WO2017099430A1 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2017099430A1
WO2017099430A1 PCT/KR2016/014112 KR2016014112W WO2017099430A1 WO 2017099430 A1 WO2017099430 A1 WO 2017099430A1 KR 2016014112 W KR2016014112 W KR 2016014112W WO 2017099430 A1 WO2017099430 A1 WO 2017099430A1
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aryl
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박우재
엄민식
김태형
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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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/24—Polycyclic condensed hydrocarbons containing two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • 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
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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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
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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
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

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 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
  • 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 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;
  • Arylamine group, alkylsilyl group, 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 groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • 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.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, 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 such as N, O, S or Se.
  • a form in which two or more rings are simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group.
  • 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 represented by Chemical Formula 1 according to the present invention exhibits high efficiency device characteristics due to excellent electrical stability and tilted structural properties.
  • 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 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
  • 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 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;
  • Arylamine group, alkylsilyl group, 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 groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • the novel organic compound according to the present invention has a structure in which various fluorene groups and hetero rings are bonded to a binaphthalene moiety.
  • Electron-withdrawing electrons (EWGs) with high electron absorption such as aromatic rings (eg phenyl, fluorene) or nitrogen-containing heterocycles (eg pyrimidine, triazine, quinazoline, quinoline, triazolopyridinyl, etc.) It forms the basic backbone connected by various linkers (phenyl, biphenyl, naphthalene, fluorene, carbazolyl, phenanthrene, etc.). Specifically, it is characterized in that the compound represented by the 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 60 carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
  • 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 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;
  • Arylamine group, alkylsilyl group, 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 groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • the compound of the present invention As a material for the electron transporting layer or the electron transporting auxiliary layer of the organic light emitting device, it is possible to improve the efficiency and life characteristics of the organic light emitting device.
  • the compound of the present invention can improve the life characteristics by the center of the binaphthalene structure, the binaphthalene has a steric hindrance by the substitution structure, thereby having a high triplet energy, excitons generated in the light emitting layer to the light emitting layer Diffusion to adjacent electron transporting layers or hole transporting layers can be prevented.
  • the number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased.
  • the compound represented by Formula 1 may be a compound represented by any one of the following Formulas 2 to 4:
  • L 1 to L 4 , R 1 to R 4 are each as defined in Chemical Formula 1.
  • L 1 to L 4 may be 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.
  • each of R 1 to R 4 may be independently selected from the group consisting of hydrogen and a substituent represented by the formula 5 to 17:
  • Z 1 to Z 8 are each independently N or C (R 5 );
  • T 1 is N (R 6 ) or C (R 7 ) (R 8 );
  • T 1 When T 1 is bonded to L 1 , L 2 , L 3 or L 4 in Formulas 8 and 9, when T 1 is N (R 6 ), R 6 is absent, or T 1 is C (R 7 ) (R 8 ) any one of R 7 and R 8 is absent;
  • Y 1 is N or C (R 5 );
  • R 5 to R 8 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, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ C 60 selected from an aryl silyl group the group consisting of or of, the adjacent groups (e. g., L 1, L
  • 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 5 to R 8 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
  • each of R 1 to R 4 is independently selected from the group consisting of hydrogen and substituents represented by the following formula F-1 to F-17 to the organic electroluminescent device When applied, it is preferred for, but not limited to, extending life, improving luminous efficiency, and lowering driving voltage:
  • n is an integer from 0 to 4.
  • n is an integer from 0 to 3;
  • p is an integer from 0 to 2;
  • R 9 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 6 ⁇ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, A C 6 -C 60 mono or diarylphosphinyl group and C 6 -C 60 arylsilyl group, or an adjacent group (e.g., L 1 , L 2 , adjacent R 5 to R 8 , Or
  • R 5 to R 8 are as defined in the formula 5 to 17.
  • R 1 and R 2 are each independently a substituent selected from the group consisting of F-3, F-5, F-6, F-14 and F-15
  • R 1 and R 2 are each independently a substituent selected from the group consisting of F-3, F-5, F-6, F-14 and F-15
  • each of R 5 to R 9 is independently hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected from the group.
  • R 5 to R 9 are each independently hydrogen, phenyl group, biphenyl group, naphthalenyl group, carbazolyl group, fluorenyl group, pyridinyl group and pyrimidinyl group Can be selected.
  • 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 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 organic material layer including the compound represented by Chemical Formula 1 may be an electron transport layer or an electron transport auxiliary layer.
  • the compound represented by the formula (1) of the present invention can improve the life characteristics by the central binaphthalene structure, the binaphthalene has a steric hindrance by the substitution structure, thereby having a high triplet energy, generated in the light emitting layer
  • the excitons can be prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer.
  • the number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased. Therefore, by using the compound of Formula 1 of the present invention as a material for the electron transporting layer or the electron transporting auxiliary layer of the organic light emitting device, it is possible to improve the efficiency and the life characteristics of the organic light emitting device.
  • the light emitting layer of the organic EL device may include a host material, and in this case, the host material may include the compound represented by Formula 1 above.
  • 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 an electron transport layer or an electron transport aid
  • the layer may include a compound represented by Chemical 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 electroluminescent device of the present invention is a material known in the art, except that at least one of the organic material layers (for example, an electron transporting layer or an electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 above. And other organic material layers and electrodes using the method.
  • the organic material layers for example, an electron transporting layer or an electron transporting 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.
  • 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 9 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine
  • Step 15 2- (4- (4'- Bromo -[1,1'- Vinaphthalene ] -4-yl) phenyl) -4,6-diphenyl-1,3,5-triazine
  • Step 18 2- (4- (6'- Bromo -[1,1'- Vinaphthalene ] -6-yl) phenyl) -4,6-diphenyl-1,3,5-triazine
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • DS-205 Doosan Electronics, 80 nm
  • NPB 15 nm
  • ADN 5%
  • DS-405 Doosan Electronics, 30nm
  • Compounds of -20, C-1, C-16 or C-19 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.
  • a blue organic EL device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound A-1 as the electron transporting layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1 was not used as the electron transporting layer material.
  • NPB, AND and Alq 3 used in Examples 1 to 18 and Comparative Examples 1 and 2 are as follows.
  • Example 1 Compound A-1 4.1 457 7.6
  • Example 2 Compound A-2 3.8 456 8.1
  • Example 3 Compound A-3 3.3 451 7.6
  • Example 4 Compound A-4 3.7 452 8.5
  • Example 5 Compound a-16 3.6 455 9.3
  • Example 6 Compound a-19 3.9 453 8.1
  • Example 7 Compound A-20 4.2 454 8.7
  • Example 8 Compound a-21 4.3 455 8.1
  • Example 9 Compound B-1 4.0 456 7.8
  • Example 10 Compound b-2 3.9 457 8.2
  • Example 11 Compound b-16 3.2 458 8.1
  • Example 12 Compound b-17 3.1 453 8.5
  • Example 13 Compound b-18 3.7 453 7.6
  • Example 14 Compound b-19 4.2 454 8.1
  • Example 15 Compound b-20 3.5 455 8.2
  • Example 16 Compound C-1 3.9 452 8.1
  • Example 17 Compound c-16 3.8 453 7.3
  • Example 18 Compound C-19
  • the blue organic electroluminescent device (Examples 1 to 18) using the compound of the present invention in the electron transporting layer is a blue organic electroluminescent device (comparative example 1) using Alq 3 in the electron transporting layer and Compared with the blue organic electroluminescent device (Comparative Example 2) without an electron transporting layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwashin Tech
  • DS-205 Doosan Electronics 80 nm
  • NPB 15 nm
  • ADN 5%
  • DS-405 Doosan Electronics, 30 nm
  • 5 nm ) / Alq 3 (25 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 19, except that Compound A-2 was not used as an electron transport auxiliary layer material, and Alq 3 , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm. Produced.
  • Example 19 Compound A-2 4.1 455 8.1
  • Example 20 Compound A-4 3.7 451 7.6
  • Example 21 Compound a-17 3.9 454 7.7
  • Example 22 Compound a-19 3.9 453 7.3
  • Example 23 Compound a-21 3.7 455 8.3
  • Example 24 Compound B-1 3.8 452 8.1
  • Example 25 Compound b-3 3.7 458 7.9
  • Example 26 Compound b-16 4.3 454 7.8
  • Example 27 Compound b-19 4.2 455 8.6
  • Example 28 Compound b-21 3.4 456 8.1
  • Example 29 Compound C-1 3.9 458 8.3
  • Example 30 Compound c-3 3.9 459 7.8
  • Example 31 Compound c-16 4.1 455 7.5
  • Example 32 Compound C-19 4.4 454 8.6 Comparative Example 3 - 4.8 458 6.0
  • the blue organic electroluminescent devices (Examples 19 to 32) using the compound of the present invention in the electron transport auxiliary layer were compared to the blue organic electroluminescent devices (Comparative Example 3) without the electron transport auxiliary layer. It was found to exhibit excellent performance in terms of current efficiency, emission peak, and driving voltage.
  • 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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  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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  • High Energy & Nuclear Physics (AREA)
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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 peut être utilisé dans une couche organique, et de préférence dans une couche de transport d'électrons ou une couche de transport d'électrons auxiliaire dans le dispositif électroluminescent organique, ce qui permet d'améliorer l'efficacité électroluminescente, la tension d'excitation et la durée de vie, entre autres caractéristiques, du dispositif électroluminescent organique.
PCT/KR2016/014112 2015-12-08 2016-12-02 Composé organique et dispositif électroluminescent organique le comprenant WO2017099430A1 (fr)

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WO2018221985A1 (fr) * 2017-05-31 2018-12-06 주식회사 엘지화학 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
WO2018221986A1 (fr) * 2017-05-31 2018-12-06 주식회사 엘지화학 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
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KR20190111824A (ko) * 2018-03-22 2019-10-02 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
WO2019182402A1 (fr) * 2018-03-22 2019-09-26 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
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CN111263753B (zh) * 2018-03-22 2024-02-23 株式会社Lg化学 化合物和包含其的有机发光器件
CN108623430A (zh) * 2018-07-19 2018-10-09 石家庄诚志永华显示材料有限公司 联萘衍生物、包含该联萘衍生物的材料和有机电致发光器件
KR20200067043A (ko) * 2018-12-03 2020-06-11 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
KR102625755B1 (ko) 2018-12-03 2024-01-15 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자
CN113195458A (zh) * 2019-03-05 2021-07-30 株式会社Lg化学 联萘化合物及包含其的有机发光器件

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