WO2019039723A1 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2019039723A1
WO2019039723A1 PCT/KR2018/007415 KR2018007415W WO2019039723A1 WO 2019039723 A1 WO2019039723 A1 WO 2019039723A1 KR 2018007415 W KR2018007415 W KR 2018007415W WO 2019039723 A1 WO2019039723 A1 WO 2019039723A1
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group
aryl
alkyl
layer
alkenyl
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박정근
신환규
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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
    • 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
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • 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 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 of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.
  • 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 1 and R 1 to R 12 are each independently 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 blood group and
  • L 1 and L 2 of the arylene group and a heteroarylene group wherein Ar 1 and Alkyl group of R 1 to R 12, 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 arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy C 60, C 1
  • Ring A is represented by any one of the following formulas (2) to (5);
  • the dotted line means the part where the condensation is made
  • n is an integer from 0 to 4.
  • n is an integer from 0 to 6;
  • R 13 is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 A cycloalkyl group, a heterocycloalkyl 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 An aryloxy group, 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 phosphazene-aryl group, is selected from the group consisting of an aryl amine of the C 6 ⁇ C 60 mono or diaryl phosphine blood
  • 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 .
  • 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.
  • Arylamine &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.
  • novel compounds of the present invention can be represented by the following formula
  • 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 1 and R 1 to R 12 are each independently 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 blood group and
  • L 1 and L 2 of the arylene group and a heteroarylene group wherein Ar 1 and Alkyl group of R 1 to R 12, 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 arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy C 60, C 1
  • Ring A is represented by any one of the following formulas (2) to (5);
  • the dotted line means the part where the condensation is made
  • n is an integer from 0 to 4.
  • n is an integer from 0 to 6;
  • R 13 is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 A cycloalkyl group, a heterocycloalkyl 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 An aryloxy group, 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 phosphazene-aryl group, is selected from the group consisting of an aryl amine of the C 6 ⁇ C 60 mono or diaryl phosphine blood
  • the compound represented by formula (1) of the present invention has a basic skeleton of substituted or unsubstituted asymmetric dibenzocarbazole. Since the entire skeleton has a bipolar characteristic due to the binding of a substituted or unsubstituted quinoxaline group, which is one of electron-withdrawing groups (EWG) having a high electron absorbing property, it can increase the binding force between holes and electrons.
  • EWG electron-withdrawing groups
  • the core of the compound represented by formula (I) of the present invention is a structure in which two naphthalene groups having high hole mobility are condensed.
  • the stability and mobility of holes can be increased higher than those of naphthalene monohydrated skeletons.
  • a quinoxaline group having a high electron mobility as a substituent, the flow of holes and electrons can be performed well. Accordingly, the number of the excitons contributing to light emission in the light emitting layer can be increased, the light emitting efficiency of the device can be improved, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased.
  • the steric hindrance between the core and the electron drag (EDG) is further increased compared to the symmetrical dibenzocarbazole, and the luminous efficiency of the device can be improved.
  • the compound represented by the general formula (1) of the present invention is useful as an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (red phosphorescent host material), an electron transporting layer / injection layer material emitting auxiliary layer material, More preferably, it can be used as a light emitting layer material, an electron transporting layer material, and an electron transporting layer material.
  • the organic electroluminescent device including the compound of Formula 1 can be greatly improved in performance and lifetime, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize its performance.
  • the compound may be represented by any one of the following formulas (6) to (9):
  • the Ar 1 and R 1 to R 12 are each independently selected from hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and the nuclear atoms of 5 to 60 heteroaryl group the group consisting of, wherein Ar 1 and The alkyl group, aryl group and heteroaryl group of R 1 to R 12 are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they may be the same or different from each other.
  • the Ar 1 and R 1 to R 12 are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxynyl group, and is preferably a group selected from the group consisting of a methyl group,
  • a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 arylamine group, C 6 ⁇ C 60 aryl group and a nuclear atoms substituted with at least one member selected from the group consisting of 5 to 60 heteroaryl group substituent or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different from each other .
  • the Ar 1 and R 1 to R 12 are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, A dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group, and a dibenzodioxynyl group, and is preferably a group selected from the group consisting of a methyl group,
  • the Ar < 1 & A substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, terphenyl, naphthalenyl, phenanthrenyl,
  • a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, A phenyl group, a terphenyl group, a naphthalenyl group, a phenanthrenyl group, a triphenylenyl group, a pyridinyl group, a pyrimidiny
  • the Ar 1 and At least one of R 1 to R 12 may be a substituent represented by any one of the following formulas B-1 to B-12:
  • R 14 to R 16 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 ⁇ phosphazene-aryl group of C 60, the group is bonded to adjacent or selected from the group consisting of an arylamine C
  • Alkyl group of said R 14 to R 16 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 arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy C 60, C 1 ⁇ alkyloxy group of C 40 of, C 6 ⁇ C 60 arylamine group, C 3 ⁇ C
  • Ar 1 may be a substituent represented by any one of formulas B-1 to B-7, and at least one of R 1 to R 12 may be a substituent represented by any one of formulas B-8 to B- -12, more preferably the R 2 may be a substituent represented by any one of formulas B-8 to B-12.
  • each of R 14 to R 16 is independently hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, A heteroaryl group having 5 to 60 nuclear atoms;
  • the alkyl group, aryl group and heteroaryl group of R 14 to R 16 are each independently a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 An aryl group, and a heteroaryl group having 5 to 60 ring atoms, and when they are substituted with a plurality of substituents, they may be the same or different from each other.
  • each of R 14 to R 16 is independently hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, A group consisting of a phenyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, Lt; / RTI >
  • alkyl group of R 14 to R 16 examples include a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, phenanthrenyl group, triphenylenyl group, pyridinyl group, A thiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a spirofluorenyl group and a dibenzodioxinyl group are each independently a C 1 to C 40 alkyl group, a C 6 to C 60 an arylamine group, C 6 ⁇ C 60 aryl group and a nuclear atoms substituted with at least one member selected from 5 to 60 heteroaryl group the group consisting of substituted or is unsubstituted, in the case where the substitution of a
  • L 1 and L 2 are each independently a direct bond or a linker selected from the group consisting of the following formulas C-1 to C-4, preferably a direct bond or a C- 1 or C-2, more preferably L < 2 > is a direct bond or a linker represented by C-1 or C-2:
  • 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 injecting layer 36 is a layer which is stacked on the electron transporting layer to facilitate injection of electrons from the cathode to ultimately improve the power efficiency.
  • LiF, Liq, NaCl, CsF, Li 2 O, BaO, or the like 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 compound represented by the above formula (1) has a substituted or unsubstituted asymmetric dibenzocarbazole as a basic skeleton and a substituted or unsubstituted quinoxaline as an electron attracting group (EWG) Since the whole molecule has a bipolar characteristic due to the bonding of groups, it is possible to enhance the bonding force between holes and electrons.
  • EWG electron attracting group
  • the core of the compound of the present invention is a structure in which two naphthalene groups having a high hole mobility are condensed.
  • the structure and mobility of holes can be increased higher than those of the naphthalene monohydric skeleton, and quinoxaline
  • a group as a substituent holes and electrons can flow well. Accordingly, the number of the excitons contributing to light emission in the light emitting layer can be increased, the light emitting efficiency of the device can be improved, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased.
  • the steric hindrance between the core and the electron drag (EDG) is further increased compared to the symmetrical dibenzocarbazole, and the luminous efficiency of the device can be improved.
  • the compound represented by the formula (1) of the present invention can be used as any one of a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer which are organic compound layers of an organic electroluminescent device.
  • Transporting layer and an electron transporting layer and more preferably an electron transporting layer, or an electron transporting layer.
  • the compound represented by the above formula (1) can be used as a phosphorescent host, a fluorescent host or a dopant material of a light emitting layer, Preferably a red phosphorescent host material.
  • 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.
  • 2-naphthyl boronic acid (20.0 g, 116.3 mmol) and 1-bromo-2-nitro naphthalene (29.3 g, 116.3 mmol) and Pd (PPh 3) 4 (5.4 g, 4.7 mmol), NaOH (14.0 g, 348.9 mmol) were dissolved in 400 ml of tetrahydrofuran and 200 ml of water, and the mixture was stirred at 75 ° C for 4 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, 2-nitro-1,2'-binaphthalene (30.0 g, yield 86%) was obtained by column chromatography.
  • a glass substrate coated with ITO Indium Tin Oxide
  • ITO Indium Tin Oxide
  • the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
  • a solvent such as isopropyl alcohol, acetone, or methanol
  • a red organic EL device was fabricated in the same manner as in Example 1 as a light emitting host material in the formation of a light emitting layer.
  • Example 1 One 4.5 620 45.1 Example 2 2 4.3 620 46,2 Example 3 7 4.5 620 44.1 Example 4 8 4.5 620 44.3 Example 5 17 4.6 620 45.1 Example 6 18 4.7 620 45,2 Example 7 20 4.5 620 44.3 Example 8 23 4.6 620 44.1 Example 9 25 4.5 620 46.1 Example 10 30 4.6 620 47.1 Example 11 37 4.6 620 49.8 Example 12 44 4.7 620 44.3 Example 13 53 4.7 620 43.2 Example 14 65 4.6 620 41.2 Example 15 76 4.6 620 41.2 Comparative Example 1 A 5.3 620 35.2 Comparative Example 2 B 5.2 620 37.1
  • organic layer 31 hole transport layer
  • Electron transport layer 35 Electron transport layer

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé dans une couche organique d'un dispositif électroluminescent organique, de préférence une couche électroluminescente, et permet d'améliorer l'efficacité lumineuse, la tension de commande et la durée de vie du dispositif électroluminescent organique.
PCT/KR2018/007415 2017-08-25 2018-06-29 Composé organique et dispositif électroluminescent organique le comprenant WO2019039723A1 (fr)

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KR1020170107977A KR102441870B1 (ko) 2017-08-25 2017-08-25 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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CN115636823B (zh) * 2022-10-18 2024-05-28 上海和辉光电股份有限公司 一种有机电致发光化合物及其应用

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