JP2022166114A - 電子素子のための材料 - Google Patents
電子素子のための材料 Download PDFInfo
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- JP2022166114A JP2022166114A JP2022125716A JP2022125716A JP2022166114A JP 2022166114 A JP2022166114 A JP 2022166114A JP 2022125716 A JP2022125716 A JP 2022125716A JP 2022125716 A JP2022125716 A JP 2022125716A JP 2022166114 A JP2022166114 A JP 2022166114A
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- 239000000463 material Substances 0.000 title abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
- 239000011159 matrix material Substances 0.000 claims abstract description 28
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 25
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 20
- 125000004306 triazinyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims description 72
- -1 N(R 1 ) 2 Inorganic materials 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 239000000412 dendrimer Substances 0.000 claims description 14
- 229920000736 dendritic polymer Polymers 0.000 claims description 14
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 13
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000005580 triphenylene group Chemical group 0.000 claims description 6
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006619 Stille reaction Methods 0.000 claims description 2
- 238000006887 Ullmann reaction Methods 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 238000006880 cross-coupling reaction Methods 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 abstract description 3
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 89
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 19
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 18
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical class C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 230000004907 flux Effects 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical compound C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- YKCZGQXLXXMGNR-UHFFFAOYSA-N (9,9-dimethylfluoren-4-yl)boronic acid Chemical compound C1=CC=C(B(O)O)C2=C1C(C)(C)C1=CC=CC=C12 YKCZGQXLXXMGNR-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
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- IOPQERQQZZREDR-UHFFFAOYSA-N 1-bromo-3,5-diphenylbenzene Chemical compound C=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 IOPQERQQZZREDR-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- WMHZKJGIAYFAJT-UHFFFAOYSA-N 4-(9,9-dimethylfluoren-1-yl)triazine Chemical compound N1=NN=C(C=C1)C1=CC=CC=2C3=CC=CC=C3C(C1=2)(C)C WMHZKJGIAYFAJT-UHFFFAOYSA-N 0.000 description 2
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- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
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- 239000012043 crude product Substances 0.000 description 2
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- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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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
- C07D401/10—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 linked by a carbon chain containing aromatic rings
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- 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
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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Abstract
Description
Z1およびZ2は、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R1)3、B(OR1)2、B(R1)2、B(N(R1)2)2、OSO2R1、1~40のC原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、また2~40のC原子を有する、直鎖の、アルケニルもしくはアルキニル基、3~40のC原子を有する、分岐もしくは環状の、アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR1によって置換されていてもよく、ここで1以上の、好ましくは非隣接のCH2基が、(R1)C=C(R1)、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=N(R1)2、P(=O)(R1)、SO、SO2、N(R1)2、O、SまたはCON(R1)2によって置き換えられていてもよく、かつ1以上のH原子がD、F、Cl、Br、I、CNまたはNO2によって置き換えられていてもよい)、またはそれぞれのケースにおいて1以上のラジカルR1によって置換されていてもよい、5~60の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系、または1以上のラジカルR1によって置換されていてもよい、5~60の芳香族環原子を有する、アリールオキシもしくはヘテロアリールオキシ基である。
Xは、出現毎に同一であるかまたは異なり、CR1またはNであり、ただし、少なくとも1つのXがNである。
Lは、出現毎に同一であるかまたは異なり、5~30の芳香族環原子を有する、芳香族またはヘテロ芳香族環系であり、1以上の非芳香族ラジカルR1によって置換されていてもよい。
a、b、cおよびdは、それぞれ、同一であるかまたは異なり、0または1であり、ただし、a、b、cまたはdのうちの少なくとも1つが1である。
eおよびfは、それぞれ、同一であるかまたは異なり、0、1、2または3である。
nは、出現毎に同一であるかまたは異なり、0または1である。
1.蛍光または燐光発光体のためのマトリックス材料として使用される、本発明による化合物は、長い寿命をもたらす。これは、特に、化合物が燐光発光体のためのマトリックス材料として使用される場合に、あてはまる。
2.本発明による化合物は、ひじょうに高い効率をもたらす。これは、特に、化合物が、燐光発光体のためのマトリックス材料として、または正孔輸送材料として使用される場合に、あてはまる。
3.いくつかの形態において、本発明による化合物は、低電圧素子をもたらす。これは、特に、化合物が、燐光発光体のためのマトリックス材料として、または電子輸送層において、使用される場合にあてはまる。
合成例
以下の合成は、特に断らない限り、乾燥溶媒中で、保護ガス雰囲気下で行われる。溶媒および試薬は、ALDRICH社またはABCR社から購入できる。市販されている出発材料に示された数値は、対応するCAS番号である。
以下の例V1-V7およびE1-E22(表1および2参照)は、さまざまなOLEDからのデータを示す。
Claims (17)
- 式(I)の化合物。
Z1およびZ2は、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R1)3、B(OR1)2、B(R1)2、B(N(R1)2)2、OSO2R1、1~40のC原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、または2~40のC原子を有する、直鎖の、アルケニルもしくはアルキニル基、3~40のC原子を有する、分岐もしくは環状の、アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR1によって置換されていてもよく、ここで1以上のCH2基が、(R1)C=C(R1)、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=N(R1)、P(=O)(R1)、SO、SO2、N(R1)2、O、SまたはCON(R1)2によって置き換えられていてもよく、かつ1以上のH原子がD、F、Cl、Br、I、CNまたはNO2によって置き換えられていてもよい)、またはそれぞれのケースにおいて1以上のラジカルR1によって置換されていてもよい、5~60の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系、または1以上のラジカルR1によって置換されていてもよい、5~60の芳香族環原子を有する、アリールオキシもしくはヘテロアリールオキシ基であり、
Y1およびY2は、出現毎に同一であるかまたは異なり、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、(R1)C=C(R1)Ar1、CN、NO2、Si(R1)3、B(OR1)2、B(R1)2、B(N(R1)2)2、OSO2R1、1~40のC原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、または2~40のC原子を有する、直鎖の、アルケニルもしくはアルキニル基、3~40のC原子を有する、分岐もしくは環状の、アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR1によって置換されていてもよく、ここで1以上のCH2基が、(R1)C=C(R1)、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=N(R1)2、P(=O(R1)2、SO、SO2、N(R1)2、O、SまたはCON(R1)2によって置き換えられていてもよく、かつ1以上のH原子がD、F、Cl、Br、I、CNまたはNO2、によって置き換えられていてもよい)、またはそれぞれのケースにおいて1以上のラジカルR1によって置換されていてもよい、5~60の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系、または1以上のラジカルR1によって置換されていてもよい、5~60の芳香族環原子を有する、アリールオキシもしくはヘテロアリールオキシ基、またはこれらの系の組み合わせであり、2以上の隣接する置換基Y1またはY2が、縮合の、単環状もしくは多環状の、脂肪族もしくは芳香族またはヘテロ芳香族環系を互いに形成していてもよく、
Ar1およびAr2は、出現毎に同一であるかまたは異なり、ベンゼン、オルト-ビフェニル、メタ-ビフェニル、パラ-ビフェニル、オルト-ターフェニル、メタ-ターフェニル、パラ-ターフェニル、分岐のターフェニル、ナフチル、トリフェニレン、9,9-ジアルキルフルオレニル、N-フェニルカルバゾール、ジベンゾフランおよびジベンゾチオフェンからなる群から選択され、それぞれのケースにおいて1以上のラジカルR1によって置換されていてもよく、ただし、ヘテロ芳香族環系は炭素-炭素結合を介して結合されており、
R1は、出現毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、CN、Si(R2)3、1~40のC原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、3~40のC原子を有する、分岐もしくは環状の、アルキル、アルコキシもしくはチオアルコキシ基(これらは、1以上のラジカルR2によって置換されていてもよく、それぞれ1以上の非隣接のCH2基がC(R2)=C(R2)、Si(R2)2、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SまたはCONR2によって置き換えられていてもよく、かつ1以上のH原子がD、F、Cl、BrまたはIによって置き換えられていてもよい)、1以上のラジカルR2によって置換されていてもよい、6~40の炭素原子を有する、芳香族もしくはヘテロ芳香族環系、または1以上のラジカルR2によって置換されていてもよい、5~60の芳香族環原子を有するアリールオキシ基、1以上のラジカルR2によって置換されていてもよい、5~60の芳香族環原子を有するアラルキル基からなる群から選択され、ここで、所望により、2以上の隣接する置換基R1が、単環状もしくは多環状の、脂肪族、芳香族またはヘテロ芳香族環系を互いに形成していてもよく、これは1以上のラジカルR2によって置換されていてもよく、ここでR2は、H、D、F、1~20の炭素原子を有する脂肪族炭化水素ラジカル、または5~30のC原子を有する、芳香族もしくはヘテロ芳香族環系からなる群から選択され、2以上の隣接する置換基R2が、単環状もしくは多環状、脂肪族、芳香族またはヘテロ芳香族環系を互いに形成していてもよく、
Xは、出現毎に同一であるかまたは異なり、CR1またはNであり、ただし、少なくとも1つのXがNであり、
Lは、出現毎に同一であるかまたは異なり、5~30の芳香族環原子を有する、芳香族またはヘテロ芳香族環系であり、1以上の非芳香族ラジカルR1によって置換されていてもよく、
a、b、cおよびdは、それぞれ、同一であるかまたは異なり、0または1であり、ただし、a、b、cまたはdのうちの少なくとも1つが1であり、
eおよびfは、それぞれ、同一であるかまたは異なり、0、1、2または3であり、かつ
nは、出現毎に同一であるかまたは異なり、0または1である) - Z1およびZ2が、同一の置換基であり、かつフルオレン環の9位以外のどの位置においても互いに結合されていない、請求項1に記載の化合物。
- 記Xの両方が窒素である、式IX~XVIIのいずれかに記載の、請求項6に記載の化合物。
- eおよびfの両方が0である、請求項4、5および7のいずれか一項に記載の化合物。
- nが0である、請求項2~5および7のいずれか一項に記載の化合物。
- a、b、cまたdが0でないときはいつでも、両方のXが窒素である、請求項2~5および7のいずれか一項に記載の化合物。
- a、b、cまたdが0でないときはいつでも、Xのうちの1つが窒素であり、かつもう一方がCR1である、請求項2~5および7のいずれか一項に記載の化合物。
- Ar1が、N-フェニルカルバゾール、ジベンゾフランおよびジベンゾチオフェンからなる群から選択され、Ar2が、ベンゼン、オルト-ビフェニル、メタ-ビフェニル、パラ-ビフェニル、オルト-ターフェニル、メタ-ターフェニル、パラ-ターフェニル、分岐のターフェニル、ナフチル、トリフェニレン、9,9-ジアルキルフルオレニル、N-フェニルカルバゾール、ジベンゾフランおよびジベンゾチオフェンからなる群から選択される、請求項1~11のいずれか一項に記載の化合物。
- 請求項1~12のいずれか一項に記載の化合物を調製する方法であって、以下の反応ステップ:まだトリアジニルまたはピリミジニル基を含まない化合物(I)の骨格の合成;およびスズキ、ネギシ、ヤマモト、グリニャール-クロスもしくはスティルカップリングを含むC-Cカップリング、またはブッフバルトもしくはウルマンカップリングを含むC-Nカップリングの骨格の反応、を含んでなる方法。
- 請求項1~12のいずれか一項に記載の1以上の化合物を含むオリゴマー、ポリマー、またはデンドリマーであって、ポリマー、オリゴマーまたはデンドリマーへの化合物からの1以上の結合が、1以上の位置で、置換基の代わりに存在するオリゴマー、ポリマーまたはデンドリマー。
- 請求項1~12のいずれか一項に記載の少なくとも1つの化合物、または請求項14に記載のオリゴマー、ポリマーもしくはデンドリマー、および少なくとも1つの溶媒を含んでなる配合剤。
- 請求項1~12のいずれか一項に記載の少なくとも1つの化合物、または請求項14に記載のオリゴマー、ポリマーもしくはデンドリマーを含んでなる電子素子であって、有機エレクトロルミネッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機太陽電池、色素増感有機太陽電池、有機光学検査器、有機光受容器、有機電場消光素子、発光電子化学電池、有機レーザーダイオード、および有機プラズマ発光素子からなる群から選択される、電子素子。
- 請求項1~12のいずれか一項に記載の化合物または14に記載のオリゴマー、ポリマーもしくはデンドリマーが、燐光もしくは蛍光発光体、電子ブロックもしくは励起子ブロック層、電荷発生層、正孔ブロック層、または電子輸送層のための、1つ以上のマトリックス材料として使用されることを特徴とする、有機エレクトロルミネッセンス素子。
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- 2016-07-01 CN CN201680044327.6A patent/CN107922359A/zh active Pending
- 2016-07-01 EP EP16734191.6A patent/EP3328841B1/en active Active
- 2016-07-01 US US15/748,437 patent/US11098019B2/en active Active
- 2016-07-01 JP JP2018504890A patent/JP6839697B2/ja active Active
- 2016-07-01 EP EP23202035.4A patent/EP4301110A3/en active Pending
- 2016-07-01 KR KR1020187005481A patent/KR20180031766A/ko not_active Application Discontinuation
- 2016-07-01 WO PCT/EP2016/001117 patent/WO2017016630A1/en active Application Filing
- 2016-07-27 TW TW111109932A patent/TW202225147A/zh unknown
- 2016-07-27 TW TW109134170A patent/TWI761977B/zh active
- 2016-07-27 TW TW105123770A patent/TWI707845B/zh active
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2021
- 2021-02-12 JP JP2021021129A patent/JP7121817B2/ja active Active
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2022
- 2022-08-05 JP JP2022125716A patent/JP2022166114A/ja active Pending
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Also Published As
Publication number | Publication date |
---|---|
JP2018531883A (ja) | 2018-11-01 |
TWI707845B (zh) | 2020-10-21 |
EP4301110A2 (en) | 2024-01-03 |
TW202225147A (zh) | 2022-07-01 |
TWI761977B (zh) | 2022-04-21 |
EP3328841B1 (en) | 2023-10-11 |
KR20180031766A (ko) | 2018-03-28 |
TW202124366A (zh) | 2021-07-01 |
WO2017016630A1 (en) | 2017-02-02 |
EP3328841A1 (en) | 2018-06-06 |
US11098019B2 (en) | 2021-08-24 |
EP4301110A3 (en) | 2024-04-10 |
JP7121817B2 (ja) | 2022-08-18 |
JP6839697B2 (ja) | 2021-03-10 |
JP2021098707A (ja) | 2021-07-01 |
CN107922359A (zh) | 2018-04-17 |
TW201718526A (zh) | 2017-06-01 |
US20180222872A1 (en) | 2018-08-09 |
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