JP7438965B2 - 電子デバイス用材料 - Google Patents
電子デバイス用材料 Download PDFInfo
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- JP7438965B2 JP7438965B2 JP2020554119A JP2020554119A JP7438965B2 JP 7438965 B2 JP7438965 B2 JP 7438965B2 JP 2020554119 A JP2020554119 A JP 2020554119A JP 2020554119 A JP2020554119 A JP 2020554119A JP 7438965 B2 JP7438965 B2 JP 7438965B2
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- Prior art keywords
- aromatic ring
- radicals
- carbon atoms
- groups
- atoms
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- 239000000463 material Substances 0.000 title description 33
- 150000001875 compounds Chemical class 0.000 claims description 145
- 239000010410 layer Substances 0.000 claims description 130
- 125000003118 aryl group Chemical group 0.000 claims description 119
- 150000003254 radicals Chemical class 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- -1 R 11 radicals Chemical class 0.000 claims description 49
- 230000005525 hole transport Effects 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000000412 dendrimer Substances 0.000 claims description 11
- 229920000736 dendritic polymer Polymers 0.000 claims description 11
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001716 carbazoles Chemical class 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- FTMRMQALUDDFQO-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran Chemical compound C1=CC=C2C=C3C4=CC=CC=C4OC3=CC2=C1 FTMRMQALUDDFQO-UHFFFAOYSA-N 0.000 claims description 2
- UWMISBRPSJFHIR-UHFFFAOYSA-N naphtho[2,3-b][1]benzothiole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4SC3=CC2=C1 UWMISBRPSJFHIR-UHFFFAOYSA-N 0.000 claims description 2
- 150000004826 dibenzofurans Chemical class 0.000 claims 1
- 239000005486 organic electrolyte Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 239000011159 matrix material Substances 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 230000000903 blocking effect Effects 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 125000006413 ring segment Chemical group 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 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 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 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 6
- SXOUNESKHJIXNK-UHFFFAOYSA-N 4-bromo-9,9-dimethylfluorene Chemical compound C1=CC=C(Br)C2=C1C(C)(C)C1=CC=CC=C12 SXOUNESKHJIXNK-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 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 4
- 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 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000004986 diarylamino group Chemical group 0.000 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 description 4
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KMZUUSFWPQLMQE-UHFFFAOYSA-N 1-bromo-9,9-dimethylfluorene Chemical compound C1=CC(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 KMZUUSFWPQLMQE-UHFFFAOYSA-N 0.000 description 3
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 3
- VECLPBKDHAALGQ-UHFFFAOYSA-N 3-bromo-9,9-dimethylfluorene Chemical compound BrC1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 VECLPBKDHAALGQ-UHFFFAOYSA-N 0.000 description 3
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 3
- PDOQLUHQQRDCES-UHFFFAOYSA-N 4-(9-phenylcarbazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 PDOQLUHQQRDCES-UHFFFAOYSA-N 0.000 description 3
- JPNNLBQKGZVDPF-UHFFFAOYSA-N 4-dibenzofuran-4-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=CC2=C1OC1=CC=CC=C21 JPNNLBQKGZVDPF-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-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
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 229910000314 transition metal oxide Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- 238000001947 vapour-phase growth Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
R1は、それぞれの場合において同じであるかまたは異なり、H、D、F、Si(R11)3、1~20個の炭素原子を有する直鎖アルキルおよびアルコキシ基、ならびに3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基から選択され、ここで、2つ以上のR1ラジカルは、互いに結合していても、環を形成していてもよく;言及したアルキルおよびアルコキシ基は、それぞれ1つ以上のR11ラジカルにより置換されていてもよく;
ArSは、それぞれの場合において同じであるかまたは異なり、6~40個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよい芳香族環系、および5~40個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよいヘテロ芳香族環系から選択され;
Ar1は、6~40個の芳香族環原子を有し、1つ以上のR4ラジカルにより置換されていてもよい芳香族環系、および5~40個の芳香族環原子を有し、1つ以上のR4ラジカルにより置換されていてもよいヘテロ芳香族環系から選択され;
HetAr1は、13~40個の芳香族環原子を有し、1つ以上のR5ラジカルにより置換されていてもよいヘテロ芳香族環系から選択され;
R2、R3、R4、R5は、それぞれの場合において同じであるかまたは異なり、H、D、F、C(=O)R11、CN、Si(R11)3、N(R11)2、P(=O)(R11)2、OR11、S(=O)R11、S(=O)2R11、1~20個の炭素原子を有する直鎖アルキルまたはアルコキシ基、3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され;ここで、R2ラジカルから選択される2つ以上のラジカル、R3ラジカルから選択される2つ以上のラジカル、R4ラジカルから選択される2つ以上のラジカルおよびR5ラジカルから選択される2つ以上のラジカルは、各場合において互いに結合していても、環を形成していてもよく;言及したアルキル、アルコキシ、アルケニルおよびアルキニル基、ならびに言及した芳香族環系およびヘテロ芳香族環系は、それぞれ1つ以上のR11ラジカルにより置換されていてもよく;言及したアルキル、アルコキシ、アルケニルおよびアルキニル基中の1つ以上のCH2基は、-R11C=CR11-、-C≡C-、Si(R11)2、C=O、C=NR11、-C(=O)O-、-C(=O)NR11-、NR11、P(=O)(R11)、-O-、-S-、SOまたはSO2により置きかえられていてもよく;
R11は、それぞれの場合において同じであるかまたは異なり、H、D、F、C(=O)R21、CN、Si(R21)3、N(R21)2、P(=O)(R21)2、OR21、S(=O)R21、S(=O)2R21、1~20個の炭素原子を有する直鎖アルキルまたはアルコキシ基、3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され;ここで、2つ以上のR11ラジカルは、互いに結合していても、環を形成していてもよく;言及したアルキル、アルコキシ、アルケニルおよびアルキニル基、ならびに言及した芳香族環系およびヘテロ芳香族環系は、それぞれ1つ以上のR21ラジカルにより置換されていてもよく;言及したアルキル、アルコキシ、アルケニルおよびアルキニル基中の1つ以上のCH2基は、-R21C=CR21-、-C≡C-、Si(R21)2、C=O、C=NR21、-C(=O)O-、-C(=O)NR21-、NR21、P(=O)(R21)、-O-、-S-、SOまたはSO2により置きかえられていてもよく;
R21は、それぞれの場合において同じであるかまたは異なり、H、D、F、CN、1~20個の炭素原子を有するアルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、6~40個の芳香族環原子を有する芳香族環系および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され;ここで、2つ以上のR3ラジカルは、互いに結合していても、環を形成していてもよく;言及したアルキル、アルコキシ、アルケニルおよびアルキニル基、芳香族環系およびヘテロ芳香族環系は、FおよびCNから選択される1つ以上のラジカルにより置換されていてもよく;
m、nは、同じであるかまたは異なり、0、1、2および3から選択され、
ここで、添え字mおよびnのうちの少なくとも1つは0であり;
左側のフルオレニル基は、#印がついた位置のうちの1つを介してArS基またはNに結合している)
の化合物を提供する。
R4およびR5は、先に定義した通りであり、好ましくはHまたはフェニル、より好ましくはHであり;
この基は、自由結合を介して式(I)中の窒素原子に結合している)
に合致する。
である。
より詳細には、正孔注入層でも電子阻止層でもない正孔輸送層である。
A)合成例
以下に続く合成は、特に断らない限り、保護ガス雰囲気下、乾燥溶媒中で行われる。溶媒および試薬は、たとえば、Sigma-ALDRICHまたはABCRから購入することができる。角括弧内それぞれの数字または個々の化合物について引用した番号は、文献から公知の化合物のCAS番号に関する。
A-1)シントンの調製:
OLEDを、下記のように製造する:
厚さ50nmの構造化されたITO(インジウムスズ酸化物)でコーティングするガラスプラークを、コーティング前に酸素プラズマで処理した後、アルゴンプラズマで処理する。これらのプラズマ処理したガラスプラークが、OLEDが適用される基板を形成する。
Claims (14)
- 式(I-A-4)
R1は、それぞれの場合において同じであるかまたは異なり、H、D、F、Si(R11)3、1~20個の炭素原子を有する直鎖アルキルおよびアルコキシ基、ならびに3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基から選択され、ここで、2つ以上のR1ラジカルは、互いに結合して、環を形成していてもよく;言及した前記アルキルおよびアルコキシ基は、それぞれ1つ以上のR11ラジカルにより置換されていてもよく;
Ar1は、6~20個の芳香族環原子を有し、1つ以上のR4ラジカルにより置換されていてもよい芳香族環系から選択され;
HetAr1は、ジベンゾフラン、ベンゾナフトフラン、ジベンゾチオフェン、ベンゾナフトチオフェン、その炭素原子のうちの1個を介して結合しているカルバゾール、その窒素原子を介して結合しているカルバゾール、その炭素原子のうちの1個を介して結合しているベンゾカルバゾール、およびその窒素原子を介して結合しているベンゾカルバゾールから選択され、1つ以上のR5ラジカルにより置換されていてもよく;
R2は、それぞれの場合において同じであるかまたは異なり、H、D、F、C(=O)R11、CN、Si(R11)3、N(R11)2、P(=O)(R11)2、OR11、S(=O)R11、S(=O)2R11、1~20個の炭素原子を有する直鎖アルキルまたはアルコキシ基、3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され;ここで、R2ラジカルから選択される2つ以上のラジカルは、各場合において互いに結合して、環を形成していてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基、ならびに言及した前記芳香族環系およびヘテロ芳香族環系は、それぞれ1つ以上のR11ラジカルにより置換されていてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基中の1つ以上のCH2基は、-R11C=CR11-、-C≡C-、Si(R11)2、C=O、C=NR11、-C(=O)O-、-C(=O)NR11-、NR11、P(=O)(R11)、-O-、-S-、SOまたはSO2により置きかえられていてもよく;
R4は、それぞれの場合において同じであるかまたは異なり、H、D、F、C(=O)R11、CN、Si(R11)3、N(R11)2、P(=O)(R11)2、OR11、S(=O)R11、S(=O)2R11、1~20個の炭素原子を有する直鎖アルキルまたはアルコキシ基、3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され;ここで、R4ラジカルから選択される2つ以上のラジカルは、各場合において互いに結合して、環を形成していてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基、ならびに言及した前記芳香族環系およびヘテロ芳香族環系は、それぞれ1つ以上のR11ラジカルにより置換されていてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基中の1つ以上のCH2基は、-R11C=CR11-、-C≡C-、Si(R11)2、C=O、C=NR11、-C(=O)O-、-C(=O)NR11-、NR11、P(=O)(R11)、-O-、-S-、SOまたはSO2により置きかえられていてもよく;
R5は、それぞれの場合において同じであるかまたは異なり、H、D、F、C(=O)R11、CN、Si(R11)3、N(R11)2、P(=O)(R11)2、OR11、S(=O)R11、S(=O)2R11、1~20個の炭素原子を有する直鎖アルキルまたはアルコキシ基、3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、および6~40個の芳香族環原子を有する芳香族環系から選択され;ここで、R5ラジカルから選択される2つ以上のラジカルは、各場合において互いに結合して環を形成していてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基、ならびに言及した前記芳香族環系は、それぞれ1つ以上のR11ラジカルにより置換されていてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基中の1つ以上のCH2基は、-R11C=CR11-、-C≡C-、Si(R11)2、C=O、C=NR11、-C(=O)O-、-C(=O)NR11-、NR11、P(=O)(R11)、-O-、-S-、SOまたはSO2により置きかえられていてもよく;
R11は、それぞれの場合において同じであるかまたは異なり、H、D、F、C(=O)R21、CN、Si(R21)3、N(R21)2、P(=O)(R21)2、OR21、S(=O)R21、S(=O)2R21、1~20個の炭素原子を有する直鎖アルキルまたはアルコキシ基、3~20個の炭素原子を有する分枝または環状アルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され;ここで、2つ以上のR11ラジカルは、互いに結合していても、環を形成していてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基、ならびに言及した前記芳香族環系およびヘテロ芳香族環系は、それぞれ1つ以上のR21ラジカルにより置換されていてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基中の1つ以上のCH2基は、-R21C=CR21-、-C≡C-、Si(R21)2、C=O、C=NR21、-C(=O)O-、-C(=O)NR21-、NR21、P(=O)(R21)、-O-、-S-、SOまたはSO2により置きかえられていてもよく;
R21は、それぞれの場合において同じであるかまたは異なり、H、D、F、CN、1~20個の炭素原子を有するアルキルまたはアルコキシ基、2~20個の炭素原子を有するアルケニルまたはアルキニル基、6~40個の芳香族環原子を有する芳香族環系および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され;ここで、2つ以上のR3ラジカルは、互いに結合していても、環を形成していてもよく;言及した前記アルキル、アルコキシ、アルケニルおよびアルキニル基、芳香族環系およびヘテロ芳香族環系は、FおよびCNから選択される1つ以上のラジカルにより置換されていてもよい。)
の化合物。 - R1が、それぞれの場合において同じであるかまたは異なり、1~10個の炭素原子を有する直鎖アルキル基および3~10個の炭素原子を有する分枝または環状アルキル基から選択され、ここで、2つ以上のR1ラジカルは、互いに結合していても、環を形成していてもよく、前記アルキル基中の1個以上の水素原子は、Dにより置きかえられていてもよいことを特徴とする、請求項1に記載の化合物。
- Ar1が、各場合において1つ以上のR4ラジカルにより置換されていてもよいベンゼンであることを特徴とする、請求項1または2に記載の化合物。
- HetAr1が、ジベンゾフラン、ジベンゾチオフェンおよびカルバゾールから選択され、これらのそれぞれは、1つ以上のR5ラジカルにより置換されていてもよいことを特徴とする、請求項1~3の何れか1項に記載の化合物。
- R2が、それぞれの場合において同じであるかまたは異なり、H、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され、これらのそれぞれは、1つ以上のR11ラジカルにより置換されていてもよく;
R4が、それぞれの場合において同じであるかまたは異なり、H、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され、これらのそれぞれは、1つ以上のR11ラジカルにより置換されていてもよく;
R5が、それぞれの場合において同じであるかまたは異なり、H、および6~40個の芳香族環原子を有する芳香族環系から選択され、これらのそれぞれは、1つ以上のR11ラジカルにより置換されていてもよいことを特徴とする、請求項1~4の何れか1項に記載の化合物。 - R11が、それぞれの場合において同じであるかまたは異なり、H、D、F、CN、Si(R21)3、N(R21)2、1~20個の炭素原子を有する直鎖アルキル基、3~20個の炭素原子を有する分枝または環状アルキル基、6~40個の芳香族環原子を有する芳香族環系、および5~40個の芳香族環原子を有するヘテロ芳香族環系から選択され、ここで、言及した前記アルキル基、言及した前記芳香族環系および言及した前記ヘテロ芳香族環系は、それぞれ1つ以上のR21ラジカルにより置換されていてもよいことを特徴とする、請求項1~5の何れか1項に記載の化合物。
- -Ar1-HetAr1基が、式(H-1)または(H-2)
唯一つのR 4 ラジカルおよび唯一つのR 5 ラジカルが、式(H-1)および(H-2)に存在する;
前記基は、自由結合手を介して窒素原子に結合している)
に合致することを特徴とする、請求項1に記載の化合物。 - 請求項1~7の何れか1項に記載の化合物を調製するための方法であって、出現する可変基が請求項1~7の何れか1項において式(I-A-4)に関して定義した通りである化合物HetAr1-Ar1-NH2を、ブッフバルトカップリング反応で反応性X基(Xは、Cl、BrおよびIから選択される)を有するフルオレンと反応させることを特徴とする、方法。
- 請求項1~7の何れか1項に記載の1種以上の式(I-A-4)の化合物を含有するオリゴマー、ポリマーまたはデンドリマーであって、前記ポリマー、オリゴマーまたはデンドリマーへの結合(複数可)が、式(I)中のR1、R2、R4またはR5により置換されている任意所望の位置に局在していてもよい、オリゴマー、ポリマーまたはデンドリマー。
- 請求項1~7の何れか1項に記載の少なくとも1種の化合物、または請求項9に記載の1種のポリマー、オリゴマーもしくはデンドリマーと、少なくとも1種の溶媒を含む調合物。
- 請求項1~7の何れか1項に記載の少なくとも1種の化合物、または請求項9に記載の1種のポリマー、オリゴマーもしくはデンドリマーを含む電子デバイス。
- アノード、カソードおよび少なくとも1つの発光層を含む有機エレクトロルミネッセントデバイスであって、ここで、前記少なくとも1種の化合物を含むのが、発光層および正孔輸送層から選択される前記デバイスの少なくとも1つの有機層であることを特徴とする、請求項11に記載の電子デバイス。
- アノード、カソードおよび少なくとも1つの発光層を含み、前記少なくとも1種の化合物が、少なくとも1種のリン光発光体と組み合わせて発光層に存在することを特徴とする、請求項12に記載の有機エレクトロルミネッセントデバイス。
- 請求項1~7の何れか1項に記載の化合物の電子デバイスにおける使用。
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