WO2016006791A1 - 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치 - Google Patents
화합물, 이를 포함하는 유기 광전자 소자 및 표시장치 Download PDFInfo
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- WO2016006791A1 WO2016006791A1 PCT/KR2015/002638 KR2015002638W WO2016006791A1 WO 2016006791 A1 WO2016006791 A1 WO 2016006791A1 KR 2015002638 W KR2015002638 W KR 2015002638W WO 2016006791 A1 WO2016006791 A1 WO 2016006791A1
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- HJVVBGRKSBSNEA-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c(cccc2)c2N2c3cc(-c4ccccc4)cc(-c4ccccc4)n3)c3c2ncnc3c1 Chemical compound c(cc1)ccc1-c1cc(-c(cccc2)c2N2c3cc(-c4ccccc4)cc(-c4ccccc4)n3)c3c2ncnc3c1 HJVVBGRKSBSNEA-UHFFFAOYSA-N 0.000 description 1
- YZTSVBPURBNKTA-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c(cccc2)c2N2c3ccncc3)c3c2ncnc3c1 Chemical compound c(cc1)ccc1-c1cc(-c(cccc2)c2N2c3ccncc3)c3c2ncnc3c1 YZTSVBPURBNKTA-UHFFFAOYSA-N 0.000 description 1
- PHZPPXFJHZHIIO-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c2ccccc2)nc(N(c2c-3cccc2)c2cccc4nc(-c5ccccc5)nc-3c24)c1 Chemical compound c(cc1)ccc1-c1cc(-c2ccccc2)nc(N(c2c-3cccc2)c2cccc4nc(-c5ccccc5)nc-3c24)c1 PHZPPXFJHZHIIO-UHFFFAOYSA-N 0.000 description 1
- IEHRRKWZNAAXOD-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c2cncnc2N2c3ccncc3)c3c2cccc3c1 Chemical compound c(cc1)ccc1-c1cc(-c2cncnc2N2c3ccncc3)c3c2cccc3c1 IEHRRKWZNAAXOD-UHFFFAOYSA-N 0.000 description 1
- XTDQGPQKVBAMOR-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c2ncncc2N2c3ccncc3)c3c2cccc3c1 Chemical compound c(cc1)ccc1-c1cc(-c2ncncc2N2c3ccncc3)c3c2cccc3c1 XTDQGPQKVBAMOR-UHFFFAOYSA-N 0.000 description 1
- ANSFUDXMPZWKRE-UHFFFAOYSA-N c(cc1)ccc1-c1cc2cccc(Nc3cnccc3-3)c2c-3c1 Chemical compound c(cc1)ccc1-c1cc2cccc(Nc3cnccc3-3)c2c-3c1 ANSFUDXMPZWKRE-UHFFFAOYSA-N 0.000 description 1
- LXOVUAPDBVIIDB-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cccc2)c2Nc2ccc3)c2c3n1 Chemical compound c(cc1)ccc1-c1nc(-c(cccc2)c2Nc2ccc3)c2c3n1 LXOVUAPDBVIIDB-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 101150002764 purA gene Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Definitions
- a compound, an organic optoelectronic device, and a display device are provided.
- An organic optoelectric diode is a device capable of converting electrical energy and light energy.
- Organic optoelectronic devices can be divided into two types according to the principle of operation.
- One is an optoelectronic device in which an exciton formed by light energy is separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electrical energy.
- It is a light emitting device that generates light energy from electrical energy.
- Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
- the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material, and has a structure in which an organic layer is inserted between an anode and a cathode.
- the organic layer may include a light emitting layer and an optional auxiliary layer, and the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like, in order to increase the efficiency and stability of the organic light emitting device. It may comprise at least one layer selected from the hole blocking layer.
- the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, is affected by the organic material included in the organic layer.
- An organic optoelectronic device including the compound and a display device including the organic optoelectronic device are provided.
- X 1 to X 10 are each independently N, C or CR a
- At least one of X 1 to X 10 is N,
- Z is NL 4 -R b , 0, S, CL 4 -R c R d , or Si-L 4 -R e R f ,
- L 1 to L 4 are each independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted group A substituted C2 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 aryleneamine group, a substituted or unsubstituted C1 to C30 alkoxylene group : a substituted or unsubstituted C 1 to C30 aryloxyylene group, substituted or Unsubstituted C2 to C30 alkenylene group, substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof, R 1 to R 3 , and R a to R f are each independently hydrogen, hydrogen, Substituted or unsubstituted
- R 1 to R 3 are each independently present or are fused to any two adjacent groups of R 1 to R 3 to form a ring.
- the compound according to one embodiment of the present invention may be for an organic optoelectronic device.
- a display device including the organic optoelectronic device described above is provided.
- FIG. 1 and 2 are cross-sectional views illustrating various embodiments of an organic light emitting diode according to an embodiment of the present invention.
- organic light emitting element 200 organic light emitting element
- substituted means that at least one hydrogen of a substituent or compound compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C such as cyclic C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C 1 to C20 alkoxy group, fluoro group, trifluoromethyl group, etc. Mean substituted with 1 to C10 trifluoroalkyl group or cyano group.
- hetero means one to three hetero atoms selected from the group consisting of ⁇ , ⁇ , S, P, and Si in one functional group, and the remainder is carbon unless otherwise defined.
- an "alkyl group” means an aliphatic hydrocarbon group.
- the alkyl group may be a "saturated alkyl group” that does not contain any double or triple bonds.
- the alkyl group may be an alkyl group of C 1 to C20. More specifically, the alkyl group may be a C1 to C 10 alkyl group or a C 1 to C6 alkyl group.
- a C 1 to C 4 alkyl group means that the alkyl chain contains .1 to 4 carbon atoms, and methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec-butyl and t- Selected from the group consisting of butyl.
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a real pillar.
- an "aryl (ar yi) group” means a substituent in which all elements of a cyclic substituent have a P-orbital, and these P-orbitals form a conjugate, and are monocyclic or fused rings.
- heterocycle means containing at least one hetero atom selected from the group consisting of N, 0, S, P, and Si in a ring compound such as an aryl group or a cycloalkyl group, and the rest is carbon.
- a ring compound such as an aryl group or a cycloalkyl group
- the rest is carbon.
- the aryl group contains a hetero atom
- the heterocycle may include one or more heteroatoms for all or each ring.
- a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heteroaryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Cenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, ' substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group, substituted or Unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted perryleny
- Thiadiazolyl group substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted Or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted A quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group,
- Acridinyl group substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenothiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted carbazolyl group, It may be a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.
- a single bond refers to a bond directly connected without passing through carbon or a hetero atom other than carbon, and specifically, L means a single bond means that a substituent linked to L is directly connected to the central core. do. That is, in the present specification, a single bond refers to methylene or the like via carbon.
- the hole characteristic refers to a characteristic capable of forming holes by donating electrons when an electric field is applied, and conducting along the HOMO level. It is characterized by the characteristics that facilitate the injection of the holes formed in the anode into the light emitting layer, the movement of the holes formed in the light emitting layer to the anode and the movement in the light emitting layer.
- the electron characteristic refers to a characteristic that can receive electrons when an electric field is applied, and has a conductivity characteristic along the LUMO level, and injects electrons formed in the cathode into the light emitting layer, moves electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement.
- an organic compound according to one embodiment is described.
- a compound represented by the following Chemical Formula 1 may be provided.
- X 1 to X 10 are each independently N, C or CR a
- At least one of X 1 to X ′ 0 is N,
- Z is NL 4 -R b , 0, S, CL 4 -R3 ⁇ 4 d , or Si-L 4 -R e R f ,
- L 1 to L 4 are each independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted group Substituted C3 to C30 heterocyclic group, substituted or unsubstituted C6 to C30 aryleneamine group, substituted or unsubstituted C1 to C30 alkoxylene group substituted or unsubstituted C1 to C30 aryloxyylene group, substituted or unsubstituted A C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,
- R 1 to R 3 , and R a to R f are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 Heterocyclic group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted amine group, substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C2 to C30 Alkoxycarbonyl group, substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, substituted or unsubstituted C7 to C30 aryloxycarbonylamino group, substituted or unsubstituted C1 to C30 sulfamo
- R 'to R 3 are each independently present, or any two adjacent groups of R 1 to R 3 are fused to each other to form a ring.
- the compound according to an embodiment of the present invention includes a structure in which an acridan derivative and a hexagonal ring are fused, thereby controlling the flow of holes and electrons in a molecule, and thus, in the organic optoelectronic device to which the compound is applied. It has the advantages of high efficiency, long life, and low voltage driving.
- the compound since the compound has excellent charge transport characteristics and well overlaps with the absorption spectrum of the dopant, high efficiency, long life, and low voltage can be maximized.
- At least one of the X 2 to X 10 may be N.
- Formula 1 may be represented by any one of the following Formulas 2 to 14.
- Z is NL 4 -R b , and L 1 to L 4 , R r to R 3 , R a , and R b are as described above. Since the balance between holes and electrons is better when at least two of X 1 to X 10 are N, the organic optoelectronic devices to which the compounds represented by Formulas 2 to 5 are applied exhibit particularly excellent characteristics in terms of efficiency and driving voltage. .
- Formula 1 may be represented by any one of the following Formula 15, but is not limited thereto. 15] [Formula 16] [Formula 17] [Formula 18]
- Z is NL 4 -R b ,
- L 1 and L 4 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
- R 1 , and R b are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted C6 to C30 aryl group, substituted or Unsubstituted C5 to C40 fused ring, or a combination thereof.
- L 1 and L 4 are each independently a single bond or a substitution listed in Group I below. Or an unsubstituted group, but is not limited thereto.
- * is a connection point.
- R 1 and R b may be each independently selected from hydrogen, hydrogen, or a substituted or unsubstituted group listed in Group II.
- R and R are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof , * Is the connection point.
- Z in Formula 1 is NL 4 -R b , wherein R b is hydrogen, deuterium, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted C6 to C30 aryl group, ,-,
- the compound may be a substituted or unsubstituted C5 to C40 fused ring, or a combination thereof.
- the compound may be, for example, but not limited to the compounds listed in the group m.
- the above-mentioned compounds may be for organic optoelectronic devices.
- the organic layer may include a light emitting layer, and the light emitting layer may include a compound of the present invention. Specifically, the compound may be included as a host of the light emitting layer.
- the organic layer includes at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer, the auxiliary layer May be an organic optoelectronic device including the compound.
- the organic optoelectronic device is not particularly limited as long as the device can switch electrical energy and light energy. Examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.
- an organic optoelectronic device 100 includes an anode 120 and a cathode 1 10 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 1 10. ).
- the anode 120 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
- the anode 120 is, for example, a metal such as nickel, platinum, banana, chromium, copper, zinc, gold or an alloy thereof; Zinc oxide, phosphate oxide, phosphate tin oxide ( ⁇ ),
- Metal oxides such as indium zinc oxide (IZO); Of metals and oxides such as ZnO and A1 or Sn0 2 and Sb . Combination; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, and the like. It is not.
- the cathode 1 10 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
- the negative electrode ⁇ 0 may be, for example, a metal or an alloy of idol such as magnesium, calcium, natrium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or the like; Multilayer structure materials such as LiF / Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
- the organic layer 105 includes a light emitting layer 130 including the compound described above.
- the light emitting layer 130 may include, for example, the compounds described above alone or as described above. At least two kinds of the compounds may be mixed and included, or the above-described compounds and other compounds may be mixed. In the case of including a compound different from the above-mentioned compound, for example, it may be included in the form of a host and a dopant, and the above-described compound may be included as, for example, a host.
- the host can be, for example, a phosphorescent host or a fluorescent host, for example a phosphorescent host.
- the dopant may be an inorganic, organic, or inorganic compound, and may be selected from known dopants.
- the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 230.
- the hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the emission layer 230 and block electrons.
- the hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.
- the above-described compound may be included in the light emitting layer 230 and / or hole auxiliary layer 140.
- the organic layer 105 of FIG. 1 or 2 may further include an electron injection layer, an electron transport layer, an auxiliary electron transport layer, a hole transport layer, an auxiliary hole transport layer, a hole injection layer, or a combination thereof. .
- the compounds of the present invention can be included in these organic layers.
- the organic light emitting diodes 100 and 200 may be formed by forming a positive electrode or a negative electrode on a substrate, followed by a dry film method such as evaporation, sputtering, plasma plating and ion plating; Alternatively, the organic layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode or an anode thereon.
- the organic light emitting diode described above may be applied to an organic light emitting diode display.
- Second step synthesis of intermediate product (L-2)
- the crystallized solid was filtered and then dissolved in monochlorobenzene to silica gel / celite.
- Tris (dibenzylideneacetone) dipallam (0) 1.6 g (2.8 mmol), trit-butylphosphine 2.3 mL (50% in toluene) was added to 190 mL of xyl 3 ⁇ 41 and heated under nitrogen stream for 15 hours. It was refluxed. The mixture obtained therefrom was added to 500 mL of methanol, and the crystallized solid was filtered. The mixture was dissolved in dichlorobenzene, filtered through silica gel / Sela Art, an appropriate amount of an organic solvent was removed, and then recrystallized with methanol, to give Compound A-105 (9.5 g, 63% yield).
- Formula (a) was synthesized in the same manner as described in WO 2013032035.
- the energy level of each material was calculated by the Gaussian 09 method using a supercomputer GAIA (IBM power 6), and the results are shown in Table 1 below.
- the desired HOMO / LUMO energy on the simulation The level of HOMO is -5.0 to -5.5 and the LUMO is -1.4 to -2.2 is expected to show the electron transport characteristics well, when comparing the Examples 1, 2, 3 and Comparative Example 1 of the present Example 1 is the HOMO level Satisfied, but LUMO level is not satisfied, it is expected that the hole and the electron balance is not balanced.
- the compound of the present invention has an appropriate energy level as compared with Comparative Example 1, and thus the efficiency and lifespan are excellent.
- An organic light emitting device was manufactured using B-17 obtained in Example 1 as a host and using (piq) 2 Ir (acac) as a dopant.
- ITO was used as the anode at a thickness of 1000 A
- aluminum (A1) was used as the cathode at a thickness of 1000 A.
- the manufacturing method of the organic light emitting device the anode is cut into a size of 50mm x 50mm x 0.7mm ⁇ glass substrate having a sheet resistance value of 15Q / cm 2 in each of acetone, isopropyl alcohol and pure water 15 After ultrasonic cleaning for minutes, UV ozone cleaning was used for 30 minutes.
- a phosphorescent dopant (piq) 2 Ir (acac) was simultaneously deposited.
- the amount of light 3 ⁇ 4 dopyeon agent was deposited so that 3 parts by weight 0 /.
- the structure of the organic optoelectronic device is 11,0 / 1 (80 1101) / £ 1 ⁇ 1 ⁇ (8-17 (97% by weight) + (piq) was produced in the structure of 2 Ir (acac) (3 parts by weight 0/0), 30nm) / Balq (5nm) / Alq3 (20nm) / LiF (lnm) I Al (l OOnm).
- An organic light emitting diode was manufactured according to the same method as Example 4 except for using B-33 of Example 2 instead of B-17 of Example 4.
- An organic light emitting diode was manufactured according to the same method as Example 4 except for using A-105 of Example 3 instead of B-17 of Example 4.
- An organic light emitting diode was manufactured according to the same method as Example 4 except for using CBP having the following structure instead of B-17 of Example 4.
- NPB, BAlq, CBP, and (piq) 2 Ir (acac) structures used for fabricating the organic light emitting diode are as follows.
- the current value flowing through the unit device was measured using a current-voltmeter (Kekhley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
- the current efficiency (cd / A) of the same current density (10 mA / cm 2 ) was calculated using the luminance, current density and voltage measured from (1) and (2).
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Abstract
Description
Claims
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Application Number | Priority Date | Filing Date | Title |
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EP15819320.1A EP3168221B1 (en) | 2014-07-09 | 2015-03-18 | Compound, organic optoelectronic diode comprising same, and display |
CN201580030598.1A CN106414450B (zh) | 2014-07-09 | 2015-03-18 | 化合物、有机光电装置以及显示装置 |
JP2017500861A JP6564012B2 (ja) | 2014-07-09 | 2015-03-18 | 化合物、これを含む有機光電子素子および表示装置 |
US15/359,877 US20170077416A1 (en) | 2014-07-09 | 2016-11-23 | Compound, organic optoelectronic diode comprising same, and display |
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KR1020140086108A KR101850889B1 (ko) | 2014-07-09 | 2014-07-09 | 화합물, 이를 포함하는 유기 광전자 소자 및 표시장치 |
KR10-2014-0086108 | 2014-07-09 |
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US15/359,877 Continuation US20170077416A1 (en) | 2014-07-09 | 2016-11-23 | Compound, organic optoelectronic diode comprising same, and display |
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US (1) | US20170077416A1 (ko) |
EP (1) | EP3168221B1 (ko) |
JP (1) | JP6564012B2 (ko) |
KR (1) | KR101850889B1 (ko) |
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WO2017109727A1 (en) * | 2015-12-21 | 2017-06-29 | Idemitsu Kosan Co., Ltd. | Hetero-condensed phenylquinazolines and their use in electronic devices |
EP3275970A1 (en) * | 2016-07-27 | 2018-01-31 | SFC Co., Ltd. | Organic light emitting compound and organic light emitting diode including the same |
JP2018534238A (ja) * | 2016-02-23 | 2018-11-22 | エルジー・ケム・リミテッド | ヘテロ環化合物およびこれを含む有機発光素子 |
EP3608319A1 (en) | 2018-08-07 | 2020-02-12 | Idemitsu Kosan Co., Ltd. | Condensed aza cycles as organic light emitting device and materials for use in same |
US11407766B2 (en) | 2017-01-30 | 2022-08-09 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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EP3418285B1 (en) | 2017-06-20 | 2020-05-06 | Idemitsu Kosan Co., Ltd. | Composition comprising a substituted ir complex and a phenylquinazoline bridged with a heteroatom |
EP3466954A1 (en) | 2017-10-04 | 2019-04-10 | Idemitsu Kosan Co., Ltd. | Fused phenylquinazolines bridged with a heteroatom |
CN110903290B (zh) * | 2018-09-14 | 2022-11-22 | 北京鼎材科技有限公司 | 一种化合物及其应用 |
KR102647025B1 (ko) * | 2018-12-28 | 2024-03-12 | 엘지디스플레이 주식회사 | 발광 특성이 우수한 유기 화합물, 이를 포함하는 유기발광다이오드 및 유기발광장치 |
KR20200099651A (ko) * | 2019-02-14 | 2020-08-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함한 발광 장치 |
CN110835532B (zh) * | 2019-11-22 | 2022-10-28 | 吉林奥来德光电材料股份有限公司 | 有机电致发光化合物及其制备方法和有机电致发光器件 |
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US11466021B2 (en) | 2016-12-05 | 2022-10-11 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US11407766B2 (en) | 2017-01-30 | 2022-08-09 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3608319A1 (en) | 2018-08-07 | 2020-02-12 | Idemitsu Kosan Co., Ltd. | Condensed aza cycles as organic light emitting device and materials for use in same |
Also Published As
Publication number | Publication date |
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JP2017527535A (ja) | 2017-09-21 |
EP3168221A4 (en) | 2017-12-06 |
EP3168221B1 (en) | 2023-06-28 |
JP6564012B2 (ja) | 2019-08-21 |
EP3168221A1 (en) | 2017-05-17 |
KR20160006472A (ko) | 2016-01-19 |
TW201602106A (zh) | 2016-01-16 |
CN106414450B (zh) | 2020-05-19 |
US20170077416A1 (en) | 2017-03-16 |
CN106414450A (zh) | 2017-02-15 |
KR101850889B1 (ko) | 2018-04-20 |
TWI551599B (zh) | 2016-10-01 |
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