JP2018526358A - 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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- JP2018526358A JP2018526358A JP2018507008A JP2018507008A JP2018526358A JP 2018526358 A JP2018526358 A JP 2018526358A JP 2018507008 A JP2018507008 A JP 2018507008A JP 2018507008 A JP2018507008 A JP 2018507008A JP 2018526358 A JP2018526358 A JP 2018526358A
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- 239000000463 material Substances 0.000 title claims description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 238000005401 electroluminescence Methods 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims description 73
- -1 quaterphenyl Chemical group 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 239000011159 matrix material Substances 0.000 claims description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 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 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 9
- 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 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000012300 argon atmosphere Substances 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 17
- 239000003480 eluent Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000005842 heteroatom Chemical group 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 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 5
- UAVZDBIKIOWDQF-UHFFFAOYSA-N 7,7-dimethyl-5h-indeno[2,1-b]carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=C1C(C)(C)C3=CC=CC=C3C1=C2 UAVZDBIKIOWDQF-UHFFFAOYSA-N 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XRMZKCQCINEBEI-UHFFFAOYSA-N 4-bromo-2-fluoro-1-iodobenzene Chemical compound FC1=CC(Br)=CC=C1I XRMZKCQCINEBEI-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- WJEIYVAPNMUNIU-UHFFFAOYSA-N [Na].OC(O)=O Chemical compound [Na].OC(O)=O WJEIYVAPNMUNIU-UHFFFAOYSA-N 0.000 description 3
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 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
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-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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- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
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- 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
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 239000004020 conductor Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
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- 239000002019 doping agent Substances 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-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
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- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 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
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- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
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- 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
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
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- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 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
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- 230000008022 sublimation Effects 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides 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
- 238000001931 thermography Methods 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Abstract
Description
Aは、以下の式(A−1)〜(A−6)の構造から選ばれ;
Bは、夫々、1以上の非芳香族R基により置換されてよい6〜30個の芳香族環原子を有する芳香族環構造、または13〜30個の芳香族環原子を有する電子リッチ複素環式芳香族環構造であり;
Xは、出現毎に同一であるか異なり、CHまたはNであり、ここで、1個を超えないXは、Nであり;
Arは、出現毎に同一であるか異なり、1以上の非芳香族R基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;
R、R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R2)2、C(=O)R2、P(=O)R2、Si(R2)3、1〜20個の炭素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、3〜20個の炭素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キル基、2〜20個の炭素原子を有するアルケニルもしくはアルキニル基(夫々、1以上のR2基により置換されてもよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R)2、C=O、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以上の水素原子は、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R2基により置換されてよい5〜40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、または、1以上のR2基により置換されてよい5〜40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オキシ基より成る基から選ばれ;同時に、2個の隣接するR置換基もしくは2個の隣接するR1置換基は、1以上のR2基により置換されてよいモノあるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成することができ;
R2は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個の炭素原子を有する脂肪族炭化水素基および5〜30個の環原子を有する芳香族もしくは複素環式芳香族環構造(ここで、1以上の水素原子は、D、F、CNもしくは1〜10個の炭素原子を有するアルキル基で置き代えられてよい。)より成る基から選ばれ;ここで、2個以上の隣接するR2置換基は、一緒に、モノあるいはポリ環状の脂肪族環構造を形成してもよく;
nは、0または1である。
本発明の文脈では、1〜40個の炭素原子を含んでよく、個々の水素原子もしくはCH2基が、前述の基により置き代えられていてもよい脂肪族炭化水素基もしくはアルキル基もしくはアルケニル基もしくはアルキニル基は、好ましくは、メチル、エチル、n-プロピル、i-プロピル、n-ブチル、i-ブチル、s-ブチル、t-ブチル、2-メチルブチル、n-ペンチル、s-ペンチル、ネオペンチル、シクロペンチル、n-ヘキシル、ネオヘキシル、シクロヘキシル、n-ヘプチル、シクロヘプチル、n-オクチル、シクロオクチル、2-エチルヘキシル、トリフルオロメチル、ペンタフルオロエチル、2,2,2-トリフルオロエチル、エテニル、プロペニル、ブテニル、ペンテニル、シクロペンテニル、ヘキセニル、シクロヘキセニル、ヘプテニル、シクロヘプテニル、オクテニル、シクロオクテニル、エチニル、プロピニル、ブチニル、ペンチニル、ヘキシニル、ヘプチニルまたはオクチニル基の意味であると理解される。1〜40個の炭素原子を有するアルコキシ基は、好ましくは、メトキシ、トリフルオロメトキシ、エトキシ、n-プロポキシ、i-プロポキシ、n-ブトキシ、i-ブトキシ、s-ブトキシ、t-ブトキシ、n-ペントキシ、s-ペントキシ、2-メチルブトキシ、n-ヘキソキシ、シクロヘキシルオキシ、n-ヘプトキシ、シクロヘプチルオキシ、n-オクチルオキシ、シクロオクチルオキシ、2-エチルヘキシルオキシ、ペンタフルオロエトキシおよび2,2,2-トリフルオロエトキシの意味であると理解される。1〜40個の炭素原子を有するチオアルキル基は、特別に、メチルチオ、エチルチオ、n-プロピルチオ、i-プロピルチオ、n-ブチルチオ、i-ブチルチオ、s-ブチルチオ、t-ブチルチオ、n-ペンチルチオ、s-ペンチルチオ、n-ヘキシルチオ、シクロヘキシルチオ、n-ヘプチチオル、シクロヘプチルチオ、n-オクチルチオ、シクロオクチルチオ、2-エチルヘキシルチオ、トリフルオロメチルチオ、ペンタフルオロエチルチオ、2,2,2-トリフルオロエチルチオ、エテニルチオ、プロペニルチオ、ブテニルチオ、ペンテニルチオ、シクロペンテニルチオ、ヘキセニルチオ、シクロヘキセニルチオ、ヘプテニルチオ、シクロヘプテニルチオ、オクテニルチオ、シクロオクテニルチオ、エチニルチオ、プロピニルチオ、ブチニルチオ、ペンチニルチオ、ヘキシニルチオ、ヘプチニルチオまたはオクチニルチオの意味であると理解される。一般に、本発明によるアルキル、アルコキシまたはチオアルキル基は、直鎖状、分枝または環状であってよく、1以上の隣接していないCH2基は、上記基によって置きかえられていてもよく、さらに、1以上の水素原子も、D、F、Cl、Br、I、CNまたはNO2、好ましくはF、ClまたはCN、さらに好ましくは、FまたはCN、特別に好ましくは、CNによって置きかえられていてもよい。
同時に、真空蒸発から加工される化合物においては、アルキル基は、好ましくは、5個を超えない炭素原子、より好ましくは4個を超えない炭素原子、最も好ましくは1個を超えない炭素原子を有する。溶液から加工される化合物に対しては、適切な化合物は、10個までの炭素原子を有するアルキル基、特別には分岐アルキル基で置換されたものか、オリゴアリーレン基、たとえば、オルト-、メタ-、パラ-もしくは分岐テルフェニルまたはクアテルフェニル基で置換されたものである。
2.本発明の化合物は、正孔ブロックもしくは電子輸送材料として使用されると、B基ではなく水素原子を含むか、またはインデノカルバゾール基ではなく、単純なカルバゾール基を含む類似の電子輸送材料と比べて、減少した駆圧と改善されたパワー効率をもたらす。これは、A基が、電子不足基である、すなわち、式(A−1)〜(A−4)基の一つの基である本発明の化合物に特別にあてはまる。
合成例:
以下の合成を、別段の指定がない限り、保護ガス雰囲気下で無水溶媒中で実施する。溶媒および試薬を、ALDRICHまたはABCRから購入できる。市販されていない試薬について与えられている番号は対応するCAS番号である。化合物(I)、(II)、(IX)、(XIII)、(XIV)、(XIX)、(XXI)および(XXVI)は市販されている。化合物(XV)、(XXII)および(XXVIII)は、Syn. Let、2011、12、1761により合成されることができる。化合物(XII)、(XVI)、(XXIII)および(XXIX)は、Chem. Eur、J、2009、15、5482により合成されることができる。角括弧内の数値は、化合物のCAS番号である。
OLEDの製造
以下の例C1〜I40(表1および2を参照)に、種々のOLEDのデータを提示する。
燐光OLEDの電子輸送層で使用するとき、本発明の電子伝導材料は、先行技術と比べて、とくに電圧とパワー効率に関して、著しい改善を与える。LiQと組み合わせて、本発明の化合物IV1、IV2、IV3を使用することにより、先行技術PA1〜51と比べて、約10〜20%の電圧およびパワー効率の増加を実現することができる(例C1、C2、C3,C4、C5と、I1、I2、I3との比較)。
燐光OLEDの発光層で使用するとき、本発明の正孔伝導材料は、先行技術と比べて、とくに寿命に関して、著しい改善を与える。緑色発光ドーパントTEG1および電子伝導マトリックスIC1と組み合わせて、本発明の化合物IV4、IV5、IV6、IV7、IV8を使用することにより、先行技術PA7〜11と比べて、約20〜60%の寿命の増加を実現することができる(例I4とC7、I5とC8、I6とC9、I7とC10、I8とC11との比較)。
Claims (14)
- 式(1)の化合物:
Aは、式(A−1)〜(A−6)の構造から選ばれ;
Bは、夫々、1以上の非芳香族R基により置換されてよい6〜30個の芳香族環原子を有する芳香族環構造、または13〜30個の芳香族環原子を有する電子リッチ複素環式芳香族環構造であり;
Xは、出現毎に同一であるか異なり、CHまたはNであり、ここで、1個を超えないXは、Nであり;
Arは、出現毎に同一であるか異なり、1以上の非芳香族R基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;
R、R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R2)2、C(=O)R2、P(=O)R2、Si(R2)3、1〜20個の炭素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、3〜20個の炭素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キル基または2〜20個の炭素原子を有するアルケニルもしくはアルキニル基(夫々、1以上のR2基により置換されてもよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R)2、C=O、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以上の水素原子は、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R2基により置換されてよい5〜40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、または、1以上のR2基により置換されてよい5〜40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オキシ基より成る基から選ばれ;同時に、2個の隣接するR置換基もしくは2個の隣接するR1置換基は、1以上のR2基により置換されてよいモノあるいはポリ環状の脂肪族、芳香族もしくは複素環式芳香族環構造を随意に形成することができ;
R2は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個の炭素原子を有する脂肪族炭化水素基および5〜30個の環原子を有する芳香族もしくは複素環式芳香族環構造(ここで、1以上の水素原子は、D、F、CNもしくは1〜10個の炭素原子を有するアルキル基で置き代えられてよい。)より成る基から選ばれ;ここで、2個以上の隣接するR2置換基は、一緒に、モノあるいはポリ環状の脂肪族環構造を形成してもよく;
nは、0または1である。 - Arは、フェニル、ビフェニル、テルフェニル、クアテルフェニル、フルオレニル、スピロビフルオレニル、ジベンゾフラニル、ジベンゾチエニルおよびN-フェニルカルバゾリルより成る基から選ばれ、これらの基は、夫々、1以上のR基により置換されてよいことを特徴とする、請求項1〜7何れか1項記載の化合物。
- B基は、フェニル、ビフェニル、テルフェニル、クアテルフェニル、フルオレニル、スピロビフルオレニル、ナフチル、フェナントレニル、トリフェニレニル、ジベンゾフラニル、ジベンゾチエニルおよびN-フェニルカルバゾリルより成る基から選ばれ、これらの基は、夫々、1以上のR基により置換されてよいことを特徴とする、請求項1〜8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さらなる化合物、特別には、溶媒を含む、調合物。
- 請求項1〜10何れか1項記載の化合物の、電子素子での使用。
- 少なくとも一つの請求項1〜10何れか1項記載の化合物を含む電子素子であって、特別に、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、有機ソーラーセル、染料増感性有機ソーラーセル、有機光学検査器、有機光受容器、有機電場消光素子、発光電子化学セル、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、電子素子。
- 有機エレクトロルミネッセンス素子であり、請求項1〜10何れか1項記載の化合物が、発光層中で燐光エミッターのためのマトリックス材料として、または正孔ブロック層もしくは電子輸送層中で電子輸送材料として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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