WO2017111543A1 - Composé organique et dispositif électroluminescent organique comprenant ce composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant ce composé Download PDF

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WO2017111543A1
WO2017111543A1 PCT/KR2016/015198 KR2016015198W WO2017111543A1 WO 2017111543 A1 WO2017111543 A1 WO 2017111543A1 KR 2016015198 W KR2016015198 W KR 2016015198W WO 2017111543 A1 WO2017111543 A1 WO 2017111543A1
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group
aryl
alkyl
boron
independently
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이용환
김영배
김회문
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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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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 the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
  • the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of the organic material layer material which is excellent in performance is calculated
  • 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):
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • Ar 1 is a C 6 -C 60 aryl group or a heteroaryl group of 5 to 60 nuclear atoms;
  • the arylene group and heteroarylene group of L 1 to L 4, the aryl group and heteroaryl group of Ar 1 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, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyl Oxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to 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 and C 6 ⁇ C 60 arylsilyl group
  • Ar 2 and Ar 3 are each independently hydrogen or a substituent selected from the group represented by Formulas A-1 to A-24, but Ar 2 and Ar 3 are different from each other;
  • Z 1 to Z 5 are each independently N or C (R 7 );
  • Y 1 and Y 2 are each independently selected from the group consisting of a single bond, C (R 8 ) (R 9 ), N (R 10 ), O and S, but both Y 1 and Y 2 are not single bonds;
  • n are each independently an integer from 0 to 4.
  • l is an integer from 0 to 3;
  • R 1 and R 2 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 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 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 An arylphosphanyl group, a C 6 ⁇ C 60 mono or diaryl phosphinyl group, and a C 6 ⁇ C 60 arylamine group may be selected from the group consisting of or adjacent to a condensed
  • R 3 to 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 10 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • 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 C2-C40 straight or branched chain unsaturated hydrocarbon 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 at least one carbon-carbon triple bond, 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 to 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 of 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.
  • 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 since the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.
  • the present invention provides a compound represented by Formula 1:
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • Ar 1 is a C 6 -C 60 aryl group or a heteroaryl group of 5 to 60 nuclear atoms;
  • the arylene group and heteroarylene group of L 1 to L 4, the aryl group and heteroaryl group of Ar 1 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, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyl Oxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to 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 and C 6 ⁇ C 60 arylsilyl group
  • Ar 2 and Ar 3 are each independently hydrogen or a substituent selected from the group represented by Formulas A-1 to A-24, but Ar 2 and Ar 3 are different from each other;
  • Z 1 to Z 5 are each independently N or C (R 7 );
  • Y 1 and Y 2 are each independently selected from the group consisting of a single bond, C (R 8 ) (R 9 ), N (R 10 ), O and S, but both Y 1 and Y 2 are not single bonds;
  • n are each independently an integer from 0 to 4.
  • l is an integer from 0 to 3;
  • R 1 and R 2 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 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 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 An arylphosphanyl group, a C 6 ⁇ C 60 mono or diaryl phosphinyl group, and a C 6 ⁇ C 60 arylamine group may be selected from the group consisting of or adjacent to a condensed
  • R 3 to 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 10 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • novel compounds of the present invention can be represented by the following formula (1):
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • Ar 1 is C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 heteroaryl group;
  • the arylene group and heteroarylene group of L 1 to L 4, the aryl group and heteroaryl group of Ar 1 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, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyl Oxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to 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 and C 6 ⁇ C 60 arylsilyl group
  • Ar 2 and Ar 3 are each independently hydrogen or a substituent selected from the group represented by Formulas A-1 to A-24, but Ar 2 and Ar 3 are different from each other;
  • Z 1 to Z 5 are each independently N or C (R 7 );
  • Y 1 and Y 2 are each independently selected from the group consisting of a single bond, C (R 8 ) (R 9 ), N (R 10 ), O and S, but both Y 1 and Y 2 are not single bonds;
  • n are each independently an integer from 0 to 4.
  • l is an integer from 0 to 3;
  • R 1 and R 2 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 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 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 An arylphosphanyl group, a C 6 ⁇ C 60 mono or diaryl phosphinyl group, and a C 6 ⁇ C 60 arylamine group may be selected from the group consisting of or adjacent to a condensed
  • R 3 to 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 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 10 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • the compound may be a compound represented by the following formula (2):
  • L 1 to L 4 and Ar 1 to Ar 3 are each as defined in Chemical Formula 1.
  • the novel compound according to the present invention is a structure that combines various asymmetric substituents at positions 3 and 6 of the carbazole moiety, and has a larger energy bandgap than a conventional organic electroluminescent device material (eg, CBP), and a wide energy band gap. While having, it is possible to increase the binding force between the hole and the electron. Therefore, when the compound of Formula 1 is used in an organic electroluminescent device, the driving voltage, efficiency (luminescence efficiency, power efficiency), lifetime, and luminance of the device may be improved.
  • a conventional organic electroluminescent device material eg, CBP
  • the compounds of the present invention described above are relatively easy to control properties due to the asymmetric substituents bonded to the basic skeleton.
  • the triphenylene group has a relatively small difference in (singlet energy-triplet energy) when compared to biphenyls having similar triplet energy, and triphenylene group and benzo- When compared to fused thiophenyl groups, both are used as EDG, but triphenylene groups have better electron transport than hole transport, but in the case of benzo-fused thiophenyl groups, their properties are reversed. It is easy to improve.
  • the compound of the present invention when the compound of the present invention is applied to an organic electroluminescent device, since it can exhibit excellent characteristics as a host material of the light emitting layer compared to the conventional CBP, the phosphorescence properties of the device is improved, and the hole injection ability and / or transport ability, Luminous efficiency, driving voltage, lifespan characteristics and the like can be improved. And the energy level can be adjusted according to the substituents to have a wide bandgap (sky blue ⁇ red), and thus can be applied not only to the light emitting layer, but also to the electron transport auxiliary layer, electron transport layer, hole transport layer, hole injection layer, etc. Can be.
  • the glass transition temperature can be improved, thereby having a higher thermal stability than conventional CBP.
  • the thermal stability of the compound may not only be improved, but also effective in suppressing crystallization of the organic layer including the compound of Formula 1. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.
  • the compound of Formula 1 according to the present invention when adopted as a hole injection / transport layer material, an electron injection / transport layer material, a blue, green and / or red phosphorescent host material of an organic electroluminescent device, efficiency and lifespan compared to conventional CBP In terms of excellent effects can be achieved. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect in maximizing the performance in the full color organic light emitting panel.
  • Ar 2 and Ar 3 are each independently hydrogen or a substituent selected from the group consisting of Formulas A-5 and A-10 to A-24, but Ar 2 and Ar 3 Are characterized in that they are different from each other.
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group, more preferably May be selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group.
  • R 1 to R 3 are each independently selected from the group consisting of C 1 ⁇ C 10 Alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected.
  • R 1 to R 3 are each independently selected from the group consisting of methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group and naphthalenyl group,
  • the methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, and naphthalenyl group of R 1 to R 3 are each independently deuterium, halogen, C 1 -C 10 alkyl group and C 6 -C 60 aryl group If unsubstituted or substituted with one or more substituents selected from the group consisting of, they may be the same or different from each other.
  • R 1 to R 3 are each independently selected from the group consisting of methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group and naphthalenyl group,
  • the methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group and naphthalenyl group of R 1 to R 3 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen and phenyl group. , When substituted with a plurality of substituents, they may be the same or different from each other.
  • R 4 to R 6 are each independently hydrogen, C 1 ⁇ C 40 Alkyl group, C 6 ⁇ C 60 An aryl group and a nuclear atom of 5 to 60 heteroaryl group Can be selected from the group.
  • R 4 to R 6 may be independently selected from the group consisting of hydrogen, phenyl group, biphenyl group, fluorenyl group and naphthalenyl group.
  • Ar 1 is preferably a substituent selected from the group represented by the following formulas B-1 to B-9 in terms of luminous efficiency, but is not limited thereto:
  • X 1 to X 8 are each independently N or C (R 16 );
  • Any one of X 1 to X 4 connected to L 2 in Formula B-2 is C (R 16 ), wherein R 16 is absent;
  • T 1 is O, S, N (R 17 ), C (R 18 ) (R 19 ) or SO 2 ;
  • R 11 , R 14 to R 19 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, A C 6 to C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylamine group, or a group selected from or adjacent to
  • q and r are each independently integers of 0 to 4.
  • p is an integer from 0 to 3;
  • R 12 and R 13 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 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 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 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or a group selected from or adjacent to each other (for example, adjacent other R
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 11 to R 19 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, halogen C 1 -C 40 alkyl, C 2 ⁇ C 40 alkenyl group, an aryloxy group of C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60 of, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 arylamine group, C 3 ⁇
  • Ar 1 may be a substituent selected from the group consisting of Formulas B-2 to B-5 and B-9.
  • R 11 to R 16 may be each independently selected from the group consisting of C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms.
  • R 11 to R 16 are each independently selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group and a naphthalenyl group,
  • the phenyl group, biphenyl group, pyridinyl group and naphthalenyl group of R 11 to R 16 are each independently halogen, cyano group, alkyl group of C 1 to C 10 , alkyl group of halogen C 1 to C 4 and C 6 to C 60 If unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups, they may be the same or different from each other.
  • R 11 to R 16 are each independently selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group and a naphthalenyl group,
  • the phenyl group, biphenyl group, pyridinyl group and naphthalenyl group of R 11 to R 16 are each independently composed of a cyano group, a fluorine group, a methyl group, an ethyl group, a butyl group, a cyano group, a trifluoroethanyl group and a naphthalenyl group
  • substituted or unsubstituted with one or more substituents selected from the group, and substituted with a plurality of substituents they may be the same or different from each other.
  • Ar 1 may be a substituent selected from the group represented by Formula F-1 to F-26, but is not limited thereto:
  • t and x are each independently an integer from 0 to 5;
  • u, q and r are each independently integers of 0 to 4.
  • v is an integer from 0 to 3;
  • w is an integer from 0 to 2;
  • R 12 , R 13 , R 20 and R 21 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, 5 to 60 heteroaryl group of nuclear atoms, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkyl boron groups, C 6 to C 60 aryl boron groups , C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylsilyl group selected from the group consisting of, or in combination with an
  • R 11, R 16 to R 19 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 6 ⁇ C 60 aryl group, nuclear atom 5 ⁇ 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 3 ⁇ C 40 cycloalkyl group, nucleus Heterocycloalkyl group having 3 to 40 atoms, C 6 -C 60 arylamine group, C 1 -C 40 alkylsilyl 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 arylsilyl group or selected from the group consist
  • Alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 to C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 Alkoxyoxy group, C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇
  • Ar 1 is preferably a substituent selected from the group consisting of the formula F-1 to F-15, F-21, F-22 and F-26 in terms of luminous efficiency. .
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • 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 at least one organic material layer may be at least one 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 compound layer
  • the compound represented by 1 may be included, and preferably a light emitting layer may be included.
  • the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material.
  • the compound represented by Chemical Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer.
  • At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer or the electron transport layer is It may include a compound represented by the formula (1).
  • the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic EL device of the present invention is a material and method known in the art, except that at least one or more of the organic material layer (for example, the light emitting layer or the electron transport layer) is formed to include the compound represented by the formula (1) It can be prepared by forming other organic material layer and electrode using.
  • the organic material layer for example, the light emitting layer or the electron transport 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.
  • examples of the anode material 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
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • step 1> of Preparation Example 5 of ⁇ The procedure of step 1> was followed to obtain 3-chloro-6- (fluoranthen-3-yl) -9H-carbazole.
  • A-5 (5.85 g, 10.0 mmol) was used instead of A-1 and 2-bromo-4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-bis (3,5-dimethylphenyl) -1,3,5-triazine (3.68 g, 10.0 mmol) was subjected to the same process as in Synthesis Example 1 to J-5 ( 4.71 g, yield 54%) was obtained.
  • the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / 90% of the host compound + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30) nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound J-1 as the light emitting host material when the emission layer was formed.
  • Example 1 J-1 6.81 518 39.7 Example 2 J-2 6.68 518 38.9
  • Example 3 J-3 6.66 518 41.3 Example 4 J-4 6.7 517 41.3
  • Example 5 J-5 6.7 515 43.1 Example 6 J-6 6.51 518 43.5
  • Example 8 J-11 6.46 518 42.2 Example 9 J-12 6.81 517 42
  • Example 12 J-15 6.48 518 41.2 Example 13 J-16 6.86 517 41.2
  • Example 15 J-18 6.66 518 42.2 Example 16 J-19 6.81 518 39.7
  • Example 17 J-20 6.68 518 38.9 Example 18 J-21 6.66 518 41.3 Comparative Example 1 CBP 6.93 516 38.2
  • 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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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique comprenant ce composé. Le composé selon la présente invention est utilisé dans une couche organique, de préférence une couche émettant de la lumière, d'un dispositif électroluminescent organique, ce qui permet d'améliorer l'efficacité lumineuse, la tension de commande et la durée de vie du dispositif électroluminescent organique.
PCT/KR2016/015198 2015-12-23 2016-12-23 Composé organique et dispositif électroluminescent organique comprenant ce composé WO2017111543A1 (fr)

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KR102485738B1 (ko) * 2019-10-08 2023-01-06 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
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