JP2012508202A - 有機エレクトロルミネセント素子 - Google Patents
有機エレクトロルミネセント素子 Download PDFInfo
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- JP2012508202A JP2012508202A JP2011535023A JP2011535023A JP2012508202A JP 2012508202 A JP2012508202 A JP 2012508202A JP 2011535023 A JP2011535023 A JP 2011535023A JP 2011535023 A JP2011535023 A JP 2011535023A JP 2012508202 A JP2012508202 A JP 2012508202A
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- Prior art keywords
- group
- aromatic
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- substituted
- different
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 239000000126 substance Substances 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims description 150
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 85
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- -1 NR 3 Inorganic materials 0.000 claims description 47
- 150000003254 radicals Chemical group 0.000 claims description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 239000011159 matrix material Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 230000000903 blocking effect Effects 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 22
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 125000002950 monocyclic group Chemical group 0.000 claims description 20
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 125000003367 polycyclic group Chemical group 0.000 claims description 19
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 18
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 12
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229930192474 thiophene Natural products 0.000 claims description 11
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000000412 dendrimer Substances 0.000 claims description 9
- 229920000736 dendritic polymer Polymers 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 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 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052787 antimony Inorganic materials 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 44
- 239000007787 solid Substances 0.000 description 32
- 239000000463 material Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000006872 improvement Effects 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical class BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 150000007858 diazaphosphole derivatives Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- BCIDDURGCAHERU-UHFFFAOYSA-N 1,2-dibromo-4,5-dimethylbenzene Chemical compound CC1=CC(Br)=C(Br)C=C1C BCIDDURGCAHERU-UHFFFAOYSA-N 0.000 description 3
- PCHXKBMOEZRZGD-UHFFFAOYSA-N 1-n,2-n-bis(2-methylphenyl)benzene-1,2-diamine Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1NC1=CC=CC=C1C PCHXKBMOEZRZGD-UHFFFAOYSA-N 0.000 description 3
- QWGFRXKFUXRXBM-UHFFFAOYSA-N 4,5-dimethyl-1-n,2-n-bis(4-phenylphenyl)benzene-1,2-diamine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC=1C=C(C)C(C)=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 QWGFRXKFUXRXBM-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- ZQCPBFMCBBHJPV-UHFFFAOYSA-N 1-n,2-n-bis(4-phenylphenyl)benzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2C=CC(=CC=2)C=2C=CC=CC=2)C=1NC(C=C1)=CC=C1C1=CC=CC=C1 ZQCPBFMCBBHJPV-UHFFFAOYSA-N 0.000 description 2
- ZNZCBZJTANSNGL-UHFFFAOYSA-N 1-n,2-n-diphenylbenzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2C=CC=CC=2)C=1NC1=CC=CC=C1 ZNZCBZJTANSNGL-UHFFFAOYSA-N 0.000 description 2
- PZIFARYSEFVLME-UHFFFAOYSA-N 1-n,2-n-dipyridin-4-ylbenzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2C=CN=CC=2)C=1NC1=CC=NC=C1 PZIFARYSEFVLME-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
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- XGVDODZGAORRLN-UHFFFAOYSA-N 2-n-(4,6-diphenyl-1,3,5-triazin-2-yl)-1-n-phenylbenzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=1NC1=CC=CC=C1 XGVDODZGAORRLN-UHFFFAOYSA-N 0.000 description 2
- QTZAWJBRPNFBSD-UHFFFAOYSA-N 4,5-dimethyl-1-n,2-n-diphenylbenzene-1,2-diamine Chemical compound C=1C=CC=CC=1NC=1C=C(C)C(C)=CC=1NC1=CC=CC=C1 QTZAWJBRPNFBSD-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 102100036305 C-C chemokine receptor type 8 Human genes 0.000 description 2
- PODHJIQSMSGBRQ-UHFFFAOYSA-N C1=CC=CC=C1.P(O)(O)=O Chemical compound C1=CC=CC=C1.P(O)(O)=O PODHJIQSMSGBRQ-UHFFFAOYSA-N 0.000 description 2
- 0 CCCNP*ONC(C)(*)* Chemical compound CCCNP*ONC(C)(*)* 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 101000837299 Euglena gracilis Trans-2-enoyl-CoA reductase Proteins 0.000 description 2
- 101000716063 Homo sapiens C-C chemokine receptor type 8 Proteins 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
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- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 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
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007650 screen-printing 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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Abstract
Description
以下の合成は、特に断らなければ、乾燥した溶媒内において、保護ガス雰囲気の下で実施される。使用した出発化合物は、例えば、1,4-ビス(ホスホン酸)ベンゼン(Inorganic Chemistry 1996, 35(17), 4942-4949)、N,N’-ジフェニル-1,2-ベンゼンジアミン(Organic Letters 2007, 9(7), 1339-1342)又はN-フェニル-o-フェニレンジアミン(Indian Journal of Pharmaceutical Sciences 2003, 65(2), 135-138)であり得る。
同様に、以下の化合物を得ることが出来る。
1.06g(4.75mモル)のPd(OAc)2及び14.46ml(14.46mモル)のトリ第3ブチルホスフィン(1Mトルエン溶液)を660mlのガス抜きされたトルエンに加え、混合物を5時間攪拌する。次いで、240mモルの1,2-ジブロモ-ベンゼン誘導体、505mモルのアリールアミン、及び67.22g(700nモル)のナトリウム第3ブトキシドを溶液に加え、その後、ガス抜きし、保護ガス雰囲気で140℃で10時間攪拌する。溶液を冷却した後、600mlのNH4Cl溶液と150mlの酢酸エチルを加え、相分離し、水で洗浄し、MgSO4上で乾燥し、蒸発させた。固形分をトルエンに溶解し、セライト(商標)により濾過する。粗生成物を熱ヘプタンとともに攪拌することにより洗浄する。
158mモルのN,N’-ジアリール-1,2-ベンゼンジアミンを500mlのピリジンに溶解し、0℃に冷却する。この溶液に、1000mlのトルエンに溶解された74mモルの1,2-ビス(ホスホニルクロリド)ベンゼンを0℃で滴下し、激しく攪拌し、得られた混合物を1時間攪拌し、還流下で24時間加熱する。溶媒を真空中で蒸発させ、固形分を酢酸エチル内で沸騰させることにより洗浄し、吸引濾過し、100mlの酢酸エチルにより一回洗浄し、その後、ジオキサンから再結晶させる。
例12:H4の合成
例13:H5の合成
例14:H6の合成
例15:H7の合成
例16:H8の合成
例17:H9の合成
例18:H10の合成
同様に、以下の化合物が得られる。
例29:H12の合成
例30:OLEDの製造
本発明のOLED及び従来技術のOLEDを、ここに記載した環境に適合される(層の厚さの変化及び使用した物質)、WO 04/058911に従って、一般的手順で製造される。
例56−60:ジアザホスホールズの合成
下記のジアザホスホールズは、例55と類似の対応する塩化燐との反応により、対応するジアミノ芳香族化合物から製造され得る。
Claims (15)
- 下記式(1)又は式(39)の少なくとも1種の化合物を含む電子デバイス。
Yは、それぞれ現れるごとに同一か又は異なる、P(=O)、P(=S)、P、As(=O)、As(=S)、As、Sb(=O)、Sb(=S)、Sb、Bi(=O)、Bi(=S)、又はBiであり、
Arは、それぞれ現れるごとに同一か又は異なる、1つ又はそれ以上のラジカルR1と置換されてもよい、5〜60の芳香環原子を有する芳香環又はヘテロ芳香環系であり、
Ar1は、それぞれ現れるごとに同一か又は異なる、1つ又はそれ以上のラジカルR1と置換されてもよい、5〜18の芳香環原子を有するアリール又はヘテロアリール基であり、
Xは、それぞれ現れるごとに同一か又は異なる、CR1又はNであり、
Lは、単結合又は二価、三価、又は四価の基であり、
R1は、それぞれ現れるごとに同一か又は異なる、H、D、F、Cl、Br、I、CN、NO2、N(R3)2、C(=O)R3、そのそれぞれが1又はそれ以上のラジカルR3により置換されてもよく、また1つ又はそれ以上の非隣接CH2基がR3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S、又はCONR3により置換されてもよく、1つ又はそれ以上のHがD、F、Cl、Br、I、CN、又はNO2により置換されてもよい、1〜40のC原子を有する直鎖アルキル、アルコキシ又はチオアルキル基、2〜40のC原子を有するアルケニル又はアルキニル基、それぞれの場合に1つ又はそれ以上のR3により置換されてもよい5〜60の芳香環原子を有する芳香環又はヘテロ芳香環系、それぞれの場合に1つ又はそれ以上のR3により置換されてもよい5〜60の芳香環原子を有するアリールオキシ又はヘテロアリールオキシ基、又は2つ又はそれ以上の隣接する置換基R1が任意に、1つ又はそれ以上のR3により置換されてもよい、モノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成する、これらの系の組合せからなる群から選択される、
R2は、それぞれ現れるごとに同一か又は異なる、そのそれぞれが1つ又はそれ以上のラジカルR3により置換されてもよく、1つ又はそれ以上の非隣接CH2基がR3C=CR3、C≡C、C=Oにより置換されてもよく、1つ又はそれ以上のHがD、F、Cl、Br、I、CN、又はNO2により置換されてもよい、1〜40のC原子を有する直鎖アルキル又は3〜40のC原子を有する分枝又は環状アルキル基、1つ又はそれ以上のラジカルR3により置換されてもよい5〜60の芳香環原子を有する芳香環又はヘテロ芳香環系、又はこれらの系の組合せからなる群から選択され、1,2位において相互に隣接するR1及びR2は、1つ又はそれ以上のラジカルR3により置換されてもよいモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を任意に形成し、
R3は、H、D、F、CN、1〜20のC原子を有する脂肪族炭化水素ラジカル、1つ又はそれ以上のHがD、F、Cl、Br、I、又はCNにより置換されてもよい、5〜30の芳香環原子を有する芳香環又はヘテロ芳香環系からなる群から選択され、2つ又はそれ以上の隣接置換基R3は、相互にモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成し、
nは、1〜10、好ましくは1、2、3、4、5又は6であり、
mは、Lが単結合又は二価基であるならば1であり、Lが三価基であるならば2であり、Lが四価基であるならば3であり、
qは、それぞれ現れるごとに同一か又は異なる、0又は1である。 - Ar1は、それぞれ現れるごとに同一か又は異なる、5〜14個の芳香環原子、好ましくは5〜10個の芳香環原子、アリール又はヘテロアリール基を表し、特に好ましくは、ベンゼン、ピリジン、ピリミジン、ピリダジン、ピラジン、トリアジン、フラン、チオフェン、ピロール、ナフタレン、フェナントレン、キノリン、イソキノリン、キノキサリン、インドール、ベンゾフラン、ベンゾチオフェン、又はカルバゾールを表すことを特徴とする請求項1に記載の電子デバイス。
- 符号YはP(=O)を表し、符合Zは、それぞれ現れるごとに同一か又は異なる、NR2を表すことを特徴とする請求項1〜3のいずれかに記載の電子デバイス。
- R2は、それぞれ現れるごとに同一か又は異なる、それぞれの場合において、1つ又はそれ以上のR3により置換されてもよい5〜24の芳香環原子を有する芳香環又はヘテロ芳香環系からなる群から選択され、好ましくは、そのそれぞれが1つ又はそれ以上のR3により置換されてもよい、フェニル、ナフチル、ビフェニル、又はターフェニル、特に、フェニル又はビフェニルを表すことを特徴とする請求項1〜4のいずれかに記載の電子デバイス。
- Ar1は、それぞれ現れるごとに同一か又は異なる、5〜14の芳香環原子を有する、好ましくは5〜10の芳香環原子を有する、特に好ましくは6個の芳香環原子を有するアリール又はヘテロアリール基であり、
Yは、それぞれ現れるごとに同一か又は異なる、P(=O)又はP(=S)であり、
Zは、それぞれ現れるごとに同一か又は異なる、それがA又はBと式(7)の環を形成しないならば、N-R2であり、
Xは、CR1又はNを表し、最大2つの符号XがNを表し、好ましくは最大1つの符号XがNを表し、
Arは、同一か又は異なる、5〜30の芳香環原子を有する、好ましくは5〜24の芳香環原子を有する芳香環又はヘテロ芳香環系であり、好ましくは、芳香環又はヘテロ芳香環系のアリール又はヘテロアリール基のいずれもが10個を超える芳香環原子を含まず、
qは0であり、
nは、1、2、3、又は4、好ましくは1、2、又は3であり、
R1は、それぞれ現れるごとに同一か又は異なる、H、D、CN、N(R3)2、そのそれぞれが1又はそれ以上のラジカルR3により置換されてもよく、また1つ又はそれ以上の非隣接CH2基がR3C=CR3又はOにより置換されてもよく、1つ又はそれ以上のHがD又はFにより置換されてもよい、1〜20のC原子を有する直鎖アルキル又はアルコキシ基、3〜20のC原子を有する分枝又は環状アルキル基又はアルコキシ基、2〜20のC原子を有するアルケニル基、それぞれの場合に1つ又はそれ以上のR3により置換されてもよい5〜30の芳香環原子を有する芳香環又はヘテロ芳香環系、1つ又はそれ以上のR3により置換されてもよい5〜30の芳香環原子を有するアリールオキシ又はヘテロアリールオキシ基、又は2つ又はそれ以上の隣接する置換基R1が任意に、1つ又はそれ以上のR3により置換されてもよいモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成する、これらの系の組合せからなる群から選択され、
R2は、それぞれ現れるごとに同一か又は異なる、そのそれぞれが1つ又はそれ以上のR3により置換されてもよく、1つ又はそれ以上のHがF又はDにより置換されてもよい、1〜10のC原子を有する直鎖アルキル基又は3〜10のC原子を有する分枝又は環状アルキル基、それぞれの場合において、1つ又はそれ以上のR3により置換されてもよい5〜30の芳香環原子を有する芳香環又はヘテロ芳香環系、又はこれらの系の組合せからなる群から選択され、1,2位において相互に隣接するR1及びR2は、1つ又はそれ以上のラジカルR3により置換されてもよいモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成し、
他の符号又はインデックスは請求項1に示す意味を有することを特徴とする請求項1〜6のいずれかに記載の電子デバイス。 - Ar1は、それぞれ現れるごとに同一か又は異なる、ベンゼン、ピリジン、ピリミジン、ピリダジン、ピラジン、トリアジン、フラン、チオフェン、ピロール、ナフタレン、キノリン、イソキノリン、キノキサリン、インドール、ベンゾフラン、ベンゾチオフェン、及びカルバゾールから選択され、
Yは、P(=O)であり、
Zは、それぞれ現れるごとに同一か又は異なる、それがA又はBと式(7)の環を形成しないならば、N-R2であり、
Xは、それぞれ現れるごとに同一か又は異なる、CR1であり、
Arは、5〜24個の芳香環原子を有する芳香環又はヘテロ芳香環系であり、それは、それぞれの場合において、ベンゼン、ピリジン、ピリミジン、ピリダジン、ピラジン、ピロール、チオフェン、フラン、ナフタレン、トリフェニレン、キノリン、イソキノリン、キノキサリン、インドール、ベンゾチオフェン、又はベンゾフランからなる群の1つ又はそれ以上からなり、好ましくは、それぞれの場合において、ベンゼン、ピリジン、ピリミジン、ピリダジン、ピラジン、又はトリアジンからなる群の1つ又はそれ以上からなり、特にベンゼンンであり、
qは0であり、
nは、1又は2であり、
R1は、それぞれ現れるごとに同一か又は異なる、H、D、F、CN、そのそれぞれが1又はそれ以上のラジカルR3により置換されてもよく、また1つ又はそれ以上のH原子がDにより置換されてもよい、1〜10のC原子、好ましくは1〜4のC原子を有する直鎖アルキル基、3〜10のC原子を有する、特に好ましくは3〜5のC原子を有する分枝又は環状アルキル基、又は2〜10のC原子を有する、特に好ましくは2〜4のC原子を有するアルケニル基、それぞれの場合に1つ又はそれ以上のラジカルR3により置換されてもよい5〜12の芳香環原子を有する芳香環又はヘテロ芳香環系、又は2つ又はそれ以上の隣接する置換基R1が任意に、1つ又はそれ以上のR3により置換されてもよいモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成する、これらの系の組合せからなる群から選択され、
R2は、それぞれ現れるごとに同一か又は異なる、そのそれぞれが1つ又はそれ以上のR3により置換されてもよい、5〜24の芳香環原子を有する芳香環又はヘテロ芳香環系からなる群から選択され、
他の符号又はインデックスは請求項1に示す意味を有することを特徴とする請求項1〜7のいずれかに記載の電子デバイス。 - 有機エレクトロルミネセント素子(OLED)、有機集積回路(O-IC)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機発光トランジスタ(O-LET)、有機太陽電池(O-SC)、有機光検出器、有機フォトリセプタ、有機電場消光素子(O-FQD)、発光電気化学セル(LEC),有機レーザーダイオード(O-レーザー)、及び有機プラスモン放出素子からなる群から選択される請求項1〜8のいずれかに記載の電子デバイス。
- 蛍光又は燐光発光体特に燐光発光体のためのマトリックス物質として、及び又は正孔ブロッキング層における正孔ブロッキング物質として、及び/又は電子輸送層又は電子注入層における電子注入物質として、及び/又は電子ブロッキング又は励起子ブロッキング層における電子ブロッキング物質又は励起子ブロッキング物質として、及び/又は正孔輸送層又は正孔注入層における正孔輸送物質として、式(1)又は式(8)〜(18)の化合物が用いられることを特徴とする請求項1〜9のいずれかに記載の電子デバイス。
- 用いられる燐光発光体は、銅、モリブデン、タングステン、レニウム、ルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金、銀、金、又はユーロピウム、特にイリジウム又は白金を含む化合物であることを特徴とする請求項10に記載の電子デバイス。
- 下記式(1’)の化合物又は下記式(39)の化合物。
Zは、同じ基Yに結合された双方の基ZがOを表わさなければ、それぞれ現れるごとに同一か又は異なる、N-R2、O、又はSであり、又は
A-Z及びB-Zは、それぞれ現れるごとに同一か又は異なる、以下の式(7)であり、q=0であり、
Yは、それぞれ現れるごとに同一か又は異なる、P(=O)、As(=O)、As(=S)、Sb(=O)、Sb(=S)、Bi(=O)、又はBi(=S)であり、
Arは、それぞれ現れるごとに同一か又は異なる、1つ又はそれ以上のラジカルR1と置換されてもよい、5〜60の芳香環原子を有する芳香環又はヘテロ芳香環系であり、
Ar1は、それぞれ現れるごとに同一か又は異なる、1つ又はそれ以上のラジカルR1と置換されてもよい、5〜16の芳香環原子を有するアリール又はヘテロアリール基であり、
Xは、それぞれ現れるごとに同一か又は異なる、CR1又はNであり、
Lは、単結合又は二価、三価、又は四価の基であり、
R1は、それぞれ現れるごとに同一か又は異なる、H、D、F、Cl、Br、I、CN、NO2、N(R3)2、C(=O)R3、そのそれぞれが1又はそれ以上のラジカルR3により置換されてもよく、また1つ又はそれ以上の非隣接CH2基がR3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、S、又はCONR3により置換されてもよく、1つ又はそれ以上のHがD、F、Cl、Br、I、CN、又はNO2により置換されてもよい、1〜40のC原子を有する直鎖アルキル又はアルコキシ又はチオアルキル基又は3〜40のC原子を有する分枝状又は環状アルキル、アルコキシ又はチオアルキル基又は2〜40のC原子を有するアルケニル又はアルキニル基、それぞれの場合に1つ又はそれ以上のR3により置換されてもよい5〜60の芳香環原子を有する芳香環又はヘテロ芳香環系、1つ又はそれ以上のR3により置換されてもよい5〜60の芳香環原子を有するアリールオキシ又はヘテロアリールオキシ基、又は2つ又はそれ以上の隣接する置換基R1が任意に、1つ又はそれ以上のR3により置換されてもよいモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成する、これらの系の組合せからなる群から選択され、
R2は、それぞれ現れるごとに同一か又は異なる、そのそれぞれが1つ又はそれ以上のR3により置換されてもよく、1つ又はそれ以上の非隣接CH2基がR3C=CR3、C≡C、C=Oにより置換されてもよく、1つ又はそれ以上のHがD、F、Cl、Br、I、CN、又はNO2により置換されてもよい、1〜40のC原子を有する直鎖アルキル又は3〜40のC原子を有する分枝状又は環状アルキル基、1つ又はそれ以上のR3により置換されてもよい5〜60の芳香環原子を有する芳香環又はヘテロ芳香環系、又はこれらの系の組合せからなる群から選択され、1,2位において相互に隣接するR1及びR2は、1つ又はそれ以上のラジカルR3により置換されてもよいモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成し、
R3は、H、D、F、CN、1〜20のC原子を有する脂肪族炭化水素ラジカル、1つ又はそれ以上のHがD、F、Cl、Br、I、又はCNにより置換されてもよい、5〜30の芳香環原子を有する芳香環又はヘテロ芳香環系からなる群から選択され、2つ又はそれ以上の隣接置換基R3は、相互にモノ環状又はポリ環状、脂肪族、芳香環又はヘテロ芳香環系を形成し、
nは、1〜10、好ましくは1、2、3、4、5又は6であり、
mは、Lが単結合又は二価基であるならば1であり、Lが三価基であるならば2であり、Lが四価基であるならば3であり、
qは、それぞれ現れるごとに同一か又は異なる、0又は1であり、
以下の化合物は、本発明から除外される。
- 請求項12の化合物の電子デバイスにおける用途。
- アミノ基が置換されないか又はモノ置換されたオルト-ジアミノ-置換された芳香族化合物の、芳香族ホスホニルクロリド誘導体又は芳香族オリゴホスホニルクロリド誘導体との反応による、請求項12の化合物の製造方法。
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Cited By (1)
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JP2016103568A (ja) * | 2014-11-28 | 2016-06-02 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
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Publication number | Publication date |
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EP2344607B1 (de) | 2013-04-10 |
CN102076813B (zh) | 2016-05-18 |
CN102076813A (zh) | 2011-05-25 |
TW201033227A (en) | 2010-09-16 |
US8865321B2 (en) | 2014-10-21 |
KR101763422B1 (ko) | 2017-07-31 |
JP5701766B2 (ja) | 2015-04-15 |
TWI466893B (zh) | 2015-01-01 |
KR20100053454A (ko) | 2010-05-20 |
WO2010054730A1 (de) | 2010-05-20 |
EP2344607A1 (de) | 2011-07-20 |
US20110201778A1 (en) | 2011-08-18 |
KR20110097612A (ko) | 2011-08-31 |
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