WO2019103397A1 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2019103397A1
WO2019103397A1 PCT/KR2018/013975 KR2018013975W WO2019103397A1 WO 2019103397 A1 WO2019103397 A1 WO 2019103397A1 KR 2018013975 W KR2018013975 W KR 2018013975W WO 2019103397 A1 WO2019103397 A1 WO 2019103397A1
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aryl
alkyl
heteroaryl
nuclear atoms
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심재의
엄민식
박우재
한송이
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주식회사 두산
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Definitions

  • the present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.
  • the luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials to realize better natural colors. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.
  • the dopant material can 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, BCP and Alq 3 have been widely known as the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material.
  • metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like having advantages in terms of efficiency improvement in the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.
  • p and q are each independently an integer of 0 to 4.
  • r and s are each independently an integer of 0 to 3;
  • n and n are each independently an integer of 0 to 1, and necessarily one of m or n is 1;
  • R 1 and R 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkynyl group of C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, 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 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine of blood group and
  • R 3 to R 6 are each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ⁇ alkyl group of C 40, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 of A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 A C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or is selected from diaryl phosphine blood group and the group consisting of an aryl group of C 6 ⁇ C 60 of the R 3
  • R 1 to R 6 an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, an alkylsilyl group, an alkyl boron group, an aryl boron
  • Ar 1 and Ar 2 are each independently a substituent of the following formula (2) or (3);
  • L 1 and L 2 are each independently selected from the group consisting of a direct bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
  • Ar 3 to Ar 6 each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of 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 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine of blood group and a
  • Alkyl groups of the L 1 and L 2 arylene group and a heteroarylene group wherein Ar 3 to Ar 6 in the group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl alkyl group, an aryl group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6
  • the present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .
  • Halogen " in the present invention means fluorine, chlorine, bromine or iodine.
  • Alkyl in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.
  • alkenyl &quot is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.
  • " alkynyl " in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, , 2-propynyl, and the like, but are not limited thereto.
  • Aryl " in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent 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. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity).
  • heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • " aryloxy " means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms.
  • R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • " alkyloxy " in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamino &quot in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl &quot in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl &quot in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.
  • Alkylsilyl &quot in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 5 to 60 carbon atoms.
  • condensed rings means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
  • the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent 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, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.
  • FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • organic layer 31 hole transport layer
  • Electron transport layer 35 Electron transport layer
  • novel compounds of the present invention can be represented by the following formula
  • p and q are each independently an integer of 0 to 4.
  • r and s are each independently an integer of 0 to 3;
  • n and n are each independently an integer of 0 to 1, and necessarily one of m or n is 1;
  • R 1 and R 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkynyl group of C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, 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 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic the C 40 group of alkylboronic, C 6 ⁇ C 60 group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine of blood group and a C
  • R 3 to R 6 are each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ⁇ alkyl group of C 40, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 of A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 A C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or is selected from diaryl phosphine blood group and the group consisting of an aryl group of C 6 ⁇ C 60 of the R 3
  • R 1 to R 6 an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, an alkylsilyl group, an alkyl boron group, an aryl boron
  • Ar 1 and Ar 2 are each independently a substituent of the following formula (2) or (3);
  • L 1 and L 2 are each independently selected from the group consisting of a direct bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
  • Ar 3 to Ar 6 each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of 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 ⁇ alkyloxy group of C 40, C 6 ⁇ aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine of blood group and a
  • Alkyl groups of the L 1 and L 2 arylene group and a heteroarylene group wherein Ar 3 to Ar 6 in the group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl alkyl group, an aryl group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6
  • the materials based on dimethylacridine structure have excellent hole transporting ability and have excellent luminescence efficiency based on fast hole mobility.
  • lifetime can be increased by driving at a low voltage, and amorphous crystalline and high refractive index The effect is further enhanced.
  • the structures of the spiroacridine series are excellent in electrochemical stability, high in glass transition temperature and carrier transporting ability, and particularly excellent in hole transporting ability, so that the hole transporting is smooth in the light emitting layer and the luminous efficiency is enhanced .
  • the materials of the structure represented by the above formula (1) are spirally structurally characterized by at least two combinations of dimethylfluorene and arylamine, thereby forming a HOMO level which is a physicochemical characteristic suitable for transferring holes. In addition, it has characteristics of low voltage driving and high refractive index based on fast hole transporting ability and shows the high efficiency and long life physical characteristics.
  • the compound represented by the general formula (1) which is a representative claim structure of the present invention, is excellent in luminescence characteristics, and therefore, it is preferable to use any one of the hole injection layer, the hole transporting layer, the light emitting layer, the electron transporting layer, It can be used as a material.
  • a hole transporting layer and a hole assisting transporting layer material are preferable.
  • the compound may be a compound represented by the following formula 4 or 5:
  • R 1 to R 6, p, q, r, s, L 1 , L 2 and Ar 3 to Ar 6 are as defined in formula (1).
  • the compound may be a compound represented by the following formula 6 or 7:
  • R 1 to R 6, p, q, r, s and Ar 3 to Ar 6 are as defined in formula (1).
  • R 1 and R 2 each independently represent a group selected from the group consisting of a C 1 to C 30 alkyl group, a C 6 to C 30 aryl group and a heteroaryl group having 5 to 30 nuclear atoms Selected,
  • the alkyl, aryl, and heteroaryl groups of R 1 and R 2 are each independently selected from the group consisting of a C 1 to C 30 alkyl group, a C 6 to C 30 aryl group, and a heteroaryl group having 5 to 30 nucleus atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.
  • R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl and triazinyl groups ≪ / RTI >
  • Alkyl group of R 1 and R 2 of an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group and a triazole group possess each independently a C 1 ⁇ C 30, C 6 ⁇ It substituted from the group consisting of C 30 aryl group and the nuclear atoms of 5 to 30 heteroaryl group by one or more substituents selected or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same as or different from each other.
  • R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl and triazinyl groups ≪ / RTI >
  • the methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group and triazinyl group of R 1 and R 2 are each independently a methyl group, A phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.
  • each of Ar 3 to Ar 6 is independently selected from the group consisting of a C 1 to C 30 alkyl group, a C 6 to C 30 aryl group and a heteroaryl group having 5 to 30 nuclear atoms Selected,
  • the alkyl, aryl and heteroaryl groups of Ar 3 to Ar 6 are each independently selected from the group consisting of a C 1 to C 30 alkyl group, a C 6 to C 30 aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other.
  • Ar 3 to Ar 6 each independently represent a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzo A thienopyranyl group, a quinolinyl group, a quinolinyl group, a quinoxalinyl group and a quinazolinyl group in the group consisting of a thiophene group, a pyridonyl group, a pyrimidinyl group, a triazinyl group, a naphthalenyl group, a triazolopyridinyl group, Selected,
  • Examples of the substituent of Ar 3 to Ar 6 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, A thiazolyl group, a naphthalenyl group, a triazolopyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a quinoxalinyl group and a quinazolinyl group are each independently a C 1 to C 30 alkyl group, a C 6 ⁇ C 30 aryl group and a nuclear atoms substituted by one or more substituent species selected from the group consisting of 5 to 30 heteroaryl group being unsub
  • Ar 3 to Ar 6 each independently represent a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzo A thienopyranyl group, a quinolinyl group, a quinolinyl group, a quinoxalinyl group and a quinazolinyl group in the group consisting of a thiophene group, a pyridonyl group, a pyrimidinyl group, a triazinyl group, a naphthalenyl group, a triazolopyridinyl group, Selected,
  • Examples of the substituent of Ar 3 to Ar 6 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group,
  • An isoquinolinyl group, a quinolinyl group, a quinoxalinyl group and a quinazolinyl group are each independently a methyl group, ethyl group, propyl group, butyl group, isopropyl group, n-butyl group, A phenyl group, a biphenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyri
  • each of Ar 3 to Ar 6 may independently be a substituent represented by any one of the following formulas B-1 to B-7:
  • k is an integer from 0 to 5;
  • t is an integer from 0 to 4.
  • R 7 to R 11 each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ of C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, C 1 ⁇ C 40 alkyl silyl group, a alkyl boronic of C 1 ⁇ C 40, an aryl boronic a C 6 ⁇ C 60, C 6 ⁇ C A C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylsilyl group, or is bonded to an adjacent
  • each of R 7 to R 11 is independently selected from the group consisting of a C 1 to C 30 alkyl group, a C 6 to C 30 aryl group and a heteroaryl group having 5 to 30 nuclear atoms Selected,
  • the alkyl, aryl and heteroaryl groups of R 7 to R 11 are each independently selected from the group consisting of a C 1 to C 30 alkyl group, a C 6 to C 30 aryl group and a heteroaryl group having 5 to 30 nuclear atoms, And when they are substituted with a plurality of substituents, they are the same as or different from each other.
  • each of R 7 to R 11 is independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl and triazinyl groups ≪ / RTI >
  • each of R 7 to R 11 is independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl and triazinyl groups ≪ / RTI >
  • the methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group and triazinyl group of R 8 to R 11 are each independently a methyl group, A phenyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a phenylamino group and a diphenylamino group, and when they are substituted with a plurality of substituents, They are the same or different.
  • the compound is N1 - ([1,1'-biphenyl] -4-yl) -N4- (10,10- (Dibenzo [b, d] furan-3-yl) -N4- (10,10-dimethyl- (Dibenzo [b, d] thiophene-2-yl) -N, N4-diphenylbenzene-1,4-diamine or N2 ' 2-yl) -10,10-dimethyl-N2 ', N7', N7'-triphenyl-10H-spiro [anthracene-9,9'-fluorene] -2 ', 7'-diamine.
  • the compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:
  • the compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
  • organic electroluminescent device comprising the compound represented by the general formula (1) according to the present invention described above.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1).
  • the compounds may be used singly or in combination of two or more.
  • the at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI >
  • the structure of the organic electroluminescent device according to the present invention is not particularly limited.
  • the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34.
  • a hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32.
  • An electron transporting auxiliary layer 35 may be interposed between the electron transporting 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, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).
  • the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO.
  • the layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.
  • the electron injection layer 36 is a layer which is stacked on the electron transport layer 34 to facilitate injection of electrons from the cathode to ultimately improve power efficiency and is commonly used in the art .
  • materials such as LiF, Liq, NaCl, CsF, Li 2 O, and BaO can be used.
  • the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32.
  • the light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32.
  • the light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.
  • a life improving layer may be further included between the electron transporting auxiliary layer 35 and the light emitting layer 32. Holes moving in the organic light emitting device due to the ionization potential level in the light emitting layer 32 are blocked by the high energy barrier of the lifetime enhancing layer and do not diffuse or move to the electron transporting layer and consequently function to limit the holes to the light emitting layer .
  • the function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .
  • the structures of the spiroacridine series are excellent in electrochemical stability, high in glass transition temperature and carrier transporting ability, and particularly excellent in hole transporting ability, so that the hole transporting is smooth in the light emitting layer and the luminous efficiency is enhanced .
  • the compound represented by the formula (1) is characterized by substitution of two or more of spirodimethylfluorene moieties with an arylamine, and has characteristics of low voltage driving and high refractive index, thereby exhibiting high efficiency and long life physical characteristics .
  • the compound represented by the general formula (1) which is a representative claim structure of the present invention, is excellent in luminescence characteristics, and therefore, it is preferable to use any one of the hole injection layer, the hole transporting layer, the light emitting layer, the electron transporting layer, It can be used as a material.
  • a hole transporting layer and a hole assisting transporting layer material are preferable.
  • the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.
  • the organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another organic material layer and an electrode.
  • the organic material layers for example, the 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 a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.
  • the anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as 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), and indium zinc oxide (IZO)
  • ZnO Al or SnO 2: a combination of a metal and an oxide
  • the negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • Step 2 of Preparation Example 1 The procedure of Step 2 of Preparation Example 1 was followed to obtain 28.6 g (60%) of the target compound corresponding to the structural isomer of Core 1.
  • Step 2 of Preparation Example 4 The procedure of Step 2 of Preparation Example 4 was followed to obtain 28.1 g (44%) of the target compound corresponding to the structural isomer of Core 4.
  • reaction mixture was extracted with 500 mL of EA and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and then purified by silica gel column chromatography to obtain the desired compound (12.7 g, yield 72%).
  • reaction mixture was extracted with 500 mL of EA and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and then purified by silica gel column chromatography to obtain the desired compound (8.8 g, yield 71%).
  • reaction mixture was extracted with 500 mL of EA and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and then purified by silica gel column chromatography to obtain the desired compound (8.4 g, yield 66%).
  • 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, Hoshin Tech
  • ITO transparent glass substrate electrode
  • m-MTDATA 60 nm
  • m-MTDATA 60 nm
  • 1, 3, 4, 7, 9, 10, 12, 14, 19, 21, 23, 26, 28, 31, DS-H522 + 5% 80 nm
  • 40, 46, 50, 54, 58, 59, 66, 70, 76, 78, 91, 95, 98, 102, 112, 116, (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.
  • An organic EL device was prepared in the same manner as in Example 1, except that NPB was used as a hole transport layer material in place of the compound 1 used as a hole transport layer material in forming the hole transport layer in Example 1.
  • the structure of the NPB used is as follows.
  • the driving voltage, current efficiency and emission peak at current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices manufactured in Examples 1 to 36 and Comparative Example 1, and the results are shown in Table 1 below .
  • Example 1 Compound 1 4.0 26.4 Example 2 Compound 3 3.9 25.5 Example 3 Compound 4 3.8 26.9 Example 4 Compound 7 4.5 25.0 Example 5 Compound 9 4.2 27.5 Example 6 Compound 10 4.0 24.5 Example 7 Compound 12 4.1 25.6 Example 8 Compound 14 4.4 27.0 Example 9 Compound 19 4.1 25.9 Example 10 Compound 21 3.9 24.6 Example 11 Compound 23 4.3 25.0 Example 12 Compound 26 3.8 26.2 Example 13 Compound 28 3.9 25.4 Example 14 Compound 31 4.4 23.4 Example 15 Compound 33 4.1 26.1 Example 16 Compound 38 4.0 26.8 Example 17 Compound 40 3.7 25.8 Example 18 Compound 46 3.8 26.6 Example 19 Compound 50 3.9 22.5 Example 20 Compound 54 4.2 26.9 Example 21 Compound 58 4.1 24.5 Example 22 Compound 59 3.8 27.6 Example 23 Compound 66 4.5 28.0 Example 24 Compound 70 4.1 24.2 Example 25 Compound 76 3.9 27.2
  • the organic electroluminescent devices using the compounds according to the present invention as the hole transporting layer exhibited higher current density than the conventional NBP (Comparative Example 1)
  • the efficiency and the driving voltage exhibit excellent performance.

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Un composé selon la présente invention est utilisé pour une couche organique, de préférence une couche d'émission de lumière, d'un dispositif électroluminescent organique, et peut ainsi améliorer le rendement d'émission de lumière, la tension de commande, la durée de vie, etc. du dispositif électroluminescent organique.
PCT/KR2018/013975 2017-11-24 2018-11-20 Composé organique et dispositif électroluminescent organique le comprenant WO2019103397A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110872315A (zh) * 2019-11-29 2020-03-10 浙江华显光电科技有限公司 一种有机化合物和使用该化合物的有机电致发光器件

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018225943A1 (fr) * 2017-06-09 2018-12-13 주식회사 엘지화학 Nouveau composé et élément électroluminescent organique l'utilisant
CN114075112B (zh) * 2020-08-14 2023-12-01 广州华睿光电材料有限公司 芴类化合物及其应用
CN112574045B (zh) * 2020-12-08 2022-04-01 武汉华星光电半导体显示技术有限公司 空穴传输材料及其制备方法、电致发光器件
CN113314037B (zh) 2021-07-30 2022-01-04 武汉华星光电半导体显示技术有限公司 柔性显示面板、电子装置以及铰链

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130140303A (ko) * 2012-06-14 2013-12-24 (주) 에프엔지리서치 유기전계발광 소자 제조용 신규 화합물
KR20160100698A (ko) * 2015-02-16 2016-08-24 주식회사 엘지화학 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자
KR20160141361A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
CN106588674A (zh) * 2015-10-16 2017-04-26 晶宜科技股份有限公司 有机电激发光装置及其材料
CN107353893A (zh) * 2017-07-13 2017-11-17 长春海谱润斯科技有限公司 一种含芴环结构的四苯基乙烯有机电致发光材料及其有机发光器件

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102054159B1 (ko) * 2013-07-09 2019-12-10 덕산네오룩스 주식회사 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치
US20160351817A1 (en) * 2015-05-27 2016-12-01 Samsung Display Co., Ltd. Organic light-emitting device
KR102093535B1 (ko) * 2016-04-25 2020-03-25 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
WO2018225943A1 (fr) * 2017-06-09 2018-12-13 주식회사 엘지화학 Nouveau composé et élément électroluminescent organique l'utilisant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130140303A (ko) * 2012-06-14 2013-12-24 (주) 에프엔지리서치 유기전계발광 소자 제조용 신규 화합물
KR20160100698A (ko) * 2015-02-16 2016-08-24 주식회사 엘지화학 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자
KR20160141361A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
CN106588674A (zh) * 2015-10-16 2017-04-26 晶宜科技股份有限公司 有机电激发光装置及其材料
CN107353893A (zh) * 2017-07-13 2017-11-17 长春海谱润斯科技有限公司 一种含芴环结构的四苯基乙烯有机电致发光材料及其有机发光器件

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110872315A (zh) * 2019-11-29 2020-03-10 浙江华显光电科技有限公司 一种有机化合物和使用该化合物的有机电致发光器件

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