JP6250684B2 - 有機エレクトロルミネッセンス素子のための材料 - Google Patents
有機エレクトロルミネッセンス素子のための材料 Download PDFInfo
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- JP6250684B2 JP6250684B2 JP2015536005A JP2015536005A JP6250684B2 JP 6250684 B2 JP6250684 B2 JP 6250684B2 JP 2015536005 A JP2015536005 A JP 2015536005A JP 2015536005 A JP2015536005 A JP 2015536005A JP 6250684 B2 JP6250684 B2 JP 6250684B2
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- 239000000463 material Substances 0.000 title description 33
- 150000001875 compounds Chemical class 0.000 claims description 126
- 125000003118 aryl group Chemical group 0.000 claims description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 239000011159 matrix material Substances 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- -1 quaterphenyl Natural products 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 16
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 230000000903 blocking effect Effects 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 10
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 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 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 9
- 239000004305 biphenyl Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000005580 triphenylene group Chemical group 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 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 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 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 claims description 4
- 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 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 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 4
- 238000009472 formulation Methods 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 4
- 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 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000005259 triarylamine group Chemical group 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 229960005544 indolocarbazole Drugs 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 238000007689 inspection Methods 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 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
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003367 polycyclic group Polymers 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 0 *c(cc1-c(cc(*)c(*)c2)c2C2=O)cc(-c3c4cc(*)c(*)c3)c1N2C4=O Chemical compound *c(cc1-c(cc(*)c(*)c2)c2C2=O)cc(-c3c4cc(*)c(*)c3)c1N2C4=O 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
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- 239000007789 gas Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
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- 230000001681 protective effect Effects 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- PCZAIQYILJYEGO-UHFFFAOYSA-N 11-bromo-1-azapentacyclo[11.7.1.03,8.09,21.014,19]henicosa-3,5,7,9,11,13(21),14,16,18-nonaene-2,20-dione Chemical compound Brc1cc2c3ccccc3c(=O)n3c2c(c1)c1ccccc1c3=O PCZAIQYILJYEGO-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- ASNFMRWCRKAYQC-UHFFFAOYSA-N 1-azapentacyclo[11.7.1.03,8.09,21.014,19]henicosa-3,5,7,9(21),10,12,14,16,18-nonaene-2,20-dione Chemical compound O=c1c2ccccc2c2cccc3c4ccccc4c(=O)n1c23 ASNFMRWCRKAYQC-UHFFFAOYSA-N 0.000 description 4
- YQQRKUQVFWYEPV-UHFFFAOYSA-N 5,6-dihydrophenanthridine Chemical class C1=CC=C2CNC3=CC=CC=C3C2=C1 YQQRKUQVFWYEPV-UHFFFAOYSA-N 0.000 description 4
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
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- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
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- 238000006467 substitution reaction Methods 0.000 description 3
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- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 2
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- LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 description 2
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- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- SMPCEFVYTWTDRQ-UHFFFAOYSA-N 5-[(2-bromophenyl)methyl]-6H-phenanthridine Chemical compound BrC1=C(CN2C=3C=CC=CC3C3=CC=CC=C3C2)C=CC=C1 SMPCEFVYTWTDRQ-UHFFFAOYSA-N 0.000 description 2
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- 101000837299 Euglena gracilis Trans-2-enoyl-CoA reductase Proteins 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- 101000716063 Homo sapiens C-C chemokine receptor type 8 Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
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- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 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
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 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
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
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- 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 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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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
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Description
Xは、出現毎に同一であるか異なり、CRもしくはNであるか;または正確に二個の隣接する基Xは、共に、NR、OもしくはSから選ばれる基であり、その結果、五員環を形成し:
Yは、出現毎に同一であるか異なり、Z=Z、O、SまたはNRであり、ここで、RはHではなく;
Zは、出現毎に同一であるか異なり、CRもしくはNであるか、または隣接する基Z=Zは、一緒に式(2)の基であり;
Lは、n=1に対しては存在せず、n=2に対しては単結合もしくは二価基であり、n=3に対しては三価基であり、n=4に対しては四価基であり、n=5に対しては五価基であり、n=6に対しては六価基であり、ここで、Lは、基Rに代わって基本構造の任意の所望の位置に結合し;
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar1)2、N(R1)2、C(=O)Ar1、C(=O)R1、P(=O)(Ar1)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キル基、3〜40個のC原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルキル基、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、C=O、C=S、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5〜60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、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ラルキルもしくはヘテロアラルキル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、1以上の基R1で置換されてよいモノあるいはポリ環式の脂肪族、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;
Ar1は、出現毎に同一であるか異なり、1以上の非芳香族基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であり;ここで、同じN原子もしくはP原子に結合する二個の基Ar1は、また、単結合またはN(R1)、C(R1)2もしくはOから選ばれるブリッジにより互いにブリッジされてよく;
R1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、CNもしくは1〜10個のC原子を有するアルキル基もしくは2〜10個のC原子を有するアルケニル基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R1は、モノ-あるいはポリ環式の脂肪族、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;
nは、1、2、3、4、5または6であり;
ただし、以下の化合物は、本発明から除外される。
好ましい基Rは、ベンゼン、ビフェニル、特に、オルト-、メタ-もしくはパラ-ビフェニル、テルフェニル、特に、オルト-、メタ-、パラ-もしくは分岐テルフェニル、クアテルフェニル、特に、オルト-、メタ-、パラ-結合、直鎖もしくは分岐クアテルフェニル、フルオレン、特に、1-,2-,3-もしくは4-フルオレン、スピロビフルオレン、特に、1-,2-,3-もしくは4-スピロビフルオレン、1-もしくは2-ナフタレン、ピロール、フラン、チオフェン、インドール、ベンゾフラン、ベンゾチオフェン、カルバゾール、特に、1-,2-,3-もしくは4-カルバゾールもしくはN-カルバゾール、ジベンゾチオフェン、特に、1-,2-,3-もしくは4-ジベンゾチオフェン、ジベンゾフラン、特に、1-,2-,3-もしくは4-ジベンゾフラン、1,3,5-トリアジン、ピリジン、ピリミジン、ピラジン、ピリダジン、インデノカルバゾール、架橋カルバゾール、インドロカルバゾール、フェナントレン、トリフェニレンまたはこれらの二もしくは三個の組み合わせより成る基から選ばれる。これらの基は、1以上の基R1により置換されてよい。
Aは、出現毎に同一であるか異なり、CR1もしくはNであり、ただし、ゼロ、一、二もしくは三個の基Aは、Nであり;
Ar2は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい5〜16個のC原子を有する二価の芳香族もしくは複素環式芳香族環構造であり、
mは、出現毎に同一であるか異なり、0または1である。
Eは、C(R1)2、NR1、OまたはSより成る基から選ばれ;
Gは、NR1、OまたはSより成る基から選ばれる。
b)ハロゲンの位置での少なくとも一つの置換基Rの導入。
と組み合わせて、有機エレクトロルミネッセンス素子のために知られたすべての材料を使用することができる。
以下の合成を、特に断らなければ、保護ガス雰囲気下で行う。出発材料をALDRICHまたはABCRから購入することができる(酢酸パラジウム(II)、トリ-o-トリルホスフィン、無機物、溶媒)。文献公知の出発物質の場合の番号は、CAS番号である。
種々のOLEDのデータを、以下の例E1〜E7で提示する(表1と2を参照)。厚さ50nmの構造化されたITO(インジウム錫酸化物)で被覆されたガラス板が、改善された加工のために、20nmのPEDOT:PSS(ポリ(3,4-エチレンジオキシチオフェン)ポリ(スチレンスルホネート)(Heraeus Precious Metals GmbH 独からCLEVIOS(登録商標) P VP AI 4083として購入)で被覆される。これらの被覆されたガラス板はOLEDが適用される基板を形成する。OLEDは、基本的に、次の層構造を有する:基板/正孔輸送層(HTL)/中間層(IL)/電子ブロック層(EBL)/発光層(EML)/随意に、正孔ブロック層(HBL)/電子輸送層(ETL)/随意に、電子注入層(EIL)および最後にカソード。カソードは、100nm厚のアルミニウム層により形成される。OLEDの正確な構造は、表1に示されている。OLEDの製造のために必要とされる材料は、表3に示されている。ここでは「8a」などの指示は、前述の例8aからの対応する化合物を指している。このことは、使用する本発明によるすべての材料にも同じように当てはまる。
Claims (14)
- 式(1)の化合物:
Xは、出現毎に同一であるか異なり、CRもしくはNであるか;または二個の隣接する基Xは、共に、NR、OもしくはSから選ばれ、その結果五員環を形成し:
Yは、出現毎に同一であるか異なり、Z=Z、O、SまたはNRであり、ここで、RはHではなく;
Zは、出現毎に同一であるか異なり、CRもしくはNであるか、または隣接する基Z=Zは、一緒に式(2)の基であり;
Lは、n=1に対しては存在せず、n=2に対しては単結合もしくは二価基であり、n=3に対しては三価基であり、n=4に対しては四価基であり、n=5に対しては五価基であり、n=6に対しては六価基であり、ここで、Lは、基Rに代わって基本構造の任意の所望の位置に結合し;
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(Ar1)2、N(R1)2、C(=O)Ar1、C(=O)R1、P(=O)(Ar1)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キル基、3〜40個のC原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルキル基、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、C=O、C=S、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5〜60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、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ラルキルもしくはヘテロアラルキル基またはこれらの構造の組み合わせより成る基から選ばれ;ここで、2個以上の隣接する置換基Rは、1以上の基R1で置換されてよいモノあるいはポリ環式の脂肪族、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よく;
Ar1は、出現毎に同一であるか異なり、1以上の非芳香族基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であり;ここで、同じN原子もしくはP原子に結合する二個の基Ar1は、また、単結合またはN(R1)、C(R1)2もしくはOから選ばれるブリッジにより互いにブリッジされてよく;
R1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、CNもしくは1〜10個のC原子を有するアルキル基もしくは2〜10個のC原子を有するアルケニル基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R1は、モノ-あるいはポリ環式の脂肪族、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;
nは、1、2、3、4、5または6であり;
ただし、以下の化合物は、本発明から除外される。
- Lは、n=2に対して、単結合、CR2、O、NRまたはC=Oから選ばれ、n=3に対してNであり、n≧2に対して、一以上の基Rにより置換されてよい5〜24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ることを特徴とする、請求項1〜7何れか1項記載の化合物。
- 少なくとも一つの基Rは、1以上の基R1により置換されてよい5〜24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ること、および/または少なくとも一つの基Rは、C(=O)Ar1もしくはP(=O)(Ar1)2から選ばれること、および/または少なくとも一つの基Rは、トリアリールもしくはヘテロアリールアミン誘導体から選ばれることおよび/または少なくとも一つの置換基Rは、-N(Ar1)2であることを特徴とする請求項1〜7何れか1項記載の化合物。
- 少なくとも一つの基Rは、1以上の基R1により置換されてよいベンゼン、ビフェニル、テルフェニル、クアテルフェニル、フルオレン、スピロビフルオレン、ナフタレン、ピロール、フラン、チオフェン、インドール、ベンゾフラン、ベンゾチオフェン、カルバゾール、ジベンゾチオフェン、ジベンゾフラン、1,3,5-トリアジン、ピリジン、ピリミジン、ピラジン、ピリダジン、インデノカルバゾール、架橋カルバゾール、インドロカルバゾール、アントラセン、フェナントレン、ピレン、トリフェニレン、ベンズアントラセン、、キノリン、イソキノリン、フェナントリジン、フェナントロリン、アザカルバゾール、イミダゾール、ピラゾール、チアゾール、オキサゾール、オキサジアゾール、トリアゾール、ベンズイミダゾールまたはこれらの二、三もしくは四個の組み合わせから選ばれることを特徴とする、請求項1〜9何れか1項記載の化合物。
- 請求項1〜10何れか1項記載の少なくとも一つの化合物と少なくとも一つの有機溶媒とを含む、調合物。
- 請求項1〜10何れか1項記載の少なくとも一つの化合物の電子素子での使用。
- 請求項1〜10何れか1項記載の少なくとも一つの化合物を含む電子素子であって、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、有機染料増感性太陽電池、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スモン発光素子より成る群から選ばれる、電子素子。
- 請求項1〜10何れか1項記載の化合物が、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/または正孔ブロック層中でおよび/または電子輸送層中で使用されることを特徴とする、請求項13記載の電子素子。
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