TWI721121B - 電荷輸送性清漆 - Google Patents
電荷輸送性清漆 Download PDFInfo
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- TWI721121B TWI721121B TW106107061A TW106107061A TWI721121B TW I721121 B TWI721121 B TW I721121B TW 106107061 A TW106107061 A TW 106107061A TW 106107061 A TW106107061 A TW 106107061A TW I721121 B TWI721121 B TW I721121B
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- bis
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- 239000002966 varnish Substances 0.000 title claims abstract description 62
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 150000003577 thiophenes Chemical class 0.000 claims abstract description 5
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 45
- 239000000758 substrate Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000011248 coating agent Substances 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 31
- -1 n-octyl Chemical group 0.000 description 194
- 239000010410 layer Substances 0.000 description 165
- 125000004432 carbon atom Chemical group C* 0.000 description 85
- 125000005843 halogen group Chemical group 0.000 description 63
- 238000002347 injection Methods 0.000 description 56
- 239000007924 injection Substances 0.000 description 56
- 125000003118 aryl group Chemical group 0.000 description 53
- 229910052799 carbon Inorganic materials 0.000 description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 39
- 239000010408 film Substances 0.000 description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 38
- 125000001153 fluoro group Chemical group F* 0.000 description 33
- 125000001072 heteroaryl group Chemical group 0.000 description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 31
- 125000000304 alkynyl group Chemical group 0.000 description 28
- 125000004093 cyano group Chemical group *C#N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 229910052731 fluorine Inorganic materials 0.000 description 26
- 125000003342 alkenyl group Chemical group 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 150000001448 anilines Chemical class 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 21
- 241000208340 Araliaceae Species 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 19
- 235000003140 Panax quinquefolius Nutrition 0.000 description 19
- 235000008434 ginseng Nutrition 0.000 description 19
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- 239000010409 thin film Substances 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 15
- 229910052741 iridium Inorganic materials 0.000 description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 7
- CSYYQOYMUKFICA-UHFFFAOYSA-N 3-methyl-2-phenyl-2-(2-piperidin-1-ylethyl)pentanenitrile;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)CC)(C#N)CCN1CCCCC1 CSYYQOYMUKFICA-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 6
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000010405 anode material Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000010304 firing Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 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
- 235000010290 biphenyl Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UVUNZHNCNUFPQA-UHFFFAOYSA-K C(C)(=O)CC(C(=O)[O-])=O.[Ir+3].C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O Chemical compound C(C)(=O)CC(C(=O)[O-])=O.[Ir+3].C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O UVUNZHNCNUFPQA-UHFFFAOYSA-K 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Chemical group 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 150000004010 onium ions Chemical class 0.000 description 3
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 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 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 2
- 0 *[B-](c(c(F)c(c(F)c1F)F)c1F)(c(c(F)c(c(F)c1F)F)c1F)c(c(F)c(c(F)c1F)F)c1F Chemical compound *[B-](c(c(F)c(c(F)c1F)F)c1F)(c(c(F)c(c(F)c1F)F)c1F)c(c(F)c(c(F)c1F)F)c1F 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CISROCVXJOHQIK-UHFFFAOYSA-N 1-(2,4-difluorophenyl)pyridin-1-ium Chemical compound FC1=C(C=CC(=C1)F)[N+]1=CC=CC=C1 CISROCVXJOHQIK-UHFFFAOYSA-N 0.000 description 2
- COOJZGDRNSHKNW-UHFFFAOYSA-N 1-(benzylsulfanylmethyl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1CSCC1=CC=CC=C1 COOJZGDRNSHKNW-UHFFFAOYSA-N 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 2
- SXNILPAPBUZTIM-UHFFFAOYSA-N 1-benzylacridine Chemical compound C=1C=CC2=NC3=CC=CC=C3C=C2C=1CC1=CC=CC=C1 SXNILPAPBUZTIM-UHFFFAOYSA-N 0.000 description 2
- NDZFNTHGIIQMQI-UHFFFAOYSA-N 1-benzylpyridin-1-ium Chemical compound C=1C=CC=C[N+]=1CC1=CC=CC=C1 NDZFNTHGIIQMQI-UHFFFAOYSA-N 0.000 description 2
- VQGBPCIONNQYIL-UHFFFAOYSA-N 1-benzylquinolin-1-ium Chemical compound C=1C=CC2=CC=CC=C2[N+]=1CC1=CC=CC=C1 VQGBPCIONNQYIL-UHFFFAOYSA-N 0.000 description 2
- AOQAYBCERCSGDQ-UHFFFAOYSA-N 1-benzylthiolan-1-ium Chemical compound C=1C=CC=CC=1C[S+]1CCCC1 AOQAYBCERCSGDQ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- SWCAHNHHPDFYSS-UHFFFAOYSA-N 2-(benzylsulfanylmethyl)naphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1CSCC1=CC=CC=C1 SWCAHNHHPDFYSS-UHFFFAOYSA-N 0.000 description 2
- MBWYZECWEVLZGI-UHFFFAOYSA-N 2-benzyl-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1CC1=CC=CC=C1 MBWYZECWEVLZGI-UHFFFAOYSA-N 0.000 description 2
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- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
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- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
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- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
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- 150000003077 polyols Chemical class 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
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- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
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- 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
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
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- AGWJLDNNUJKAHP-UHFFFAOYSA-N tetrahexylphosphanium Chemical compound CCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC AGWJLDNNUJKAHP-UHFFFAOYSA-N 0.000 description 1
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- QQFYJXKKHBDLQV-UHFFFAOYSA-N tetrakis(2-methoxyphenyl)phosphanium Chemical compound COC1=CC=CC=C1[P+](C=1C(=CC=CC=1)OC)(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC QQFYJXKKHBDLQV-UHFFFAOYSA-N 0.000 description 1
- XLZOKVSFMDOMTL-UHFFFAOYSA-N tetrakis(3-methoxyphenyl)phosphanium Chemical compound COC1=CC=CC([P+](C=2C=C(OC)C=CC=2)(C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 XLZOKVSFMDOMTL-UHFFFAOYSA-N 0.000 description 1
- BFADQASMYNGYBX-UHFFFAOYSA-N tetrakis(4-methoxyphenyl)phosphanium Chemical compound C1=CC(OC)=CC=C1[P+](C=1C=CC(OC)=CC=1)(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFADQASMYNGYBX-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
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- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-UHFFFAOYSA-N 0.000 description 1
- FCIABWJRBPKYJO-UHFFFAOYSA-N triethoxy(furan-3-yl)silane Chemical compound CCO[Si](OCC)(OCC)C=1C=COC=1 FCIABWJRBPKYJO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- ZRQAIBMAFLMIND-UHFFFAOYSA-N triethoxy(thiophen-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CS1 ZRQAIBMAFLMIND-UHFFFAOYSA-N 0.000 description 1
- JAXKOBBGXVPAFI-UHFFFAOYSA-N triethoxy-[3-(1,1,1,2,3-pentafluoropropan-2-yloxy)propyl]silane Chemical compound FCC(C(F)(F)F)(OCCC[Si](OCC)(OCC)OCC)F JAXKOBBGXVPAFI-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical group COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 1
- KIGXXTRUJYDDKP-UHFFFAOYSA-N triphenyl-[4-[4-(4-triphenylsilylphenyl)phenyl]phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KIGXXTRUJYDDKP-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 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 1
- AXYQQAVHPAUFQX-UHFFFAOYSA-N tris(2-methylphenyl)sulfanium Chemical compound CC1=CC=CC=C1[S+](C=1C(=CC=CC=1)C)C1=CC=CC=C1C AXYQQAVHPAUFQX-UHFFFAOYSA-N 0.000 description 1
- QKFJVDSYTSWPII-UHFFFAOYSA-N tris(4-methylphenyl)sulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 QKFJVDSYTSWPII-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
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-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
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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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- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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Abstract
例如,苯胺衍生物或噻吩衍生物等電荷輸送性物質與例如,含有如下述式所示的鎓硼酸鹽與有機溶劑之電荷輸送性清漆可有效率地賦予具有優良的電荷輸送性、平坦性及均勻性之電荷輸送性薄膜的再現性。
Description
本發明係關於電荷輸送性清漆。
有機電致發光(以下稱為有機EL)元件中,作為發光層或電荷注入層,使用由有機化合物所成的電荷輸送性薄膜。特別在電洞注入層中,擔任陽極與電洞輸送層或者發光層之電荷交換,而發揮達成有機EL元件的低電壓驅動及高亮度時的重要功能。
電洞注入層的形成方法可大致分為以蒸鍍法作為代表的乾式製程,與以旋轉塗佈法作為代表的濕式製程,將這些各製程做比較時,濕式製程中比較能夠有效率地製造出大面積且平坦性高之薄膜。因此,有機EL顯示的大面積化進展中的現在,可望以濕式製程可形成之電洞注入層。
有鑑於如此情事,本發明者們對於可適用於各種濕式製程的同時,開發出賦予適用於有機EL元件的電洞注入層時可實現優良的EL元件特性的薄膜之電荷輸送性材料,或對於使用於此的有機溶劑具有良好的溶解性之化合物(例如參照專利文獻1~4)。
然而,有關電洞注入層用之濕式製程材料常被要求被
改善,特別期待可賦予優良電荷輸送性之薄膜的濕式製程材料。
[專利文獻1]國際公開2008/032616號
[專利文獻2]國際公開2008/129947號
[專利文獻3]國際公開2006/025342號
[專利文獻4]國際公開2010/058777號
[專利文獻5]日本特開2014-205624號公報
本發明為有鑑於上述情事者,以提供將優良的電荷輸送性、平坦性及均勻性的電荷輸送性薄膜可具有良好再現性之電荷輸送性清漆為目的。
本發明者們,欲達成上述目的重複進行詳細檢討的結果,發現由將電荷輸送性物質與所定鎓硼酸鹽溶解於有機溶劑所得之清漆,可得到具有優良電荷輸送性、平坦性及均勻性之電荷輸送性薄膜的優良再現性,以及將該薄膜作為電洞注入層使用時,可得到優良亮度特性之有機EL元件,進而完成本發明。
即,本發明為提供以下者。
(式中,R表示碳數1~10的烷基、碳數1~10的氟烷基、碳數7~10的芳烷基或碳數7~10的氟芳烷基)
2.前述電荷輸送性物質為選自苯胺衍生物及噻吩衍生物的至少1種之1.所示電荷輸送性清漆、
3.前述電荷輸送性物質為苯胺衍生物之2.所示電荷輸送性清漆、
4.使用1.~3.中任一電荷輸送性清漆所製作的電荷輸送性薄膜、
5.具有4.的電荷輸送性薄膜之有機電致發光元件、
6.將1.~3.中任一電荷輸送性清漆塗佈於基材上,並將溶劑蒸發者為特徵之電荷輸送性薄膜的製造方法。
藉由使用本發明之電荷輸送性清漆,可得到
具有優良的電荷輸送性、平坦性及均勻性的電荷輸送性薄膜。
又,具有如此特性的電荷輸送性薄膜可作為以有機EL元件為始的電子裝置用薄膜使用為佳。特別因將此薄膜使用於有機EL元件的電洞注入層,可得到低驅動電壓之有機EL元件。
且,本發明之電荷輸送性清漆即使使用旋轉塗佈法或狹縫塗佈法等可成膜為大面積之各種濕式製程時,亦可再現性良好下製造出電荷輸送性優良的薄膜,故對於近年來的有機EL元件領域中的進展有充分的對應性。
而由本發明之電荷輸送性清漆所得的薄膜因具有優良電荷輸送性,故期待可作為有機薄膜太陽電池之陽極緩衝層、帶電防止膜等使用。
以下對於本發明做詳細說明。
有關本發明之電荷輸送性清漆為含有電荷輸送性物質、鎓硼酸鹽與有機溶劑,鎓硼酸鹽係含有由式(a1)所示負離子與反陽離子所成的鎓硼酸鹽者。
且,所謂電荷輸送性與導電性同義,亦與電洞輸送性同義。又,本發明之電荷輸送性清漆可其自體為具有電荷輸送性者,亦可為使用清漆所得之固體膜為電荷輸送性者。
式(a1)中,R表示碳數1~10的烷基、碳數1~10的氟烷基、碳數7~10的芳烷基或碳數7~10的氟芳烷基。
作為碳數1~10的烷基,可為直鏈狀、分支鏈狀、環狀中任一種,例如可舉出甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、s-丁基、t-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等碳數1~10的直鏈或分支鏈狀烷基;環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、聯環丁基、聯環戊基、聯環己基、聯環庚基、聯環辛基、聯環壬基、聯環癸基等碳數3~10的環狀烷基等,以碳數1~8的烷基為佳,以碳數1~6的烷基為較佳。
作為碳數7~10的芳烷基,可舉出將烷基的氫原子至少1個以芳基進行取代的基,例如可舉出苯甲基、1-萘伸甲基、2-萘伸甲基、苯基伸乙基、1-萘伸乙基、2-萘伸甲基等,以碳數7~9的芳烷基為佳。
作為碳數1~10的氟烷基之具體例子,可舉出碳數1~10的烷基之氫原子至少1個由氟原子所取代的
基。
作為該具體例子,可舉出氟甲基、二氟甲基、三氟甲基、五氟乙基、2,2,2-三氟乙基、五氟丙基、2,2,3,3,3-五氟丙基、2,2,3,3-四氟丙基、2,2,2-三氟-1-(三氟甲基)乙基、九氟丁基、4,4,4-三氟丁基、十一氟戊基、2,2,3,3,4,4,5,5,5-九氟戊基、2,2,3,3,4,4,5,5-八氟戊基、十三氟己基、2,2,3,3,4,4,5,5,6,6,6-十一氟己基、2,2,3,3,4,4,5,5,6,6-十氟己基、3,3,4,4,5,5,6,6,6-九氟己基等。
作為碳數7~10的氟芳烷基之具體例子,可舉出碳數7~10的芳烷基之氫原子至少1個由氟原子所取代的基。
作為該具體例子,可舉出全氟苯甲基、五氟苯基伸甲基、五氟-1-萘伸甲基、五氟-2-萘伸甲基、五氟-1-萘伸乙基、五氟-2-萘伸乙基等。
作為可適用於本發明的烷基芳基硼酸鹽,可舉出下述式所示者,但並未限定於此等。
另一方面,反陽離子雖無特別限定,以式(c1)所示陽離子為佳。
式(c1)中之E表示15~17族的原子價n之元素,因此n表示對應E的原子價之1~3的整數。
上述R’為n+1個鍵結於E,彼等互相獨立表示一價有機基,或2個以上的R’互相直接或介著-O-、-S-、-SO-、-SO2-、-NH-、-CO-、-COO-、-CONH-、伸烷基或者伸苯基進行鍵結,亦與元素E共同可形成環結構。
作為一價有機基,雖無特別限定,但以碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基或可由Z進行取代的碳數6~20的芳基為佳,以可由Z所取代的碳數6~14的芳基為較佳。
作為碳數1~20的烷基,可為直鏈狀、分支鏈狀、環狀中任一種,除在上述碳數1~10的烷基所例示的基以外,例如可舉出n-十一烷基、n-十二烷基、n-十三烷基、n-四癸基、n-十五烷基、n-十六烷基、n-十七烷基、n-十八烷基、n-十九烷基、n-二十烷基等,但以碳數1~18的烷基為佳,以碳數1~8的烷基為較佳。
作為碳數2~20的烯基之具體例子,可舉出乙烯基、n-1-丙烯基、n-2-丙烯基、1-甲基乙烯基、n-1-丁烯基、n-2-丁烯基、n-3-丁烯基、2-甲基-1-丙烯基、2-甲
基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、n-1-戊烯基、n-1-癸烯基、n-1-二十碳烯基等。
作為碳數2~20的炔基之具體例子,可舉出乙炔基、n-1-丙炔基、n-2-丙炔基、n-1-丁炔基、n-2-丁炔基、n-3-丁炔基、1-甲基-2-丙炔基、n-1-戊炔基、n-2-戊炔基、n-3-戊炔基、n-4-戊炔基、1-甲基-n-丁炔基、2-甲基-n-丁炔基、3-甲基-n-丁炔基、1,1-二甲基-n-丙炔基、n-1-己炔基、n-1-癸炔基、n-1-十五炔基、n-1-二十炔基等。
作為碳數6~20的芳基之具體例子,可舉出苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等,以碳數6~14的芳基為佳。
Z表示碳數1~20的烷基、碳數1~8的鹵烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基、碳數2~20的雜芳基、硝基、羥基、氰基、碳數1~8的烷氧基、碳數6~20的芳基氧基、碳數1~20的醯基、碳數1~20的醯氧基、碳數1~8的烷基硫基、碳數6~20的芳基硫基、二碳數1~8烷基胺基、二碳數6~20芳基胺基、胺基或鹵素原子。
彼等中作為烷基、烯基、炔基、芳基,可舉出與上述相同者。
作為鹵素原子,可舉出氟原子、氯原子、溴原子、碘原子等,以氟原子為佳。
作為碳數2~20的雜芳基之具體例子,可舉
出2-噻吩基、3-噻吩基、2-呋喃基、3-呋喃基、2-噁唑基、4-噁唑基、5-噁唑基、3-異噁唑基、4-異噁唑基、5-異噁唑基等含氧雜芳基、2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基等含硫雜芳基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基、2-吡嗪基、3-吡嗪基、5-吡嗪基、6-吡嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基、6-嘧啶基、3-噠嗪基、4-噠嗪基、5-噠嗪基、6-噠嗪基、1,2,3-三嗪-4-基、1,2,3-三嗪-5-基、1,2,4-三嗪-3-基、1,2,4-三嗪-5-基、1,2,4-三嗪-6-基、1,3,5-三嗪-2-基、1,2,4,5-四嗪-3-基、1,2,3,4-四嗪-5-基、2-喹啉基、3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基、1-異喹啉基、3-異喹啉基、4-異喹啉基、5-異喹啉基、6-異喹啉基、7-異喹啉基、8-異喹啉基、2-喹喔啉基、5-喹喔啉基、6-喹喔啉基、2-喹唑啉基、4-喹唑啉基、5-喹唑啉基、6-喹唑啉基、7-喹唑啉基、8-喹唑啉基、3-噌啉基、4-噌啉基、5-噌啉基、6-噌啉基、7-噌啉基、8-噌啉基等含氮雜芳基等。
作為碳數1~8的鹵烷基之具體例子,可舉出在上述所例示的烷基中,碳數1~8的烷基之氫原子至少1個由鹵素原子所取代的基等。且,鹵素原子可為氯、溴、碘、氟原子中任一。其中以氟烷基為佳,以全氟烷基為較佳。
作為氟烷基之具體例子,可舉出與上述同樣者。
作為碳數1~8的烷氧基之具體例子,可舉出
甲氧基、乙氧基、n-丙氧基、i-丙氧基、c-丙氧基、n-丁氧基、i-丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、n-己氧基、n-庚基氧基、n-辛基氧基等。
作為碳數6~20的芳基氧基之具體例子,可舉出苯氧基、1-萘氧基、2-萘氧基、1-蒽基氧基、2-蒽基氧基、9-蒽基氧基、1-菲基氧基、2-菲基氧基、3-菲基氧基、4-菲基氧基、9-菲基氧基等。
碳數1~20的醯基之具體例子,可舉出甲醯基、乙醯基、丙醯基、丁醯基、異丁醯基、香草基、異香草基、苯甲醯基等。
作為碳數1~20的醯氧基之具體例,可舉出甲醯基氧基、乙醯氧基、丙醯基氧基、丁醯基氧基、異丁醯基氧基、香草基氧基、異香草基氧基、苯甲醯基氧基等。
作為碳數1~8的烷基硫基之具體例,可舉出甲基硫基、乙基硫基、n-丙基硫基、異丙基硫基、n-丁基硫基、異丁基硫基、s-丁基硫基、t-丁基硫基、n-戊基硫基、n-己基硫基、n-庚基硫基、n-辛基硫基等。
作為碳數6~20的芳基硫基之具體例,可舉出苯基硫基、1-萘硫基、2-萘硫基、1-蒽基硫基、2-蒽基硫基、9-蒽基硫基、1-菲基硫基、2-菲基硫基、3-菲基硫基、4-菲基硫基、9-菲基硫基等。
作為二碳數1~8烷基胺基之具體例,可舉出二甲基胺基、二乙基胺基、二n-丙基胺基、二i-丙基胺基、二n-丁基胺基、二i-丁基胺基、二n-戊基胺基、二
n-己基胺基、二n-庚基胺基、二n-辛基胺基、甲基乙基胺基等。
作為二碳數6~20芳基胺基之具體例,可舉出二苯基胺基、1-萘苯基胺基、二(1-萘)胺基、1-萘-2-萘胺基、二(2-萘)胺基等。
作為上述E,15~17族之元素中,特別以O(氧)、N(氮)、P(磷)、S(硫)或I(碘)為佳,特別以可賦予安定且容易處理的鎓離子之S、I、N、P為較佳,S、I為更一層佳。對應的鎓離子為氧鎓、銨、鏻、硫鎓、碘鎓。
上述(R’)n+1-E+所示鎓離子之具體例,可舉出下述者,但並未受限定於此等。
作為氧鎓離子之具體例,可舉出三甲基氧鎓、二乙基甲基氧鎓、三乙基氧鎓、四伸甲基甲基氧鎓等氧鎓;4-甲基吡喃鎓、2,4,6-三甲基吡喃鎓、2,6-二-t-丁基吡喃鎓、2,6-二苯基吡喃鎓等吡喃鎓;2,4-二甲基苯並吡喃鎓(Chromenium)、1,3-二甲基異苯並吡喃鎓等苯並吡喃鎓(Chromenium)及異苯並吡喃鎓等。
作為銨離子之具體例,可舉出四甲基銨、乙基三甲基銨、二乙基二甲基銨、三乙基甲基銨、四乙基銨等四烷基銨;N,N-二甲基吡咯烷鎓、N-乙基-N-甲基吡咯烷鎓、N,N-二乙基吡咯烷鎓等吡咯烷鎓;N,N’-二甲基咪唑鎓、N,N’-二乙基咪唑鎓、N-乙基-N’-甲基咪唑鎓、1,3,4-三甲基咪唑鎓、1,2,3,4-四甲基咪唑鎓等咪唑鎓;N,N’-二甲基四氫嘧啶鎓等四氫嘧啶鎓;N,N’-二甲基嗎啉
鎓等嗎啉鎓;N,N’-二乙基哌啶鎓等哌啶鎓;N-甲基吡啶鎓、N-苯甲基吡啶鎓、N-苯甲醯基吡啶鎓等吡啶鎓;N,N’-二甲基咪唑鎓等咪唑鎓;N-甲基喹啉鎓、N-苯甲基喹啉鎓、N-苯甲醯基喹啉鎓等喹啉鎓;N-甲基異喹啉鎓等異喹啉鎓;苯甲基苯並噻唑鎓、苯甲醯基苯並噻唑鎓等噻唑鎓;苯甲基吖啶鎓、苯甲醯基吖啶鎓等吖啶鎓等。
作為鏻離子之具體例,可舉出四苯基鏻、四-p-甲苯基鏻、肆(2-甲氧基苯基)鏻、肆(3-甲氧基苯基)鏻、肆(4-甲氧基苯基)鏻等四芳基鏻;三苯基苯甲基鏻、三苯基苯甲醯基鏻、三苯基甲基鏻、三苯基丁基鏻等三芳基鏻;三乙基苯甲基鏻、三丁基苯甲基鏻、四乙基鏻、四丁基鏻、四己基鏻、三乙基苯甲醯基鏻、三丁基苯甲醯基鏻等四烷基鏻等。
作為硫鎓離子之具體例,可舉出三苯基硫鎓、三-p-甲苯基硫鎓、三-o-甲苯基硫鎓、參(4-甲氧基苯基)硫鎓、1-萘二苯基硫鎓、2-萘二苯基硫鎓、參(4-氟苯基)硫鎓、三-1-萘硫鎓、三-2-萘硫鎓、參(4-羥基苯基)硫鎓、4-(苯基硫基)苯基二苯基硫鎓、4-(p-甲苯基硫基)苯基二-p-甲苯基硫鎓、4-(4-甲氧基苯基硫基)苯基雙(4-甲氧基苯基)硫鎓、4-(苯基硫基)苯基雙(4-氟苯基)硫鎓、4-(苯基硫基)苯基雙(4-甲氧基苯基)硫鎓、4-(苯基硫基)苯基二-p-甲苯基硫鎓、〔4-(4-聯苯基硫基)苯基〕-4-聯苯基苯基硫鎓、〔4-(2-噻噸酮基硫基)苯基〕二苯基硫鎓、雙〔4-(二苯基鎏)苯基〕硫化物、雙〔4-{雙〔4-(2-羥基乙氧基)苯
基〕鎏}苯基〕硫化物、雙{4-〔雙(4-氟苯基)鎏〕苯基}硫化物、雙{4-〔雙(4-甲基苯基)鎏〕苯基}硫化物、雙{4-〔雙(4-甲氧基苯基)鎏〕苯基}硫化物、4-(4-苯甲醯基-2-氯苯基硫基)苯基雙(4-氟苯基)硫鎓、4-(4-苯甲醯基-2-氯苯基硫基)苯基二苯基硫鎓、4-(4-苯甲醯基苯基硫基)苯基雙(4-氟苯基)硫鎓、4-(4-苯甲醯基苯基硫基)苯基二苯基硫鎓、7-異丙基-9-氧代-10-硫雜-9,10-二氫蒽-2-基二-p-甲苯基硫鎓、7-異丙基-9-氧代-10-硫雜-9,10-二氫蒽-2-基二苯基硫鎓、2-〔(二-p-甲苯基)鎏〕噻噸酮、2-〔(二苯基)鎏〕噻噸酮、4-(9-氧代-9H-硫基呫噸-2-基)噻吩基-9-氧代-9H-硫基呫噸-2-基苯基硫鎓、4-〔4-(4-t-丁基苯甲醯基)苯基硫基〕苯基二-p-甲苯基硫鎓、4-〔4-(4-t-丁基苯甲醯基)苯基硫基〕苯基二苯基硫鎓、4-〔4-(苯甲醯基苯基硫基)〕苯基二-p-甲苯基硫鎓、4-〔4-(苯甲醯基苯基硫基)〕苯基二苯基硫鎓、5-(4-甲氧基苯基)噻蒽鎓、5-苯基噻蒽鎓、5-甲苯基噻蒽鎓、5-(4-乙氧基苯基)噻蒽鎓、5-(2,4,6-三甲基苯基)噻蒽鎓等三芳基硫鎓;二苯基苯甲醯基硫鎓、二苯基4-硝基苯甲醯基硫鎓、二苯基苯甲基硫鎓、二苯基甲基硫鎓等二芳基硫鎓;苯基甲基苯甲基硫鎓、4-羥基苯基甲基苯甲基硫鎓、4-甲氧基苯基甲基苯甲基硫鎓、4-乙醯羰基氧基苯基甲基苯甲基硫鎓、4-羥基苯基(2-萘甲基)甲基硫鎓、2-萘甲基苯甲基硫鎓、2-萘甲基(1-乙氧基羰基)乙基硫鎓、苯基甲基苯甲醯基硫鎓、4-羥基苯基甲基苯甲醯基硫鎓、4-甲氧基苯基甲基苯甲醯基硫鎓、4-乙
醯羰基氧基苯基甲基苯甲醯基硫鎓、2-萘甲基苯甲醯基硫鎓、2-萘十八烷基苯甲醯基硫鎓、9-蒽甲基苯甲醯基硫鎓等單芳基硫鎓;二甲基苯甲醯基硫鎓、苯甲醯基四氫噻吩鎓、二甲基苯甲基硫鎓、苯甲基四氫噻吩鎓、十八烷基甲基苯甲醯基硫鎓等三烷基硫鎓等。
作為碘鎓離子之具體例,可舉出二苯基碘鎓、二-p-甲苯基碘鎓、雙(4-十二烷基苯基)碘鎓、雙(4-甲氧基苯基)碘鎓、(4-辛基氧基苯基)苯基碘鎓、雙(4-癸基氧基)苯基碘鎓、4-(2-羥基四癸基氧基)苯基苯基碘鎓、4-異丙基苯基(p-甲苯基)碘鎓、4-異丁基苯基(p-甲苯基)碘鎓等。
對於本發明,上述鎓硼酸鹽可單獨使用1種,或組合2種以上使用。
又,視必要可併用公知的其他鎓硼酸鹽。
且,上述鎓硼酸鹽,例如可藉由於日本特開2014-205624號公報等所記載的公知方法進行合成。
上述鎓硼酸鹽欲使電荷輸送性清漆之溶解變得容易,可預先溶解在有機溶劑中。
作為如此有機溶劑,可舉出伸丙基碳酸酯、伸乙基碳酸酯、1,2-伸丁基碳酸酯、二甲基碳酸酯、二乙基碳酸酯等碳酸酯類;丙酮、甲基乙基酮、環己酮、甲基異戊基酮、2-庚酮等酮類;乙二醇、乙二醇單乙酸酯、二乙二醇、二乙二醇單乙酸酯、丙二醇、丙二醇單乙酸酯、二丙二醇、二丙二醇單乙酸酯的單甲基醚、單乙基醚、單丙基
醚、單丁基醚或單苯基醚等多元醇及其衍生物類;二噁烷等環式醚類;甲酸乙酯、乳酸甲酯、乳酸乙酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、丙酮酸甲酯、乙醯乙酸甲酯、乙醯乙酸乙酯、丙酮酸乙酯、乙氧基乙酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯、2-羥基丙酸甲酯、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、2-羥基-3-甲基丁烷酸甲酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯等酯類;甲苯、二甲苯等芳香族烴類等,這些可單獨使用,亦可組合2種以上使用。
使用有機溶劑時,該使用比例對於上述鎓硼酸鹽100質量份而言,以15~1000質量份為佳,以30~500質量份為較佳。
作為在本發明使用的電荷輸送性物質,並無特別限定,可使用適宜地選自過去有機EL之領域等中公知者。
該具體例,可舉出寡苯胺衍生物、N,N’-二芳基聯苯胺衍生物、N,N,N’,N’-四芳基聯苯胺衍生物等芳基胺衍生物、寡聚噻吩衍生物、噻吩並噻吩衍生物、噻吩並噻吩衍生物等噻吩衍生物、寡聚吡咯等吡咯衍生物等之各種電洞輸送性物質,其中亦以芳基胺衍生物、噻吩衍生物為佳,以芳基胺衍生物為較佳,以式(1)或(2)所示苯胺衍生物為更一層佳。
又,電荷輸送性物質的分子量亦無特別限定,由可調製出賦予平坦性高的薄膜的均勻清漆之觀點來
看,以200~9,000為佳,由可得到耐溶劑性高之電荷輸送性的觀點來看,以300以上為較佳,以400以上為更一層佳,由可調製出可更良好再現性地賦予平坦性高之薄膜的均勻清漆之觀點來看,以8,000以下為較佳,以7,000以下為更一層佳,以6,000以下更佳,以5,000以下為最佳。
且,由在進行薄膜化時防止電荷輸送性物質分離之觀點來看,電荷輸送性物質以無分子量分布者(分散度為1)為佳(即,單一分子量者為佳)。
式(2)中,R1及R2為互相獨立表示氫原子、鹵素原子、硝基、氰基或可由鹵素原子所取代之碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基或者碳數2~20的雜芳基,這些具體例,可舉出與上述式(c1)所說明的相同基。
其中,R1及R2亦以氫原子、氟原子、氰基、可由鹵素原子所取代的碳數1~20的烷基、可由鹵素原子所取代的碳數6~20的芳基、可由鹵素原子所取代的碳數2~20的雜芳基為佳,以氫原子、氟原子、氰基、可由鹵素原子所取代的碳數1~10的烷基、可由鹵素原子所取代
的苯基為較佳,以氫原子、氟原子、甲基、三氟甲基為更一層佳,以氫原子為最佳。
上述式(1)及(2)中之Ph1表示式(P1)所示基。
其中,R3~R6為互相獨立表示氫原子、鹵素原子、硝基、氰基或可由鹵素原子所取代的碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基或者碳數2~20的雜芳基,這些具體例,可舉出與在上述式(c1)所說明的相同基。
特別作為R3~R6,以氫原子、氟原子、氰基、可由鹵素原子所取代的碳數1~20的烷基、可由鹵素原子所取代的碳數6~20的芳基、可由鹵素原子所取代的碳數2~20的雜芳基為佳,以氫原子、氟原子、氰基、可由鹵素原子所取代的碳數1~10的烷基、可由鹵素原子所取代的苯基為較佳,以氫原子、氟原子、甲基、三氟甲基為更一層佳,以氫原子為最佳。
以下,雖舉出作為Ph1的較佳基之具體例子,但並無限定於此等。
上述式(1)中之Ar1為互相獨立表示式(B1)~(B11)中任一所示基,但特別以式(B1’)~(B11’)中任一所示基為佳。
其中,R7~R27、R30~R51及R53~R154為互相獨立表示氫原子、鹵素原子、硝基、氰基或可由鹵素原子所取代的二苯基胺基、碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基或者碳數2~20的雜芳基,R28及R29為互相獨立表示可由Z1所取代的碳數6~20的芳基或碳數2~20的雜芳基,R52表示氫原子、可由Z4所取代的碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基或可由Z1所取代的碳數6~20的芳基或者碳數2~20的雜芳基,Z1表示可由鹵素原
子、硝基、氰基或Z2所取代的碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基,Z2表示可由鹵素原子、硝基、氰基或Z3所取代的碳數6~20的芳基或者碳數2~20的雜芳基,Z3表示鹵素原子、硝基或氰基,Z4表示可由鹵素原子、硝基、氰基或Z5所取代的碳數6~20的芳基或者碳數2~20的雜芳基,Z5表示可由鹵素原子、硝基、氰基或Z3所取代的碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基,這些鹵素原子、碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基及碳數2~20的雜芳基之具體例,可舉出與上述式(c1)所說明的相同基。
特別作為R7~R27、R30~R51及R53~R154,以氫原子、氟原子、氰基、可由鹵素原子所取代的二苯基胺基、可由鹵素原子所取代的碳數1~20的烷基、可由鹵素原子所取代的碳數6~20的芳基、可由鹵素原子所取代的碳數2~20的雜芳基為佳,以氫原子、氟原子、氰基、可由鹵素原子所取代的碳數1~10的烷基、可由鹵素原子所取代的苯基為較佳,以氫原子、氟原子、甲基、三氟甲基為更一層佳,以氫原子為最佳。
又,作為R28及R29,以可由Z1所取代的碳數6~14的芳基、可由Z1所取代的碳數2~14的雜芳基為佳,以可由Z1所取代的碳數6~14的芳基為較佳,可由Z1所取代的苯基、可由Z1所取代的1-萘基、可由Z1所取代的2-萘基為更一層佳。
而作為R52,以氫原子、可由Z1所取代的碳數6~20的芳基、可由Z1所取代的碳數2~20的雜芳基、可由Z4所取代的碳數1~20的烷基為佳,以氫原子、可由Z1所取代的碳數6~14的芳基、可由Z1所取代的碳數2~14的雜芳基、可由Z4所取代的碳數1~10的烷基為較佳,以氫原子、可由Z1所取代的碳數6~14的芳基、可由Z1所取代的碳數2~14的含氮雜芳基、可由Z4所取代的碳數1~10的烷基為更一層佳,以氫原子、可由Z1所取代的苯基、可由Z1所取代的1-萘基、可由Z1所取代的2-萘基、可由Z1所取代的2-吡啶基、可由Z1所取代的3-吡啶基、可由Z1所取代的4-吡啶基、可由Z4所取代的甲基為更佳。
又,Ar4為互相獨立表示可由二碳數6~20的芳基胺基所取代的碳數6~20的芳基。
碳數6~20的芳基、二碳數6~20的芳基胺基之具體例,可舉出與式(c1)中所說明的相同基。
作為Ar4,以苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、p-(二苯基胺基)苯基、p-(1-萘苯基胺基)苯基、p-(二(1-萘)胺基)苯基、p-(1-萘-2-萘胺基)苯基、p-(二(2-萘)胺基)苯基為佳,以p-(二苯基胺基)苯基為較佳。
以下,舉出作為Ar1的較佳基之具體例子,但並未限定於此等。
(式中,R52表示與上述相同意思)
上述式(1)中之Ar2為互相獨立表示式(A1)~(A18)中任一所示基。
其中,式中,R155表示氫原子、可由Z4所取代的碳數1~20的烷基、碳數2~20的烯基或者碳數2~20的炔基或可由Z1所取代的碳數6~20的芳基或者碳數2~20的雜芳基,R156及R157為互相獨立表示可由Z1所取代的碳數6~20的芳基或碳數2~20的雜芳基,DPA表示二苯基胺基,Ar4、Z1,Z4表示與上述相同意思。這些鹵素原子、碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基及碳數2~20的雜芳基之具體例,可舉出與上述式(c1)所說明的相同基。
特別作為R155,以氫原子、可由Z1所取代的碳數6~20的芳基、可由Z1所取代的碳數2~20的雜芳基、可由Z4所取代的碳數1~20的烷基為佳,以氫原子、可由Z1所取代的碳數6~14的芳基、可由Z1所取代的碳數2~14的雜芳基、可由Z4所取代的碳數1~10的烷基為較佳,以氫原子、可由Z1所取代的碳數6~14的芳基、可由Z1所取代的碳數2~14之含氮雜芳基、可由Z4所取代的碳數1~10的烷基為更一層佳,以氫原子、可由Z1所取代的苯基、可由Z1所取代的1-萘基、可由Z1所取代的2-萘基、可由Z1所取代的2-吡啶基、可由Z1所取代的3-吡啶基、可由Z1所取代的4-吡啶基、可由Z4所取代的甲基為更佳。
又,作為R156及R157,以可由Z1所取代的碳數6~14的芳基、可由Z1所取代的碳數2~14的雜芳基為佳,以可由Z1所取代的碳數6~14的芳基為較佳,以可由Z1
所取代的苯基、可由Z1所取代的1-萘基、可由Z1所取代的2-萘基為更一層佳。
以下,雖舉出作為Ar2的較佳基之具體例子,但並未限定於此等。
(式中,R155表示與上述相同意思)
且,式(1)中,若考慮到所得之苯胺衍生物的合成之容易性,以Ar1皆為相同基,Ar2皆為相同基者為佳,以Ar1及Ar2皆為相同基者為較佳。即,式(1)所示苯胺衍生物以式(1-1)所示苯胺衍生物為較佳。
又,如後述,作為原料化合物可使用比較便宜的雙
(4-胺基苯基)胺以比較簡單的方法進行合成,而同時對於有機溶劑之溶解性為優良,故式(1)所示苯胺衍生物以式(1-1)所示苯胺衍生物為佳。
式(1-1)中,Ph1及k表示與上述相同意思,Ar5同時表示式(D1)~(D13)中任一所示基時,特別以式(D1’)~(D13’)中任一所示基者為佳。
且,作為Ar5之具體例,可舉出與作為Ar1的較佳基之具體例子而在上述所舉出者相同者。
(式中,R28、R29、R52、Ar4及DPA表示與上述相同
意思)
(式中,R28、R29、R52、Ar4及DPA表示與上述相同意思)
又,如後述作為原料化合物使用比較便宜的雙(4-胺基苯基)胺,以比較簡便的方法進行合成之同時,所得之苯胺衍生物對於有機溶劑的溶解性為優良,故式(1)所示苯胺衍生物以式(1-2)所示苯胺衍生物為佳。
上述Ar6同時表示式(E1)~(E14)中任一所示基。
(式中,R52表示與上述相同意思)
上述式(2)中之Ar3表示式(C1)~(C8)中任一所示基,特別以(C1’)~(C8’)中任一所示基為佳。
上述式(1)中之k表示1~10的整數,但由提高化合物對於有機溶劑的溶解性之觀點來看,以1~5為佳,以1~3為較佳,以1或2為更一層佳,以1最佳。
上述式(2)中之l表示1或2。
且,對於R28、R29、R52及R155~R157,Z1以鹵素原子、硝基、氰基、可由Z2所取代的碳數1~10的烷基、可由Z2所取代的碳數2~10的烯基、可由Z2所取代的碳數2~10的炔基為佳,以鹵素原子、硝基、氰基、可由Z2所取代的碳數1~3的烷基、可由Z2所取代的碳數2~3的烯基、可由Z2所取代的碳數2~3的炔基為較佳,以氟原子、可由Z2所取代的碳數1~3的烷基、可由Z2所取代的碳數2~3的烯基、可由Z2所取代的碳數2~3的炔基為更一層佳。
對於R28、R29、R52及R155~R157,Z4以鹵素
原子、硝基、氰基、可由Z5所取代的碳數6~14的芳基為佳,以鹵素原子、硝基、氰基、可由Z5所取代的碳數6~10的芳基為較佳,以氟原子、可由Z5所取代的碳數6~10的芳基為更一層佳,以氟原子、可由Z5所取代的苯基為更佳。
對於R28、R29、R52及R155~R157,Z2以鹵素原子、硝基、氰基、可由Z3取代的碳數6~14的芳基為佳,以鹵素原子、硝基、氰基、可由Z3所取代的碳數6~10的芳基為較佳,以氟原子、可由Z3所取代的碳數6~10的芳基為更一層佳,以氟原子、可由Z3所取代的苯基為更佳。
對於R28、R29、R52及R155~R157,Z5以鹵素原子、硝基、氰基、可由Z3所取代的碳數1~10的烷基、可由Z3所取代的碳數2~10的烯基、可由Z3所取代的碳數2~10的炔基為佳,以鹵素原子、硝基、氰基、可由Z3所取代的碳數1~3的烷基、可由Z3所取代的碳數2~3的烯基、可由Z3所取代的碳數2~3的炔基為較佳,以氟原子、可由Z3所取代的碳數1~3的烷基、可由Z3所取代的碳數2~3的烯基、可由Z3所取代的碳數2~3的炔基為更一層佳。
對於R28、R29、R52及R155~R157,Z3以鹵素原子為佳,以氟原子為較佳。
另一方面,對於R7~R27、R30~R51及R53~R154,Z1以鹵素原子、硝基、氰基、可由Z2所取代的碳
數1~3的烷基、可由Z2所取代的碳數2~3的烯基、可由Z2所取代的碳數2~3的炔基為佳,以鹵素原子、可由Z2所取代的碳數1~3的烷基為較佳,以氟原子、可由Z2所取代的甲基為更一層佳。
對於R7~R27、R30~R51及R53~R154,Z4以鹵素原子、硝基、氰基、可由Z5所取代的碳數6~10的芳基為佳,以鹵素原子、可由Z5所取代的碳數6~10的芳基為較佳,以氟原子、可由Z5所取代的苯基為更一層佳。
對於R7~R27、R30~R51及R53~R154,Z2以鹵素原子、硝基、氰基、可由Z3所取代的碳數6~10的芳基為佳,以鹵素原子、可由Z3所取代的碳數6~10的芳基為較佳,以氟原子、可由Z3所取代的苯基為更一層佳。
對於R7~R27、R30~R51及R53~R154,Z5以鹵素原子、硝基、氰基、可由Z3所取代的碳數1~3的烷基、可由Z3所取代的碳數2~3的烯基、可由Z3所取代的碳數2~3的炔基為佳,以鹵素原子、可由Z3所取代的碳數1~3的烷基為較佳,以氟原子、可由Z3所取代的甲基為更一層佳。
對於R7~R27、R30~R51及R53~R154,Z3以鹵素原子為佳,以氟原子為較佳。
作為上述R52及R155的較佳基之具體例,可舉出以下所舉出的基,但並未限定於此等。
上述烷基、烯基及炔基的碳數,較佳為10以下,更佳為6以下,更一層較佳為4以下。
又,上述芳基及雜芳基的碳數,較佳為14以下,更佳為10以下,更一層較佳為6以下。
上述式(1)所示苯胺衍生物係可將式(3)所示胺化合物與式(4)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X表示鹵素原子或擬鹵素基,Ar1、Ar2、Ph1及k表示與上述相同意思)
特別式(1-1)所示苯胺衍生物係由將式(5)所示胺化合物與式(6)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X、Ar5、Ph1及k表示與上述相同意思)
又,式(1-2)所示苯胺衍生物係可由將雙(4-胺基苯基)胺與式(7)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X及Ar6表示與上述相同意思)
另一方面,上述式(2)所示苯胺衍生物係可由將式(8)所示胺化合物與式(9)所示芳基化合物在觸媒存在下進行反應而製造。
(式中,X、R1、R2、Ar3、Ph1及l表示與上述相同意思)
作為鹵素原子可舉出與上述相同者。
作為擬鹵素基,可舉出甲烷磺醯基氧基、三氟甲烷磺醯基氧基、九氟丁烷磺醯基氧基等(氟)烷基磺醯基氧基;苯磺醯基氧基、甲苯磺醯基氧基等芳香族磺醯基氧基等。
式(3)、(5)或者(8)所示胺化合物或雙(4-胺基苯基)胺與式(4)、(6)、(7)或(9)所示芳基化合物的裝入比,對於胺化合物或雙(4-胺基苯基)胺的全NH基之物質量而言,可使芳基化合物為當量以上,但以1~1.2當量程度為佳。
作為使用於上述反應的觸媒,例如可舉出氯化銅、溴化銅、碘化銅等銅觸媒;Pd(PPh3)4(肆(三苯基膦)鈀)、Pd(PPh3)2Cl2(雙(三苯基膦)二氯鈀)、Pd(dba)2(雙(二苯亞甲基丙酮)鈀)、Pd2(dba)3(參(二苯亞甲基丙酮)二鈀)、Pd(P-t-Bu3)2(雙(三(t-丁基膦))鈀)、Pd(OAc)2(乙酸鈀)等鈀觸媒等。這些觸媒可單獨使用,亦可組合2種以上使用。又,這些觸媒可與公知的適當配位子同時使用。
作為如此配位子,可舉出三苯基膦、三-o-甲苯基膦、二苯基甲基膦、苯基二甲基膦、三甲基膦、三乙基膦、三丁基膦、三-tert-丁基膦、二-t-丁基(苯基)膦、二-tert-丁基(4-二甲基胺基苯基)膦、1,2-雙(二苯基膦)乙烷、1,3-雙(二苯基膦)丙烷、1,4-雙(二苯基膦)丁烷、1,1’-雙(二苯基膦)二茂鐵等3級膦、三甲基亞磷酸酯、三乙基亞
磷酸酯、三苯基亞磷酸酯等3級亞磷酸酯等。
觸媒之使用量對於式(4)、(6)、(7)或(9)所示芳基化合物1mol而言,可為0.2mol程度,但以0.15mol程度為較佳。
又,使用配位子時,該使用量對於所使用的金屬錯體而言,可為0.1~5當量,但以1~2當量為佳。
由原料化合物全為固體之情況或者可有效率得到作為目的的苯胺衍生物之觀點,上述各反應在溶劑中進行。使用溶劑時,該種類若未對反應造成壞影響者即可並無特別限制。具體例可舉出脂肪族烴類(戊烷、n-己烷、n-辛烷、n-癸烷、十氫萘等)、鹵素化脂肪族烴類(氯仿、二氯甲烷、二氯乙烷、四氯化碳等)、芳香族烴類(苯、硝基苯、甲苯、o-二甲苯、m-二甲苯、p-二甲苯、三甲苯等)、鹵素化芳香族烴類(氯苯、溴苯、o-二氯苯、m-二氯苯、p-二氯苯等)、醚類(二乙基醚、二異丙基醚、t-丁基甲基醚、四氫呋喃、二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、酮類(丙酮、甲基乙基酮、甲基異丁基酮、二-n-丁基酮、環己酮等)、醯胺類(N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等)、內醯胺及內酯類(N-甲基吡咯啶酮、γ-丁內酯等)、尿素類(N,N-二甲基咪唑啉酮、四甲基脲等)、亞碸類(二甲基亞碸、環丁碸等)、腈類(乙腈、丙腈、丁腈等)等,這些溶劑可單獨使用,亦可混合2種以上使用。
反應溫度可適宜地設定在溶劑的熔點至沸點
之範圍即可,特別以0~200℃程度為佳,以20~150℃為較佳。
反應終了後依據常法進行後處理,可得到目的之苯胺衍生物。
對於上述式(1)所示苯胺衍生物的製造方法,作為原料所使用的式(3’)所示胺化合物可由將式(10)所示胺化合物與式(11)所示芳基化合物在觸媒存在下進行反應而有效率地製造。
(式中,X、Ar1、Ph1及k表示與上述相同意思。但,2個Ar1不會同時為式(B1)所示基)
式(3’)所示胺化合物之上述製造方法為可使式(10)所示胺化合物與式(11)所示芳基化合物進行偶合反應者,但式(10)所示胺化合物與式(11)所示芳基化合物的裝入比例為,在物質量比下對於胺化合物1而言芳基化合物2~2.4程度為佳。
其他,有關於該偶合反應中之觸媒、配位子、溶劑、反應溫度等各條件係如式(1)所示苯胺衍生物之製造方法中所說明的上述相同條件。
且,對於式(1),製造Ar1係R52為氫原子之
式(B4)所示基或式(B10)所示基或者Ar2為式(A12)所示基或R155(含有式(1-1)中之R52)為氫原子之式(A16)所示基的苯胺衍生物時,對於上述反應,亦可使用於胺基上具有公知保護基的芳基化合物。
以下雖舉出式(1)或(2)所示苯胺衍生物之具體例子,但並未限定於此等。且,式及表中,「Me」表示甲基,「Et」表示乙基,「Prn」表示n-丙基,「Pri」表示i-丙基,「Bun」表示n-丁基,「Bui」表示i-丁基,「Bus」表示s-丁基,「But」表示t-丁基,「DPA」表示二苯基胺基,「SBF」表示9,9’-螺雙〔9H-芴〕-2-基。
本發明中,上述鎓硼酸鹽與電荷輸送性物質的比率在物質量(莫耳)比時,電荷輸送性物質:鎓硼酸鹽=1:0.1~10程度。
作為使用於調製電荷輸送性清漆時的有機溶劑,可使用可良好地溶解電荷輸送性物質及鎓硼酸鹽的高溶解性溶劑。
作為如此高溶解性溶劑,例如可舉出環己酮、N,N-二
甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-咪唑啉酮、二乙二醇單甲基醚等有機溶劑,但並未限定於此等。這些溶劑可單獨使用1種或混合2種以上使用,該使用量對於使用於清漆的溶劑全體而言可為5~100質量%。
又,對於本發明,於清漆可含有在25℃為10~200mPa.s,特別為具有35~150mPa.s的黏度之在常壓(大氣壓)的沸點50~300℃,特別為150~250℃之高黏度有機溶劑的至少1種類,藉此可容易進行清漆黏度之調整,其結果可調製出再現性良好下賦予高平坦性之薄膜的對應塗佈方法之清漆。
作為高黏度有機溶劑,例如可舉出環己醇、乙二醇、乙二醇二縮水甘油基醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、丙二醇、己二醇等,但並未限定於此等。這些溶劑可單獨使用,亦可混合2種以上使用。
對於使用於本發明之清漆的溶劑全體之高黏度有機溶劑的添加比例,以固體不會析出的範圍內者為佳,僅不析出固體即可,該添加比例以5~90質量%為佳。
且,對於基板的濕潤性之提高,以溶劑表面張力之調整、極性之調整、沸點之調整等目的下,可將其他溶劑以對於使用於清漆的溶劑全體而言以1~90質量%,較佳為1~50質量%的比例下混合。
作為如此溶劑,例如可舉出丙二醇單甲基醚、乙二醇
單丁基醚、二乙二醇二乙基醚、二乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二乙二醇單乙基醚、二丙酮醇、γ-丁內酯、乙基乳酸酯、n-己基乙酸酯等,但並未限定於此等。這些溶劑可單獨使用1種或混合2種以上後使用。
又,本發明之電荷輸送性清漆可含有有機矽烷化合物。因含有有機矽烷化合物,對於將自清漆所得之薄膜作為有機EL元件的電洞注入層使用時,於與所謂電洞輸送層或發光層之陽極的反側上欲銜接電洞注入層,可提高被層合的對層之電洞注入能。
作為該有機矽烷化合物,可舉出二烷氧基矽烷化合物、三烷氧基矽烷化合物或四烷氧基矽烷化合物,這些可單獨使用,亦可組合2種以上後使用。
對於本發明,有機矽烷化合物係以含有選自二烷氧基矽烷化合物及三烷氧基矽烷化合物的1種者為佳,以含有三烷氧基矽烷化合物者為較佳,以含有具有氟原子之三烷氧基矽烷化合物者為更一層佳。
作為這些烷氧基矽烷化合物,例如可舉出式(S1)~(S3)所示者。
Si(OR)4 (S1)
SiR’(OR)3 (S2)
Si(R’)2(OR)2 (S3)
式中,R為互相獨立表示可由Z6所取代的碳
數1~20的烷基、可由Z6所取代的碳數2~20的烯基、可由Z6所取代的碳數2~20的炔基、可由Z7所取代的碳數6~20的芳基或Z7所取代的碳數2~20的雜芳基,R’為互相獨立表示可由Z8所取代的碳數1~20的烷基、可由Z8所取代的碳數2~20的烯基、可由Z8所取代的碳數2~20的炔基、可由Z9所取代的碳數6~20的芳基或Z9所取代的碳數2~20的雜芳基。
Z6表示鹵素原子、可由Z10所取代的碳數6~20的芳基或Z10所取代的碳數2~20的雜芳基,Z7表示鹵素原子、可由Z10所取代的碳數1~20的烷基、可由Z10所取代的碳數2~20的烯基或Z10所取代的碳數2~20的炔基。
Z8表示鹵素原子、可由Z10所取代的碳數6~20的芳基、可由Z10所取代的碳數2~20的雜芳基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸酯基(-NCO)、胺基、-NHY1基或-NY2Y3基,Z9表示鹵素原子、可由Z10所取代的碳數1~20的烷基、可由Z10所取代的碳數2~20的烯基、可由Z10所取代的碳數2~20的炔基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸酯基(-NCO)、胺基、-NHY1基或-NY2Y3基,Y1~Y3為互相獨立表示可由Z10所取代的碳數1~20的烷基、可由Z10所取代的碳數2~20的烯基、可由Z10所取代的碳數2~20的炔基、可由Z10所取代的碳數6~
20的芳基或可由Z10所取代的碳數2~20的雜芳基。
Z10表示鹵素原子、胺基、硝基、氰基或硫醇基。
式(S1)~(S3)中,作為鹵素原子、碳數1~20的烷基、碳數2~20的烯基、碳數2~20的炔基、碳數6~20的芳基、及碳數2~20的雜芳基可舉出與上述相同者。
對於R及R’,烷基、烯基及炔基的碳數較佳為10以下,更佳為6以下,更一層較佳為4以下。
又,芳基及雜芳基的碳數較佳為14以下,更佳為10以下,更一層較佳為6以下。
作為R,以可由Z6所取代的碳數1~20的烷基或者碳數2~20的烯基或可由Z7所取代的碳數6~20的芳基為佳,以可由Z6所取代的、碳數1~6的烷基或者碳數2~6的烯基或可由Z7所取代的苯基為較佳,以可由Z6所取代的碳數1~4的烷基或可由Z7所取代的苯基為更一層佳,以可由Z6所取代的、甲基或乙基為更佳。
又,作為R’,以可由Z8所取代的碳數1~20的烷基或可由Z9所取代的碳數6~20的芳基為佳,以可由Z8所取代的碳數1~10的烷基或可由Z9所取代的碳數6~14的芳基為較佳,以可由Z8所取代的碳數1~6的烷基或可由Z9所取代的碳數6~10的芳基為更一層佳,以可由Z8所取代的碳數1~4的烷基或可由Z9所取代的苯基為更佳。
且,複數R可皆相同或相異,複數的R’亦可皆為相
同或相異。
作為Z6以鹵素原子或可由Z10所取代的碳數6~20的芳基為佳,以氟原子或可由Z10所取代的苯基為較佳,以不存在者(即,非取代者)為最佳。
又,作為Z7以鹵素原子或可由Z10所取代的碳數6~20的烷基為佳,以氟原子或可由Z10所取代的碳數1~10的烷基為較佳,以不存在者(即,非取代者)為最佳。
另一方面,作為Z8以鹵素原子、可由Z10所取代的苯基、可由Z10所取代的呋喃基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、可由Z10所取代的苯基胺基或可由Z10所取代的二苯基胺基為佳,以鹵素原子為較佳,以氟原子或不存在者(即,非取代者)為更一層佳。
又,作為Z9以鹵素原子、可由Z10所取代的碳數1~20的烷基、可由Z10所取代的呋喃基、環氧環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、可由Z10所取代的苯基胺基或可由Z10所取代的二苯基胺基為佳,以鹵素原子為較佳,以氟原子或不存在者(即,非取代者)為更一層佳。
而作為Z10以鹵素原子為佳,以氟原子或不存在者(即,非取代者)為較佳。
以下,雖舉出在本發明可使用的有機矽烷化合物之具體例子,但並未限定於此等。
二烷氧基矽烷化合物之具體例,可舉出二甲基二甲氧
基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基丙基二甲氧基矽烷、甲基丙基二乙氧基矽烷、二異丙基二甲氧基矽烷、苯基甲基二甲氧基矽烷、乙烯基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二乙氧基矽烷、3-(3,4-環氧環己基)乙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-巰基丙基甲基二甲氧基矽烷、γ-胺基丙基甲基二乙氧基矽烷、N-(2-胺基乙基)胺基丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷等。
三烷氧基矽烷化合物之具體例,可舉出甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、戊基三甲氧基矽烷、戊基三乙氧基矽烷、庚基三甲氧基矽烷、庚基三乙氧基矽烷、辛基三甲氧基矽烷、辛基三乙氧基矽烷、十二烷基三甲氧基矽烷、十二烷基三乙氧基矽烷、十六烷基三甲氧基矽烷、十六烷基三乙氧基矽烷、十八烷基三甲氧基矽烷、十八烷基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、γ-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-
甲基丙烯醯氧基丙基三乙氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、十二烷基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、(三乙氧基矽基)環己烷、全氟辛基乙基三乙氧基矽烷、三乙氧基氟矽烷、十三氟-1,1,2,2-四氫辛基三乙氧基矽烷、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷、3-(五氟異丙氧基)丙基三乙氧基矽烷、十七氟-1,1,2,2-四氫癸基三乙氧基矽烷、三乙氧基-2-噻吩基矽烷、3-(三乙氧基矽基)呋喃等。
四烷氧基矽烷化合物之具體例,可舉出四乙氧基矽烷、四甲氧基矽烷、四丙氧基矽烷等。
彼等中,亦以3,3,3-三氟丙基甲基二甲氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、3,3,3-三氟丙基三甲氧基矽烷、全氟辛基乙基三乙氧基矽烷或五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷為佳。
本發明之電荷輸送性清漆為含有有機矽烷化合物時,該含有量對於電荷輸送性物質之質量(含有摻合物質時為電荷輸送性物質及摻合物物質之合計質量),通常為0.1~50質量%程度,可抑制所得之薄膜的電荷輸送性之降低,且考慮到於上述陰極側上欲銜接由自該清漆所得之薄膜而成的電洞注入層等,而提高對於被層合的層之電洞注入能時,較佳為0.5~40質量%程度,更佳為0.8~30質量%程度,更一層較佳為1~20質量%程度。
本發明之清漆的黏度為配合製作的薄膜之厚度等或固體成分濃度而做適宜設定,通常為在25℃下1~
50mPa.s,該表面張力通常為20~50mN/m。
又,電荷輸送性清漆之固體成分濃度雖有鑑於清漆的黏度及表面張力等或所製作的薄膜厚度等而進行適宜設定者,通常為0.1~10.0質量%程度,若考慮到提高清漆之塗佈性時,較佳為0.5~5.0質量%程度,更佳為1.0~3.0質量%程度。
作為清漆之調製法,雖無特別限定,例如可舉出先將上述鎓硼酸鹽溶解於溶劑中,對此依序加入電荷輸送性物質的方法,或將上述鎓硼酸鹽與電荷輸送性物質之混合物溶解於溶劑的方法。
又,有機溶劑為複數種時,例如於將上述鎓硼酸鹽與電荷輸送性物質仔細溶解的溶劑中,首先溶解此等,於此可加入其他溶劑,於複數種有機溶劑之混合溶劑中,可將上述鎓硼酸鹽、電荷輸送性物質依序或者同時將此等進行溶解。
對於本發明,電荷輸送性清漆由可良好再現性地得到高平坦性薄膜之觀點來看,將上述鎓硼酸鹽、電荷輸送性化合物等溶解於有機溶劑後,使用亞微米級之濾器等進行過濾為佳。
本發明之電荷輸送性薄膜可將上述說明的電荷輸送性清漆塗佈於基材上而燒成後可於基材上形成。
作為清漆之塗佈方法,雖無特別限定,可舉出浸漬法、旋轉塗佈法、轉印印刷法、輥塗佈法、刷毛塗佈、噴墨法、噴霧法、狹縫塗佈法等,對應塗佈方法可調節清漆
之黏度及表面張力者為佳。
又,使用於本發明之清漆時,燒成環境亦無特別限定,不僅可在大氣環境,亦可在氮等惰性氣體或真空中得到均勻成膜面及具有高電荷輸送性之薄膜,但依據電荷輸送性化合物等種類,將清漆在大氣環境下進行燒成時,可良好再現性下得到具有更高電荷輸送性之薄膜。
就燒成溫度,考慮到所得之薄膜的用途、賦予所得之薄膜的電荷輸送性程度、溶劑種類或沸點等,可在100~260℃程度之範圍內進行適宜設定,但將所得之薄膜作為有機EL元件的電洞注入層使用時,以140~250℃程度為佳,以145~240℃程度為較佳。
且,燒成時,以可表現較高均勻成膜性,在基材上可進行反應作為目的下,可設定2階段以上之溫度變化,加熱例如可使用加熱板或烤箱等適當機器進行。
電荷輸送性薄膜之膜厚雖無特別限定,作為有機EL元件之電洞注入層、電洞輸送層或者電洞注入輸送層使用時,以5~200nm為佳。作為使膜厚產生變化的方法,有使清漆中之固體成分濃度產生變化,或使塗佈時之基板上的溶液量產生變化等方法。
本發明之有機EL元件為具有一對電極,於這些電極之間,具有上述本發明之電荷輸送性薄膜者。
作為有機EL元件之代表性構成,可舉出以下(a)~(f),但並未限定於此等。且,對於下述構成,視必要可於發光層與陽極之間設置電子阻擋層等,於發光層與陰極之
間設置孔(電洞)阻擋層等。又,電洞注入層、電洞輸送層或者電洞注入輸送層亦可兼備作為電子阻擋層等功能,電子注入層、電子輸送層或者電子注入輸送層亦可兼備作為孔(電洞)阻擋層等功能。
(a)陽極/電洞注入層/電洞輸送層/發光層/電子輸送層/電子注入層/陰極
(b)陽極/電洞注入層/電洞輸送層/發光層/電子注入輸送層/陰極
(c)陽極/電洞注入輸送層/發光層/電子輸送層/電子注入層/陰極
(d)陽極/電洞注入輸送層/發光層/電子注入輸送層/陰極
(e)陽極/電洞注入層/電洞輸送層/發光層/陰極
(f)陽極/電洞注入輸送層/發光層/陰極
所謂「電洞注入層」、「電洞輸送層」及「電洞注入輸送層」為於發光層與陽極之間所形成的層,其為具有將電洞自陽極輸送至發光層的功能者,於發光層與陽極之間,僅設置1層電洞輸送性材料的層時,其為「電洞注入輸送層」,於發光層與陽極之間設置2層以上的電洞輸送性材料之層時,接近陽極的層為「電洞注入層」,此以外的層為「電洞輸送層」。特別為電洞注入(輸送)層所使用的薄膜並非僅在自陽極的電洞受容性,在對電洞輸送(發光)層的電洞注入性方面亦為優良。
所謂「電子注入層」、「電子輸送層」及「電子注入
輸送層」為於發光層與陰極之間所形成的層,其為具有將電子自陰極輸送至發光層的功能者,於發光層與陰極之間,僅設置1層的電子輸送性材料之層時,此為「電子注入輸送層」,於發光層與陰極之間設置2層以上的電子輸送性材料之層時,接近陰極的層為「電子注入層」,此以外的層為「電子輸送層」。
所謂「發光層」表示具有發光功能之有機層,採用摻合系統時,含有主材料與摻合物材料。此時,主材料主要為促進電子與電洞之再結合,其具有將激子封閉於發光層內之功能,摻合物材料為具有有效率地使在再鍵結所得之激子發光的功能。燐光元件之情況為,主材料主要為具有將在摻合物所生成的激子封閉於發光層內之功能。
本發明之電荷輸送性薄膜於有機EL元件,可作為電洞注入層、電洞輸送層、電洞注入輸送層適用,可適用於作為電洞注入層較佳者。
作為使用本發明之電荷輸送性清漆製作有機EL元件時的使用材料,或作為製作方法可舉出如下述者,但並未限定於此等。
所使用的電極基板以洗劑、醇、純水等預先以液體進行洗淨使其淨化者為佳,例如在陽極基板時於使用前進行UV臭氧處理、氧-電漿處理等表面處理者為佳。但陽極材料係以有機物作為主成分時,亦可不進行表面處理。
具有由本發明之電荷輸送性清漆所得之薄膜而成的電洞注入層之有機EL元件的製作方法之例子如以
下所示。
藉由上述方法,於陽極基板上塗佈本發明之電荷輸送性清漆並燒成後於電極上製作出電洞注入層。
於該電洞注入層之上,以電洞輸送層、發光層、電子輸送層、電子注入層、陰極之順序設置。電洞輸送層、發光層、電子輸送層及電子注入層可配合所使用的材料之特性等,以蒸鍍法、塗佈法(濕式製程)中任一形式形成。
作為陽極材料,可舉出以銦錫氧化物(ITO)、銦鋅氧化物(IZO)作為代表的透明電極,或以鋁作為代表的金屬或由這些合金等所構成的金屬陽極,進行平坦化處理者為佳。亦可使用具有高電荷輸送性之聚噻吩衍生物或聚苯胺衍生物。
且,作為構成金屬陽極之其他金屬,可舉出鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鑭、鈰、鐠、釹、鉤、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或這些合金等,但並未限定於此等。
作為形成電洞輸送層的材料,可舉出(三苯基胺)二聚物衍生物、〔(三苯基胺)二聚物〕螺二聚物、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-聯苯胺(α-NPD)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-螺雙芴、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-螺
雙芴、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二甲基-芴、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二甲基-芴、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二苯基-芴、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二苯基-芴、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-2,2’-二甲基聯苯胺、2,2’,7,7’-肆(N,N-二苯基胺基)-9,9-螺雙芴、9,9-雙〔4-(N,N-雙-聯苯基-4-基-胺基)苯基〕-9H-芴、9,9-雙〔4-(N,N-雙-萘-2-基-胺基)苯基〕-9H-芴、9,9-雙〔4-(N-萘-1-基-N-苯基胺基)-苯基〕-9H-芴、2,2’,7,7’-肆〔N-萘基(苯基)-胺基〕-9,9-螺雙芴、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙〔N,N-雙(聯苯基-4-基)胺基〕-9,9-螺雙芴、2,2’-雙(N,N-二苯基胺基)-9,9-螺雙芴、二-〔4-(N,N-二(p-甲苯基)胺基)-苯基〕環己烷、2,2’,7,7’-四(N,N-二(p-甲苯基))胺基-9,9-螺雙芴、N,N,N’,N’-四-萘-2-基-聯苯胺、N,N,N’,N’-四-(3-甲基苯基)-3,3’-二甲基聯苯胺、N,N’-二(萘基)-N,N’-二(萘-2-基)-聯苯胺、N,N,N’,N’-四(萘基)-聯苯胺、N,N’-二(萘-2-基)-N,N’-二苯基聯苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(m-甲苯基)苯-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-二胺、參(4-(喹啉-8-基)苯基)胺、2,2’-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯基、4,4’,4”-參〔3-甲基苯基(苯基)胺基〕三苯基胺(m-MTDATA)、4,4’,4”-參〔1-萘(苯基)胺基〕三苯基胺(1-TNATA)等三芳基胺類、5,5”-雙-{4-〔雙(4-甲基苯基)胺基〕苯基}-2,2’:5’,2”-三噻吩(BMA-3T)等寡聚噻吩類等電洞輸送性低分子材料等。
作為形成發光層之材料,可舉出參(8-羥基喹啉)鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)-4-(p-苯基苯酚)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯基、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙〔9,9-二(4-甲基苯基)-芴-2-基〕-9,9-二(4-甲基苯基)芴、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-螺雙芴-2-基)-9,9-螺雙芴、2,7-雙(9,9-螺雙芴-2-基)-9,9-螺雙芴、2-〔9,9-二(4-甲基苯基)-芴-2-基〕-9,9-二(4-甲基苯基)芴、2,2’-二芘基-9,9-螺雙芴、1,3,5-參(芘-1-基)苯、9,9-雙〔4-(芘基)苯基〕-9H-芴、2,2’-雙(9,10-二苯基蒽)、2,7-二芘基-9,9-螺雙芴、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯基-4-基)五苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、參〔4-(芘基)-苯基〕胺、10,10’-二(聯苯基-4-基)-9,9’-雙蒽、N,N’-二(萘-1-基)-N,N’-二苯基-〔1,1’:4’,1”:4”,1”’-季苯基〕-4,4”’-二胺、4,4’-二〔10-(萘-1-基)蒽-9-基〕聯苯基、二苯並{〔f,f’〕-4,4’,7,7’-四苯基}二茚並〔1,2,3-cd:1’,2’,3’-lm〕苝、1-(7-(9,9’-雙蒽-10-基)-9,9-二甲基-9H-芴-2-基)芘、1-(7-(9,9’-雙蒽-10-基)-9,9-二己基-9H-芴-2-基)芘、1,3-雙(咔唑-9-基)苯、1,3,5-參(咔唑-9-基)苯、4,4’,4”-參(咔唑-9-基)三苯基胺、4,4’-雙(咔唑-9-基)聯苯基(CBP)、4,4’-雙(咔唑-9-基)-2,2’-二甲基聯苯基、2,7-雙(咔唑-9-基)-9,9-二甲基芴、2,2’,7,7’-肆(咔唑-9-基)-9,9-螺雙芴、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)芴、9,9-雙〔4-(咔唑-9-基)-苯基〕
芴、2,7-雙(咔唑-9-基)-9,9-螺雙芴、1,4-雙(三苯基矽基)苯、1,3-雙(三苯基矽基)苯、雙(4-N,N-二乙基胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基芴、4,4”-二(三苯基矽基)-p-三聯苯、4,4’-二(三苯基矽基)聯苯基、9-(4-t-丁基苯基)-3,6-雙(三苯基矽基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-芴-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-芴-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯並〔d〕咪唑-2-基)苯基)-9H-芴-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-螺雙芴-2-基-二苯基-膦氧化物、9,9’-(5-(三苯基矽基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(二苯基磷醯基)-9-苯基-9H-芴-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯並〔cd,mn〕芘、4,7-二(9H-咔唑-9-基)-1,10-菲咯啉、2,2’-雙(4-(咔唑-9-基)苯基)聯苯基、2,8-雙(二苯基磷醯基)二苯並〔b,d〕噻吩、雙(2-甲基苯基)二苯基矽烷、雙〔3,5-二(9H-咔唑-9-基)苯基〕二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷醯基)-9-(4-(二苯基磷醯基)苯基)-9H-咔唑、3,6-雙〔(3,5-二苯基)苯基〕-9-苯基咔唑等,藉由與發光性摻合物進行共蒸鍍可形成發光層。
作為發光性摻合物,可舉出3-(2-苯並噻唑基)-7-(二乙基胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-
1H,5H,11H-10-(2-苯並噻唑基)喹嗪並〔9,9a,1gh〕香豆素、喹吖啶酮、N,N’-二甲基-喹吖啶酮、參(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯丙酮酸鹽)銥(III)(Ir(ppy)2(acac))、參〔2-(p-甲苯基)吡啶〕銥(III)(Ir(mppy)3)、9,10-雙〔N,N-二(p-甲苯基)胺基〕蒽、9,10-雙〔苯基(m-甲苯基)胺基〕蒽、雙〔2-(2-羥基苯基)苯並噻唑根〕鋅(II)、N10,N10,N10’,N10’-四(p-甲苯基)-9,9’-雙蒽-10,10’-二胺、N10,N10,N10’,N10’-四苯基-9,9’-雙蒽-10,10’-二胺、N10,N10’-二苯基-N10,N10’-二萘基-9,9’-雙蒽-10,10’-二胺、4,4’-雙(9-乙基-3-咔唑並乙烯基)-1,1’-聯苯基、苝、2,5,8,11-四-t-丁基苝、1,4-雙〔2-(3-N-乙基咔唑基)乙烯基〕苯、4,4’-雙〔4-(二-p-甲苯基胺基)苯乙烯〕聯苯基、4-(二-p-甲苯基胺基)-4’-〔(二-p-甲苯基胺基)苯乙烯〕芪、雙〔3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)〕銥(III)、4,4’-雙〔4-(二苯基胺基)苯乙烯〕聯苯基、雙(2,4-二氟苯基吡啶根)肆(1-吡唑基)硼酸鹽銥(III)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-參(9,9-二甲基芴)、2,7-雙{2-〔苯基(m-甲苯基)胺基〕-9,9-二甲基-芴-7-基}-9,9-二甲基-芴、N-(4-((E)-2-(6((E)-4-(二苯基胺基)苯乙烯)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯並咪唑啉-2-亞基-C,C2’)、mer-銥(III)參(1-苯基-3-甲基苯並咪唑啉-2-亞基-C,C2’)、2,7-雙〔4-(二苯基胺基)苯乙烯〕-9,9-螺雙芴、6-甲基-2-(4-(9-(4-(6-甲基苯並〔d〕噻唑-2-基)苯基)蒽-10-基)苯基)苯並〔d〕噻唑、1,4-二
〔4-(N,N-二苯基)胺基〕苯乙烯苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯)苯、(E)-6-(4-(二苯基胺基)苯乙烯)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶根)(5-(吡啶-2-基)-1H-四偶氮酸鹽)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苯甲基)二苯基膦酸鹽(Phosphinate))銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑鹽)(苯甲基二苯基膦酸鹽(Phosphinate))銥(III)、雙(1-(2,4-二氟苯甲基)-3-甲基苯並咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三偶氮酸鹽)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑鹽)(4’,6’-二氟苯基吡啶鹽)銥(III)、雙(4’,6’-二氟苯基吡啶根)(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯鹽)銥(III)、雙(4’,6’-二氟苯基吡啶根)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三偶氮酸鹽)銥(III)、(Z)-6-三甲苯基-N-(6-三甲苯基喹啉-2(1H)-亞基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基胺基)苯乙烯)-6-甲基-4H-吡喃-4-亞基)丙二腈、4-(二氰基伸甲基)-2-甲基-6-久洛尼定基(Julolidyl)-9-烯基-4H-吡喃、4-(二氰基伸甲基)-2-甲基-6-(1,1,7,7-四甲基久洛尼定基(Julolidyl)-9-烯基)-4H-吡喃、4-(二氰基伸甲基)-2-t-丁基-6-(1,1,7,7-四甲基久洛尼定(Julolidine)-4-基-乙烯基)-4H-吡喃、參(二苯甲醯基甲烷)菲咯啉銪(III)、5,6,11,12-四苯基萘並萘、雙(2-苯並〔b〕噻吩-2-基-吡啶)(乙醯丙酮酸鹽)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮酸鹽)銥(III)、雙〔1-(9,9-二甲基-9H-芴-2-基)-異喹啉〕(乙醯丙酮酸鹽)銥(III)、雙〔2-(9,9-二甲基-9H-芴-2-基)喹啉〕(乙醯
丙酮酸鹽)銥(III)、參〔4,4’-二-t-丁基-(2,2’)-雙吡啶〕釕(III).雙(六氟磷酸酯)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸鹽)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基四苯、雙(2-苯基苯並噻唑根)(乙醯丙酮酸鹽)銥(III)、5,10,15,20-四苯基四苯並卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑鹽)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三偶氮酸鹽)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三偶氮酸鹽)二甲基苯基膦、雙〔2-(4-n-己基苯基)喹啉〕(乙醯丙酮酸鹽)銥(III)、參〔2-(4-n-己基苯基)喹啉〕銥(III)、參〔2-苯基-4-甲基喹啉〕銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶鹽)銥(III)、雙(2-(9,9-二乙基-芴-2-基)-1-苯基-1H-苯並〔d〕咪唑根(imidazolato))(乙醯丙酮酸鹽)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-色烯-2-酮酸鹽)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸鹽)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸鹽)銥(III)、銥(III)雙(4-苯基噻吩並〔3,2-c〕吡啶根-N,C2’)乙醯丙酮酸鹽、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯並〔3,2,1-ij〕喹啉-8-基)乙烯基)-4H-吡喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑鹽)(甲基二苯基膦)釕、雙〔(4-n-己基苯基)異喹啉〕(乙醯丙酮酸鹽)銥(III)、鉑(II)八乙基卟吩(Porphin)、雙(2-甲基二苯並〔f,h〕喹喔啉)(乙醯丙酮酸
鹽)銥(III)、參〔(4-n-己基苯基)氧代喹啉〕銥(III)等。
作為形成電子輸送層之材料,可舉出、8-羥基羥基喹啉根(quinolinolato)-鋰、2,2’,2”-(1,3,5-苯甲苯甲醯基)-參(1-苯基-1-H-苯並咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-噁二唑、2,9-二甲基-4,7-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、雙(2-甲基-8-羥基喹啉根(quinolinolato))-4-(苯基苯酚根)鋁、1,3-雙〔2-(2,2’-雙吡啶-6-基)-1,3,4-噁二唑-5-基〕苯、6,6’-雙〔5-(聯苯基-4-基)-1,3,4-噁二唑-2-基〕-2,2’-雙吡啶、3-(4-聯苯基)-4-苯基-5-t-丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-菲咯啉、2,7-雙〔2-(2,2’-雙吡啶-6-基)-1,3,4-噁二唑-5-基〕-9,9-二甲基芴、1,3-雙〔2-(4-t-丁基苯基)-1,3,4-噁二唑-5-基〕苯、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑並〔4,5f〕〔1,10〕菲咯啉、2-(萘-2-基)-4,7-二苯基-1,10-菲咯啉、苯基-二芘基氧化膦、3,3’,5,5’-四〔(m-吡啶基)-苯-3-基〕聯苯基、1,3,5-參〔(3-吡啶基)-苯-3-基〕苯、4,4’-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯基、1,3-雙〔3,5-二(吡啶-3-基)苯基〕苯、雙(10-羥基苯並〔h〕喹啉根)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
作為形成電子注入層之材料,可舉出氧化鋰(Li2O)、氧化鎂(MgO)、氧化鋁(Al2O3)、氟化鋰(LiF)、氟化鈉(NaF)、氟化鎂(MgF2)、氟化銫(CsF)、氟化鍶
(SrF2)、三氧化鉬(MoO3)、鋁、Li(acac)、乙酸鋰、安息香酸鋰等。
作為陰極材料,可舉出鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
又,具有由本發明之電荷輸送性清漆所得之薄膜而成的電洞注入層之有機EL元件的其他製作方法例子,如以下所示。
對於上述EL元件製作,取代進行電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作,藉由依序形成電洞輸送層(以下稱為電洞輸送性高分子層)、發光層(以下稱為發光性高分子層),可製造出具有由本發明之電荷輸送性清漆所形成的電荷輸送性薄膜之有機EL元件。
具體而言,於陽極基板上塗佈本發明之電荷輸送性清漆,藉由上述方法製作出電洞注入層,於該上面,依序形成電洞輸送性高分子層、發光性高分子層,進一步蒸鍍陰極電極後做成有機EL元件。
作為使用的陰極及陽極材料,可使用與上述相同者,進行相同的洗淨處理、表面處理。
作為電洞輸送性高分子層及發光性高分子層之形成法,可舉出於電洞輸送性高分子材料或者發光性高分子材料或於此等加入摻合物物質的材料中,加入溶劑進行溶解,或均勻地分散後塗佈於電洞注入層或電洞輸送性高分子層上後,藉由各燒成後成膜的方法。
作為電洞輸送性高分子材料,可舉出聚〔
(9,9-二己基芴基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)〕、聚〔(9,9-二辛基芴基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,1’-亞聯苯-4,4-二胺)〕、聚〔(9,9-雙{1’-戊烯-5’-基}芴基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)〕、聚〔N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺〕-用聚矽氧烷封閉、聚〔(9,9-二辛基芴基-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯基胺)〕等。
作為發光性高分子材料,可舉出聚(9,9-二烷基芴)(PDAF)等聚芴衍生物、聚(2-甲氧基-5-(2’-乙基己氧基)-1,4-伸苯基亞乙烯)(MEH-PPV)等聚伸苯基亞乙烯衍生物、聚(3-烷基噻吩)(PAT)等聚噻吩衍生物、聚乙烯咔唑(PVCz)等。
作為溶劑,可舉出甲苯、二甲苯、氯仿等,作為溶解或均勻分散法,可舉出攪拌、加熱攪拌、超音波分散等方法。
作為塗佈方法,並無特別限定,可舉出噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗佈法、刷毛塗佈等。且塗佈可在氮、氬等惰性氣體下進行者為佳。
作為燒成方法,可舉出在惰性氣體下或真空中、烤箱或加熱板中進行加熱的方法。
具有由本發明之電荷輸送性清漆所得的薄膜而成之電洞輸送層的EL元件之製作方法例子,如以下所示。
於陽極基板上形成電洞注入層。於該層上面,藉由上述方法塗佈本發明之電荷輸送性清漆後燒成,製作電洞輸送層。
於該電洞輸送層之上面,將發光層、電子輸送層、電子注入層、陰極以該順序設置。發光層、電子輸送層及電子注入層之形成方法及具體例子可舉出與上述相同者。又,電洞注入層為配合所使用的材料特性等,可藉由蒸鍍法、塗佈法(濕式製程)中任一方法形成。
作為形成電洞注入層之材料,可舉出銅酞菁、氧化鈦酞菁、鉑酞菁、吡嗪並〔2,3-f〕〔1,10〕菲咯啉-2,3-二甲腈、N,N,N’,N’-肆(4-甲氧基苯基)聯苯胺、2,7-雙〔N,N-雙(4-甲氧基-苯基)胺基〕-9,9-螺雙芴、2,2’-雙〔N,N-雙(4-甲氧基-苯基)胺基〕-9,9-螺雙芴、N,N’-二苯基-N,N’-二〔4-(N,N-二甲苯基胺基)苯基〕聯苯胺、N,N’-二苯基-N,N’-二〔4-(N,N-二苯基胺基)苯基〕聯苯胺、N4,N4’-(聯苯基-4,4’-二基)雙(N4,N4’,N4’-三苯基聯苯基-4,4’-二胺)N1,N1’-(聯苯基-4,4’-二基)雙(N1-苯基-N4,N4’-二-m-甲苯基苯-1,4-二胺)、國際公開第2004/043117號、國際公開第2004/105446號、國際公開第2005/000832號、國際公開第2005/043962號、國際公開第2005/042621號、國際公開第2005/107335號、國際公開第2006/006459號、國際公開第2006/025342號、國際公開第2006/137473號、國際公開第2007/049631號、國際公開第2007/099808號、國際公開第2008/010474號、國際
公開第2008/032617號、國際公開第2008/032616號、國際公開第2008/129947號、國際公開第2009/096352號、國際公開第2010/041701號、國際公開第2010/058777號、國際公開第2010/058776號、國際公開第2013/042623號、國際公開第2013/129249號、國際公開第2014/115865號、國際公開第2014/132917號、國際公開第2014/141998號及國際公開2014/132834號所記載的電荷輸送材料等。
作為形成陽極材料、發光層、發光性摻合物、電子輸送層及電子阻擋層之材料,及作為陰極材料可舉出與上述相同。
具有由本發明之電荷輸送性清漆所得之薄膜而成的電洞注入輸送層之有機EL元件的製作方法的例子如以下所示。
於陽極基板上形成電洞注入輸送層,於該電洞注入輸送層的上面,以發光層、電子輸送層、電子注入層、陰極的順序設置。發光層、電子輸送層及電子注入層之形成方法及具體例子可舉出與上述相同者。
作為形成陽極材料、發光層、發光性摻合物、電子輸送層及電子阻擋層之材料、陰極材料,可舉出與上述相同者。
且,於電極及上述各層之間的任意間,視必要可設置電洞阻擋層、電子阻擋層等。例如作為形成電子阻擋層之材料可舉出參(苯基吡唑)銥等。
構成於陽極與陰極及此等間所形成的層之材料因會依製造具備底部發射(Bottom emission)結構、頂部發射(Top emission)結構中任一者的元件而相異,可考慮到此點而做適宜材料之選擇。
通常在底部發射結構之元件中,於基板側使用透明陽極,而自基板側取光,相較之下,在頂部發射結構之元件,使用由金屬所成的反射陽極,由與基板為反方向的透明電極(陰極)側取光,故例如對於陽極材料而言,製造底部發射結構之元件時,使用ITO等透明陽極,而在製造頂部發射結構的元件時,則使用Al/Nd等反射陽極。
本發明之有機EL元件欲防止特性惡化,依據定法可視必要與捕水劑等同時進行封止。
以下舉出實施例及比較例,更具體說明本發明,但本發明並未限定於此下述實施例。且,所使用的裝置如以下所示。
(1)1H,19F-NMR:JEOL(股)製 核磁共振裝置AL-300
(2)基板洗淨:長州產業(股)製 基板洗淨裝置(減壓電漿方式)
(3)清漆之塗佈:Mikasa(股)製 旋轉塗佈機MS-A100
(4)膜厚測定:(股)小坂研究所製 微細形狀測定機Surf coderET-4000
(5)膜之表面觀察:雷射帝克公司製 共焦點雷射顯微
鏡real time掃描型雷射顯微鏡1LM21D
(6)EL元件之製作:長州產業(股)製 多功能蒸鍍裝置系統C-E2L1G1-N
(7)EL元件之亮度等測定:(有)Tech World製I-V-L測定系統
(8)EL元件之壽命測定(亮度半衰期測定):(股)E-etch Sea製 有機EL亮度壽命評估系統PEL-105S
〔1〕鎓硼酸鹽之合成
〔合成例1〕(4-苯基硫基苯基)二苯基硫鎓n-丁基參(五氟苯基)硼酸鹽之合成
將參(五氟苯基)硼烷(東京化成工業(股)製)38.1質量份、戊烷1200質量份裝入於反應容器,攪拌下在室溫滴入n-丁基鋰的己烷溶液(1.6M)38.8質量份,在室溫進行3小時反應後得到泥漿狀反應液。
將過濾反應液所得之結晶物以戊烷洗淨,在60℃進行減壓乾燥後得到中間體之鋰n-丁基參(五氟苯基)硼酸鹽38.1質量份(產率89%)。
繼續於將(4-苯基硫基苯基)二苯基硫鎓六氟磷
酸鹽(san-apro(股)製)22.5質量份溶解於二氯甲烷530質量份之溶液中,加入將上述所得之硼酸鹽30質量份溶解於離子交換水400質量份之水溶液,攪拌經1小時混合。混合後,靜置並除去水層,將二氯甲烷溶液以離子交換水400質量份進行5次洗淨。將水洗後的二氯甲烷溶液在減壓下進行脫溶劑,得到目的物之(4-苯基硫基苯基)二苯基硫鎓n-丁基參(五氟苯基)硼酸鹽之淡黃色固體40質量份(產率97%)。所得之目的物以1H-NMR及19F-NMR鑑定。
1H-NMR(DMSO-d6):δ 7.6~7.8(12H,m),7.4~7.5(5H,m),7.3(2H,d),1.0~1.2(4H,m),0.6~0.8(5H,m)ppm。
19F-NMR(DMSO-d6):δ-132(6F,d),-159.5(3F,t),-163(6F,t)ppm。
〔2〕電荷輸送性清漆之調製
〔實施例1-1〕
於依據國際公開第2015/050253號之製造例18記載的方法所合成的下述式所示PCZ5 158mg與在合成例1所得之(4-苯基硫基苯基)二苯基硫鎓n-丁基參(五氟苯基)硼酸鹽105mg的混合物中,加入二甲苯5g,在室溫下一邊照射超音波一邊攪拌並溶解,將所得之溶液以孔徑0.2μm的注射器濾器進行過濾後得到電荷輸送性清漆。
〔3〕有機EL元件之製作及特性評估
〔實施例2-1〕
將在實施例1-1所得之清漆,使用旋轉塗佈機塗佈於ITO基板後,在80℃進行1分鐘乾燥,再於大氣環境下在150℃下進行10分鐘燒成,於ITO基板上形成100nm的均勻薄膜。作為ITO基板,使用銦錫氧化物(ITO)於表面上製圖成膜厚150nm的25mm×25mm×0.7t之玻璃基板,於使用前藉由O2電漿洗淨裝置(150W、30秒)除去表面上的雜質。
其次,對於形成薄膜之ITO基板,使用蒸鍍裝置(真空度1.0×10-5Pa),將α-NPD(N,N’-二(1-萘)-N,N’-二苯基聯苯胺)以0.2nm/秒成膜為30nm。其次將CBP與Ir(PPy)3進行共蒸鍍。共蒸鍍為將蒸鍍速率控制在Ir(PPy)3的濃度成為6%,層合為40nm。其次,將BAlq、氟化鋰及鋁的薄膜依序層合後得到有機EL元件。此時,蒸鍍速率對於BAlq及鋁以0.2nm/秒的條件,對於氟化鋰以0.02nm/秒的條件進行,得到各膜厚為20nm、0.5nm及120nm者。
且,欲防止藉由空氣中的氧、水等影響所造成的特性
劣化,有機EL元件藉由封止基板進行封止後,評估其特性。封止藉由以下程序進行。在氧濃度2ppm以下,露點-85℃以下之氮環境中,將有機EL元件收集在封止基板之間,將封止基板藉由接著材(Nagase Chemtex(股)製,XNR5516Z-B1)進行貼合。此時,將捕水劑(Dynic(股)製,HD-071010W-40)與有機EL元件同時收集在封止基板內。對於貼合封止基板,照射UV光(波長:365nm、照射量:6,000mJ/cm2)後,在80℃進行1小時的熱處理(annealing)處理使接著材硬化。
對於實施例2-1之元件,測定在亮度5000cd/m2下驅動時的驅動電壓、電流密度及發光效率以及亮度半衰期(初期亮度5000cd/m2達到一半時所需要的時間)。結果如表19所示。
如表19所示,具備本發明之電荷輸送性薄膜的EL元件可適當地驅動。且其亦具有優良的壽命特性。
Claims (6)
- 如請求項1之電洞輸送性清漆,其中前述電洞輸送性物質係由選自苯胺衍生物及噻吩衍生物的至少1種。
- 如請求項2之電洞輸送性清漆,其中前述電洞輸送性物質為苯胺衍生物。
- 一種電洞輸送性薄膜,其特徵為使用如請求項1~3中任1項之電洞輸送性清漆所製作。
- 一種有機電致發光元件,其特徵為具有如請求項4之 電洞輸送性薄膜。
- 一種電洞輸送性薄膜之製造方法,其特徵為將如請求項1~3中任1之電洞輸送性清漆塗佈於基材上,使溶劑蒸發者。
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JP6717372B2 (ja) | 2020-07-01 |
US20190062351A1 (en) | 2019-02-28 |
JPWO2017150412A1 (ja) | 2018-12-27 |
CN108886103A (zh) | 2018-11-23 |
TW201802099A (zh) | 2018-01-16 |
WO2017150412A1 (ja) | 2017-09-08 |
EP3425689A4 (en) | 2019-04-17 |
KR20180117176A (ko) | 2018-10-26 |
KR102656454B1 (ko) | 2024-04-12 |
EP3425689A1 (en) | 2019-01-09 |
CN108886103B (zh) | 2020-12-18 |
EP3425689B1 (en) | 2019-10-23 |
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