JP6009435B2 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP6009435B2 JP6009435B2 JP2013508381A JP2013508381A JP6009435B2 JP 6009435 B2 JP6009435 B2 JP 6009435B2 JP 2013508381 A JP2013508381 A JP 2013508381A JP 2013508381 A JP2013508381 A JP 2013508381A JP 6009435 B2 JP6009435 B2 JP 6009435B2
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- 238000005401 electroluminescence Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 239000011159 matrix material Substances 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- -1 NR 2 Inorganic materials 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 17
- 230000004888 barrier function Effects 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 13
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 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 claims description 3
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 238000007689 inspection Methods 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000000463 material Substances 0.000 description 42
- 239000000460 chlorine Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000000412 dendrimer Substances 0.000 description 7
- 229920000736 dendritic polymer Polymers 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QYBJUTSQRXNWMP-UHFFFAOYSA-N 3-phenyl-4h-furo[3,4-b]indole Chemical compound C=12NC3=CC=CC=C3C2=COC=1C1=CC=CC=C1 QYBJUTSQRXNWMP-UHFFFAOYSA-N 0.000 description 4
- 0 CC1=C2NC=CC2=NN=CC*C1 Chemical compound CC1=C2NC=CC2=NN=CC*C1 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004696 coordination complex 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- JSKPHZKTZRJYJN-UHFFFAOYSA-N (2-bromophenyl)-(3-phenylfuro[3,4-b]indol-4-yl)methanone Chemical compound BrC1=CC=CC=C1C(=O)N1C2=C(C=3C=CC=CC=3)OC=C2C2=CC=CC=C21 JSKPHZKTZRJYJN-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 125000004429 atom Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 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
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000002950 deficient Effects 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
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- QJVZUBLEWURBDT-UHFFFAOYSA-N (1-chloro-[1]benzofuro[3,2-b]indol-10-yl)-phenylmethanone Chemical compound C1=2C(Cl)=CC=CC=2C=2OC3=CC=CC=C3C=2N1C(=O)C1=CC=CC=C1 QJVZUBLEWURBDT-UHFFFAOYSA-N 0.000 description 1
- YXGNBDOMJCXYGL-UHFFFAOYSA-N (2-bromophenyl)-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C(=CC=CC=1)Br)(Cl)C1=CC=CC=C1 YXGNBDOMJCXYGL-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- OLROCKKMZHTZFM-UHFFFAOYSA-N 1,2-oxazole;1,2-thiazole Chemical compound C=1C=NOC=1.C=1C=NSC=1 OLROCKKMZHTZFM-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 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
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-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
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 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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Description
Xは、C=O、C(R)2、NR、O、S、C=S、C=NR、C=C(R)2、Si(R)2、BR、PR、P(=O)R、SOまたはSO2であり;
Yは、Ar1が、六員アリールもしくはヘテロアリール環基であるならば、Cであり、Ar1が、五員アリールもしくはヘテロアリール環基であるならば、CまたはNRであり;
Eは、単結合、C(R)2、NR、O、S、C=O、C=S、C=NR、C=C(R)2、Si(R)2、BR、PR、P(=O)R、SOまたはSO2であり;
Ar1は、基Yと明示的な炭素原子と一緒になって、1以上の基Rで置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり、
Ar2、Ar3は、出現毎に同一であるか異なり、明示的な炭素原子と一緒になって、1以上の基Rで置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり、
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R1)2、C(=O)Ar4、C(=O)R1、P(=O)(Ar4)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R1により置換されてよく、1以上の隣接しないCH2基は、R1C=CR1、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SもしくはCONR1で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R1により置換されてよい5〜80個、好ましくは、5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R1で置換されてよい5〜60個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構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rは、一以上の置換基R1により置換されてよいモノ環状あるいはポリ環状脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R2)2、C(=O)Ar4、C(=O)R2、P(=O)(Ar4)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個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、またはこれらの構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rは、一以上の置換基R2により置換されてよいモノ環状あるいはポリ環状脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;
Ar4は、出現毎に同一であるか異なり、1以上の非芳香族基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって;ここで、同じN原子もしくはP原子に結合する2個の基Ar4は、単結合またはN(R2)、C(R2)2もしくはOから選ばれるブリッジにより互いに架橋されてもよく;
R2は、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上のH原子は、D、F、Cl、Br、I、もしくはCNで置き代えられてよく、ここで、2個以上の隣接する置換基R2はモノ-あるいはポリ環状脂肪族、芳香族もしくは複素環式芳香族環構造を互いに形成してもよい。
Vは、NR、OまたはSである。
Xは、C=O、CR2、SiR2、P(=O)RまたはSO2であり;
Eは、出現毎に同一であるか異なり、単結合、CR2、C=O、NR、OまたはSであり;
Ar1は、上記言及した式(2)、(3)、(4)、(5)または(6)の基から選ばれ、
Ar2は、上記言及した式(9)、(10)または(11)の基から選ばれ、
Ar3は、上記言及した式(12)、(13)、(14)または(15)の基から選ばれる。
Xは、C=O、SiR2またはSO2であり;
Eは、出現毎に同一であるか異なり、単結合、CR2、C=OまたはNRであり、好ましくは、単結合、CR2またはC=Oであり、特に、好ましくは、単結合である。
Ar2は、上記言及した式(9)、(10)または(11)の基から選ばれ、
Ar3は、上記言及した式(12)、(13)、(14)または(15)の基から選ばれる。
Xは、C=O、C(R)2、NR、O、S、C=S、C=NR、C=C(R)2、Si(R)2、BR、PR、P(=O)R、SOまたはSO2であり;
Yは、Ar1が、六員アリールもしくはヘテロアリール環基であるならば、Cであり、Ar1が、五員アリールもしくはヘテロアリール環基であるならば、CまたはNRであり;
Eは、出現毎に同一であるか異なり、単結合、C(R)2、NR、O、S、C=O、C=S、C=NR、C=C(R)2、Si(R)2、BR、PR、P(=O)R、SOまたはSO2であり;
Ar1は、基Yと明示的な炭素原子と一緒になって、1以上の基Rで置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり、
Ar2は、明示的な炭素原子と一緒になって、1以上の基Rで置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;Ar2が、芳香族もしくは複素環式芳香族環構造基Rにより置換される少なくとも一つの窒素原子を有する芳香族環構造であるならば、そこで、この基Rは、6個未満の芳香族C原子を含み;
Ar3は、明示的な炭素原子と一緒になって、1以上の基Rで置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R1)2、C(=O)Ar4、C(=O)R1、P(=O)(Ar4)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R1により置換されてよく、1以上の隣接しないCH2基は、R1C=CR1、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SもしくはCONR1で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R1により置換されてよい5〜80個、好ましくは、5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R1で置換されてよい5〜60個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構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rは、一以上の置換基R1により置換されてよいモノ環状あるいはポリ環状脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R2)2、C(=O)Ar4、C(=O)R2、P(=O)(Ar4)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個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、またはこれらの構造の組み合わせより成る群から選ばれ;ここで、2個以上の隣接する置換基Rは、一以上の置換基R2により置換されてよいモノ環状あるいはポリ環状脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成してもよく;
Ar4は、出現毎に同一であるか異なり、1以上の非芳香族基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって;ここで、同じN原子もしくはP原子に結合する2個の基Ar4は、単結合によりまたはN(R2)、C(R2)2もしくはOから選ばれるブリッジにより互いに架橋されてもよく;
R2は、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造から選ばれ、ここで、1以上のH原子は、D、F、Cl、Br、I、もしくはCNで置き代えられてよく、ここで、2個以上の隣接する置換基R2はモノ-あるいはポリ環状脂肪族、芳香族もしくは複素環式芳香族環構造を互いに形成してもよく、
以下の化合物は、除外される。
a)基Rに代えて、反応性脱離基を有する骨格の合成;および
b)好ましくは、カップリング反応、たとえば、スズキカップリングまたはハートウイッグ-ブフバルトカップリングによる基Rの導入
の反応工程を含む、式(1’)の化合物の製造方法に関する。
以下の合成は、他に断らない限り、保護ガス雰囲気下で行われる。出発物質は、アルドリッチ(ALDRICH)またはABCR(酢酸パラジウム(II)、トリ-o-トリルホスフィン、無機化学物質、溶媒)から購入することができる。3-フェニル-4-(フェニルスルホニル)-4H-フルオロ[3,4-b]インドールの合成は、文献(Journal of Organic Chemistry 2002,67(3),1001-1003)にしたがって、実行することができる。11,12-ジヒドロ-11-フェニルインドロ[2,3-a] カルバゾール(WO 2009/136595)および2,12-ジメチル-10-フェニル-10,12-ジヒドロ-10-アザインデノ[2,1-b]フルオレン(未公開出願DE 102009023155.2)の合成は、同様に、文献から知られている。
本発明によるOLEDと先行技術によるOLEDが、WO 2004/058911にしたがう一般的プロセスにより製造されるが、ここに記載される特別な状況(層の厚さの変化、材料)に適合される。
本発明の材料の電子輸送層中での使用は、良好な電圧、効率と寿命を生み出す。青色蛍光ドーパントD1との組み合わせにおいて、たとえば、4.9Vの電圧が、得られる(例l5)。LiQと材料8nの混合層の使用については、5.3%の外部量子効率が得られる(例l6)。例l4にしたがうOLEDは、一定電流での約170時間の駆動持続後に、6000〜3000cd/m2(「LT50」)の輝度低下を示すが、非常に良好な値である。これは、1000cd/m2で約6000時間の寿命に対応する。
本発明による材料の燐光エミッターのためのマトリックス材料としての使用について、非常に良好な特性データが、同様に得られる。
化合物3lを、青色蛍光ドーパントとして使用することができる。この場合に、CIEx/y=0.14/0.14の深青色色座標と4.7%の外部量子効率が、4.4Vの電圧で得られる(例I20)。
Claims (8)
- 少なくとも一つの式(1)の化合物を含む電子素子;
Xは、C=O、CR2、SiR2、P(=O)RまたはSO2であり;
Yは、Ar1が、六員アリールもしくはヘテロアリール環基であるならば、Cであり、Ar1が、五員アリールもしくはヘテロアリール環基であるならば、CまたはNRであり;
Eは、出現毎に同一であるか異なり、単結合、CR2、C=O、NR、OまたはSであり;
Ar1は、式(2)、(3)、(4)、(5)または(6)の一つの基であり、
Wは、出現毎に同一であるか異なり、CRまたはNであるか、二個の隣接する基Wは、式(7)または(8)の基であり、
Vは、NR、OまたはSであり、
Ar2は、式(9)、(10)または(11)の一つの基であり、
Ar3は、式(12)、(13)、(14)または(15)の一つの基であり、
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、CN、N(Ar 4 ) 2 、C(=O)Ar 4 、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜10個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R1により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、DもしくはFで置き代えられてよい。)、各場合に、1以上の基R1により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R1で置換されてよい5〜30個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より成る群から選ばれ、
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R2)2、C(=O)Ar4、C(=O)R2、P(=O)(Ar4)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個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より成る群から選ばれ;
Ar4は、出現毎に同一であるか異なり、1以上の非芳香族基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって;ここで、同じN原子もしくはP原子に結合する2個の基Ar4は、単結合またはN(R2)、C(R2)2もしくはOから選ばれるブリッジにより互いに架橋されてもよく;
R2は、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上のH原子は、D、F、Cl、Br、I、もしくはCNで置き代えられてよい。 - 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、有機染料感受性太陽電池、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モン発光素子より成る群から選ばれる、請求項1記載の電子素子。
- 有機エレクトロルミネッセンス素子であり、式(1)の化合物が、蛍光もしくは燐光エミッターのためのマトリックス材料として、および/または正孔障壁層中でおよび/または電子輸送層中でおよび/または電子障壁層中でおよび/または励起子障壁層中でおよび/または正孔輸送中でおよび/または光学アウトカップリング層中で使用されることを特徴とする請求項1〜5何れか1項記載の電子素子。
- 式(1’)の化合物;
Xは、C=O、CR2、SiR2、P(=O)RまたはSO2であり;
Yは、Ar1が、六員アリールもしくはヘテロアリール環基であるならば、Cであり、Ar1が、五員アリールもしくはヘテロアリール環基であるならば、CまたはNRであり;
Eは、出現毎に同一であるか異なり、単結合、CR2、C=O、NR、OまたはSであり;
Ar1は、式(2)、(3)、(4)、(5)または(6)の一つの基であり、
Wは、出現毎に同一であるか異なり、CRまたはNであるか、二個の隣接する基Wは、式(7)または(8)の基であり、
Vは、NR、OまたはSであり、
Ar2は、式(9)、(10)または(11)の一つの基であり、
Ar3は、式(12)、(13)、(14)または(15)の一つの基であり、
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、CN、N(Ar 4 ) 2 、C(=O)Ar 4 、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜10個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R1により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、DもしくはFで置き代えられてよい。)、各場合に、1以上の基R1により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R1で置換されてよい5〜30個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より成る群から選ばれ、ここで、式(1’)中の少なくとも一つのRは、それぞれ、炭素原子または窒素原子を介して結合してよい置換あるいは非置換カルバゾール、インデノカルバゾールもしくはインドロカルバゾールから選ばれる複素環式芳香族環構造であり;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar4)2、N(R2)2、C(=O)Ar4、C(=O)R2、P(=O)(Ar4)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々は、1以上の基R2により置換されてよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜60個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造、1以上の基R2で置換されてよい5〜60個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より成る群から選ばれる。
Ar 4 は、出現毎に同一であるか異なり、1以上の非芳香族基R 2 により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって;ここで、同じN原子もしくはP原子に結合する2個の基Ar 4 は、単結合またはN(R 2 )、C(R 2 ) 2 もしくはOから選ばれるブリッジにより互いに架橋されてもよく;
R 2 は、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であって、ここで、1以上のH原子は、D、F、Cl、Br、I、もしくはCNで置き代えられてよい。 - 請求項7記載の化合物の、有機エレクトロルミネッセンス素子での使用。
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CN102869662A (zh) | 2013-01-09 |
JP2013531617A (ja) | 2013-08-08 |
US20130053555A1 (en) | 2013-02-28 |
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