently selected from the following structures:
Figure imgf000170_0001
[Claim 3]
The organic electroluminescent compound according to claim 1, wherein Ar1 is selected from the following structures:
Figure imgf000171_0001
wherein
R51 through R67 independently represent hydrogen, deuterium, halogen,
(Cl-C60)alkyl, halo(Cl-C60)alkyl , (C6-C60)aryl , (C3-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3~C60)cycloalkyl , tr i (Cl- C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl , tri(C6-C60)arylsilyl , adamantyl, (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2-C60)alkynyl , cyano, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl , (Cl- C60)alkyloxy, (Cl-CβO)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl, (Cl-C60)alkylcarbonyl , (C6-C60)arylcarbony1 , carboxyl , nitro or hydroxy1 , or R51 and Rs2, R53 and R54, R55 and R56, Reo and R6I, Rδ3 and RM, and R65 and R6e may be linked via (C3~C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; and the alkyl, aryl , heteroaryl, heterocycloalkyl , cycloalkyl, trialky1 si 1y1 , dialkylarylsi IyI , triarylsi IyI , adamantyl, bicycloalkyl , alkenyl , aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkylamino, arylamino, alkoxycarbonyl , alkylcarbonyl or arylcarbonyl of R51 through Rβ7 may be further substituted by one or more substituent(s) selected from a group consisting of halogen, (Cl-CδO)alkyl with or without halogen substituent (s) , (C6-C60)aryl , (C3-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S with or without (C6-C60)aryl subst ituent (s) , morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60)cycloalkyl , tr i (Cl- C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsi IyI , tri(C6-C60)arylsi IyI , adamantyl, (C7~C60)bicycloalkyl , (C2-C60)alkenyl , (C2-C60)alkynyl , cyano, carbazolyl, (Cl-C60)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl , (Cl-C60)alkyl(C6-C60)aryl, (C1-C60)alkyloxy, (Cl-C60)alkylthio, (C6- C60)aryloxy, (C6-C60)arylthio, (Cl-C60)alkoxycarbonyl , (C1-C60)alkylcarbonyl , (C6-C60)arylcarbonyl , carboxyl, nitro and hydroxy1.
[Claim 4] An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 3.
[Claim 5] The organic electroluminescent device according to claim 4, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) according to any of claims 1 to 3 and one or more host(s) selected from the compounds represented by Chemical Formula 2 or 3: (Arn)a-L1-(Ar12)b (2) (Ar13)c-L2-(Ari4)d (3) wherein Li represents (C6-C60)arylene or (C4-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S; L2 represents anthracenylene; Arii through Ar14 independently represent hydrogen, deuterium, (Cl-
C60)alkyl, (Cl-C60)alkoxy, halogen, (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C5-C60)cycloalkyl or (C6-C60)aryl , and the arylene, heteroarylene or anthracenylene of Li and L2, and the cycloalkyl, aryl or heteroaryl of Arn through Ar14 may be further substituted by one or more subst ituent(s) selected from a group consisting of (C6- C60)aryl with or without one or more subst ituent(s) selected from a group consisting of (Cl-CβO)alkyl with or without halogen subst ituent(s) , (Cl- C60)alkoxy, (C3-C60)cycloalkyl , halogen, cyano, tri(Cl-C60)alkylsilyl, di(Cl- C60)alkyl(C6-C60)arylsilyl and tri(C6-C60)arylsilyl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (Cl-C60)alkyl with or without halogen subst ituent(s), (Cl-CΘO)alkoxy, (C3-C60)cycloalkyl , halogen, cyano, tri(Cl-C60)alkylsilyl , di(Cl-C60)alkyl(C6-C60)arylsilyl and tri(C6-C60)arylsilyl; and a, b, c and d independently represent an integer from 0 to 4.
[Claim 6]
The organic electroluminescent device according to claim 5, wherein the host is selected from anthracene derivatives or benz[a]anthracene derivatives represented by Chemical Formulas 4 to T-
Figure imgf000174_0001
wherein
Rioi and R102 independently represent hydrogen, (Cl-CΘO)alkyl , halogen,
(C6-C60)aryl , (C4-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) selected from N, 0 and S or (C3-C60)cycloalkyl , and the aryl or heteroaryl of R101 and R102 may be further substituted by one or more substituent(s) selected from a group consisting of (Cl-C60)alkyl, halo(Cl- C60)alkyl, (Cl-CβO)alkoxy, (C3-C60)cycloalkyl , (C6-C60)aryl , (C4- C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, halogen, cyano, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsi IyI and tri(C6-C60)arylsilyl; R103 through Rioβ independently represent hydrogen, (Cl-CβO)alkyl , (Cl-
C60)alkoxy, halogen, (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, (C5-C60)cycloalkyl or (C6-C60)aryl , and the heteroaryl, cycloalkyl or aryl of R103 through RiO6 may be further substituted by one or more substituent(s) selected from a group consisting of (Cl- C60)alkyl with or without halogen substituent(s) , (Cl-C60)alkoxy, (C3- C60)cycloalkyl, halogen, cyano, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6- C60)arylsilyl and tri(C6-C60)arylsi IyI ; P1 and P2 independently represent a chemical bond or (C6-C60)arylene with or without one or more subst ituent(s) selected from (Cl-CΘO)alkyl , (Cl- C60)alkoxy, (C6-C60)aryl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S and halogen;
Ar21 and Ar22 are independently selected from the following structures:
Figure imgf000176_0002
Lu represents (C6-C60)arylene, (C4-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S or a compound the following formula:
Figure imgf000176_0001
the arylene or heteroarylene of Lu may be substituted by one or more substituent(s) selected from (Cl-CΘO)alkyl , (Cl-C60)alkoxy, (C6-C60)aryl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S and halogen;
Rm, R112, Rii3 and Rn4 independently represent hydrogen, (Cl-CβO)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 ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
Rm, R122, R123 and R124 independently represent hydrogen, (Cl-C60)alkyl ,
(Cl-CΘO)alkoxy, (C6-C60)aryl , (C4-C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S 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 ring or a mono- or polycyclic aromatic ring:
Figure imgf000177_0001
wherein L2I and L22 independently represent a chemical bond, (C6-C60)arylene or
(C3-C60)heteroarylene containing one or more heteroatom(s) selected from N, 0 and S, and the arylene or heteroarylene of L2i and L2? may be further substituted by one or more substituent (s) selected from (Cl-CβO)alkyl , halogen, cyano, (Cl-C60)alkoxy, (C3-C60)cycloalkyl , (C6-C60)aryl , (C3- C60)heteroaryl containing one or more heteroatom(s) selected from N, 0 and S, tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsi IyI and tri(C6- C30)arylsilyl;
R201 through R219 independently represent hydrogen, halogen, (Cl-
C60)alkyl, (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl , tri(C6-C60)arylsilyl, adamantyl , (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, (Cl-CβO)alkoxy, cyano, (Cl-CδO)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl , nitro or hydroxyl , or each of R201 through R219 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 mono- or polycyclic aromatic ring;
Ar3I represents (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl , adamantyl, (C7-C60)bicycloalkyl or a substituent selected from the following structures:
Figure imgf000178_0001
wherein
R220 through R232 independently represent hydrogen, halogen, (Cl-
C60)alkyl, (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6-C60)arylsilyl , tri(C6-C60)arylsilyl, adamantyl, (C7-C60)bicycloalkyl , (C2-C60)alkenyl , (C2- C60)alkynyl, (Cl-CβO)alkoxy, cyano, (Cl-CβO)alkylamino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl, nitro or hydroxyl;
Ei and E2 independently represent a chemical bond, -(CR233R234)q ~, -N(R23s)~ , -(S)-, -(0)-, -Si(R236)(R237)", -P(R38)-, -CC=O)- , -B(R239)-, -In(R240)-, -Se-, -Ge(R24I)(R242)-, -Sn(R243)(R244)-, -Ga(R245)- or -(R246 )C=C(R247)-; R233 through R247 independently represent hydrogen, halogen, (Cl-
C60)alkyl, (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3- C60)cycloalkyl, tri(Cl-C60)alkylsilyl , di(Cl-C60)alkyl(C6-C60)arylsilyl , tri(C6-C60)arylsilyl, adamantyl , (C7-C60)bicycloalkyl , (C2-C60)alkenyl , CC2- C60)alkynyl, (Cl-CΘO)alkoxy, cyano, (Cl-CβO)alkyl amino, (C6-C60)arylamino, (C6-C60)ar(Cl-C60)alkyl, (C6-C60)aryloxy, (C6-C60)arylthio, (Cl- C60)alkoxycarbonyl , carboxyl , nitro or hydroxyl , or each of R233 through R247 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 mono- or polycyclic aromatic ring! the aryl , heteroaryl, heterocycloalkyl, adamantyl or bicycloalkyl of Ar3i, or the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylsilyl, alkyl si IyI , alkylamino or arylamino of R2oi through R232 may be further substituted by one or more substituent Cs) selected from halogen, (Cl-CΘO)alkyl , (C6-C60)aryl , (C4-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) selected from N, 0 and S, (C3-C60)cycloalkyl, tri(Cl-C60)alkylsilyl, di(Cl-C60)alkyl(C6- C60)arylsilyl, tri(C6-C60)arylsilyl , adamantyl, (C7-C60)bicycloalkyl , (02- C60)alkenyl, (C2-C60)alkynyl , (Cl-CβO)alkoxy, cyano, (Cl-CΘO)alkylamino, (C6- C60)arylamino, (C6-C60)ar(Cl-C60)alkyl , (C6-C60)aryloxy, (C6-C60)arylthio, (Cl-CβO)alkoxycarbonyl , carboxyl, nitro and hydroxyl; p represents an integer from 1 to 4; and q represents an integer from 0 to 4.
[Claim 7] The organic electroluminescent device according to claim 5, wherein the organic layer comprises one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds.
[Claim 8] The organic electroluminescent device according to claim 5, wherein the organic layer further comprises 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.
[Claim 9] The organic electroluminescent device according to claim 5, wherein the organic layer comprises an electroluminescent layer and a charge generating 1ayer .
[Claim 10] A white-emitting electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 3.
PCT/KR2009/006353 2008-10-30 2009-10-30 Novel organic electroluminescent compounds and organic electroluminescent device using the same WO2010050781A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN200980143444.8A CN102203076B (en) 2008-10-30 2009-10-30 Novel organic electroluminescent compounds and organic electroluminescent device using the same
JP2011534396A JP2012507508A (en) 2008-10-30 2009-10-30 NOVEL ORGANIC LIGHT EMITTING COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME AS LIGHT EMITTING MATERIAL

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020080107245A KR20100048203A (en) 2008-10-30 2008-10-30 Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR10-2008-0107245 2008-10-30

Publications (1)

Publication Number Publication Date
WO2010050781A1 true WO2010050781A1 (en) 2010-05-06

Family

ID=41334447

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2009/006353 WO2010050781A1 (en) 2008-10-30 2009-10-30 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Country Status (5)

Country Link
EP (1) EP2182038A1 (en)
JP (1) JP2012507508A (en)
KR (1) KR20100048203A (en)
CN (1) CN102203076B (en)
WO (1) WO2010050781A1 (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010140801A1 (en) * 2009-06-02 2010-12-09 Dow Advanced Display Materials, Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
EP2574608A1 (en) * 2011-09-28 2013-04-03 Solvay Sa Spirobifluorene compounds for light emitting devices
WO2013045410A1 (en) * 2011-09-28 2013-04-04 Solvay Sa Spirobifluorene compounds for light emitting devices
JP2014521593A (en) * 2011-05-05 2014-08-28 メルク パテント ゲーエムベーハー Compounds for electronic devices
CN105777715A (en) * 2016-03-30 2016-07-20 阜阳欣奕华材料科技有限公司 Compound, organic light emitting display (OLED) and display device
CN105859687A (en) * 2016-03-30 2016-08-17 阜阳欣奕华材料科技有限公司 Compound, organic electroluminescent device and display device
US9680108B2 (en) 2014-06-11 2017-06-13 Samsung Display Co., Ltd. Organic light-emitting device
US10026906B2 (en) 2015-01-12 2018-07-17 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US10062850B2 (en) 2013-12-12 2018-08-28 Samsung Display Co., Ltd. Amine-based compounds and organic light-emitting devices comprising the same
US10147882B2 (en) 2013-05-09 2018-12-04 Samsung Display Co., Ltd. Styrl-based compound and organic light emitting diode comprising the same
US10256416B2 (en) 2013-07-01 2019-04-09 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US10290811B2 (en) 2014-05-16 2019-05-14 Samsung Display Co., Ltd. Organic light-emitting device
US10388882B2 (en) 2013-03-04 2019-08-20 Samsung Display Co., Ltd. Anthracene derivatives and organic light emitting devices comprising the same
US10538538B2 (en) 2017-01-13 2020-01-21 Samsung Display Co., Ltd. Polycyclic compound and organic electroluminescence device including the same
US10673000B2 (en) 2016-11-14 2020-06-02 Samsung Display Co., Ltd. Heterocyclic compound and organic electroluminescence device including the same

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2436679B1 (en) 2009-05-29 2016-01-06 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescent element using the same
CN103450883B (en) * 2012-05-30 2016-03-02 京东方科技集团股份有限公司 Organic electronic material
CN103456897B (en) * 2012-05-30 2016-03-09 京东方科技集团股份有限公司 Organic electroluminescence device
US9312500B2 (en) 2012-08-31 2016-04-12 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
JP6023635B2 (en) * 2013-04-15 2016-11-09 出光興産株式会社 Fused ring amine compound and organic electroluminescence device using the same
WO2015175680A1 (en) * 2014-05-14 2015-11-19 President And Fellows Of Harvard College Organic light-emitting diode materials
KR102291487B1 (en) * 2014-12-10 2021-08-20 삼성디스플레이 주식회사 Condensed-cyclic compound and organic light emitting device comprising the same
CN105777628B (en) * 2016-03-30 2018-06-26 阜阳欣奕华材料科技有限公司 A kind of compound, organic electroluminescence device and display device
CN111777609B (en) * 2020-07-23 2021-06-11 吉林奥来德光电材料股份有限公司 Anthracene-containing derivative and preparation method and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004269696A (en) * 2003-03-10 2004-09-30 Toyo Ink Mfg Co Ltd Organic electroluminescent device material and electroluminescent device using the same

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3890686B2 (en) * 1997-07-22 2007-03-07 東洋インキ製造株式会社 Organic electroluminescence device
JP3693224B2 (en) * 1999-05-17 2005-09-07 富士写真フイルム株式会社 Organic electroluminescence device
JP2003020469A (en) * 2001-07-06 2003-01-24 Fuji Photo Film Co Ltd Biphoton absorption composition
US7001708B1 (en) * 2001-11-28 2006-02-21 University Of Central Florida Research Foundation, Inc. Photosensitive polymeric material for worm optical data storage with two-photon fluorescent readout
JP2004224746A (en) * 2003-01-24 2004-08-12 Fuji Photo Film Co Ltd Method for carrying out two-photon fluorescent labeling and two-photon absorption compound
JP4363133B2 (en) * 2003-09-09 2009-11-11 東洋インキ製造株式会社 Organic electroluminescent device material and organic electroluminescent device using the same
KR100812178B1 (en) * 2006-01-27 2008-03-12 (주)그라쎌 Electroluminescent compounds comprising fluorene group and organic electroluminescent device using the same
JP5221061B2 (en) * 2006-06-15 2013-06-26 三星ディスプレイ株式會社 Cyclopentaphenanthrene compound and organic electroluminescence device using the same
JP2008021687A (en) * 2006-07-10 2008-01-31 Mitsubishi Chemicals Corp Material for organic electric field light emitting element, composition for organic electric field light emitting element and organic electric field light emitting element

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004269696A (en) * 2003-03-10 2004-09-30 Toyo Ink Mfg Co Ltd Organic electroluminescent device material and electroluminescent device using the same

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHI, CHIH-CHIN ET AL.: "Achieving high-efficiency non-doped blue organic light- emitting diodes: charge-balance control of bipolar blue fluorescent materials with reduced hole-mobility", JOURNAL OF MATERIALS CHEMISTRY, vol. 19, no. 31, 2009, pages 5561 - 5571 *
PATENT ABSTRACTS OF JAPAN *

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010140801A1 (en) * 2009-06-02 2010-12-09 Dow Advanced Display Materials, Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
JP2014521593A (en) * 2011-05-05 2014-08-28 メルク パテント ゲーエムベーハー Compounds for electronic devices
US10056549B2 (en) 2011-05-05 2018-08-21 Merck Patent Gmbh Compounds for electronic devices
TWI551666B (en) * 2011-09-28 2016-10-01 首威公司 Spirobifluorene compounds for light emitting devices
CN106986842A (en) * 2011-09-28 2017-07-28 住友化学株式会社 The fluorene compound of spiral shell two for luminescent device
CN103958486A (en) * 2011-09-28 2014-07-30 索尔维公司 Spirobifluorene compounds for light emitting devices
US20140231713A1 (en) * 2011-09-28 2014-08-21 Solvay Sa Spirobifluorene compounds for light emitting devices
WO2013045411A1 (en) * 2011-09-28 2013-04-04 Solvay Sa Spirobifluorene compounds for light emitting devices
JP2014534950A (en) * 2011-09-28 2014-12-25 ソルヴェイ（ソシエテ アノニム） Spirobifluorene compounds for light emitting devices
JP2015500793A (en) * 2011-09-28 2015-01-08 ソルヴェイ（ソシエテ アノニム） Spirobifluorene compounds for light emitting devices
US10825992B2 (en) 2011-09-28 2020-11-03 Sumitomo Chemical Co., Ltd Spirobifluorene compounds for light emitting devices
EP2574608A1 (en) * 2011-09-28 2013-04-03 Solvay Sa Spirobifluorene compounds for light emitting devices
WO2013045410A1 (en) * 2011-09-28 2013-04-04 Solvay Sa Spirobifluorene compounds for light emitting devices
CN103958485A (en) * 2011-09-28 2014-07-30 索尔维公司 Spirobifluorene compounds for light emitting devices
US10388882B2 (en) 2013-03-04 2019-08-20 Samsung Display Co., Ltd. Anthracene derivatives and organic light emitting devices comprising the same
US10147882B2 (en) 2013-05-09 2018-12-04 Samsung Display Co., Ltd. Styrl-based compound and organic light emitting diode comprising the same
US10256416B2 (en) 2013-07-01 2019-04-09 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
US10062850B2 (en) 2013-12-12 2018-08-28 Samsung Display Co., Ltd. Amine-based compounds and organic light-emitting devices comprising the same
US10290811B2 (en) 2014-05-16 2019-05-14 Samsung Display Co., Ltd. Organic light-emitting device
US9680108B2 (en) 2014-06-11 2017-06-13 Samsung Display Co., Ltd. Organic light-emitting device
US10026906B2 (en) 2015-01-12 2018-07-17 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN105859687A (en) * 2016-03-30 2016-08-17 阜阳欣奕华材料科技有限公司 Compound, organic electroluminescent device and display device
CN105777715A (en) * 2016-03-30 2016-07-20 阜阳欣奕华材料科技有限公司 Compound, organic light emitting display (OLED) and display device
US10673000B2 (en) 2016-11-14 2020-06-02 Samsung Display Co., Ltd. Heterocyclic compound and organic electroluminescence device including the same
US10538538B2 (en) 2017-01-13 2020-01-21 Samsung Display Co., Ltd. Polycyclic compound and organic electroluminescence device including the same

Also Published As

Publication number Publication date
EP2182038A1 (en) 2010-05-05
CN102203076B (en) 2015-01-14
JP2012507508A (en) 2012-03-29
CN102203076A (en) 2011-09-28
KR20100048203A (en) 2010-05-11

Similar Documents

Publication Publication Date Title
WO2010050781A1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR101376530B1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR101551207B1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR101178219B1 (en) Electroluminescent device using the electroluminescent compounds
KR100910150B1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
JP5797672B2 (en) Novel organic electroluminescent compound and organic electroluminescent device using the same
KR100901887B1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
EP2161320A2 (en) Fluorene derivatives and organic electroluminescent device using the same
KR101495547B1 (en) Novel compounds for electronic material and organic electronic device using the same
EP2281862A2 (en) Fluorene-derivatives and organic electroluminescent device using the same
WO2010064871A1 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100041043A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
EP2194110A1 (en) Electroluminescent device using electroluminescent compounds
JP5554914B2 (en) Novel organic electroluminescent compound and organic electroluminescent device using the same
KR20100000121A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20090100013A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20090098585A (en) Organic electroluminescent device using the organic electroluminescent compounds
JP2009249385A (en) New organic electroluminescent compound, and organic electroluminescent element using the same
JP2009228004A (en) Novel organic electroluminescent compound, and organic electroluminescent device using the same
KR20100086972A (en) Organic electroluminescent device using the organic electroluminescent compounds

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200980143444.8

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09823861

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2011534396

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 09823861

Country of ref document: EP

Kind code of ref document: A1