JP2018104413A - 有機化合物、発光素子、発光装置、電子機器、及び照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器、及び照明装置 Download PDFInfo
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- JP2018104413A JP2018104413A JP2017244746A JP2017244746A JP2018104413A JP 2018104413 A JP2018104413 A JP 2018104413A JP 2017244746 A JP2017244746 A JP 2017244746A JP 2017244746 A JP2017244746 A JP 2017244746A JP 2018104413 A JP2018104413 A JP 2018104413A
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- 150000002991 phenoxazines Chemical class 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960000286 proflavine Drugs 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000004549 pulsed laser deposition Methods 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- OQRNKLRIQBVZHK-UHFFFAOYSA-N selanylideneantimony Chemical compound [Sb]=[Se] OQRNKLRIQBVZHK-UHFFFAOYSA-N 0.000 description 1
- YWDGEUIDOIIHTK-UHFFFAOYSA-N selanylidenebarium Chemical compound [Ba]=[Se] YWDGEUIDOIIHTK-UHFFFAOYSA-N 0.000 description 1
- UKGBSHWRVFPDKV-UHFFFAOYSA-N selanylideneberyllium Chemical compound [Se]=[Be] UKGBSHWRVFPDKV-UHFFFAOYSA-N 0.000 description 1
- OMEPJWROJCQMMU-UHFFFAOYSA-N selanylidenebismuth;selenium Chemical compound [Se].[Bi]=[Se].[Bi]=[Se] OMEPJWROJCQMMU-UHFFFAOYSA-N 0.000 description 1
- AHMCFSORHHSTSB-UHFFFAOYSA-N selanylidenecalcium Chemical compound [Se]=[Ca] AHMCFSORHHSTSB-UHFFFAOYSA-N 0.000 description 1
- GGYFMLJDMAMTAB-UHFFFAOYSA-N selanylidenelead Chemical compound [Pb]=[Se] GGYFMLJDMAMTAB-UHFFFAOYSA-N 0.000 description 1
- YQMLDSWXEQOSPP-UHFFFAOYSA-N selanylidenemercury Chemical compound [Hg]=[Se] YQMLDSWXEQOSPP-UHFFFAOYSA-N 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- MFIWAIVSOUGHLI-UHFFFAOYSA-N selenium;tin Chemical compound [Sn]=[Se] MFIWAIVSOUGHLI-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052566 spinel group Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 description 1
- UQMCSSLUTFUDSN-UHFFFAOYSA-N sulfanylidenegermane Chemical compound [GeH2]=S UQMCSSLUTFUDSN-UHFFFAOYSA-N 0.000 description 1
- SMDQFHZIWNYSMR-UHFFFAOYSA-N sulfanylidenemagnesium Chemical compound S=[Mg] SMDQFHZIWNYSMR-UHFFFAOYSA-N 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- UCMJLSDIXYLIDJ-UHFFFAOYSA-N tellanylidenebarium Chemical compound [Ba]=[Te] UCMJLSDIXYLIDJ-UHFFFAOYSA-N 0.000 description 1
- PUZSUGPVBHGJRE-UHFFFAOYSA-N tellanylideneberyllium Chemical compound [Te]=[Be] PUZSUGPVBHGJRE-UHFFFAOYSA-N 0.000 description 1
- UFTQLBVSSQWOKD-UHFFFAOYSA-N tellanylidenecalcium Chemical compound [Te]=[Ca] UFTQLBVSSQWOKD-UHFFFAOYSA-N 0.000 description 1
- UURRKPRQEQXTBB-UHFFFAOYSA-N tellanylidenestannane Chemical compound [Te]=[SnH2] UURRKPRQEQXTBB-UHFFFAOYSA-N 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
- XPDICGYEJXYUDW-UHFFFAOYSA-N tetraarsenic tetrasulfide Chemical compound S1[As]2S[As]3[As]1S[As]2S3 XPDICGYEJXYUDW-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ALRFTTOJSPMYSY-UHFFFAOYSA-N tin disulfide Chemical compound S=[Sn]=S ALRFTTOJSPMYSY-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical compound [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 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
- 150000003752 zinc compounds Chemical class 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- H10K2101/00—Properties of the organic materials covered by group H10K85/00
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/166—Electron transporting layers comprising a multilayered structure
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- 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
Abstract
Description
本実施の形態では、本発明の一態様に係る有機化合物について、以下説明する。
一般式(G0)乃至(G7)として表される化合物の具体的な構造としては、下記構造式(101)乃至(152)で表される化合物等を挙げることができる。なお、一般式(G0)乃至(G7)として表される化合物は、下記例示に限られない。
本実施の形態では、本発明の一態様である一般式(G0)で表される有機化合物の合成方法について説明する。なお、本発明の一態様である化合物の合成方法は、以下の合成方法に限定されない。
本実施の形態では、本発明の一態様である有機化合物を有する発光素子の構成例を、図1、図2を用いて以下に説明する。
図1(B)は、図1(A)に示す発光層130の一例を示す断面模式図である。図1(B)に示す発光層130は、材料131と、ホスト材料132と、を有する。
・TADF(131):材料131
・Host(132):ホスト材料132
・SA:材料131のS1準位
・TA:材料131のT1準位
・SH:ホスト材料132のS1準位
・TH:ホスト材料132のT1準位
次に、上記構成と異なる構成の発光素子について、図2(A)(B)を用いて以下説明を行う。なお、本構成例において、先の構成と同様の構成についての詳細は、先の構成例を参酌すればよい。
・TADF(131):材料131
・Guest(134):ゲスト材料134(燐光材料)
・SA:材料131のS1準位
・TA:材料131のT1準位
・TPG:ゲスト材料134(燐光材料)のT1準位
次に、本発明の一態様に係わる発光素子の構成要素の詳細について、以下説明を行う。
発光層130に用いることができる材料について、それぞれ以下に説明する。
材料131は、S1準位とT1準位とのエネルギー差が小さいことが好ましく、具体的には、S1準位とT1準位とのエネルギー差が、好ましくは0eVより大きく0.3eV以下であり、より好ましくは0eVより大きく0.2eV以下、さらに好ましくは0eVより大きく0.1eV以下である。このような材料としては、熱活性化遅延蛍光材料が挙げられる。熱活性化遅延蛍光材料としては、実施の形態1で示した化合物が好適である。
ゲスト材料134としては、イリジウム、ロジウム、または白金系の有機金属錯体、あるいは金属錯体が挙げられ、中でも有機イリジウム錯体、例えばイリジウム系オルトメタル錯体が好ましい。オルトメタル化する配位子としては4H−トリアゾール配位子、1H−トリアゾール配位子、イミダゾール配位子、ピリジン配位子、ピリミジン配位子、ピラジン配位子、あるいはイソキノリン配位子などが挙げられる。金属錯体としては、ポルフィリン配位子を有する白金錯体などが挙げられる。
ホスト材料132に用いることができる化合物としては、特に限定はないが、亜鉛やアルミニウム系金属錯体の他、オキサジアゾール誘導体、トリアゾール誘導体、ベンゾイミダゾール誘導体、キノキサリン誘導体、ジベンゾキノキサリン誘導体、ジベンゾチオフェン誘導体、ジベンゾフラン誘導体、ピリミジン誘導体、トリアジン誘導体、ピリジン誘導体、ビピリジン誘導体、フェナントロリン誘導体などが挙げられる。他の例としては、芳香族アミンやカルバゾール誘導体などが挙げられる。
正孔注入層111は、一対の電極の一方(電極101または電極102)からのホール注入障壁を低減することでホール注入を促進する機能を有し、例えば遷移金属酸化物、フタロシアニン誘導体、あるいは芳香族アミンなどによって形成される。遷移金属酸化物としては、モリブデン酸化物やバナジウム酸化物、ルテニウム酸化物、タングステン酸化物、マンガン酸化物などが挙げられる。フタロシアニン誘導体としては、フタロシアニンや金属フタロシアニンなどが挙げられる。芳香族アミンとしてはベンジジン誘導体やフェニレンジアミン誘導体などが挙げられる。ポリチオフェンやポリアニリンなどの高分子化合物を用いることもでき、例えば自己ドープされたポリチオフェンであるポリ(エチレンジオキシチオフェン)/ポリ(スチレンスルホン酸)などがその代表例である。
正孔輸送層112は正孔輸送性材料を含む層であり、正孔注入層111の材料として例示した正孔輸送性材料を使用することができる。正孔輸送層112は正孔注入層111に注入された正孔を発光層130へ輸送する機能を有するため、正孔注入層111の最高被占軌道(Highest Occupied Molecular Orbital、HOMOともいう)準位と同じ、あるいは近いHOMO準位を有することが好ましい。
電子輸送層118は、電子注入層119を経て一対の電極の他方(電極101または電極102)から注入された電子を発光層130へ輸送する機能を有する。電子輸送性材料としては、正孔よりも電子の輸送性の高い材料を用いることができ、1×10−6cm2/Vs以上の電子移動度を有する材料であることが好ましい。電子を受け取りやすい化合物(電子輸送性を有する材料)としては、含窒素複素芳香族化合物のようなπ電子不足型複素芳香族化合物や金属錯体などを用いることができる。具体的には、発光層130に用いることができる電子輸送性材料として挙げたキノリン配位子、ベンゾキノリン配位子、オキサゾール配位子、あるいはチアゾール配位子を有する金属錯体、オキサジアゾール誘導体、トリアゾール誘導体、フェナントロリン誘導体、ピリジン誘導体、ビピリジン誘導体、ピリミジン誘導体などが挙げられる。また、1×10−6cm2/Vs以上の電子移動度を有する物質であることが好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、上記以外の物質を電子輸送層として用いても構わない。また、電子輸送層118は、単層だけでなく、上記物質からなる層が二層以上積層してもよい。
電子注入層119は電極102からの電子注入障壁を低減することで電子注入を促進する機能を有し、例えば第1族金属、第2族金属、あるいはこれらの酸化物、ハロゲン化物、炭酸塩などを用いることができる。また、先に示す電子輸送性材料と、これに対して電子供与性を示す材料の複合材料を用いることもできる。電子供与性を示す材料としては、第1族金属、第2族金属、あるいはこれらの酸化物などを挙げることができる。具体的には、フッ化リチウム(LiF)、フッ化ナトリウム(NaF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。また、電子注入層119にエレクトライドを用いてもよい。該エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。また、電子注入層119に、電子輸送層118で用いることが出来る物質を用いても良い。
電極101及び電極102は、発光素子の陽極または陰極としての機能を有する。電極101及び電極102は、金属、合金、導電性化合物、及びこれらの混合物や積層体などを用いて形成することができる。
また、本発明の一態様に係る発光素子は、ガラス、プラスチックなどからなる基板上に作製すればよい。基板上に作製する順番としては、電極101側から順に積層しても、電極102側から順に積層しても良い。
本実施の形態においては、実施の形態3に示す発光素子の構成と異なる構成の発光素子、及び該発光素子の発光機構について、図3(A)乃至図3(C)を用いて、以下説明を行う。なお、図3(A)、図3(B)において、図1(A)乃至図1(C)に示す符号と同様の機能を有する箇所には、同様のハッチパターンとし、符号を省略する場合がある。また、同様の機能を有する箇所には、同様の符号を付し、その詳細な説明は省略する場合がある。
図3(A)は、発光素子250の断面模式図である。
次に、発光層120の発光機構及び材料構成について、以下説明を行う。
・Host(121_1):有機化合物121_1(ホスト材料)
・Host(121_2):有機化合物121_2(ホスト材料)
・Guest(122):発光性材料122(燐光性化合物)
・SPH1:有機化合物121_1(ホスト材料)のS1準位
・TPH1:有機化合物121_1(ホスト材料)のT1準位
・SPH2:有機化合物121_2(ホスト材料)のS1準位
・TPH2:有機化合物121_2(ホスト材料)のT1準位
・TPG:発光性材料122(燐光性化合物)のT1準位
・SPE:励起錯体のS1準位
・TPE:励起錯体のT1準位
本実施の形態では実施の形態3及び実施の形態4で説明した発光素子を用いた発光装置について、図4(A)及び図4(B)を用いて説明する。
図5には発光装置の一例として、白色発光を呈する発光素子を形成し、着色層(カラーフィルタ)を形成した発光装置の例を示す。
トップエミッション型の発光装置の断面図を図6に示す。この場合、基板1001は光を通さない基板を用いることができる。TFTと発光素子の陽極とを接続する接続電極を作製するまでは、ボトムエミッション型の発光装置と同様に形成する。その後、第3の層間絶縁膜1037を電極1022を覆って形成する。この絶縁膜は平坦化の役割を担っていても良い。第3の層間絶縁膜1037は第2の層間絶縁膜1021と同様の材料の他、他の様々な材料を用いて形成することができる。
本実施の形態では、本発明の一態様の電子機器について説明する。
本実施の形態では、本発明の一態様の発光素子を様々な照明装置に適用する一例について、図9及び図10を用いて説明する。
<ステップ1:8−クロロ−4−(9’−フェニル−2,3’−ビ−9H−カルバゾール−9−イル)ベンゾフロ[3,2−d]ピリミジンの合成>
窒素で置換した200mLの三口フラスコに水素化ナトリウム(60%)0.30gを入れ、攪拌しながらN,N−ジメチルホルムアミド(略称:DMF)30mLを滴下した。三口フラスコを0℃に氷冷し、9’−フェニル−2,3’−ビ−9H−カルバゾール1.8gと、DMF15mlとの溶液を滴下して加え、室温に昇温し、1時間攪拌した。攪拌後、反応容器を0℃に氷冷し、4,8−ジクロロ[1]ベンゾフロ[3,2−d]ピリミジン0.82gと、DMF20mLとの溶液を滴下して加え、室温に昇温し、20時間攪拌した。得られた反応液を氷水に入れ、これをトルエンにて抽出し、抽出液を飽和食塩水にて洗浄し、硫酸マグネシウムを加え、ろ過した。得られたろ液の溶媒を留去した。得られた反応混合物を、シリカゲルカラムクロマトグラフィーにて精製した。展開溶媒はヘキサン:トルエン=1:1から始め、徐々にトルエンの割合を増やすことで精製を行った。得られたろ液を濃縮することで、目的物である8−クロロ−4−(9’−フェニル−2,3’−ビ−9H−カルバゾール−9−イル)ベンゾフロ[3,2−d]ピリミジンの黄色固体を1.1g、収率45%で得た。ステップ1の合成スキームを下記式(A−1)に示す。
200mL三口フラスコに、上記ステップ1で得た8−クロロ−4−(9’−フェニル−2,3’−ビ−9H−カルバゾール−9−イル)ベンゾフロ[3,2−d]ピリミジン1.6g、9H−カルバゾール0.53g、ナトリウム−t−ブトキシド0.61g、メシチレン50mlを加え、フラスコ内を窒素置換し、ジ−tert−ブチル(1−メチル−2,2−ジフェニルシクロプロピル)ホスフィン(略称:cBRIDP)37mg、アリルパラジウム(II)クロリドダイマー10mgを加え、窒素気流下にて160℃にて4時間加熱した。得られた反応混合物をろ過し、水、次いでエタノールにて洗浄し、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。展開溶媒はトルエンのみから始め、酢酸エチルの割合を徐々に上げ、トルエン:酢酸エチル=10:1で精製を行った。得られたろ液を濃縮することで固体を得て、この固体をトルエンとエタノールにて再結晶することにより、目的物である、8Cz−4PCCzBfpm−02の黄色固体を0.98g、収率50%で得た。本ステップの合成スキームを下記式(A−2)に示す。
なお、2.33、7.13−7.17及び7.23−7.26付近のピークはトルエン由来である。
次に、本実施例で得られた8Cz−4PCCzBfpm−02を液体クロマトグラフ質量分析(Liquid Chromatography Mass Spectrometry,略称:LC/MS分析)によって分析した。
<4,8−ビス(9’−フェニル−2,3’−ビ−9H−カルバゾール−9−イル)ベンゾフロ[3,2−d]ピリミジン(略称:4,8PCCz2Bfpm−02)の合成>
還流管を付けた200mLの三口フラスコに、4,8−ジクロロ[1]ベンゾフロ[3,2−d]ピリミジン1.0g、9’−フェニル−2,3’−ビ−9H−カルバゾール3.8g、ナトリウム−t−ブトキシド1.8g、メシチレン130mlを入れ、フラスコ内を窒素置換し、cBRIDP(略称)120mg、アリルパラジウム(II)クロリドダイマー31mgを加え、140℃にて7時間加熱撹拌した。得られた反応混合物から溶媒を留去した後、濃縮した反応混合物をトルエンに溶解し、セライト・アルミナ・セライトを通してろ過した。得られたろ液を濃縮することにより、目的物である4,8PCCz2Bfpm−02の黄色固体を1.8g、収率41%で得た。本ステップの合成スキームを下記式(B−1)に示す。
次に、本実施例で得られた4,8PCCz2Bfpm−02をLC/MS分析によって分析した。その結果を図15に示す。なお、分析方法は先の実施例と同様である。m/z=987.34の成分をTargeted−MS2法を用いて測定を行った。
基板200上に電極101として、ITSO膜を厚さが70nmになるように形成した。なお、電極101の電極面積は、4mm2(2mm×2mm)とした。
比較発光素子2は、先に示す発光素子1と、発光層130及び電子輸送層118の形成工程のみ異なり、それ以外の工程は発光素子1と同様の作製方法とした。
作製した発光素子1及び比較発光素子2の電流効率−輝度特性を図17に示す。また、輝度−電圧特性を図18に示す。また、外部量子効率−輝度特性を図19に示す。なお、各発光素子の測定は室温(23℃に保たれた雰囲気)で行った。また、発光素子1及び比較発光素子2にそれぞれ2.5mA/cm2の電流密度で電流を流した際の電界発光スペクトルを図20に示す。なお、測定は室温で行った。
次に、発光素子1、比較発光素子2の2mAにおける定電流駆動試験を行った。その結果を図21に示す。図21から分かるように発光素子1の輝度半減寿命は比較発光素子2の輝度半減寿命と比較し、2倍程向上していることが分かった。これは、本発明の一態様である8Cz−4PCCzBfpm−02は、ベンゾフロ[3,2−d]ピリミジン骨格の6乃至9位に縮合環の一つであるカルバゾール骨格を有するため、電気化学的な安定性が高いためである。
<ステップ1:9−(3−ブロモフェニル)−9’−フェニル−2,3’−ビ−9H−カルバゾールの合成>
9’−フェニル−2,3’−ビ−9H−カルバゾール16g、3ーブロモヨードベンゼン14g、リン酸三カリウム12gを、500mL三口フラスコに入れ、フラスコ内を窒素置換した。ここに1,4−ジオキサン190mL、trans−1,2−ジアミノシクロヘキサン0.65g、ヨウ化銅(I)0.54gを加え、窒素気流下で120℃にて8時間加熱した。さらに、リン酸三カリウム3.0g、trans−1,2−ジアミノシクロヘキサン0.16g、ヨウ化銅(I)0.13gを加え、窒素気流下で120℃にて14時間加熱した。得られた反応混合物に水とエタノールを加え、ろ過した。ろ液をトルエンにて抽出し、抽出液を飽和食塩水にて洗浄し、硫酸マグネシウムを加え、ろ過した。ろ液の溶媒を留去し、残留物を熱トルエンに溶かした。これを、トルエン:ヘキサン=1:2を展開溶媒としたシリカゲルカラムクロマトグラフィーにて精製することにより目的物の淡い黄色固体を16g、収率72%で得た。ステップ1の合成スキームを下記式(C−1)に示す。
次に、上記ステップ1で得た9−(3−ブロモフェニル)−9’−フェニル−2,3’−ビ−9H−カルバゾール16g、ビス(ピナコラート)ジボロン9.1g、酢酸カリウム9.1gを500mL三口フラスコに入れ、フラスコ内を窒素置換した。ここに、ジメチルスルホキシド(略称:DMSO)150mL、[1,1’−ビス(ジフェニルホスフィノ)フェロセン]ジクロロパラジウム(II)(略称:Pd(dppf)2Cl2)1.1gを加え、110℃で13時間加熱撹拌した。得られた反応混合物に水を加え、ろ過した。ろ液をトルエンにて抽出し、抽出液を飽和食塩水にて洗浄し、硫酸マグネシウムを加え、ろ過した。得られたろ液の溶媒を留去し、残渣を中性シリカゲルカラムクロマトグラフィーにて精製した。展開溶媒はトルエン:ヘキサン=1:10から、徐々にトルエンの割合を増やすことで精製を行った。得られたフラクションの溶媒を留去し、得られた固体をトルエンとヘキサンの混合溶媒にて再結晶することにより目的物の淡黄色固体を9.7g、収率58%で得た。ステップ2の合成スキームを下記式(C−2)に示す。
次に、4,8−ジクロロ[1]ベンゾフロ[3,2−d]ピリミジン1.1g、上記ステップ2で得た9−[3−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)フェニル]−9’−フェニル−2,3’−ビ−9H−カルバゾール3.7g、2Mフッ化セシウム水溶液1,7g、トルエン50mL、エタノール5mLを100mL三口フラスコに入れ、フラスコ内を窒素置換し、酢酸パラジウム(II)21mg、ジ(1−アダマンチル)−n−ブチルホスフィン67mgを加え、90℃で21時間加熱した。得られた反応混合物に水、エタノールを加え、ろ過し、ろ物をエタノールで洗浄した。このろ物を中性シリカゲルカラムクロマトグラフィーにて精製した。展開溶媒は、トルエンから徐々に酢酸エチルを加え最終的にトルエン:酢酸エチル=1:10にすることで精製を行った。得られたフラクションを乾固することで、目的物の淡黄色固体を1.9g、収率59%で得た。また、同様の合成法を行い、追加で目的物の淡黄色固体を1g合成した。ステップ3の合成スキームを下記式(C−3)に示す。
次に、上記ステップ3で得た8−クロロ−4−[3−(9’−フェニル−2,3’−ビ−9H−カルバゾール−9−イル)フェニル]ベンゾフロ[3,2−d]ピリミジン2.9g、9H−カルバゾール0.84g、ナトリウム−t−ブトキシド0.97g、メシチレン100mLを、200mL三口フラスコに入れ、フラスコ内を窒素置換した。これに、ジ−tert−ブチル(1−メチル−2,2−ジフェニルシクロプロピル)ホスフィン(略称:cBRIDP)59mg、アリルパラジウム(II)クロリドダイマー15mgを加え、160℃で21時間加熱した。得られた反応混合物に水を加え、ろ過した。ろ液をトルエンにて抽出し、抽出液を飽和食塩水にて洗浄し、硫酸マグネシウムを加え、ろ過した。得られたろ液の溶媒を留去した。得られた反応混合物を、トルエンから徐々に酢酸エチルを加え、最終的にトルエン:酢酸エチル=1:10を展開溶媒としたシリカゲルカラムクロマトグラフィーにて精製した。得られたフラクションの溶媒を留去し、得られた固体をトルエンとヘキサンの混合溶媒にて再結晶することにより目的物である8Cz−4mPCCzPBfpmの淡黄色固体を1.0g、収率29%で得た。ステップ4の合成スキームを下記式(C−4)に示す。
次に、トルエン溶液中の8Cz−4mPCCzPBfpmの吸収スペクトル及び発光スペクトルを図23に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。なお、測定方法は先の実施例と同様に行った。
基板200上に電極101として、ITSO膜を厚さが70nmになるように形成した。なお、電極101の電極面積は、4mm2(2mm×2mm)とした。
発光素子4は、先に示す比較発光素子3と、発光層130及び電子輸送層118の形成工程のみ異なり、それ以外の工程は比較発光素子3と同様の作製方法とした。
発光素子5は、先に示す比較発光素子3と、発光層130及び電子輸送層118の形成工程のみ異なり、それ以外の工程は比較発光素子3と同様の作製方法とした。
作製した比較発光素子3、発光素子4及び発光素子5の電流効率−輝度特性を図25に示す。また、電流密度−電圧特性を図26に示す。また、外部量子効率−輝度特性を図27に示す。なお、各発光素子の測定は室温(23℃に保たれた雰囲気)で行った。また、比較発光素子3、発光素子4及び発光素子5にそれぞれ2.5mA/cm2の電流密度で電流を流した際の電界発光スペクトルを図28に示す。なお、測定は室温で行った。
次に、比較発光素子3、発光素子4及び発光素子5の2mAにおける定電流駆動試験を行った。その結果を図29に示す。図29から分かるように、比較発光素子3と比較し発光素子4、発光素子5は信頼性が向上していることが分かった。よって、ベンゾフロ[3,2−d]ピリミジン骨格の6乃至9位に縮合環を有する有機化合物は、ベンゾフロ[3,2−d]ピリミジン骨格の6乃至9位に縮合環を有さない有機化合物よりも信頼性が良好であることが示唆される。また、発光素子4よりも発光素子5の方が信頼性が良好であることが分かった。よって、ベンゾフロ[3,2−d]ピリミジン骨格の4位に直接正孔輸送性骨格であるカルバゾール骨格が結合するよりも、アリール基の一つであるフェニル基を介して、ベンゾフロ[3,2−d]ピリミジン骨格とカルバゾール骨格が結合した構造の方が信頼性が良好であることが示唆される。
101 電極
102 電極
106 発光ユニット
110 発光ユニット
111 正孔注入層
112 正孔輸送層
113 電子輸送層
114 電子注入層
115 電荷発生層
116 正孔注入層
117 正孔輸送層
118 電子輸送層
119 電子注入層
120 発光層
121 ホスト材料
121_1 有機化合物
121_2 有機化合物
122 発光性材料
130 発光層
131 材料
132 ホスト材料
134 ゲスト材料
150 発光素子
170 発光層
200 基板
220 基板
250 発光素子
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 電極
614 絶縁物
616 EL層
617 電極
618 発光素子
623 nチャネル型TFT
624 pチャネル型TFT
900 携帯情報端末
901 筐体
902 筐体
903 表示部
905 ヒンジ部
910 携帯情報端末
911 筐体
912 表示部
913 操作ボタン
914 外部接続ポート
915 スピーカ
916 マイク
917 カメラ
920 カメラ
921 筐体
922 表示部
923 操作ボタン
924 シャッターボタン
926 レンズ
1001 基板
1002 下地絶縁膜
1003 ゲート絶縁膜
1006 ゲート電極
1007 ゲート電極
1008 ゲート電極
1020 層間絶縁膜
1021 層間絶縁膜
1022 電極
1024B 電極
1024G 電極
1024R 電極
1025B 下部電極
1025G 下部電極
1025R 下部電極
1026 隔壁
1028 EL層
1029 電極
1031 封止基板
1032 シール材
1033 基材
1034B 着色層
1034G 着色層
1034R 着色層
1035 黒色層
1036 オーバーコート層
1037 層間絶縁膜
1040 画素部
1041 駆動回路部
1042 周辺部
3500 多機能端末
3502 筐体
3504 表示部
3506 カメラ
3508 照明
3600 ライト
3602 筐体
3608 照明
3610 スピーカ
8501 照明装置
8502 照明装置
8503 照明装置
8504 照明装置
9000 筐体
9001 表示部
9003 スピーカ
9005 操作キー
9006 接続端子
9007 センサ
9008 マイクロフォン
9055 ヒンジ
9200 携帯情報端末
9201 携帯情報端末
9202 携帯情報端末
Claims (17)
- 下記一般式(G0)で表される有機化合物。
(一般式(G0)において、Aは、一つまたは二つの縮合環を含む置換基を少なくとも有するベンゾフロ[3,2−d]ピリミジン骨格、もしくは、一つまたは二つの縮合環を含む置換基を少なくとも有するベンゾチエノ[3,2−d]ピリミジン骨格を表し、R1乃至R15は、それぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表す。) - 請求項1において、
前記Arは前記ベンゾフロ[3,2−d]ピリミジン骨格、若しくは前記ベンゾチエノ[3,2−d]ピリミジン骨格の4位に結合している、有機化合物。 - 下記一般式(G1)で表される有機化合物。
(一般式(G1)において、Qは、酸素または硫黄を表し、R1乃至R15は、それぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、R16乃至R20のいずれか一つは、一つまたは二つの縮合環を含む置換基を表し、その他はそれぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは、置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表す。) - 下記一般式(G2)で表される有機化合物。
(一般式(G2)において、Qは、酸素または硫黄を表し、R1乃至R19は、それぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは、置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表し、Bは一つまたは二つの縮合環を含む置換基を表す。) - 下記一般式(G3)で表される有機化合物。
(一般式(G3)において、Qは、酸素または硫黄を表し、R1乃至R19はそれぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは、置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表し、Bは一つまたは二つの縮合環を含む置換基を表す。) - 請求項1乃至請求項5において、
前記縮合環を形成する炭素数が10乃至20である、有機化合物。 - 請求項1乃至請求項6において、
前記縮合環がカルバゾール骨格、ベンゾチオフェン骨格、ジベンゾフラン骨格のいずれか一つを含む、有機化合物。 - 下記一般式(G4)で表される有機化合物。
(一般式(G4)において、Qは、酸素または硫黄を表し、R1乃至R27はそれぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは、置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表す。) - 下記一般式(G5)で表される有機化合物。
(一般式(G5)において、Qは、酸素または硫黄を表し、R1乃至R34はそれぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは、置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表す。) - 下記一般式(G6)で表される有機化合物。
(一般式(G6)において、Qは、酸素または硫黄を表し、R15は、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは、置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表す。) - 下記一般式(G7)で表される有機化合物。
(一般式(G7)において、Qは、酸素または硫黄を表し、R15及びR34はそれぞれ独立に、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数3乃至7のシクロアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基、のいずれかを表し、Arは、置換もしくは無置換の炭素数6乃至25のアリーレン基、または単結合を表す。) - 請求項1乃至請求項11のいずれか一項に記載の有機化合物を有する発光素子。
- 請求項12において、
遅延蛍光を含む成分を有する発光、
を呈する機能を有する発光素子。 - 請求項12において、
さらに、燐光材料を有する発光素子。 - 請求項12乃至請求項14いずれか一項に記載の発光素子を有する発光部と、
基板と、を有する発光装置。 - 請求項15に記載の発光装置と、
筐体及びタッチセンサの少なくとも一と、
を有する電子機器。 - 請求項15に記載の発光装置と、
筐体、接続端子、または、保護カバーと、
を備えることを特徴とする照明装置。
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CN108239094A (zh) | 2018-07-03 |
US20180182976A1 (en) | 2018-06-28 |
KR20180074582A (ko) | 2018-07-03 |
JP2022079492A (ja) | 2022-05-26 |
KR102616441B1 (ko) | 2023-12-26 |
US10868258B2 (en) | 2020-12-15 |
JP7330322B2 (ja) | 2023-08-21 |
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