WO2018117493A1 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2018117493A1
WO2018117493A1 PCT/KR2017/014266 KR2017014266W WO2018117493A1 WO 2018117493 A1 WO2018117493 A1 WO 2018117493A1 KR 2017014266 W KR2017014266 W KR 2017014266W WO 2018117493 A1 WO2018117493 A1 WO 2018117493A1
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group
aryl
alkyl
boron
groups
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김회문
김영배
손호준
배형찬
한송이
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주식회사 두산
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • 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
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
  • metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
  • the conventional organic material has an advantageous aspect in terms of the light emission characteristics, but because the glass transition temperature is low thermal stability is not very good, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
  • an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1):
  • R 1 and R 2 , R 2 and R 3, and R 3 and R 4 combine with a ring represented by the following Formula 2 to form a condensed ring;
  • R 1 to R 4 which do not form a ring and a condensed ring represented by the following Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of the aryloxy group, C 3 ⁇ C 40 alkylsilyl group, a group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 alkyl sulfonyl group , C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron
  • n are each independently an integer from 0 to 2;
  • L 1 and L 2 are each independently C 6 ⁇ C 18 aryl group and a nuclear atoms selected from 5 to 18 heteroaryl group consisting of alkylene groups, wherein L 1 and when L 2 each of a plurality individual which the same or another Different;
  • p is an integer from 0 to 5;
  • R 5 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C C 3 -C 40 alkylsilyl group, C 6 -C 60 arylsilyl group, C 1 -C 40 alkylsulfonyl group, C 6 -C 60 arylsulfonyl group, C 1 -C 40 alkylboron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diaryl phosphinyl group, C 1 to C 40 alkylcarbon
  • Ar 1 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkylsulfonyl group, C 6 ⁇ C 60 Arylsulfonyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group, C 1 ⁇ C 40 Alky
  • the arylene group and heteroarylene group of L 1 and L 2 the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group and cycloalkyl group of R 1 to R 5 and Ar 1 , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and
  • the arylsilyl groups are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group , Heter
  • Dashed line means a part where condensation is carried out in Formula 1;
  • Z 1 to Z 4 are each independently N or C (R 6 );
  • R 6 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkylsulfonyl group, C 6 ⁇ C 60 Arylsulfonyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group, C 1 ⁇ C 40 Alky
  • An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R 6 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylsulfonyl group, an arylsulfonyl group, Alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group, alkyl carbonyl group, aryl carbonyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
  • the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1-40 alkyl, and is linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
  • Aromaatic ring in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • aromatic rings include phenyl, naphthyl, phenanthrenyl, anthrenyl, and the like, but are not limited thereto.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel and the like by greatly improving aspects such as light emission performance, driving voltage, lifetime, and efficiency.
  • FIG. 1 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • organic layer 31 hole transport layer
  • R 1 and R 2 , R 2 and R 3, and R 3 and R 4 combine with a ring represented by the following Formula 2 to form a condensed ring;
  • R 1 to R 4 which do not form a ring and a condensed ring represented by the following Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of the aryloxy group, C 3 ⁇ C 40 alkylsilyl group, a group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 alkyl sulfonyl group , C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron
  • n are each independently an integer from 0 to 2;
  • L 1 and L 2 are each independently C 6 ⁇ C 18 aryl group and a nuclear atoms selected from 5 to 18 heteroaryl group consisting of alkylene groups, wherein L 1 and when L 2 each of a plurality individual which the same or another Different;
  • p is an integer from 0 to 5;
  • R 5 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C C 3 -C 40 alkylsilyl group, C 6 -C 60 arylsilyl group, C 1 -C 40 alkylsulfonyl group, C 6 -C 60 arylsulfonyl group, C 1 -C 40 alkylboron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diaryl phosphinyl group, C 1 to C 40 alkylcarbon
  • Ar 1 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkylsulfonyl group, C 6 ⁇ C 60 Arylsulfonyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group, C 1 ⁇ C 40 Alky
  • the arylene group and heteroarylene group of L 1 and L 2 the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group and cycloalkyl group of R 1 to R 5 and Ar 1 , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and
  • the arylsilyl groups are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group , Heter
  • Dashed line means a part where condensation is carried out in Formula 1;
  • Z 1 to Z 4 are each independently N or C (R 6 );
  • R 6 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkylsulfonyl group, C 6 ⁇ C 60 Arylsulfonyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group, C 1 ⁇ C 40 Alky
  • An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R 6 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylsulfonyl group, an arylsulfonyl group, Alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group, alkyl carbonyl group, aryl carbonyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • the present invention provides a compound represented by Formula 1:
  • R 1 and R 2 , R 2 and R 3, and R 3 and R 4 combine with a ring represented by the following Formula 2 to form a condensed ring;
  • R 1 to R 4 which do not form a ring and a condensed ring represented by the following Formula 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of the aryloxy group, C 3 ⁇ C 40 alkylsilyl group, a group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 alkyl sulfonyl group , C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron
  • n are each independently an integer from 0 to 2;
  • L 1 and L 2 are each independently C 6 ⁇ C 18 aryl group and a nuclear atoms selected from 5 to 18 heteroaryl group consisting of alkylene groups, wherein L 1 and when L 2 each of a plurality individual which the same or another Different;
  • p is an integer from 0 to 5;
  • R 5 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C C 3 -C 40 alkylsilyl group, C 6 -C 60 arylsilyl group, C 1 -C 40 alkylsulfonyl group, C 6 -C 60 arylsulfonyl group, C 1 -C 40 alkylboron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diaryl phosphinyl group, C 1 to C 40 alkylcarbon
  • Ar 1 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkylsulfonyl group, C 6 ⁇ C 60 Arylsulfonyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group, C 1 ⁇ C 40 Alky
  • the arylene group and heteroarylene group of L 1 and L 2 the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group and cycloalkyl group of R 1 to R 5 and Ar 1 , Heterocycloalkyl group, arylamine group, alkylsilyl group, alkylsulfonyl group, arylsulfonyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, alkylcarbonyl group, arylcarbonyl group and
  • the arylsilyl groups are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group , Heter
  • Dashed line means a part where condensation is carried out in Formula 1;
  • Z 1 to Z 4 are each independently N or C (R 6 );
  • R 6 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkylsulfonyl group, C 6 ⁇ C 60 Arylsulfonyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group, C 1 ⁇ C 40 Alky
  • An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R 6 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylsulfonyl group, an arylsulfonyl group, Alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group, alkyl carbonyl group, aryl carbonyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
  • the compound represented by Chemical Formula 1 forms a structure in which benzene is located on the opposite side of carbazole to a structure in which phenyl oxazole and carbazole are bonded as a basic skeleton.
  • an electron withdrawal group (EWG) having a high electron absorption such as a nitrogen-containing heterocyclic ring (for example, a pyridine group, a pyrimidine group, a triazine group, etc.) is bonded to the basic skeleton, so that the entire molecule has a bipolar characteristic. Therefore, the bonding force between the holes and the electrons can be increased.
  • the compound may be represented by any one of the following Formulas 3 to 5:
  • q is an integer from 0 to 4.
  • R 7 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C C 3 -C 40 alkylsilyl group, C 6 -C 60 arylsilyl group, C 1 -C 40 alkylsulfonyl group, C 6 -C 60 arylsulfonyl group, C 1 -C 40 alkylboron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diaryl phosphinyl group, C 1 to C 40 alkylcarbon
  • R 1 to R 4 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkylsulfonyl group, C 6 ⁇ C 60 arylsulfonyl group, C 1 ⁇ C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group, C 1
  • Neyl group, arylsulfonyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group, alkyl carbonyl group, arylcarbonyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group , C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 60
  • n, p, L 1 , L 2 , Ar 1 and R 5 are each as defined in Chemical Formula 1.
  • m and n may be each independently 0 or 1.
  • L 1 and L 2 may be a linker of a conventional divalent group known in the art, and more specifically, L 1 and L 2 are each Independently, a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, pyranthrenylene group, carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroyl It may be selected from the group consisting of a ethylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group and pyrimidinylene group, more preferably the L 1 and L 2 are each independently It may be a linker selected from the group consisting of Formulas A-1 to A-4:
  • Ar 1 is an alkyl group of C 1 ⁇ C 40 , C 6 ⁇ C 60 An aryl group and a nuclear atom having 5 to 60 heteroaryl groups, and more preferably a C 6 to C 60 aryl group or a nuclear atom having 5 to 60 heteroaryl groups;
  • the alkyl group, aryl group and heteroaryl group of Ar 1 are each independently one or more substituents selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl groups When substituted with or unsubstituted with a plurality of substituents, they may be the same or different from each other.
  • Ar 1 is a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene , Cryzene, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, Thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinno
  • Ar 1 is a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene , Cryzene, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, Thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinno
  • Ar 1 may be a substituent represented by Formula 6 below:
  • Z 5 to Z 9 are each independently N or C (R 8 );
  • R 8 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and when R 8 is a plurality, Same or different from each other
  • the substituent represented by Formula 6 may be a substituent represented by the following Formula 7:
  • R 9 and R 10 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
  • Z 5 , Z 7 and Z 9 are each as defined in Chemical Formula 6.
  • the substituent represented by Formula 6 may be a substituent represented by any one of the following formulas B-1 to B-3:
  • R 9 and R 10 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
  • R 9 and R 10 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Selected;
  • the alkyl group, aryl group and heteroaryl group of R 9 and R 10 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
  • R 9 and R 10 are each independently methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, Phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole , Dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline , Quinazo
  • R 9 and R 10 are each independently methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, Phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole , Dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline , Quinazo
  • R 5 and R 6 methyl groups, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, Creative Zen, dibenzothiophene , Carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine , Pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinn
  • R 9 and R 10 are each independently phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, di Benzofuran, pyridine, pyridazine, pyrimidine, pyrazine and triazine;
  • the azine is independently methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, di
  • substituents selected from the group consisting of benzofuran, pyridine, pyridazine, pyrimidine, pyrazine and triazine, they may be the same or different from each other.
  • the compound is preferably represented by the following formula (8) in the light emitting properties, but is not limited thereto:
  • Z 5 , Z 7 and Z 9 are each independently N or C (R 8 );
  • R 8 and R 11 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, is selected from the group consisting of an aryl amine of the C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of the R 8 in this case
  • o is an integer from 0 to 4.
  • R 12 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , C 6 ⁇ C 60 Mono or diaryl phosphinyl group and C 6 ⁇ C 60 It is selected from the group consisting of an arylamine group, when there are a plurality of R
  • n, p, L 1 , L 2 and R 1 to R 5 are each as defined in Chemical Formula 1.
  • R 11 may be an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 or a heteroaryl group of 5 to 60 nuclear atoms.
  • R 11 is a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, Dibenzothiophene, carbazole, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine and triazine, preferably phenyl, biphenyl, terphenyl, naphthalene, triphenylene, It may be selected from the group consisting of phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine and triazine, more preferably phenyl, biphenyl or terphenyl Can be.
  • the compound is preferably represented by the following formula (9) in the light emitting properties, but is not limited thereto:
  • Z 5 , Z 7 and Z 9 are each independently N or C (R 8 );
  • R 8 , R 13 and R 14 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 Mono or diaryl phosphinyl group and C 6 ⁇ C 60 An arylamine group, and when a plurality of R 8 They
  • n, L 1 , L 2 and R 1 to R 4 are each as defined in Chemical Formula 1.
  • R 13 and R 14 may each independently be an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 or a heteroaryl group of 5 to 60 nuclear atoms.
  • R 13 and R 14 are each independently a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, Phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine and triazine, preferably phenyl, biphenyl, terphenyl, Naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine and triazine, more preferably phenyl , Biphenyl or terphenyl.
  • the ring represented by Formula 2 may be represented by the following Formula 10, but is not limited thereto:
  • the dotted line means the part where condensation takes place
  • s is an integer of 0 or 1;
  • R 13 is a C 1 to C 40 alkyl group, C 6 to C 60 aryl group or a nuclear atom of 5 to 60 heteroaryl groups.
  • any one of the R 1 and R 2 , R 2 and R 3 and R 3 and R 4 is bonded to the ring represented by the formula (10) It is preferable to form a condensed ring in the light emitting characteristics, but is not limited thereto.
  • Z 5 , Z 7 and Z 9 are each independently N or C (R 8 ), wherein R 8 may be hydrogen, It is not limited to this.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone or mixed two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them.
  • the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34.
  • a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
  • an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode
  • the electron injection layer 36 may be further included between the holes 20.
  • the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31.
  • the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.
  • the electron injection layer 36 is a layer that is stacked on top of the electron transport layer 34 to facilitate the injection of electrons from the cathode to ultimately improve the power efficiency, commonly used in the art.
  • materials such as LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
  • a light emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light emitting layer 32.
  • the emission auxiliary layer may serve to transport holes to the emission layer 32 and to adjust the thickness of the organic layer 30.
  • the emission auxiliary layer may include a hole transport material, and may be made of the same material as the hole transport layer 31.
  • a life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes traveling through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer, and thus do not diffuse or move to the electron transport layer, and consequently, the holes are limited to the light emitting layer. .
  • Such a function of limiting holes to the light emitting layer prevents holes from diffusing into the electron transporting layer that moves electrons by reduction, thereby suppressing the lifespan phenomenon through irreversible decomposition reaction by oxidation and contributing to improving the life of the organic light emitting device. Can be.
  • the compound represented by Chemical Formula 1 forms a structure in which benzene is located on the opposite side of carbazole to a structure in which phenyl oxazole and carbazole are bonded as a basic skeleton.
  • an electron withdrawal group (EWG) having a high electron absorption such as a nitrogen-containing heterocyclic ring (for example, a pyridine group, a pyrimidine group, a triazine group, etc.) is bonded to the basic skeleton, so that the entire molecule has a bipolar characteristic. Therefore, the bonding force between the holes and the electrons can be increased. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
  • the compound represented by Chemical Formula 1 may introduce a specific substituent into a condensed indole derivative having a broad singlet energy level and a high triplet energy level, whereby the energy level may be controlled to be higher than that of the dopant.
  • a specific substituent into a condensed indole derivative having a broad singlet energy level and a high triplet energy level, whereby the energy level may be controlled to be higher than that of the dopant.
  • the carbazole moiety is a chemically weak point. It is a compound that is expected to increase the life compared to the previous compound by blocking the weak point by replacing it with a benzene ring.
  • the compound represented by Chemical Formula 1 in the present invention may improve phosphorescence characteristics of the organic EL device, and may improve hole injection / transport ability, emission efficiency, driving voltage, lifetime characteristics, and the like. Depending on the type of the substituent, the electron transport ability and the like can also be improved.
  • the compound of formula 1 according to the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer (blue, green and / or red phosphorescent host material), a hole transport layer, an electron transport layer, a hole injection layer, an electron injection layer Or it can be used as a material of the life improvement layer, more preferably can be used as a material of the light emitting layer, more preferably can be used as a phosphorescent light emitting layer material.
  • a light emitting layer blue, green and / or red phosphorescent host material
  • a hole transport layer an electron transport layer
  • a hole injection layer an electron injection layer
  • it can be used as a material of the life improvement layer, more preferably can be used as a material of the light emitting layer, more preferably can be used as a phosphorescent light emitting layer material.
  • the organic electroluminescent device may not only sequentially stack an anode, at least one organic material layer, and a cathode as described above, but may further include an insulating layer or an adhesive layer at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (for example, an electron transport auxiliary layer) is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming other organic material layer and electrode using.
  • the organic material layers for example, an electron transport auxiliary layer
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • the positive electrode material may be made of a high work function conductor, for example, to facilitate hole injection, and may include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • the cathode material may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • 2,4-Dibromoaniline 250.9 g, 1.0 mol
  • methylene chloride 1,000 ml
  • Benzoyl chloride 116 mL, 1.0 mol
  • pyridine 161.8 mL, 2.0 mol
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
  • ITO Indium tin oxide
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1-1 as a light emitting host material when forming the emission layer.
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-1, instead of Compound 1-1, was used to form the EML.
  • the structure of A is as follows:
  • Example 1 1-1 6.42 517 49.4
  • Example 2 1-2 6.47 518 47.3
  • Example 3 1-3 6.69 516 47.4
  • Example 4 1-4 6.34 516 48.3
  • Example 5 1-5 6.13 517 43.4
  • Example 6 1-6 6.64 516 42.2
  • Example 7 1-8 6.35 517 47.4
  • Example 8 1-10 6.62 518 49.2
  • Example 9 1-14 6.53 516 44.8
  • Example 10 1-16 6.36 517 43.1
  • Example 11 1-17 6.74 516 47.6
  • Example 12 1-19 6.71 518 43.2
  • Example 13 1-20 6.38 516 47.4
  • Example 14 1-23 6.54 518 44.1
  • Example 15 2-1 6.67 517 42.4
  • Example 16 2-2 6.32 517 46.7
  • Example 17 2-3 6.55 516 44.8
  • Example 18 2-4 6.83 518 43.5
  • Example 19 2-5 6.16 516 48.1
  • Example 20 6 6.24 516 49.6
  • Example 21 2-8 6.26 517
  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Le composé, selon la présente invention, est utilisé dans une couche de matière organique, de préférence dans une couche émettrice de lumière, du dispositif électroluminescent organique, ce qui permet d'améliorer l'efficacité d'émission de lumière, la tension de commande, la durée de vie et similaire du dispositif électroluminescent organique à perfectionner.
PCT/KR2017/014266 2016-12-23 2017-12-07 Composé organique et dispositif électroluminescent organique le comprenant WO2018117493A1 (fr)

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KR102446406B1 (ko) * 2019-07-09 2022-09-22 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자

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KR20130139412A (ko) * 2012-02-13 2013-12-23 덕산하이메탈(주) 오원자 헤테로 고리를 포함하는 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치
KR20140006201A (ko) * 2012-06-27 2014-01-16 덕산하이메탈(주) 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20150016833A (ko) * 2013-08-05 2015-02-13 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20150061177A (ko) * 2013-11-26 2015-06-04 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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CN114369088A (zh) * 2020-10-15 2022-04-19 江苏三月科技股份有限公司 一种含三嗪结构的化合物及其应用
CN114369088B (zh) * 2020-10-15 2024-04-23 江苏三月科技股份有限公司 一种含三嗪结构的化合物及其应用

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