WO2015053320A1 - アリールスルホン酸化合物及びその利用並びにアリールスルホン酸化合物の製造方法 - Google Patents
アリールスルホン酸化合物及びその利用並びにアリールスルホン酸化合物の製造方法 Download PDFInfo
- Publication number
- WO2015053320A1 WO2015053320A1 PCT/JP2014/076959 JP2014076959W WO2015053320A1 WO 2015053320 A1 WO2015053320 A1 WO 2015053320A1 JP 2014076959 W JP2014076959 W JP 2014076959W WO 2015053320 A1 WO2015053320 A1 WO 2015053320A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- formula
- group
- charge transporting
- represented
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 22
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- -1 Aryl sulfonic acid compounds Chemical class 0.000 claims description 48
- 239000002966 varnish Substances 0.000 claims description 44
- 239000010409 thin film Substances 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 26
- 239000002019 doping agent Substances 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 238000005401 electroluminescence Methods 0.000 claims description 3
- 238000005342 ion exchange Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 150
- 238000002347 injection Methods 0.000 description 52
- 239000007924 injection Substances 0.000 description 52
- 229910052741 iridium Inorganic materials 0.000 description 46
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 43
- 238000000034 method Methods 0.000 description 36
- 239000000463 material Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 239000000758 substrate Substances 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 16
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000010304 firing Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 239000002861 polymer material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 4
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 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
- 239000003729 cation exchange resin Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- QBUMGIJMHQGHEF-UHFFFAOYSA-N O.[Na].[Na].NC=1C=C2C=C(C=C(C2=CC1)S(=O)(=O)O)S(=O)(=O)O Chemical compound O.[Na].[Na].NC=1C=C2C=C(C=C(C2=CC1)S(=O)(=O)O)S(=O)(=O)O QBUMGIJMHQGHEF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003577 thiophenes Chemical class 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 0 *c(cc1)ccc1-c(cc1)ccc1Nc1ccccc1 Chemical compound *c(cc1)ccc1-c(cc1)ccc1Nc1ccccc1 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WFQFDAGQJUVDKP-UHFFFAOYSA-N 2,8-ditert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC(=CC=C2C(C=2C=CC(=CC=2)C(C)(C)C)=C11)C(C)(C)C)=C(C=CC(=C2)C(C)(C)C)C2=C1C1=CC=CC=C1 WFQFDAGQJUVDKP-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- RPQWXGVZELKOEU-UHFFFAOYSA-N 3,4-difluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1F RPQWXGVZELKOEU-UHFFFAOYSA-N 0.000 description 2
- OYZWEOORLJBPMA-UHFFFAOYSA-N 3,5-difluorobenzoyl chloride Chemical compound FC1=CC(F)=CC(C(Cl)=O)=C1 OYZWEOORLJBPMA-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000005362 aryl sulfone group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 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 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- LQFIGPLAXNTNNT-UHFFFAOYSA-N (2-benzylphenyl)-phenylphosphinic acid 5-pyridin-2-yl-3-(trifluoromethyl)pyrazole-3-carboxylic acid Chemical compound C(C1=CC=CC=C1)C1=C(C=CC=C1)P(O)(=O)C1=CC=CC=C1.FC(C1(N=NC(=C1)C1=NC=CC=C1)C(=O)O)(F)F.FC(C1(N=NC(=C1)C1=NC=CC=C1)C(=O)O)(F)F LQFIGPLAXNTNNT-UHFFFAOYSA-N 0.000 description 1
- YLGQLQSDQXOIBI-UHFFFAOYSA-N (29h,31h-phthalocyaninato(2-)-n29,n30,n31,n32)platinum Chemical compound [Pt+2].[N-]1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)[N-]3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 YLGQLQSDQXOIBI-UHFFFAOYSA-N 0.000 description 1
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 1
- DTZWGKCFKSJGPK-VOTSOKGWSA-N (e)-2-(2-methyl-6-(2-(1,1,7,7-tetramethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4h-pyran-4-ylidene)malononitrile Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 DTZWGKCFKSJGPK-VOTSOKGWSA-N 0.000 description 1
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- IOYYUNPMQBXJMX-UHFFFAOYSA-N 1,3-diphenylpropane-1,3-dione europium 1,10-phenanthroline Chemical compound [Eu].c1cnc2c(c1)ccc1cccnc21.O=C(CC(=O)c1ccccc1)c1ccccc1.O=C(CC(=O)c1ccccc1)c1ccccc1.O=C(CC(=O)c1ccccc1)c1ccccc1 IOYYUNPMQBXJMX-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- GHDZTXRYFQBMKP-UHFFFAOYSA-N 1-(3-pyren-1-ylphenyl)pyrene Chemical compound C1=C2C(C=3C=CC=C(C=3)C=3C4=CC=C5C=CC=C6C=CC(C4=C65)=CC=3)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 GHDZTXRYFQBMKP-UHFFFAOYSA-N 0.000 description 1
- IJJYNFWMKNYNEW-UHFFFAOYSA-N 1-(4-pyren-1-ylphenyl)pyrene Chemical compound C1=CC(C=2C=CC(=CC=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)=C2C=CC3=CC=CC4=CC=C1C2=C43 IJJYNFWMKNYNEW-UHFFFAOYSA-N 0.000 description 1
- JWNKSVWLGXYZGW-UHFFFAOYSA-N 1-N,4-N-bis(3-methylphenyl)-1-N,4-diphenylcyclohexa-1,5-diene-1,4-diamine Chemical compound C1(=CC=CC=C1)C1(CC=C(C=C1)N(C=1C=C(C=CC=1)C)C1=CC=CC=C1)NC=1C=C(C=CC=1)C JWNKSVWLGXYZGW-UHFFFAOYSA-N 0.000 description 1
- HDMYKJVSQIHZLM-UHFFFAOYSA-N 1-[3,5-di(pyren-1-yl)phenyl]pyrene Chemical compound C1=CC(C=2C=C(C=C(C=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)=C2C=CC3=CC=CC4=CC=C1C2=C43 HDMYKJVSQIHZLM-UHFFFAOYSA-N 0.000 description 1
- WHLKCPQPGTUZBU-UHFFFAOYSA-N 1-[4-[9-(4-pyren-1-ylphenyl)fluoren-9-yl]phenyl]pyrene Chemical compound C1=C2C(C3=CC=C(C=C3)C3(C=4C=CC(=CC=4)C=4C5=CC=C6C=CC=C7C=CC(C5=C76)=CC=4)C4=CC=CC=C4C=4C3=CC=CC=4)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WHLKCPQPGTUZBU-UHFFFAOYSA-N 0.000 description 1
- WMZCREDANYEXRT-UHFFFAOYSA-N 1-[phenyl(pyren-1-yl)phosphoryl]pyrene Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1P(C=1C2=CC=C3C=CC=C4C=CC(C2=C43)=CC=1)(=O)C1=CC=CC=C1 WMZCREDANYEXRT-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 1
- MGNMGUIBVXLCKB-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(2-methyl-n-(2-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(2-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC=C1N(C=1C(=CC=CC=1)C)C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C(=CC=CC=2)C)C=2C(=CC=CC=2)C)C=C1 MGNMGUIBVXLCKB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- JUXFRTZAPVOOCK-UHFFFAOYSA-N 10-(10-amino-10-benzo[a]anthracen-1-yl-1H-anthracen-9-yl)anthracen-9-amine Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)C1(C2=CC=CCC2=C(C2=CC=CC=C12)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)N)N JUXFRTZAPVOOCK-UHFFFAOYSA-N 0.000 description 1
- KLSGQSYYPQUISP-UHFFFAOYSA-N 10-[10-naphthalen-1-yl-10-(naphthalen-1-ylamino)-1H-anthracen-9-yl]anthracen-9-amine Chemical compound C1(=CC=CC2=CC=CC=C12)C1(C2=CC=CCC2=C(C2=CC=CC=C12)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)N)NC1=CC=CC2=CC=CC=C12 KLSGQSYYPQUISP-UHFFFAOYSA-N 0.000 description 1
- MJXRNMQMLMXICM-UHFFFAOYSA-N 2',7'-di(pyren-1-yl)-9,9'-spirobi[fluorene] Chemical compound C1=C2C(C=3C=C4C5(C6=CC(=CC=C6C4=CC=3)C=3C4=CC=C6C=CC=C7C=CC(C4=C76)=CC=3)C3=CC=CC=C3C=3C5=CC=CC=3)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 MJXRNMQMLMXICM-UHFFFAOYSA-N 0.000 description 1
- MAPCFLKVLLDGMV-UHFFFAOYSA-N 2,2'-di(pyren-1-yl)-9,9'-spirobi[fluorene] Chemical compound C1=C2C(C3=CC=C4C=5C(C6(C7=CC(=CC=C7C7=CC=CC=C76)C=6C7=CC=C8C=CC=C9C=CC(C7=C98)=CC=6)C4=C3)=CC=CC=5)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 MAPCFLKVLLDGMV-UHFFFAOYSA-N 0.000 description 1
- RUGZVPRCKQMYAZ-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-6-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=C(F)C(F)=C(F)C(F)=C1C(Cl)=O RUGZVPRCKQMYAZ-UHFFFAOYSA-N 0.000 description 1
- XWCKIXLTBNGIHV-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(F)C(F)=C1F XWCKIXLTBNGIHV-UHFFFAOYSA-N 0.000 description 1
- NXRQXCFBZGIRGN-UHFFFAOYSA-N 2,3,4-trifluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(F)=C1F NXRQXCFBZGIRGN-UHFFFAOYSA-N 0.000 description 1
- SCFPILCRJUUNLP-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-methylbenzoyl chloride Chemical compound CC1=C(F)C(F)=C(C(Cl)=O)C(F)=C1F SCFPILCRJUUNLP-UHFFFAOYSA-N 0.000 description 1
- QTIPHWWHHRFTNO-UHFFFAOYSA-N 2,3,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(F)C(C(Cl)=O)=C1 QTIPHWWHHRFTNO-UHFFFAOYSA-N 0.000 description 1
- DMUGJQMADYEWSQ-UHFFFAOYSA-N 2,3,6-trifluorobenzoyl chloride Chemical compound FC1=CC=C(F)C(C(Cl)=O)=C1F DMUGJQMADYEWSQ-UHFFFAOYSA-N 0.000 description 1
- CDCFERWURRNLLA-UHFFFAOYSA-N 2,3-difluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1F CDCFERWURRNLLA-UHFFFAOYSA-N 0.000 description 1
- IGBLDVIZBYMRCW-UHFFFAOYSA-N 2,4,5-trifluoro-3-methyl-6-nitrobenzoyl chloride Chemical compound CC1=C(F)C(F)=C([N+]([O-])=O)C(C(Cl)=O)=C1F IGBLDVIZBYMRCW-UHFFFAOYSA-N 0.000 description 1
- STBGCAUUOPNJBH-UHFFFAOYSA-N 2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C=C1F STBGCAUUOPNJBH-UHFFFAOYSA-N 0.000 description 1
- YETUQCIZTJPWRS-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-4-nitrocyclohexa-1,5-diene-1-carbonyl chloride Chemical compound ClC1=C(C(=O)Cl)C=C(C(C1)([N+](=O)[O-])Cl)F YETUQCIZTJPWRS-UHFFFAOYSA-N 0.000 description 1
- JSWRVDNTKPAJLB-UHFFFAOYSA-N 2,4-difluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(F)=C1 JSWRVDNTKPAJLB-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- RLRUKKDFNWXXRT-UHFFFAOYSA-N 2,5-difluorobenzoyl chloride Chemical compound FC1=CC=C(F)C(C(Cl)=O)=C1 RLRUKKDFNWXXRT-UHFFFAOYSA-N 0.000 description 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 description 1
- ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 2,8-bis(diphenylphosphoryl)dibenzothiophene Chemical compound C=1C=CC=CC=1P(C=1C=C2C3=CC(=CC=C3SC2=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 1
- XANIFASCQKHXRC-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2s1.Oc1ccccc1-c1nc2ccccc2s1 XANIFASCQKHXRC-UHFFFAOYSA-N 0.000 description 1
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- CRGSMSNUTNRNQM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=CO1 CRGSMSNUTNRNQM-UHFFFAOYSA-N 0.000 description 1
- RASFLGVDOLMZBD-UHFFFAOYSA-N 2-(9,9'-spirobi[fluorene]-2-yl)-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C1=C2)C3=CC=CC=C3C1=CC=C2C(C=C12)=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 RASFLGVDOLMZBD-UHFFFAOYSA-N 0.000 description 1
- WHHNAXUPYPAMDD-UHFFFAOYSA-N 2-(9,9-dimethylfluoren-2-yl)quinoline Chemical compound C1=CC=CC2=NC(C3=CC=C4C5=CC=CC=C5C(C4=C3)(C)C)=CC=C21 WHHNAXUPYPAMDD-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- KSSABTOENVKMLW-UHFFFAOYSA-N 2-N,2-N,2-N',2-N'-tetrakis(4-phenylphenyl)-9,9'-spirobi[fluorene]-2,2'-diamine Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C3C4(C5=CC(=CC=C5C5=CC=CC=C54)N(C=4C=CC(=CC=4)C=4C=CC=CC=4)C=4C=CC(=CC=4)C=4C=CC=CC=4)C4=CC=CC=C4C3=CC=2)C=C1 KSSABTOENVKMLW-UHFFFAOYSA-N 0.000 description 1
- UICMBMCOVLMLIE-UHFFFAOYSA-N 2-[4-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine Chemical group C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 UICMBMCOVLMLIE-UHFFFAOYSA-N 0.000 description 1
- BIXGISJFDUHZEB-UHFFFAOYSA-N 2-[9,9-bis(4-methylphenyl)fluoren-2-yl]-9,9-bis(4-methylphenyl)fluorene Chemical compound C1=CC(C)=CC=C1C1(C=2C=CC(C)=CC=2)C2=CC(C=3C=C4C(C5=CC=CC=C5C4=CC=3)(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=C2C2=CC=CC=C21 BIXGISJFDUHZEB-UHFFFAOYSA-N 0.000 description 1
- BIDXHLMXMWMYJC-UHFFFAOYSA-N 2-bromo-3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1Br BIDXHLMXMWMYJC-UHFFFAOYSA-N 0.000 description 1
- AXZRUTPBQMAWLP-UHFFFAOYSA-N 2-bromo-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(Br)=C1 AXZRUTPBQMAWLP-UHFFFAOYSA-N 0.000 description 1
- QIFDGTIOMAVGAQ-UHFFFAOYSA-N 2-bromo-5-fluorobenzoyl chloride Chemical compound FC1=CC=C(Br)C(C(Cl)=O)=C1 QIFDGTIOMAVGAQ-UHFFFAOYSA-N 0.000 description 1
- ZQOQNOOLDFFUDH-UHFFFAOYSA-N 2-bromo-6-fluorobenzoyl chloride Chemical compound FC1=CC=CC(Br)=C1C(Cl)=O ZQOQNOOLDFFUDH-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- DIUKLCJZYOPHGW-UHFFFAOYSA-N 2-chloro-3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1Cl DIUKLCJZYOPHGW-UHFFFAOYSA-N 0.000 description 1
- POIAZJJVWRVLBO-UHFFFAOYSA-N 2-chloro-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(Cl)=C1 POIAZJJVWRVLBO-UHFFFAOYSA-N 0.000 description 1
- KTHNITVDTYAHFF-UHFFFAOYSA-N 2-chloro-4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C(Cl)=C1 KTHNITVDTYAHFF-UHFFFAOYSA-N 0.000 description 1
- SGZSJPBASHYOHQ-UHFFFAOYSA-N 2-chloro-5-fluorobenzoyl chloride Chemical compound FC1=CC=C(Cl)C(C(Cl)=O)=C1 SGZSJPBASHYOHQ-UHFFFAOYSA-N 0.000 description 1
- GFNAJZAKJGKJCS-UHFFFAOYSA-N 2-chloro-6-fluorobenzoyl chloride Chemical compound FC1=CC=CC(Cl)=C1C(Cl)=O GFNAJZAKJGKJCS-UHFFFAOYSA-N 0.000 description 1
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
- RIKGRFSGIOOYEK-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC1=C(C(Cl)=O)C=CC=C1C(F)(F)F RIKGRFSGIOOYEK-UHFFFAOYSA-N 0.000 description 1
- SVSVOPWCUHQFAM-UHFFFAOYSA-N 2-fluoro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C(F)=C1 SVSVOPWCUHQFAM-UHFFFAOYSA-N 0.000 description 1
- BUBMAUUSVWQBMS-UHFFFAOYSA-N 2-fluoro-4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C(F)=C1 BUBMAUUSVWQBMS-UHFFFAOYSA-N 0.000 description 1
- OFVKAIZITGCCDN-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(F)(F)F)C=C1C(Cl)=O OFVKAIZITGCCDN-UHFFFAOYSA-N 0.000 description 1
- CEMYZMDITJKYDA-UHFFFAOYSA-N 2-fluoro-5-iodobenzoyl chloride Chemical compound FC1=CC=C(I)C=C1C(Cl)=O CEMYZMDITJKYDA-UHFFFAOYSA-N 0.000 description 1
- SXJNRYPVXFTJOU-UHFFFAOYSA-N 2-fluoro-5-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(F)C(C(Cl)=O)=C1 SXJNRYPVXFTJOU-UHFFFAOYSA-N 0.000 description 1
- ZDRYDSJMVRRAAF-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=CC(C(F)(F)F)=C1C(Cl)=O ZDRYDSJMVRRAAF-UHFFFAOYSA-N 0.000 description 1
- KUULKUHCAMRGCF-UHFFFAOYSA-N 2-fluoro-6-iodobenzoyl chloride Chemical compound FC1=CC=CC(I)=C1C(Cl)=O KUULKUHCAMRGCF-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- TZYPEOJJHBWOKE-UHFFFAOYSA-N 2-methyl-4-[3-methyl-4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]-n,n-bis(3-methylphenyl)aniline Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C(=CC(=CC=2)C=2C=C(C)C(N(C=3C=C(C)C=CC=3)C=3C=C(C)C=CC=3)=CC=2)C)=C1 TZYPEOJJHBWOKE-UHFFFAOYSA-N 0.000 description 1
- HNWFFTUWRIGBNM-UHFFFAOYSA-N 2-methyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C)=CC=C21 HNWFFTUWRIGBNM-UHFFFAOYSA-N 0.000 description 1
- LZHVTCXAXYYCIF-UHFFFAOYSA-N 2-n',2-n',7-n',7-n'-tetrakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2',7'-diamine Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC(=CC=C3C2=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 LZHVTCXAXYYCIF-UHFFFAOYSA-N 0.000 description 1
- QZTQQBIGSZWRGI-UHFFFAOYSA-N 2-n',7-n'-bis(3-methylphenyl)-2-n',7-n'-diphenyl-9,9'-spirobi[fluorene]-2',7'-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=C3C4(C5=CC=CC=C5C5=CC=CC=C54)C4=CC(=CC=C4C3=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QZTQQBIGSZWRGI-UHFFFAOYSA-N 0.000 description 1
- ZDAWFMCVTXSZTC-UHFFFAOYSA-N 2-n',7-n'-dinaphthalen-1-yl-2-n',7-n'-diphenyl-9,9'-spirobi[fluorene]-2',7'-diamine 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)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 ZDAWFMCVTXSZTC-UHFFFAOYSA-N 0.000 description 1
- BXSXNLBKCNVUGA-UHFFFAOYSA-N 2-n,2-n,2-n',2-n'-tetrakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2'-diamine Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C4=CC=CC=C43)N(C=3C=CC(OC)=CC=3)C=3C=CC(OC)=CC=3)C3=CC=CC=C3C2=CC=1)C1=CC=C(OC)C=C1 BXSXNLBKCNVUGA-UHFFFAOYSA-N 0.000 description 1
- ZOSISXPKNIMGRP-UHFFFAOYSA-N 2-n,2-n,2-n',2-n'-tetraphenyl-9,9'-spirobi[fluorene]-2,2'-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C4=CC=CC=C43)N(C=3C=CC=CC=3)C=3C=CC=CC=3)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 ZOSISXPKNIMGRP-UHFFFAOYSA-N 0.000 description 1
- LEXCBRKPOZULQO-UHFFFAOYSA-N 2-n,2-n,6-n,6-n-tetraphenylnaphthalene-2,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC(=CC2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LEXCBRKPOZULQO-UHFFFAOYSA-N 0.000 description 1
- NFZUWPDINLFCGG-UHFFFAOYSA-N 2-n,7-n-bis(3-methylphenyl)-2-n,7-n,9,9-tetraphenylfluorene-2,7-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=C3C(C4=CC(=CC=C4C3=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NFZUWPDINLFCGG-UHFFFAOYSA-N 0.000 description 1
- PQCAURRJHOJJNQ-UHFFFAOYSA-N 2-n,7-n-dinaphthalen-1-yl-2-n,7-n,9,9-tetraphenylfluorene-2,7-diamine 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)C2(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 PQCAURRJHOJJNQ-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- CELPGKFEUDCZOU-UHFFFAOYSA-N 2-naphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 CELPGKFEUDCZOU-UHFFFAOYSA-N 0.000 description 1
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 1
- VRSVVHUWDXKOIB-UHFFFAOYSA-N 3,10-dinaphthalen-2-ylperylene Chemical group C=12C3=CC=C(C=4C=C5C=CC=CC5=CC=4)C2=CC=CC=1C1=CC=CC2=C1C3=CC=C2C1=CC2=CC=CC=C2C=C1 VRSVVHUWDXKOIB-UHFFFAOYSA-N 0.000 description 1
- YRUNCQNKZIQTEO-UHFFFAOYSA-N 3,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC(F)=C1F YRUNCQNKZIQTEO-UHFFFAOYSA-N 0.000 description 1
- YNTQHSDEZACXAP-UHFFFAOYSA-N 3,5-di(pyren-1-yl)pyridine Chemical compound c1cc2ccc3ccc(-c4cncc(c4)-c4ccc5ccc6cccc7ccc4c5c67)c4ccc(c1)c2c34 YNTQHSDEZACXAP-UHFFFAOYSA-N 0.000 description 1
- GWHSOUPRKHXZPK-UHFFFAOYSA-N 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=C3C4=CC(=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=2C=C(C=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GWHSOUPRKHXZPK-UHFFFAOYSA-N 0.000 description 1
- WVEOTOUYEMTBJP-UHFFFAOYSA-N 3,9-dinaphthalen-2-ylperylene Chemical group C1=CC=CC2=CC(C3=C4C=CC=C5C6=CC=C(C=7C=CC=C(C6=7)C(C=C3)=C54)C3=CC4=CC=CC=C4C=C3)=CC=C21 WVEOTOUYEMTBJP-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- VQCRGBGOKRVGOG-UHFFFAOYSA-K 3-(2,4-difluorophenyl)pyridine-2-carboxylate iridium(3+) 5-pyridin-2-yl-3-(trifluoromethyl)pyrazole-3-carboxylate Chemical compound [Ir+3].FC1=CC=C(C(=C1)F)C=1C(=NC=CC1)C(=O)[O-].FC(C1(N=NC(=C1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC(C1(N=NC(=C1)C1=NC=CC=C1)C(=O)[O-])(F)F VQCRGBGOKRVGOG-UHFFFAOYSA-K 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- CWKORCBYPSSTRH-UHFFFAOYSA-N 3-[2,7-bis(diphenylphosphoryl)-9-phenylfluoren-9-yl]-9-phenylcarbazole Chemical compound O=P(c1ccccc1)(c1ccccc1)c1ccc2-c3ccc(cc3C(c2c1)(c1ccccc1)c1ccc2n(-c3ccccc3)c3ccccc3c2c1)P(=O)(c1ccccc1)c1ccccc1 CWKORCBYPSSTRH-UHFFFAOYSA-N 0.000 description 1
- GFMFFNAOXIHABA-UHFFFAOYSA-N 3-[2-[2-[3-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]phenyl]-n,n-bis(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1N(C=1C=C(C=CC=1)C=1C(=CC=CC=1)C=1C(=CC=CC=1)C=1C=C(C=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GFMFFNAOXIHABA-UHFFFAOYSA-N 0.000 description 1
- WCXKTQVEKDHQIY-UHFFFAOYSA-N 3-[3-[3-(3,5-dipyridin-3-ylphenyl)phenyl]-5-pyridin-3-ylphenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=NC=CC=2)=C1 WCXKTQVEKDHQIY-UHFFFAOYSA-N 0.000 description 1
- MCRKBWVSQZTERQ-UHFFFAOYSA-N 3-bromo-2-fluorobenzoyl chloride Chemical compound FC1=C(Br)C=CC=C1C(Cl)=O MCRKBWVSQZTERQ-UHFFFAOYSA-N 0.000 description 1
- RGMMCYNLNAUIJX-UHFFFAOYSA-N 3-bromo-5-fluorobenzoyl chloride Chemical compound FC1=CC(Br)=CC(C(Cl)=O)=C1 RGMMCYNLNAUIJX-UHFFFAOYSA-N 0.000 description 1
- DLZUHSFUBZTBQZ-UHFFFAOYSA-N 3-chloro-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1Cl DLZUHSFUBZTBQZ-UHFFFAOYSA-N 0.000 description 1
- CQQPZYVMGWYJOO-UHFFFAOYSA-N 3-chloro-5-fluorobenzoyl chloride Chemical compound FC1=CC(Cl)=CC(C(Cl)=O)=C1 CQQPZYVMGWYJOO-UHFFFAOYSA-N 0.000 description 1
- WLBLIJUBANCKOH-UHFFFAOYSA-N 3-cyano-5-fluorobenzoyl chloride Chemical compound FC1=CC(C#N)=CC(C(Cl)=O)=C1 WLBLIJUBANCKOH-UHFFFAOYSA-N 0.000 description 1
- SLYUKEJWEOFDHR-UHFFFAOYSA-N 3-diphenylphosphoryl-9-(4-diphenylphosphorylphenyl)carbazole Chemical compound C=1C=CC=CC=1P(C=1C=CC(=CC=1)N1C2=CC=C(C=C2C2=CC=CC=C21)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 SLYUKEJWEOFDHR-UHFFFAOYSA-N 0.000 description 1
- VVFRPFIZSXRDJH-UHFFFAOYSA-N 3-fluoro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=C(F)C=CC=C1C(Cl)=O VVFRPFIZSXRDJH-UHFFFAOYSA-N 0.000 description 1
- DPDAEMNQJYDHRQ-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC=C1C(F)(F)F DPDAEMNQJYDHRQ-UHFFFAOYSA-N 0.000 description 1
- DPWCZSXNEGNALT-UHFFFAOYSA-N 3-fluoro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1F DPWCZSXNEGNALT-UHFFFAOYSA-N 0.000 description 1
- DPAMLESDGWVDBW-UHFFFAOYSA-N 3-fluoro-4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1F DPAMLESDGWVDBW-UHFFFAOYSA-N 0.000 description 1
- BGAKSLBTFLVNAH-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC(C(F)(F)F)=C1 BGAKSLBTFLVNAH-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- BSVILDUORGWESI-UHFFFAOYSA-N 3-methyl-2-(4-naphthalen-2-ylphenyl)imidazo[4,5-f][1,10]phenanthroline Chemical compound C1=CC=CC2=CC(C3=CC=C(C=C3)C=3N(C4=C(C5=CC=CN=C5C5=NC=CC=C54)N=3)C)=CC=C21 BSVILDUORGWESI-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- DCPGBPKLXYETTA-UHFFFAOYSA-N 3-methylphenanthro[9,10-b]pyrazine Chemical compound C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1 DCPGBPKLXYETTA-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MZKXTXKVGSAPEG-UHFFFAOYSA-N 325722-28-9 Chemical compound C1CC(C)(C)C2=CC=CC3=C2N1CCC3(C)C MZKXTXKVGSAPEG-UHFFFAOYSA-N 0.000 description 1
- ZEPNEZBNLFFDDA-UHFFFAOYSA-N 4,7-di(carbazol-9-yl)-1,10-phenanthroline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=NC2=C1C=CC1=C(N3C4=CC=CC=C4C4=CC=CC=C43)C=CN=C21 ZEPNEZBNLFFDDA-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- RUERFVDCGFKEJD-UHFFFAOYSA-N 4-(4-aminophenyl)-1-N',4-N-dinaphthalen-2-yl-1-N',4-N-diphenylcyclohexa-2,5-diene-1,1,4-triamine Chemical compound C1=C(C=CC2=CC=CC=C12)N(C1(C=CC(N)(C=C1)N(C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C1)C1=CC=C(N)C=C1)C1=CC=CC=C1 RUERFVDCGFKEJD-UHFFFAOYSA-N 0.000 description 1
- ZNJRONVKWRHYBF-VOTSOKGWSA-N 4-(dicyanomethylene)-2-methyl-6-julolidyl-9-enyl-4h-pyran Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-VOTSOKGWSA-N 0.000 description 1
- WPUSEOSICYGUEW-UHFFFAOYSA-N 4-[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WPUSEOSICYGUEW-UHFFFAOYSA-N 0.000 description 1
- KBXXZTIBAVBLPP-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-(4-methylphenyl)methyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(C)C=C1 KBXXZTIBAVBLPP-UHFFFAOYSA-N 0.000 description 1
- PCFIABOQFAFDAU-UHFFFAOYSA-N 4-bromo-2-fluorobenzoyl chloride Chemical compound FC1=CC(Br)=CC=C1C(Cl)=O PCFIABOQFAFDAU-UHFFFAOYSA-N 0.000 description 1
- NTHPXJQLZIGPLM-UHFFFAOYSA-N 4-bromo-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1C(Cl)=O NTHPXJQLZIGPLM-UHFFFAOYSA-N 0.000 description 1
- LGDCSNDMFFFSHY-UHFFFAOYSA-N 4-butyl-n,n-diphenylaniline Polymers C1=CC(CCCC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 LGDCSNDMFFFSHY-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- WUFOPFHPVDSXHL-UHFFFAOYSA-N 4-cyano-2-fluorobenzoyl chloride Chemical compound FC1=CC(C#N)=CC=C1C(Cl)=O WUFOPFHPVDSXHL-UHFFFAOYSA-N 0.000 description 1
- OEYHURRIOWWRMD-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(C(F)(F)F)=C1 OEYHURRIOWWRMD-UHFFFAOYSA-N 0.000 description 1
- KZUXJRQQHJREGH-UHFFFAOYSA-N 4-fluoro-2-methylbenzoyl chloride Chemical compound CC1=CC(F)=CC=C1C(Cl)=O KZUXJRQQHJREGH-UHFFFAOYSA-N 0.000 description 1
- NQMGZEFEQXWOAT-UHFFFAOYSA-N 4-fluoro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1C(Cl)=O NQMGZEFEQXWOAT-UHFFFAOYSA-N 0.000 description 1
- BUDISZQHCHGLJW-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1C(F)(F)F BUDISZQHCHGLJW-UHFFFAOYSA-N 0.000 description 1
- FMFLKTDRPXYUGP-UHFFFAOYSA-N 4-fluoro-3-methylbenzoyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC=C1F FMFLKTDRPXYUGP-UHFFFAOYSA-N 0.000 description 1
- OJNVFOHHRJZBEG-UHFFFAOYSA-N 4-fluoro-3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC=C1F OJNVFOHHRJZBEG-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 description 1
- NXVNUSIHWZLMGF-UHFFFAOYSA-N 4-phenyl-N-(4-phenylphenyl)-N-[4-[9-[4-(4-phenyl-N-(4-phenylphenyl)anilino)phenyl]fluoren-9-yl]phenyl]aniline Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 NXVNUSIHWZLMGF-UHFFFAOYSA-N 0.000 description 1
- SKODVKMYBGXHOZ-UHFFFAOYSA-N 4-pyren-1-yl-n,n-bis(4-pyren-1-ylphenyl)aniline Chemical compound C1=CC(C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)C=2C=CC(=CC=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)=C2C=CC3=CC=CC4=CC=C1C2=C43 SKODVKMYBGXHOZ-UHFFFAOYSA-N 0.000 description 1
- JIPXYKHMDJAJNU-UHFFFAOYSA-N 4-quinolin-8-yl-n,n-bis(4-quinolin-8-ylphenyl)aniline Chemical compound C1=CN=C2C(C3=CC=C(C=C3)N(C=3C=CC(=CC=3)C=3C4=NC=CC=C4C=CC=3)C3=CC=C(C=C3)C=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 JIPXYKHMDJAJNU-UHFFFAOYSA-N 0.000 description 1
- SCZWJXTUYYSKGF-UHFFFAOYSA-N 5,12-dimethylquinolino[2,3-b]acridine-7,14-dione Chemical compound CN1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3N(C)C1=C2 SCZWJXTUYYSKGF-UHFFFAOYSA-N 0.000 description 1
- LEGBISULKASFCD-UHFFFAOYSA-N 5-bromo-2-fluorobenzoyl chloride Chemical compound FC1=CC=C(Br)C=C1C(Cl)=O LEGBISULKASFCD-UHFFFAOYSA-N 0.000 description 1
- VWGAATKTEAKOCO-UHFFFAOYSA-N 5-chloro-2-fluorobenzoyl chloride Chemical compound FC1=CC=C(Cl)C=C1C(Cl)=O VWGAATKTEAKOCO-UHFFFAOYSA-N 0.000 description 1
- VHTVVTDYYXQDHS-UHFFFAOYSA-N 5-fluoro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(F)(F)F)C(C(Cl)=O)=C1 VHTVVTDYYXQDHS-UHFFFAOYSA-N 0.000 description 1
- HBAQRSDZSVESSF-UHFFFAOYSA-N 5-fluoro-2-methylbenzoyl chloride Chemical compound CC1=CC=C(F)C=C1C(Cl)=O HBAQRSDZSVESSF-UHFFFAOYSA-N 0.000 description 1
- DHNJQRSDZABGBP-UHFFFAOYSA-N 5-fluoro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1C(Cl)=O DHNJQRSDZABGBP-UHFFFAOYSA-N 0.000 description 1
- PZPCFCMBWVLRFR-UHFFFAOYSA-N 6,13-bis(4-phenylphenyl)pentacene Chemical compound C1=CC=CC=C1C1=CC=C(C=2C3=CC4=CC=CC=C4C=C3C(C=3C=CC(=CC=3)C=3C=CC=CC=3)=C3C=C4C=CC=CC4=CC3=2)C=C1 PZPCFCMBWVLRFR-UHFFFAOYSA-N 0.000 description 1
- YJULTVLLOWTBRW-UHFFFAOYSA-N 6-(2,4,6-trimethylphenyl)-n-[6-(2,4,6-trimethylphenyl)quinolin-2-yl]quinolin-2-amine Chemical compound CC1=CC(C)=CC(C)=C1C1=CC=C(N=C(NC=2N=C3C=CC(=CC3=CC=2)C=2C(=CC(C)=CC=2C)C)C=C2)C2=C1 YJULTVLLOWTBRW-UHFFFAOYSA-N 0.000 description 1
- UBFXCBRNQSHADT-UHFFFAOYSA-N 6-methyl-2-[4-[10-[4-(6-methyl-1,3-benzothiazol-2-yl)phenyl]anthracen-9-yl]phenyl]-1,3-benzothiazole Chemical compound C12=CC=CC=C2C(C2=CC=C(C=C2)C2=NC3=CC=C(C=C3S2)C)=C(C=CC=C2)C2=C1C1=CC=C(C=2SC3=CC(C)=CC=C3N=2)C=C1 UBFXCBRNQSHADT-UHFFFAOYSA-N 0.000 description 1
- XLITZAVSBAQYNG-UHFFFAOYSA-N 7-[7-[9,9-dimethyl-7-(N-naphthalen-2-ylanilino)fluoren-2-yl]-9,9-dimethylfluoren-2-yl]-9,9-dimethyl-N-naphthalen-2-yl-N-phenylfluoren-2-amine Chemical compound CC1(C)C2=C(C=CC(=C2)N(C2=CC=CC=C2)C2=CC3=CC=CC=C3C=C2)C2=C1C=C(C=C2)C1=CC2=C(C=C1)C1=C(C=C(C=C1)C1=CC3=C(C=C1)C1=C(C=C(C=C1)N(C1=CC=CC=C1)C1=CC=C4C=CC=CC4=C1)C3(C)C)C2(C)C XLITZAVSBAQYNG-UHFFFAOYSA-N 0.000 description 1
- YDLBBFQXZLLOCM-UHFFFAOYSA-N 7-[7-[9,9-dimethyl-7-(n-(3-methylphenyl)anilino)fluoren-2-yl]-9,9-dimethylfluoren-2-yl]-9,9-dimethyl-n-(3-methylphenyl)-n-phenylfluoren-2-amine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=C3C(C)(C)C4=CC(=CC=C4C3=CC=2)C=2C=C3C(C)(C)C4=CC(=CC=C4C3=CC=2)C=2C=C3C(C)(C)C4=CC(=CC=C4C3=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 YDLBBFQXZLLOCM-UHFFFAOYSA-N 0.000 description 1
- MPMSFLAIOPUDMV-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid;sodium Chemical compound [Na].[Na].C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 MPMSFLAIOPUDMV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- YUBXDAMWVRMLOG-UHFFFAOYSA-N 9,9-dimethyl-2-n,7-n-bis(3-methylphenyl)-2-n,7-n-diphenylfluorene-2,7-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=C3C(C)(C)C4=CC(=CC=C4C3=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 YUBXDAMWVRMLOG-UHFFFAOYSA-N 0.000 description 1
- KJEQVQJWXVHKGT-UHFFFAOYSA-N 9,9-dimethyl-2-n,7-n-dinaphthalen-1-yl-2-n,7-n-diphenylfluorene-2,7-diamine Chemical compound C1=C2C(C)(C)C3=CC(N(C=4C=CC=CC=4)C=4C5=CC=CC=C5C=CC=4)=CC=C3C2=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 KJEQVQJWXVHKGT-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- KIQHGZHPNCGQJY-UHFFFAOYSA-N 9-(4-phenylphenyl)-10-[10-(4-phenylphenyl)anthracen-9-yl]anthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C(C=4C=CC(=CC=4)C=4C=CC=CC=4)=C4C=CC=CC4=3)=C3C=CC=CC3=2)C=C1 KIQHGZHPNCGQJY-UHFFFAOYSA-N 0.000 description 1
- RIFLTHUXOHHZQV-UHFFFAOYSA-N 9-(4-tert-butylphenyl)-3,6-bis[9-(4-methoxyphenyl)fluoren-9-yl]carbazole Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C3C4=CC(=CC=C4N(C=4C=CC(=CC=4)C(C)(C)C)C3=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(OC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RIFLTHUXOHHZQV-UHFFFAOYSA-N 0.000 description 1
- XUPHFLNNUVKICJ-UHFFFAOYSA-N 9-(4-tert-butylphenyl)-3,6-ditritylcarbazole Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C2=CC=C(C(C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2C2=CC(C(C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C21 XUPHFLNNUVKICJ-UHFFFAOYSA-N 0.000 description 1
- UDECBOWBCXTHEY-UHFFFAOYSA-N 9-(7'-carbazol-9-yl-9,9'-spirobi[fluorene]-2'-yl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(C34C5=CC=CC=C5C=5C3=CC=CC=5)=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C4=C1 UDECBOWBCXTHEY-UHFFFAOYSA-N 0.000 description 1
- IEQGNDONCZPWMW-UHFFFAOYSA-N 9-(7-carbazol-9-yl-9,9-dimethylfluoren-2-yl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(C3(C)C)=CC(=CC=2)N2C4=CC=CC=C4C4=CC=CC=C42)C3=C1 IEQGNDONCZPWMW-UHFFFAOYSA-N 0.000 description 1
- PUMJBASCKOPOOW-UHFFFAOYSA-N 9-[2',7,7'-tri(carbazol-9-yl)-9,9'-spirobi[fluorene]-2-yl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C23C4=CC(=CC=C4C4=CC=C(C=C42)N2C4=CC=CC=C4C4=CC=CC=C42)N2C4=CC=CC=C4C4=CC=CC=C42)C3=C1 PUMJBASCKOPOOW-UHFFFAOYSA-N 0.000 description 1
- DVNOWTJCOPZGQA-UHFFFAOYSA-N 9-[3,5-di(carbazol-9-yl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 DVNOWTJCOPZGQA-UHFFFAOYSA-N 0.000 description 1
- VDHOGVHFPFGPIP-UHFFFAOYSA-N 9-[3-[5-(3-carbazol-9-ylphenyl)pyridin-3-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=NC=C(C=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 VDHOGVHFPFGPIP-UHFFFAOYSA-N 0.000 description 1
- UFWDOFZYKRDHPB-UHFFFAOYSA-N 9-[3-[6-(3-carbazol-9-ylphenyl)pyridin-2-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(N=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 UFWDOFZYKRDHPB-UHFFFAOYSA-N 0.000 description 1
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]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)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 description 1
- ZWHCLDHSEXFKIK-MBALSZOMSA-N 9-[4-[(e)-2-[4-[(e)-2-(4-carbazol-9-ylphenyl)ethenyl]phenyl]ethenyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1/C=C/C(C=C1)=CC=C1/C=C/C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 ZWHCLDHSEXFKIK-MBALSZOMSA-N 0.000 description 1
- UXJDSNKBYFJNDO-UHFFFAOYSA-N 9-[4-[2-[2-(4-carbazol-9-ylphenyl)phenyl]phenyl]phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UXJDSNKBYFJNDO-UHFFFAOYSA-N 0.000 description 1
- GFEWJHOBOWFNRV-UHFFFAOYSA-N 9-[4-[9-(4-carbazol-9-ylphenyl)fluoren-9-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C2=CC=CC=C2C2=CC=CC=C12 GFEWJHOBOWFNRV-UHFFFAOYSA-N 0.000 description 1
- MKOZLTYWWOHJAU-UHFFFAOYSA-N 9-[7-carbazol-9-yl-9,9-bis(4-methylphenyl)fluoren-2-yl]carbazole Chemical compound C1=CC(C)=CC=C1C1(C=2C=CC(C)=CC=2)C2=CC(N3C4=CC=CC=C4C4=CC=CC=C43)=CC=C2C2=CC=C(N3C4=CC=CC=C4C4=CC=CC=C43)C=C21 MKOZLTYWWOHJAU-UHFFFAOYSA-N 0.000 description 1
- RAPHUPWIHDYTKU-WXUKJITCSA-N 9-ethyl-3-[(e)-2-[4-[4-[(e)-2-(9-ethylcarbazol-3-yl)ethenyl]phenyl]phenyl]ethenyl]carbazole Chemical group C1=CC=C2C3=CC(/C=C/C4=CC=C(C=C4)C4=CC=C(C=C4)/C=C/C=4C=C5C6=CC=CC=C6N(C5=CC=4)CC)=CC=C3N(CC)C2=C1 RAPHUPWIHDYTKU-WXUKJITCSA-N 0.000 description 1
- LMTXHBDTVAIIQY-UHFFFAOYSA-N 9-n,10-n-bis(3-methylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C(N(C=3C=CC=CC=3)C=3C=C(C)C=CC=3)=C3C=CC=CC3=2)=C1 LMTXHBDTVAIIQY-UHFFFAOYSA-N 0.000 description 1
- FWXNJWAXBVMBGL-UHFFFAOYSA-N 9-n,9-n,10-n,10-n-tetrakis(4-methylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C2C=CC=CC2=1)C1=CC=C(C)C=C1 FWXNJWAXBVMBGL-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GLTXHVSLRASWCR-UHFFFAOYSA-N C1(=CC=C(C=C1)N(C1=CC=C(C=C1)N(C=1C=C(C=CC1)C)C=1C=C(C=CC1)C)C1=CC=CC=C1)C1=CC=C(C=C1)N(C1=CC=C(C=C1)N(C=1C=C(C=CC1)C)C=1C=C(C=CC1)C)C1=CC=CC=C1.C1(=CC=CC=C1)NC1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)NC1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)N(C1=CC=C(C=C1)N(C=1C=C(C=CC1)C)C=1C=C(C=CC1)C)C1=CC=CC=C1)C1=CC=C(C=C1)N(C1=CC=C(C=C1)N(C=1C=C(C=CC1)C)C=1C=C(C=CC1)C)C1=CC=CC=C1.C1(=CC=CC=C1)NC1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)NC1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 GLTXHVSLRASWCR-UHFFFAOYSA-N 0.000 description 1
- RYTWPHNDIYUFKY-UHFFFAOYSA-L C1(=CC=CC=C1)C(C1=CC=CC=C1)P.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.[Os+2] Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)P.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.[Os+2] RYTWPHNDIYUFKY-UHFFFAOYSA-L 0.000 description 1
- WYAYWGVTBFYERV-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](C1=CC=C(C=C1)C1=CC=C(C=C1)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[Si](C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=CC=2C3=CC=CC=C3N(C12)C1=CC=2C(C3=CC(=CC=C3C2C=C1)N1C2=CC=CC=C2C=2C=CC=CC12)(CCCCCCCC)CCCCCCCC Chemical group C1(=CC=CC=C1)[Si](C1=CC=C(C=C1)C1=CC=C(C=C1)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[Si](C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=CC=2C3=CC=CC=C3N(C12)C1=CC=2C(C3=CC(=CC=C3C2C=C1)N1C2=CC=CC=C2C=2C=CC=CC12)(CCCCCCCC)CCCCCCCC WYAYWGVTBFYERV-UHFFFAOYSA-N 0.000 description 1
- BFDFHGPJXDFXBA-UHFFFAOYSA-N C12=CC=CC=C2C2=CC=CC=C2C1(C1=C2)C3=CC=CC=C3C1=CC=C2C(C=C1C2(C3=CC=CC=C3C3=CC=CC=C32)C2=C3)=CC=C1C2=CC=C3C(C=C12)=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C1=C2)C3=CC=CC=C3C1=CC=C2C(C=C1C2(C3=CC=CC=C3C3=CC=CC=C32)C2=C3)=CC=C1C2=CC=C3C(C=C12)=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 BFDFHGPJXDFXBA-UHFFFAOYSA-N 0.000 description 1
- HFPKZKXVTHRNFZ-UHFFFAOYSA-N C1=CC(C)=CC=C1C1(C=2C=CC(C)=CC=2)C2=CC(C=3C=C4C(C5=CC(=CC=C5C4=CC=3)C=3C=C4C(C5=CC=CC=C5C4=CC=3)(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=C2C2=CC=CC=C21 Chemical compound C1=CC(C)=CC=C1C1(C=2C=CC(C)=CC=2)C2=CC(C=3C=C4C(C5=CC(=CC=C5C4=CC=3)C=3C=C4C(C5=CC=CC=C5C4=CC=3)(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=C2C2=CC=CC=C21 HFPKZKXVTHRNFZ-UHFFFAOYSA-N 0.000 description 1
- VMPLMOXGWULJTH-UHFFFAOYSA-N C1=CC(C)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 Chemical compound C1=CC(C)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 VMPLMOXGWULJTH-UHFFFAOYSA-N 0.000 description 1
- DZGMBCXPLCKERU-UHFFFAOYSA-N C1=CC=CC2=C(C3=CC=CC=C3C(=C12)C=1C2=CC=CC=C2C=C2C=CC=CC12)C1=CC=C2C=3C=CC(=CC3C(C2=C1)(CCCCCC)CCCCCC)C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34.C3=CC=CC4=C(C2=CC=CC=C2C(=C34)C=3C4=CC=CC=C4C=C4C=CC=CC34)C3=CC=C4C=2C=CC(=CC2C(C4=C3)(C)C)C3=CC=C4C=CC2=CC=CC1=CC=C3C4=C21 Chemical compound C1=CC=CC2=C(C3=CC=CC=C3C(=C12)C=1C2=CC=CC=C2C=C2C=CC=CC12)C1=CC=C2C=3C=CC(=CC3C(C2=C1)(CCCCCC)CCCCCC)C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34.C3=CC=CC4=C(C2=CC=CC=C2C(=C34)C=3C4=CC=CC=C4C=C4C=CC=CC34)C3=CC=C4C=2C=CC(=CC2C(C4=C3)(C)C)C3=CC=C4C=CC2=CC=CC1=CC=C3C4=C21 DZGMBCXPLCKERU-UHFFFAOYSA-N 0.000 description 1
- LFIYMKYMOHCZMO-UHFFFAOYSA-N 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)C23C4=CC(=CC=C4C4=CC=C(C=C42)N(C=2C=CC=CC=2)C=2C4=CC=CC=C4C=CC=2)N(C=2C=CC=CC=2)C=2C4=CC=CC=C4C=CC=2)C3=C1 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)C23C4=CC(=CC=C4C4=CC=C(C=C42)N(C=2C=CC=CC=2)C=2C4=CC=CC=C4C=CC=2)N(C=2C=CC=CC=2)C=2C4=CC=CC=C4C=CC=2)C3=C1 LFIYMKYMOHCZMO-UHFFFAOYSA-N 0.000 description 1
- SUMCCQSRZIWCIX-UHFFFAOYSA-N CC1(C2=CC(=CC=C2C=2C=CC(=CC12)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=NC2=C(N1C1=CC=CC=C1)C=CC=C2)C Chemical compound CC1(C2=CC(=CC=C2C=2C=CC(=CC12)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=NC2=C(N1C1=CC=CC=C1)C=CC=C2)C SUMCCQSRZIWCIX-UHFFFAOYSA-N 0.000 description 1
- ZWKWCYYURIJPHF-UHFFFAOYSA-N CC=1C=C(C=CC1)C1(NC=CC=C1)C(=O)O.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C=C1.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C=C1 Chemical compound CC=1C=C(C=CC1)C1(NC=CC=C1)C(=O)O.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C=C1.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C=C1 ZWKWCYYURIJPHF-UHFFFAOYSA-N 0.000 description 1
- FSLBFWSUIWMADR-UHFFFAOYSA-L CP(C1=CC=CC=C1)C.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.[Os+2] Chemical compound CP(C1=CC=CC=C1)C.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.FC(C1(N=NC(=N1)C1=NC=CC(=C1)C(C)(C)C)C(=O)[O-])(F)F.[Os+2] FSLBFWSUIWMADR-UHFFFAOYSA-L 0.000 description 1
- JHFOWEGCZWLHNW-UHFFFAOYSA-N Cc(cc(cc1)F)c1[N+]([O-])=O Chemical compound Cc(cc(cc1)F)c1[N+]([O-])=O JHFOWEGCZWLHNW-UHFFFAOYSA-N 0.000 description 1
- XUCYJGMIICONES-UHFFFAOYSA-N Cc(cc(cc1)[N+]([O-])=O)c1F Chemical compound Cc(cc(cc1)[N+]([O-])=O)c1F XUCYJGMIICONES-UHFFFAOYSA-N 0.000 description 1
- WZMOWQCNPFDWPA-UHFFFAOYSA-N Cc(cc1)cc(F)c1[N+]([O-])=O Chemical compound Cc(cc1)cc(F)c1[N+]([O-])=O WZMOWQCNPFDWPA-UHFFFAOYSA-N 0.000 description 1
- OORBDHOQLZRIQR-UHFFFAOYSA-N Cc(cc1)cc([N+]([O-])=O)c1F Chemical compound Cc(cc1)cc([N+]([O-])=O)c1F OORBDHOQLZRIQR-UHFFFAOYSA-N 0.000 description 1
- KZNXALJXBRSMFL-UHFFFAOYSA-N Cc(ccc(Br)c1)c1[N+]([O-])=O Chemical compound Cc(ccc(Br)c1)c1[N+]([O-])=O KZNXALJXBRSMFL-UHFFFAOYSA-N 0.000 description 1
- KUQQONVKIURIQU-UHFFFAOYSA-N Cc(ccc(C#N)c1)c1F Chemical compound Cc(ccc(C#N)c1)c1F KUQQONVKIURIQU-UHFFFAOYSA-N 0.000 description 1
- SKWTUNAAJNDEIK-UHFFFAOYSA-N Cc(ccc(F)c1)c1[N+]([O-])=O Chemical compound Cc(ccc(F)c1)c1[N+]([O-])=O SKWTUNAAJNDEIK-UHFFFAOYSA-N 0.000 description 1
- LLYXJBROWQDVMI-UHFFFAOYSA-N Cc(ccc([N+]([O-])=O)c1)c1Cl Chemical compound Cc(ccc([N+]([O-])=O)c1)c1Cl LLYXJBROWQDVMI-UHFFFAOYSA-N 0.000 description 1
- WIQISTBTOQNVCE-UHFFFAOYSA-N Cc(ccc([N+]([O-])=O)c1)c1F Chemical compound Cc(ccc([N+]([O-])=O)c1)c1F WIQISTBTOQNVCE-UHFFFAOYSA-N 0.000 description 1
- JSXAJLMUBSEJFF-UHFFFAOYSA-N Cc(cccc1F)c1[N+]([O-])=O Chemical compound Cc(cccc1F)c1[N+]([O-])=O JSXAJLMUBSEJFF-UHFFFAOYSA-N 0.000 description 1
- GKUQCZSZQBEHCP-UHFFFAOYSA-N Cc1cc(C#N)cc(F)c1 Chemical compound Cc1cc(C#N)cc(F)c1 GKUQCZSZQBEHCP-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- WIIALIIXFFZGJZ-UHFFFAOYSA-N FC1=C(C(=O)Cl)C(=C(C=C1F)F)F.FC1=C(C(=O)Cl)C=C(C(=C1F)F)F Chemical compound FC1=C(C(=O)Cl)C(=C(C=C1F)F)F.FC1=C(C(=O)Cl)C=C(C(=C1F)F)F WIIALIIXFFZGJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- MMGCHKNLJDQCDF-JWTBXLROSA-N N,N-diphenyl-4-[(E)-2-[7'-[(E)-2-[4-(N-phenylanilino)phenyl]ethenyl]-9,9'-spirobi[fluorene]-2'-yl]ethenyl]aniline Chemical compound C(=C/C1=CC=C2C3=C(C=C(\C=C\C4=CC=C(C=C4)N(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)C3(C4=CC=CC=C4C4=C3C=CC=C4)C2=C1)\C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 MMGCHKNLJDQCDF-JWTBXLROSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052773 Promethium Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- GWFGARXUJNKOMY-UHFFFAOYSA-N [3,5-di(carbazol-9-yl)phenyl]-triphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=C(C=1)N1C2=CC=CC=C2C2=CC=CC=C21)N1C2=CC=CC=C2C2=CC=CC=C21)(C=1C=CC=CC=1)C1=CC=CC=C1 GWFGARXUJNKOMY-UHFFFAOYSA-N 0.000 description 1
- WIHKEPSYODOQJR-UHFFFAOYSA-N [9-(4-tert-butylphenyl)-6-triphenylsilylcarbazol-3-yl]-triphenylsilane Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C2=CC=C([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2C2=CC([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C21 WIHKEPSYODOQJR-UHFFFAOYSA-N 0.000 description 1
- NSTHTAKLHRZVCQ-UHFFFAOYSA-K [Ir+3].CC(C(=O)[O-])(C(CC(C(C)(C)C)=O)=O)C.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.CC(C(=O)[O-])(C(CC(C(C)(C)C)=O)=O)C.CC(C(=O)[O-])(C(CC(C(C)(C)C)=O)=O)C Chemical compound [Ir+3].CC(C(=O)[O-])(C(CC(C(C)(C)C)=O)=O)C.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.CC(C(=O)[O-])(C(CC(C(C)(C)C)=O)=O)C.CC(C(=O)[O-])(C(CC(C(C)(C)C)=O)=O)C NSTHTAKLHRZVCQ-UHFFFAOYSA-K 0.000 description 1
- UHMVYRVEAXSAEB-UHFFFAOYSA-K [Ir+3].FC(C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-] Chemical compound [Ir+3].FC(C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-] UHMVYRVEAXSAEB-UHFFFAOYSA-K 0.000 description 1
- CLTCRQSHMJEQEB-UHFFFAOYSA-I [Ir+3].FC(C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC1=C(C[N+]2=CN(C3=C2C=CC=C3)C)C=CC(=C1)F.FC1=C(C[N+]3=CN(C2=C3C=CC=C2)C)C=CC(=C1)F.FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-] Chemical compound [Ir+3].FC(C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-])(F)F.FC1=C(C[N+]2=CN(C3=C2C=CC=C3)C)C=CC(=C1)F.FC1=C(C[N+]3=CN(C2=C3C=CC=C2)C)C=CC(=C1)F.FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-].FC(F)(F)C1(N=NC(=N1)C1=NC=CC=C1)C(=O)[O-] CLTCRQSHMJEQEB-UHFFFAOYSA-I 0.000 description 1
- MBJRWUAYUSRWCK-UHFFFAOYSA-K [Ir+3].FC1=C(CC2=C(C=CC=C2)P([O-])(=O)C2=CC=CC=C2)C=CC(=C1)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC1=C(CC2=C(C=CC=C2)P([O-])(=O)C2=CC=CC=C2)C=CC(=C1)F.FC1=C(CC2=C(C=CC=C2)P([O-])(=O)C2=CC=CC=C2)C=CC(=C1)F Chemical compound [Ir+3].FC1=C(CC2=C(C=CC=C2)P([O-])(=O)C2=CC=CC=C2)C=CC(=C1)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC(C1=NNC(=C1)C1=NC=CC=C1)(F)F.FC1=C(CC2=C(C=CC=C2)P([O-])(=O)C2=CC=CC=C2)C=CC(=C1)F.FC1=C(CC2=C(C=CC=C2)P([O-])(=O)C2=CC=CC=C2)C=CC(=C1)F MBJRWUAYUSRWCK-UHFFFAOYSA-K 0.000 description 1
- QKSLHVHBIFQZQX-UHFFFAOYSA-K [Ir+3].N1=C(C=CC=C1)C1(C(OC2=CC=CC=C2C1)=O)C(=O)[O-].N1=C(C=CC=C1)C1(C(OC2=CC=CC=C2C1)=O)C(=O)[O-].N1=C(C=CC=C1)C1(C(OC2=CC=CC=C2C1)=O)C(=O)[O-] Chemical compound [Ir+3].N1=C(C=CC=C1)C1(C(OC2=CC=CC=C2C1)=O)C(=O)[O-].N1=C(C=CC=C1)C1(C(OC2=CC=CC=C2C1)=O)C(=O)[O-].N1=C(C=CC=C1)C1(C(OC2=CC=CC=C2C1)=O)C(=O)[O-] QKSLHVHBIFQZQX-UHFFFAOYSA-K 0.000 description 1
- SMFQHVSXWABQAU-UHFFFAOYSA-K [Ir+3].N1=C(C=CC=C1)C1(N=NNN1)C(=O)[O-].N1=C(C=CC=C1)C1(N=NNN1)C(=O)[O-].N1=C(C=CC=C1)C1(N=NNN1)C(=O)[O-] Chemical compound [Ir+3].N1=C(C=CC=C1)C1(N=NNN1)C(=O)[O-].N1=C(C=CC=C1)C1(N=NNN1)C(=O)[O-].N1=C(C=CC=C1)C1(N=NNN1)C(=O)[O-] SMFQHVSXWABQAU-UHFFFAOYSA-K 0.000 description 1
- GJNGTALCSUHZRC-UHFFFAOYSA-N [Ir].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C Chemical compound [Ir].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C GJNGTALCSUHZRC-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- OWWNJDFZTCNNNX-UHFFFAOYSA-N [Na].[Na].OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 Chemical compound [Na].[Na].OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OWWNJDFZTCNNNX-UHFFFAOYSA-N 0.000 description 1
- GBKYFASVJPZWLI-UHFFFAOYSA-N [Pt+2].N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 Chemical compound [Pt+2].N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 GBKYFASVJPZWLI-UHFFFAOYSA-N 0.000 description 1
- KQSSJPPOALYJCF-UHFFFAOYSA-L [Ru+2].CP(C1=CC=CC=C1)C1=CC=CC=C1.FC(C1(N=NC(=C1)C1=NC=CC2=CC=CC=C12)C(=O)[O-])(F)F.FC(C1(N=NC(=C1)C1=NC=CC2=CC=CC=C12)C(=O)[O-])(F)F Chemical compound [Ru+2].CP(C1=CC=CC=C1)C1=CC=CC=C1.FC(C1(N=NC(=C1)C1=NC=CC2=CC=CC=C12)C(=O)[O-])(F)F.FC(C1(N=NC(=C1)C1=NC=CC2=CC=CC=C12)C(=O)[O-])(F)F KQSSJPPOALYJCF-UHFFFAOYSA-L 0.000 description 1
- HDGNFKSZZTUTIF-UHFFFAOYSA-N [Ru+3].CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1.CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1.CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 Chemical compound [Ru+3].CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1.CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1.CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 HDGNFKSZZTUTIF-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- QJXVCEINEQQSPK-UHFFFAOYSA-N bis(2-methylphenyl)-diphenylsilane Chemical compound CC1=CC=CC=C1[Si](C=1C(=CC=CC=1)C)(C=1C=CC=CC=1)C1=CC=CC=C1 QJXVCEINEQQSPK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FCDNEESKPPIAJZ-UHFFFAOYSA-N bis[3,5-di(carbazol-9-yl)phenyl]-diphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=C(C=1)N1C2=CC=CC=C2C2=CC=CC=C21)N1C2=CC=CC=C2C2=CC=CC=C21)(C=1C=C(C=C(C=1)N1C2=CC=CC=C2C2=CC=CC=C21)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 FCDNEESKPPIAJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- JVXKMWXCWDWQLA-UHFFFAOYSA-N butane-1,3-diol;2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)CCO.CC(O)COC(C)COC(C)CO JVXKMWXCWDWQLA-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- FDRNXKXKFNHNCA-UHFFFAOYSA-N c(cc1)ccc1Nc(cc1)ccc1-c(cc1)ccc1Nc1ccccc1 Chemical compound c(cc1)ccc1Nc(cc1)ccc1-c(cc1)ccc1Nc1ccccc1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 1
- HFUZCVTVOQHYBZ-UHFFFAOYSA-N c1ccc2c(cccc2c1)-c1c2ccccc2c(-c2ccc(cc2)-c2ccc(cc2)-c2c3ccccc3c(-c3cccc4ccccc34)c3ccccc23)c2ccccc12 Chemical group c1ccc2c(cccc2c1)-c1c2ccccc2c(-c2ccc(cc2)-c2ccc(cc2)-c2c3ccccc3c(-c3cccc4ccccc34)c3ccccc23)c2ccccc12 HFUZCVTVOQHYBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- AFBMXTJJCXKVRZ-UHFFFAOYSA-N dimethyl(phenyl)phosphane osmium(2+) 2-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]pyridine Chemical compound [Os+2].CP(C)C1=CC=CC=C1.FC(F)(F)C1=NNC(C=2N=CC=CC=2)=N1.FC(F)(F)C1=NNC(C=2N=CC=CC=2)=N1 AFBMXTJJCXKVRZ-UHFFFAOYSA-N 0.000 description 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- UIJLKECZHOSSHF-UHFFFAOYSA-N diphenyl-bis(4-pyridin-3-ylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=NC=CC=1)(C=1C=CC(=CC=1)C=1C=NC=CC=1)C1=CC=CC=C1 UIJLKECZHOSSHF-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QYUDDCLXBAJUNA-UHFFFAOYSA-L disodium;2-aminobenzene-1,4-disulfonate Chemical compound [Na+].[Na+].NC1=CC(S([O-])(=O)=O)=CC=C1S([O-])(=O)=O QYUDDCLXBAJUNA-UHFFFAOYSA-L 0.000 description 1
- ACBJGAPIXKDCRP-UHFFFAOYSA-L disodium;2-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC2=C(S([O-])(=O)=O)C(N)=CC=C21 ACBJGAPIXKDCRP-UHFFFAOYSA-L 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- YCBINYVMSDDQKZ-UHFFFAOYSA-L disodium;3-aminonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N)=CC2=C1 YCBINYVMSDDQKZ-UHFFFAOYSA-L 0.000 description 1
- OIZLWWGSWBNNAM-UHFFFAOYSA-L disodium;4-aminobenzene-1,3-disulfonate Chemical compound [Na+].[Na+].NC1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O OIZLWWGSWBNNAM-UHFFFAOYSA-L 0.000 description 1
- QJEOKSBCNIUFDS-UHFFFAOYSA-L disodium;4-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC(S([O-])(=O)=O)=C2C(N)=CC=C(S([O-])(=O)=O)C2=C1 QJEOKSBCNIUFDS-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical group S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- BNASDYJRNOLPQY-UHFFFAOYSA-N iridium 2-phenylquinoline Chemical compound [Ir].c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1 BNASDYJRNOLPQY-UHFFFAOYSA-N 0.000 description 1
- QTRRAHGRSMFAKW-UHFFFAOYSA-N iridium(3+);1-phenylpyrazole Chemical compound [Ir+3].C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1 QTRRAHGRSMFAKW-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- ZQNWVCDSOIVSDI-UHFFFAOYSA-M lithium;8-hydroxyquinolin-2-olate Chemical compound [Li+].C1=C([O-])N=C2C(O)=CC=CC2=C1 ZQNWVCDSOIVSDI-UHFFFAOYSA-M 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- YPJRZWDWVBNDIW-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[4-[4-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-MBALSZOMSA-N 0.000 description 1
- NRKQPQQULQMWBV-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-yl]ethenyl]aniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 NRKQPQQULQMWBV-MBALSZOMSA-N 0.000 description 1
- NJWJVPXCXKIBJD-QURGRASLSA-N n,n-diphenyl-6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 NJWJVPXCXKIBJD-QURGRASLSA-N 0.000 description 1
- ZJFKMIYGRJGWIB-UHFFFAOYSA-N n-[3-methyl-4-[2-methyl-4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=CC=C1C(C(=C1)C)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ZJFKMIYGRJGWIB-UHFFFAOYSA-N 0.000 description 1
- CLTPAQDLCMKBIS-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-1-ylamino)phenyl]phenyl]-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CLTPAQDLCMKBIS-UHFFFAOYSA-N 0.000 description 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 description 1
- PKQHEBAYOGHIPX-UHFFFAOYSA-N n-[4-[9-[4-(dinaphthalen-2-ylamino)phenyl]fluoren-9-yl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=C4C=CC=CC4=CC=3)C3=CC=C(C=C3)C3(C=4C=CC(=CC=4)N(C=4C=C5C=CC=CC5=CC=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=CC=C4C=4C3=CC=CC=4)=CC=C21 PKQHEBAYOGHIPX-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 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
- LYKXFSYCKWNWEZ-UHFFFAOYSA-N pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile Chemical compound N1=CC=CC2=C(N=C(C(C#N)=N3)C#N)C3=C(C=CC=N3)C3=C21 LYKXFSYCKWNWEZ-UHFFFAOYSA-N 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 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
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- GBSZYMVOJYAZPH-UHFFFAOYSA-N thieno[2,3-e][1]benzothiole Chemical class S1C=CC2=C1C=CC1=C2SC=C1 GBSZYMVOJYAZPH-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical class S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-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
- 238000001771 vacuum deposition 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
- 239000008096 xylene Substances 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
- 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 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- 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
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
Definitions
- the present invention relates to an aryl sulfonic acid compound, use of this compound, and a method for producing an aryl sulfonic acid compound.
- organic electroluminescence element In an organic electroluminescence (hereinafter referred to as organic EL) element, a charge transporting thin film made of an organic compound is used as a light emitting layer or a charge injection layer.
- the hole injection layer is responsible for charge transfer between the anode and the hole transport layer or the light emitting layer, and plays an important function to achieve low voltage driving and high luminance of the organic EL element.
- the method of forming the hole injection layer is roughly divided into a dry process typified by vapor deposition and a wet process typified by spin coating. When these processes are compared, the wet process is more flat in a larger area. Can be manufactured efficiently. Therefore, at the present time when the area of the organic EL display is being increased, a hole injection layer that can be formed by a wet process is desired.
- the present inventor is applicable to various wet processes and provides a charge transport material that provides a thin film that can realize excellent EL element characteristics when applied to a hole injection layer of an organic EL element.
- compounds suitable for charge transporting substances and dopants that exhibit solubility in organic solvents used therefor have been developed (see, for example, Patent Documents 1 to 7).
- the present invention also provides an aryl sulfone that exhibits good solubility in an organic solvent and can realize a thin film excellent in charge transportability when used together with a charge transport material, as in the technology of the above-mentioned patent document that has been developed so far. It aims at providing an acid compound and its manufacturing method.
- the present inventor has found that the above object can be achieved with the following aryl sulfonic acid compound, and that the aryl sulfonic acid compound can be efficiently produced at low cost. Completed the invention.
- this invention provides the following aryl sulfonic acid compound, its utilization, and the manufacturing method of an aryl sulfonic acid compound.
- a dopant comprising an aryl sulfonic acid compound according to any one of 1 to 3.
- a charge transporting varnish comprising 5.4 dopant, a charge transporting substance and an organic solvent.
- An organic electroluminescence device having a charge transporting thin film of 7.6.
- a method for producing a charge transporting thin film characterized by using a dopant of 8.4.
- a method for producing a charge transporting thin film comprising using the charge transporting varnish of 9.5. 10.
- X represents a halogen atom.
- Ar 1 and Ar 3 are the same as above.
- 12 A method for producing an aryl sulfonic acid compound according to 1, wherein the aryl sulfonate represented by the formula (1 ′) is subjected to an ion exchange treatment.
- Ar 1 is the same as above.
- Ar 3 represents a group represented by the formula (3 ′) or (4 ′).
- M represents an alkali metal atom.
- the arylsulfonic acid compound of the present invention exhibits good solubility in an organic solvent, and can realize a thin film having excellent charge transportability when used with a charge transporting substance. Moreover, according to the method for producing an aryl sulfonic acid compound of the present invention, an aryl sulfonic acid compound can be produced efficiently at low cost.
- arylsulfonic acid compound The arylsulfonic acid compound of the present invention is represented by the formula (1).
- Ar 1 represents a group represented by the formula (2).
- R 1 to R 5 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a methyl group or a trifluoromethyl group, and at least one of R 1 to R 5 represents a halogen atom.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
- At least one of R 1 to R 5 is a fluorine atom, and at least the other one has a high electron withdrawing property. It is preferable that the group has
- R 1 ⁇ R 5 is a fluorine atom
- at least the other is a halogen atom, a nitro group, a cyano group or a trifluoromethyl group
- a R 1 ⁇ R 5 More preferably, at least one of them is a fluorine atom, and at least the other one is a fluorine atom, a cyano group, a nitro group or a trifluoromethyl group, and at least the other one is a fluorine atom, a cyano group or a nitro group. It is even more preferable that at least two of R 1 to R 5 are fluorine atoms.
- Preferred examples of the group represented by formula (2) include, but are not limited to, the following.
- Ar 2 represents a group represented by formula (3) or (4).
- Ar 2 is preferably a group represented by the formula (4) from the viewpoint of obtaining a charge transporting thin film having higher durability when used together with a charge transporting substance.
- Ar 2 for example, a group represented by the formula (4 ′′) is preferable.
- the following groups are preferred as the group represented by the formula (4), but are not limited thereto.
- the arylsulfonic acid compound represented by the formula (1) of the present invention is obtained by reacting an amine compound represented by the formula (5) with an acid halide represented by the formula (6).
- the aryl sulfonate represented can be obtained and this salt can be obtained by an ion exchange treatment.
- Ar 1 and Ar 2 are the same as above.
- Ar 3 represents a group represented by the formula (3 ′) or (4 ′).
- M represents an alkali metal atom such as sodium or potassium.
- Examples of the amine compound represented by the formula (5) include disodium aniline-2,4-disulfonate, disodium aniline-2,5-disulfonate, disodium 8-amino-naphthalene-1,5-disulfonate, 2-amino-naphthalene-1,5-disulfonic acid disodium salt, 2-amino-naphthalene-3,6-disulfonic acid disodium salt, 7-aminonaphthalene-1,5-disulfonic acid disodium salt, 7-aminonaphthalene-2 , 4-disulfonic acid disodium, 7-aminonaphthalene-1,3-disulfonic acid disodium, and the like, but are not limited thereto.
- the amine compound represented by Formula (5) may use a hydrate.
- Examples of the acid halide represented by the formula (6) include 2-fluorobenzoyl chloride, 3-fluorobenzoyl chloride, 4-fluorobenzoyl chloride, 2-fluoro-4-methylbenzoyl chloride, 2-fluoro-5-methylbenzoyl.
- the reaction solvent is preferably an aprotic polar organic solvent, for example, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, tetrahydrofuran And dioxane.
- N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, dioxane and the like are preferable.
- the reaction temperature is usually from ⁇ 50 ° C. to the boiling point of the solvent used, but is preferably in the range of 0 to 140 ° C.
- the reaction time is usually 0.1 to 100 hours.
- the aryl sulfonate represented by the formula (1 ′) is recovered by filtration, evaporation of the reaction solvent, and the like, and then, for example, the sulfonate is protonated with a cation exchange resin to obtain the formula ( The aryl sulfonic acid compound represented by 1) can be produced.
- the acid halide represented by the formula (6) is an electrophilic halogenating agent such as thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, or phosphorus pentachloride. Can be obtained by reacting with.
- the charge transport varnish of the present invention contains the aryl sulfonic acid compound as a dopant, and further contains a charge transport material and an organic solvent.
- the charge transporting substance contained in the charge transporting varnish of the present invention is a substance having a charge transporting property, that is, conductivity, and may have a charge transporting property by itself. There may be something. In particular, a substance having a hole transporting property is preferable.
- charge transporting substance those conventionally used in the field of organic EL and the like can be used.
- Specific examples thereof include oligoamine derivatives, N, N′-diarylbenzidine derivatives, arylamine derivatives (aniline derivatives) such as N, N, N ′, N′-tetraarylbenzidine derivatives, oligothiophene derivatives, thienothiophene derivatives.
- various charge transporting compounds such as thiophene derivatives such as thienobenzothiophene derivatives and pyrrole derivatives such as oligopyrrole, among which arylamine derivatives and thiophene derivatives are preferable.
- the molecular weight of the charge transporting compound is usually about 200 to 9,000 from the viewpoint of preparing a uniform varnish that gives a thin film with high flatness, but from the viewpoint of obtaining a thin film with more excellent charge transporting properties. 300 or more, preferably 400 or more, and preferably 8,000 or less, more preferably 7,000 or less, and 6,000 from the viewpoint of preparing a uniform varnish that gives a highly flat thin film with good reproducibility. The following is more preferable, and 5,000 or less is still more preferable.
- the charge transporting compound preferably has no molecular weight distribution (dispersity is 1) (that is, preferably has a single molecular weight). ).
- the charge transporting substance include an oligoaniline derivative described in JP-A No. 2002-151272, an oligoaniline compound described in WO 2004/105446, and 1,4-described in WO 2005/043962.
- Examples include compounds having a dithiine ring, oligoaniline compounds described in WO2008 / 032617, oligoaniline compounds described in WO2008 / 032616, aryldiamine compounds described in WO2013 / 042623, and the like. It is not limited to these.
- DPA represents a diphenylamino group.
- Ph represents a phenyl group
- TPA represents a p- (diphenylamino) phenyl group.
- n-Hex represents an n-hexyl group
- TPA represents a p- (diphenylamino) phenyl group.
- the ratio of the charge transporting substance to the aryl sulfonic acid compound in the charge transporting varnish of the present invention is not particularly limited, but considering the point of improving the characteristics of the organic EL device comprising the resulting charge transporting thin film, the charge transporting property
- the aryl sulfonic acid compound is preferably 0.25 to 5 equivalents, more preferably 0.5 to 2 equivalents, relative to the substance.
- organic solvent used when preparing the charge transporting varnish a highly soluble solvent that can dissolve the charge transporting substance and the dopant satisfactorily can be used.
- Examples of such highly soluble solvents include organic solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, and diethylene glycol monomethyl ether. Can be used. These solvents can be used singly or in combination of two or more, and the amount used can be 5 to 100% by mass with respect to the total solvent used in the varnish.
- both the charge transporting substance and the dopant are completely dissolved.
- the varnish has a viscosity of 10 to 200 mPa ⁇ s, particularly 35 to 150 mPa ⁇ s at 25 ° C., and a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure (atmospheric pressure).
- a viscosity 10 to 200 mPa ⁇ s, particularly 35 to 150 mPa ⁇ s at 25 ° C., and a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure (atmospheric pressure).
- the high-viscosity organic solvent is not particularly limited.
- cyclohexanol ethylene glycol, ethylene glycol diglycidyl ether, 1,3-octylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, propylene glycol, hexylene glycol and the like.
- These solvents can be used alone or in combination of two or more.
- the addition ratio of the high-viscosity organic solvent to the entire solvent used in the varnish of the present invention is preferably in the range where no solid precipitates, and the addition ratio is preferably 5 to 80% by mass as long as no solid precipitates.
- solvents are used in an amount of 1 to 90% by mass, preferably based on the total solvent used in the varnish. It is also possible to mix at a ratio of 1 to 50% by mass.
- solvents examples include ethylene glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether, diethylene glycol Examples include, but are not limited to, acetone alcohol, ⁇ -butyrolactone, ethyl lactate, n-hexyl acetate, propylene glycol monomethyl ether, and the like. These solvents can be used alone or in combination of two or more.
- the viscosity of the varnish of the present invention is appropriately set according to the thickness of the thin film to be produced and the solid content concentration, but is usually 1 to 50 mPa ⁇ s at 25 ° C. Further, the solid content concentration of the charge transporting varnish in the present invention is appropriately set in consideration of the viscosity and surface tension of the varnish, the thickness of the thin film to be produced, etc., but is usually from 0.1 to 10 In consideration of improving the coatability of the varnish, it is preferably about 0.5 to 5.0% by mass, and more preferably about 1.0 to 3.0% by mass.
- the charge transporting varnish is dissolved using a sub-micron order filter or the like after dissolving the charge transporting material, dopant and the like in an organic solvent. It is desirable.
- a charge transporting thin film can be formed on a base material by applying the charge transporting varnish of the present invention on the base material and baking it.
- Examples of the varnish coating method include, but are not limited to, a dip method, a spin coating method, a transfer printing method, a roll coating method, a brush coating method, an ink jet method, and a spray method. It is preferable to adjust the viscosity and surface tension of the varnish depending on the coating method.
- the type of the charge transporting substance or solvent contained in the varnish together with the aryl sulfonic acid of the present invention is selected.
- a firing atmosphere in an air atmosphere, under an inert gas such as nitrogen, in a vacuum, etc.
- firing in an air atmosphere makes it uniform and charge transportable. An excellent thin film can be obtained.
- the firing temperature is appropriately set within a range of about 100 to 260 ° C. in consideration of the use of the obtained thin film, the degree of charge transportability imparted to the obtained thin film, and the like.
- the temperature is preferably about 140 to 250 ° C, more preferably about 145 to 240 ° C.
- two or more steps of temperature change may be applied for the purpose of developing a higher uniform film forming property or causing the reaction to proceed on the substrate.
- the heating may be performed using an appropriate device such as a hot plate or an oven.
- the thickness of the charge transporting thin film is not particularly limited, but is preferably 5 to 200 nm when used as a hole injection layer in an organic EL device.
- a method of changing the film thickness there are methods such as changing the solid content concentration in the varnish and changing the amount of the solution on the substrate during coating.
- Organic EL device has a pair of electrodes, and has the above-described charge transporting thin film of the present invention between these electrodes.
- Typical examples of the organic EL element include (a) to (f) below, but are not limited thereto.
- an electron blocking layer or the like can be provided between the light emitting layer and the anode
- a hole (hole) blocking layer or the like can be provided between the light emitting layer and the cathode.
- the hole injection layer, the hole transport layer, or the hole injection transport layer may have a function as an electron block layer or the like
- the electron injection layer, the electron transport layer, or the electron injection transport layer is a hole. It may have a function as a block layer or the like.
- A Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
- b Anode / hole injection layer / hole transport layer / light emission layer / electron injection transport layer / Cathode
- c anode / hole injection transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
- d anode / hole injection transport layer / light emitting layer / electron injection transport layer / cathode
- e anode / positive Hole injection layer / hole transport layer / light emitting layer / cathode
- f anode / hole injection transport layer / light emitting layer / cathode
- “Hole injection layer”, “hole transport layer” and “hole injection transport layer” are layers formed between a light emitting layer and an anode, and transport holes from the anode to the light emitting layer.
- a hole injection transport layer In the case where only one layer of a hole transporting material is provided between the light emitting layer and the anode, it is a “hole injection transport layer”, and between the light emitting layer and the anode,
- the layer close to the anode is a “hole injection layer”, and the other layers are “hole transport layers”.
- the hole injection (transport) layer a thin film that is excellent not only in accepting holes from the anode but also injecting holes into the hole transport (light emitting) layer is used.
- Electrode injection layer “Electron injection layer”, “electron transport layer” and “electron injection transport layer” are layers formed between a light emitting layer and a cathode, and have a function of transporting electrons from the cathode to the light emitting layer.
- the layer of the electron transporting material is disposed between the light emitting layer and the cathode.
- the layer close to the cathode is an “electron injection layer” and the other layers are “electron transport layers”.
- the “light emitting layer” is an organic layer having a light emitting function, and includes a host material and a dopant material when a doping system is employed.
- the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
- the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
- the charge transporting thin film of the present invention can be suitably used as a hole injection layer, a hole transport layer, and a hole injection transport layer in an organic EL device, and can be more suitably used as a hole injection layer.
- Examples of materials used and methods for producing organic EL elements using the charge transporting varnish of the present invention include the following, but are not limited thereto.
- the electrode substrate to be used is preferably cleaned in advance by liquid cleaning with a detergent, alcohol, pure water or the like.
- the anode substrate is subjected to surface treatment such as UV ozone treatment or oxygen-plasma treatment immediately before use. It is preferable.
- the surface treatment may not be performed.
- An example of a method for producing an organic EL element having a hole injection layer made of a thin film obtained from the charge transporting varnish of the present invention is as follows.
- the charge transporting varnish of the present invention is applied to the anode substrate and baked to form a hole injection layer on the electrode.
- a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are provided in this order.
- the hole transport layer, the light-emitting layer, the electron transport layer, and the electron injection layer may be formed by either a vapor deposition method or a coating method (wet process) depending on the characteristics of the material used.
- anode material examples include transparent electrodes typified by indium tin oxide (ITO) and indium zinc oxide (IZO), metal anodes typified by aluminum, alloys thereof, and the like. What performed the chemical conversion process is preferable. Polythiophene derivatives and polyaniline derivatives having high charge transporting properties can also be used.
- metals constituting the metal anode include scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, gallium, yttrium, zirconium, niobium, molybdenum, ruthenium, rhodium, palladium, cadmium.
- Materials for forming the hole transport layer include (triphenylamine) dimer derivatives, [(triphenylamine) dimer] spirodimers, N, N′-bis (naphthalen-1-yl) -N, N′-bis (Phenyl) -benzidine ( ⁇ -NPD), N, N′-bis (naphthalen-2-yl) -N, N′-bis (phenyl) -benzidine, N, N′-bis (3-methylphenyl)- N, N′-bis (phenyl) -benzidine, N, N′-bis (3-methylphenyl) -N, N′-bis (phenyl) -9,9-spirobifluorene, N, N′-bis ( Naphthalen-1-yl) -N, N′-bis (phenyl) -9,9-spirobifluorene, N, N′-bis (3-methylphenyl) -N, N′-bis (phenyl) -9,9-s
- Materials for forming the light emitting layer include tris (8-quinolinolato) aluminum (III) (Alq 3 ), bis (8-quinolinolato) zinc (II) (Znq 2 ), bis (2-methyl-8-quinolinolato)- 4- (p-phenylphenolate) aluminum (III) (BAlq), 4,4′-bis (2,2-diphenylvinyl) biphenyl, 9,10-di (naphthalen-2-yl) anthracene, 2-t -Butyl-9,10-di (naphthalen-2-yl) anthracene, 2,7-bis [9,9-di (4-methylphenyl) -fluoren-2-yl] -9,9-di (4- Methylphenyl) fluorene, 2-methyl-9,10-bis (naphthalen-2-yl) anthracene, 2- (9,9-spirobifluoren-2-yl) -9,9-spir
- Materials for forming the electron injection layer include lithium oxide (Li 2 O), magnesium oxide (MgO), alumina (Al 2 O 3 ), lithium fluoride (LiF), sodium fluoride (NaF), magnesium fluoride ( MgF 2 ), cesium fluoride (CsF), strontium fluoride (SrF 2 ), molybdenum trioxide (MoO 3 ), aluminum, Li (acac), lithium acetate, lithium benzoate and the like.
- cathode material examples include aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium and the like.
- a hole transport layer (hereinafter referred to as a hole transporting polymer layer), a light emitting layer (hereinafter referred to as a “light emitting layer”).
- the organic EL device having a charge transporting thin film formed by the charge transporting varnish of the present invention can be produced by sequentially forming the light emitting polymer layer. Specifically, the charge transporting varnish of the present invention is applied on the anode substrate to prepare a hole injection layer by the above method, and a hole transporting polymer layer and a light emitting polymer layer are sequentially formed thereon. Then, a cathode electrode is vapor-deposited to obtain an organic EL element.
- the same materials as described above can be used, and the same cleaning treatment and surface treatment can be performed.
- the hole transporting polymer layer and the light emitting polymer layer can be formed by adding a solvent to a hole transporting polymer material or a light emitting polymer material, or a material obtained by adding a dopant substance to the hole transporting polymer material. And a method in which the film is formed by uniformly dispersing, coating the film on a hole injection layer or a hole transporting polymer layer, and firing each of them.
- Examples of the light-emitting polymer material include polyfluorene derivatives such as poly (9,9-dialkylfluorene) (PDAF), poly (2-methoxy-5- (2′-ethylhexoxy) -1,4-phenylenevinylene) (MEH). -PPV) and the like, polythiophene derivatives such as poly (3-alkylthiophene) (PAT), polyvinylcarbazole (PVCz) and the like.
- PDAF poly (9,9-dialkylfluorene)
- MEH 2-methoxy-5- (2′-ethylhexoxy) -1,4-phenylenevinylene
- PVT polythiophene derivatives
- PVCz polyvinylcarbazole
- Examples of the solvent include toluene, xylene, chloroform and the like.
- Examples of the dissolution or uniform dispersion method include methods such as stirring, heating and stirring, and ultrasonic dispersion.
- the coating method is not particularly limited, and examples include an inkjet method, a spray method, a dip method, a spin coating method, a transfer printing method, a roll coating method, and a brush coating.
- the application is preferably performed under an inert gas such as nitrogen or argon.
- the firing method a method of heating with an oven or a hot plate under an inert gas or in a vacuum can be mentioned.
- An example of a method for producing an EL element having a hole transport layer composed of a thin film obtained from the charge transport varnish of the present invention is as follows.
- a hole injection layer is formed on the anode substrate.
- the charge transporting varnish of the present invention is applied and baked by the above-described method to produce a hole transporting layer.
- a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are provided in this order. Examples of the formation method and specific examples of the light emitting layer, the electron transport layer, and the electron injection layer are the same as described above.
- the hole injection layer may be formed by either a vapor deposition method or a coating method (wet process) depending on the characteristics of the material used.
- a material for forming the hole injection layer copper phthalocyanine, titanium oxide phthalocyanine, platinum phthalocyanine, pyrazino [2,3-f] [1,10] phenanthroline-2,3-dicarbonitrile, N, N, N ′ , N′-Tetrakis (4-methoxyphenyl) benzidine, 2,7-bis [N, N-bis (4-methoxy-phenyl) amino] -9,9-spirobifluorene, 2,2′-bis [N , N-bis (4-methoxy-phenyl) amino] -9,9-spirobifluorene, N, N′-diphenyl-N, N′-di [4- (N, N-ditolylamino) phenyl] benzidine, N , N′-diphenyl-N, N′-di [4- (N, N-diphenylamino) phenyl] benzidine, N 4 , N
- Examples of the anode material, the light emitting layer, the light emitting dopant, the material for forming the electron transport layer and the electron block layer, and the cathode material include the same materials as described above.
- An example of a method for producing an organic EL device having a hole injecting and transporting layer made of a thin film obtained from the charge transporting varnish of the present invention is as follows.
- a hole injection transport layer is formed on the anode substrate, and a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are provided in this order on the hole injection transport layer. Examples of the formation method and specific examples of the light emitting layer, the electron transport layer, and the electron injection layer are the same as described above.
- Examples of the anode material, the light emitting layer, the light emitting dopant, the material for forming the electron transport layer and the electron block layer, and the cathode material include the same materials as described above.
- a hole block layer, an electron block layer, or the like may be provided between the electrode and any of the above layers as necessary.
- a hole block layer, an electron block layer, or the like may be provided between the electrode and any of the above layers as necessary.
- tris (phenylpyrazole) iridium etc. are mentioned as a material which forms an electronic block layer.
- the materials constituting the anode and the cathode and the layer formed between them differ depending on whether a device having a bottom mission structure or a top emission structure is manufactured, the material is appropriately selected in consideration of this point.
- a transparent anode is used on the substrate side, and light is extracted from the substrate side
- a reflective anode made of metal is used in the opposite direction to the substrate. Because light is extracted from a certain transparent electrode (cathode) side, for example, regarding the anode material, a transparent anode such as ITO is used when manufacturing a device with a bottom emission structure, and Al is used when manufacturing a device with a top emission structure. A reflective anode such as / Nd is used.
- the organic EL device of the present invention may be sealed together with a water catching agent or the like according to a standard method in order to prevent deterioration of characteristics.
- the solvent was distilled off from the cooled reaction mixture under reduced pressure, the resulting residue was mixed with 20 mL of methanol, and the mixture was filtered. And 300 mL of isopropanol was kept stirring, the filtrate obtained was dripped there slowly, and then it was further stirred for 30 minutes. After completion of the stirring, the obtained suspension was filtered, the solvent was removed from the filtrate under reduced pressure, and the resulting residue was dissolved in 20 mL of water. And the column chromatography by cation exchange resin Dowex 650C (H type about 200 mL, distillate solvent: water) using the obtained solution was performed.
- Example 5 A charge transporting varnish 2 was obtained in the same manner as in Example 4 except that 0.168 g of arylsulfonic acid 3 was used instead of arylsulfonic acid 1.
- Examples 6 and 7 The varnishes obtained in Examples 4 and 5 were each applied to an ITO substrate using a spin coater, then dried at 50 ° C. for 5 minutes, and further baked at 230 ° C. for 15 minutes in an air atmosphere. A uniform thin film of 30 nm was formed.
- ITO indium tin oxide
- N, N′-bis (naphthalen-1-yl) -N, N′-bis (phenyl) is applied to the ITO substrate on which the thin film has been formed using a vapor deposition apparatus (vacuum degree 1.0 ⁇ 10 ⁇ 5 Pa).
- a vapor deposition apparatus vacuum degree 1.0 ⁇ 10 ⁇ 5 Pa.
- -Benzidine ( ⁇ -NPD) tris (8-quinolinolato) aluminum (III) (Alq 3 ), lithium fluoride, and an aluminum thin film were sequentially laminated to obtain an organic EL device.
- the deposition rate is 0.2 nm / second for ⁇ -NPD, Alq 3 and aluminum, 0.02 nm / second for lithium fluoride, and the film thickness is 30 nm, 40 nm, 0.5 nm and 120 nm, respectively.
- the characteristic was evaluated. Sealing was performed according to the following procedure.
- the organic EL element was placed between the sealing substrates, and the sealing substrate was bonded with an adhesive (XNR5516Z-B1 manufactured by Nagase ChemteX Corporation). .
- an adhesive XNR5516Z-B1 manufactured by Nagase ChemteX Corporation.
- a water catching agent (HD-071010W-40 manufactured by Dynic Co., Ltd.) was placed in the sealing substrate together with the organic EL element.
- the bonded sealing substrate was irradiated with UV light (wavelength 365 nm, irradiation amount 6,000 mJ / cm 2 ), and then annealed at 80 ° C. for 1 hour to cure the adhesive.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
1.式(1)で表されることを特徴とするアリールスルホン酸化合物。
Ar2は、式(3)又は(4)
2.前記Ar2が、式(3-1)~(3-2)及び式(4-1)~(4-6)のいずれかで表される基である1のアリールスルホン酸化合物。
4.1~3のいずれかのアリールスルホン酸化合物からなるドーパント。
5.4のドーパント、電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニス。
6.5の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
7.6の電荷輸送性薄膜を有する有機エレクトロルミネッセンス素子。
8.4のドーパントを用いることを特徴とする電荷輸送性薄膜の製造方法。
9.5の電荷輸送性ワニスを用いることを特徴とする電荷輸送性薄膜の製造方法。
10.式(1')で表されることを特徴とするアリールスルホン酸塩。
Ar3は、式(3')又は(4')で表される基を表す。
11.式(5)で表されるアミンと、式(6)で表される酸ハライド化合物とを反応させることを特徴とする10のアリールスルホン酸塩の製造方法。
12.式(1')で表されるアリールスルホン酸塩をイオン交換処理することを特徴とする1のアリールスルホン酸化合物の製造方法。
また、本発明のアリールスルホン酸化合物の製造方法によれば、安価に効率よくアリールスルホン酸化合物を製造できる。
本発明の式(1)で表されるアリールスルホン酸化合物は、式(5)で表されるアミン化合物と式(6)で表される酸ハロゲン化物とを反応させて式(1')で表されるアリールスルホン酸塩を得、この塩をイオン交換処理することで得ることができる。
本発明の電荷輸送性ワニスは、ドーパントとして上記アリールスルホン酸化合物を含み、更に電荷輸送性物質及び有機溶媒を含む。
また、本発明における電荷輸送性ワニスの固形分濃度は、ワニスの粘度及び表面張力等や、作製する薄膜の厚み等を勘案して適宜設定されるものではあるが、通常、0.1~10.0質量%程度であり、ワニスの塗布性を向上させることを考慮すると、好ましくは0.5~5.0質量%程度、より好ましくは1.0~3.0質量%程度である。
本発明の電荷輸送性ワニスを基材上に塗布して焼成することで、基材上に電荷輸送性薄膜を形成させることができる。
本発明の有機EL素子は、一対の電極を有し、これら電極の間に、上述の本発明の電荷輸送性薄膜を有するものである。
(a)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(b)陽極/正孔注入層/正孔輸送層/発光層/電子注入輸送層/陰極
(c)陽極/正孔注入輸送層/発光層/電子輸送層/電子注入層/陰極
(d)陽極/正孔注入輸送層/発光層/電子注入輸送層/陰極
(e)陽極/正孔注入層/正孔輸送層/発光層/陰極
(f)陽極/正孔注入輸送層/発光層/陰極
次いで、放冷した反応混合物から減圧下で溶媒を留去し、得られた残渣とメタノール20mLとを混合し、その混合物をろ過した。そして、イソプロパノール及びn-ヘキサンの混合溶媒400mL(イソプロパノール/n-ヘキサン=3/1(v/v))を攪拌した状態に保ち、そこへ得られたろ液をゆっくりと滴下し、その後更に30分間攪拌した。
攪拌終了後、得られた懸濁液をろ過し、ろ物から減圧下で溶媒を除去し、得られた残渣を水とメタノールの混合溶媒50mL(水/メタノール=1/1(v/v)に溶解させた。そして、得られた溶液を用いた陽イオン交換樹脂ダウエックス650C(Hタイプ約200mL、留出溶媒:水/メタノール=1/1(v/v))によるカラムクロマトグラフィーを行った。
最後に、減圧下で溶媒を留去し、得られた固体を減圧下でよく乾燥し、目的とするアリールスルホン酸化合物1を得た(収量12.5g)。1H-NMRの測定結果を以下に示す。
1H-NMR (400MHz, DMSO-d6) δ[ppm]: 8.77(d, J=9.2Hz, 1H), 8.39(d, J=2.4Hz, 1H), 8.15(d, J=1.6Hz, 1H), 8.10-8.13(m, 1H), 7.99-8.00(s, 1H), 7.93-7.97(m, 1H), 7.85(dd, J=9.2, 2.4Hz, 1H), 7.62-7.69(m, 1H)
次いで、放冷した反応混合物から減圧下で溶媒を留去し、得られた残渣とメタノール20mLとを混合し、その混合物をろ過した。そして、イソプロパノール300mLを攪拌した状態に保ち、そこへ得られたろ液をゆっくりと滴下し、その後更に30分間攪拌した。
攪拌終了後、得られた懸濁液をろ過し、ろ物から減圧下で溶媒を除去し、得られた残渣を水及びメタノールの混合溶媒50mL(水/メタノール=1/1(v/v))に溶解させた。そして、得られた溶液を用いた陽イオン交換樹脂ダウエックス650C(Hタイプ約200mL、留出溶媒:水/メタノール=1/1(v/v))によるカラムクロマトグラフィーを行った。
最後に、減圧下で溶媒を留去し、得られた固体を減圧下でよく乾燥し、目的とするアリールスルホン酸化合物2を得た(収量6.2g)。1H-NMRの測定結果を以下に示す。
1H-NMR (400MHz, DMSO-d6) δ[ppm]: 10.60(s, 1H), 8.77(d, J=9.2Hz, 1H), 8.40(d, J=2.0Hz, 1H), 8.15(s, 1H), 7.99(s, 1H), 7.84(dd, J=9.2, 2.4Hz, 1H), 7.78-7.75(m, 2H), 7.58-7.53(m, 1H)
次いで、放冷した反応混合物から減圧下で溶媒を留去し、得られた残渣とメタノール20mLとを混合し、その混合物をろ過した。そして、イソプロパノール300mLを攪拌した状態に保ち、そこへ得られたろ液をゆっくりと滴下し、その後更に30分間攪拌した。
攪拌終了後、得られた懸濁液をろ過し、ろ物から減圧下で溶媒を除去し、得られた残渣を水20mLに溶解させた。そして、得られた溶液を用いた陽イオン交換樹脂ダウエックス650C(Hタイプ約200mL、留出溶媒:水)によるカラムクロマトグラフィーを行った。
最後に、減圧下で溶媒を留去し、得られた固体を減圧下でよく乾燥し、目的とするアリールスルホン酸化合物3を得た(収量10g)。1H-NMRの測定結果を以下に示す。
1H-NMR (400MHz, DMSO-d6) δ[ppm]: 10.8(s, 1H), 8.78(d, J=9.2Hz, 1H), 8.34(d, J=2.0Hz, 1H), 8.15(d, J=1.6Hz, 1H), 7.98-7.99(m, 1H), 7.87-7.89(m, 1H), 7.73(dd, J=9.2, 2.4Hz, 1H)
[実施例4]
ブレティン・オブ・ケミカル・ソサエティ・オブ・ジャパン(Bulletin of Chemical Society of Japan)、1994年、第67巻、p.1749-1752に記載されている方法に従って合成した下記式で表されるアニリン誘導体0.077gと、アリールスルホン酸1 0.163gとを1,3-ジメチル-2-イミダゾリジノン4gに溶解させ、そこへシクロヘキサノール6gとプロピレングリコール2gを加えて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いて濾過し、電荷輸送性ワニス1を得た。
アリールスルホン酸1の代わりに、アリールスルホン酸3を0.168g用いた以外は、実施例4と同じ方法で電荷輸送性ワニス2を得た。
[実施例6、7]
実施例4、5で得られたワニスを、それぞれスピンコーターを用いてITO基板に塗布した後、50℃で5分間乾燥し、更に、大気雰囲気下、230℃で15分間焼成し、ITO基板上に30nmの均一な薄膜を形成した。ITO基板として、インジウム錫酸化物(ITO)が表面上に膜厚150nmでパターニングされた25mm×25mm×0.7tのガラス基板を用い、使用前にO2プラズマ洗浄装置(150W、30秒間)によって表面上の不純物を除却した。
次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いてN,N'-ビス(ナフタレン-1-イル)-N,N'-ビス(フェニル)-ベンジジン(α-NPD)、トリス(8-キノリノラート)アルミニウム(III)(Alq3)、フッ化リチウム、及びアルミニウムの薄膜を順次積層し、有機EL素子を得た。この際、蒸着レートは、α-NPD、Alq3及びアルミニウムについては0.2nm/秒、フッ化リチウムについては0.02nm/秒とし、膜厚は、それぞれ30nm、40nm、0.5nm及び120nmとした。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、有機EL素子は封止基板により封止した後、その特性を評価した。封止は、以下の手順で行った。
酸素濃度2ppm以下、露点-85℃以下の窒素雰囲気中で、有機EL素子を封止基板の間に収め、封止基板を接着材(ナガセケムテックス(株)製XNR5516Z-B1)により貼り合わせた。この際、捕水剤(ダイニック(株)製HD-071010W-40)を有機EL素子と共に封止基板内に収めた。
貼り合わせた封止基板に対し、UV光を照射(波長365nm、照射量6,000mJ/cm2)した後、80℃で1時間、アニーリング処理して接着材を硬化させた。
Claims (12)
- 前記R1~R5のうちの少なくとも1つはフッ素原子であり、少なくとも他の1つはハロゲン原子、ニトロ基、シアノ基又はトリフルオロメチル基であることを特徴とする請求項1又は2記載のアリールスルホン酸化合物。
- 請求項1~3のいずれか1項記載のアリールスルホン酸化合物からなるドーパント。
- 請求項4記載のドーパント、電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニス。
- 請求項5記載の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
- 請求項6記載の電荷輸送性薄膜を有する有機エレクトロルミネッセンス素子。
- 請求項4記載のドーパントを用いることを特徴とする電荷輸送性薄膜の製造方法。
- 請求項5記載の電荷輸送性ワニスを用いることを特徴とする電荷輸送性薄膜の製造方法。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015541613A JP6368943B2 (ja) | 2013-10-09 | 2014-10-08 | アリールスルホン酸化合物及びその利用並びにアリールスルホン酸化合物の製造方法 |
KR1020167011796A KR102257239B1 (ko) | 2013-10-09 | 2014-10-08 | 아릴설폰산 화합물 및 그 이용 그리고 아릴설폰산 화합물의 제조 방법 |
US15/028,239 US10177315B2 (en) | 2013-10-09 | 2014-10-08 | Arylsulfonic acid compound, use thereof, and method for producing arylsulfonic acid compound |
EP14853056.1A EP3056484A4 (en) | 2013-10-09 | 2014-10-08 | Arylsulfonic acid compound, use thereof, and method for producing arylsulfonic acid compound |
CN201480055509.4A CN105612146B (zh) | 2013-10-09 | 2014-10-08 | 芳基磺酸化合物及其利用以及芳基磺酸化合物的制备方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013-211829 | 2013-10-09 | ||
JP2013211829 | 2013-10-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015053320A1 true WO2015053320A1 (ja) | 2015-04-16 |
Family
ID=52813135
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2014/076959 WO2015053320A1 (ja) | 2013-10-09 | 2014-10-08 | アリールスルホン酸化合物及びその利用並びにアリールスルホン酸化合物の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10177315B2 (ja) |
EP (1) | EP3056484A4 (ja) |
JP (1) | JP6368943B2 (ja) |
KR (1) | KR102257239B1 (ja) |
CN (1) | CN105612146B (ja) |
TW (1) | TWI619696B (ja) |
WO (1) | WO2015053320A1 (ja) |
Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002151272A (ja) | 2000-11-09 | 2002-05-24 | Nissan Chem Ind Ltd | 電界発光素子 |
WO2004043117A1 (ja) | 2002-11-07 | 2004-05-21 | Nissan Chemical Industries,Ltd. | 電荷輸送性ワニス |
WO2004105446A1 (ja) | 2003-05-20 | 2004-12-02 | Nissan Chemical Industries, Ltd. | 電荷輸送性ワニス |
WO2005000832A1 (ja) | 2003-06-25 | 2005-01-06 | Nissan Chemical Industries, Ltd. | 1,4-ベンゾジオキサンスルホン酸化合物及び電子受容性物質としての利用 |
WO2005043962A1 (ja) | 2003-10-31 | 2005-05-12 | Nissan Chemical Industries, Ltd. | 1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 |
WO2005042621A1 (ja) | 2003-10-30 | 2005-05-12 | Nissan Chemical Industries, Ltd. | 電荷輸送性化合物、電荷輸送性材料、電荷輸送性ワニス、電荷輸送性薄膜及び有機エレクトロルミネッセンス素子 |
WO2005107335A1 (ja) | 2004-04-30 | 2005-11-10 | Nissan Chemical Industries, Ltd. | 良溶媒及び貧溶媒を含有するワニス |
WO2006006459A1 (ja) | 2004-07-09 | 2006-01-19 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物の精製方法およびオリゴアニリン化合物 |
WO2006025342A1 (ja) | 2004-08-31 | 2006-03-09 | Nissan Chemical Industries, Ltd. | アリールスルホン酸化合物及び電子受容性物質としての利用 |
WO2006137473A1 (ja) | 2005-06-24 | 2006-12-28 | Nissan Chemical Industries, Ltd. | 芳香族スルホン酸化合物の製造法 |
WO2007049631A1 (ja) | 2005-10-28 | 2007-05-03 | Nissan Chemical Industries, Ltd. | スプレー又はインクジェット塗布用電荷輸送性ワニス |
WO2007099808A1 (ja) | 2006-02-23 | 2007-09-07 | Nissan Chemical Industries, Ltd. | スルホン酸エステル化合物およびその利用 |
WO2008010474A1 (fr) | 2006-07-18 | 2008-01-24 | Nissan Chemical Industries, Ltd. | Vernis contenant des charges |
WO2008032616A1 (en) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Oligoaniline compounds |
WO2008032617A1 (fr) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Composé d'oligoaniline et son utilisation |
WO2008129947A1 (ja) | 2007-04-12 | 2008-10-30 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物 |
WO2009096352A1 (ja) | 2008-01-29 | 2009-08-06 | Nissan Chemical Industries, Ltd. | アリールスルホン酸化合物および電子受容性物質としての利用 |
WO2010041701A1 (ja) | 2008-10-09 | 2010-04-15 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2010058777A1 (ja) | 2008-11-19 | 2010-05-27 | 日産化学工業株式会社 | 電荷輸送性材料および電荷輸送性ワニス |
WO2010058776A1 (ja) | 2008-11-19 | 2010-05-27 | 日産化学工業株式会社 | 電荷輸送性材料および電荷輸送性ワニス |
WO2013042623A1 (ja) | 2011-09-21 | 2013-03-28 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2013129249A1 (ja) | 2012-03-02 | 2013-09-06 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014115865A1 (ja) | 2013-01-28 | 2014-07-31 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014132834A1 (ja) | 2013-02-26 | 2014-09-04 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014132917A1 (ja) | 2013-02-28 | 2014-09-04 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014141998A1 (ja) | 2013-03-11 | 2014-09-18 | 日産化学工業株式会社 | 電荷輸送性ワニス |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2844574A (en) * | 1953-06-03 | 1958-07-22 | Azo dyes and their method of | |
DE2400259A1 (de) * | 1973-01-08 | 1974-07-18 | Ciba Geigy Ag | Photographisches material und farbstoffe hierfuer |
JPS58176265A (ja) * | 1982-04-09 | 1983-10-15 | Canon Inc | 記録液 |
US4544620A (en) * | 1984-05-25 | 1985-10-01 | Minnesota Mining And Manufacturing Company | Tannable multi-colored material |
GB9225475D0 (en) | 1992-12-05 | 1993-01-27 | Imp Cancer Res Tech | Compounds to combat angiogenesis |
JP5110282B2 (ja) | 2005-06-03 | 2012-12-26 | 日産化学工業株式会社 | 電荷輸送性ポリマーを含有する電荷輸送性ワニス及びそれを用いた有機エレクトロルミネッセンス素子 |
-
2014
- 2014-10-08 EP EP14853056.1A patent/EP3056484A4/en not_active Withdrawn
- 2014-10-08 JP JP2015541613A patent/JP6368943B2/ja active Active
- 2014-10-08 CN CN201480055509.4A patent/CN105612146B/zh active Active
- 2014-10-08 WO PCT/JP2014/076959 patent/WO2015053320A1/ja active Application Filing
- 2014-10-08 KR KR1020167011796A patent/KR102257239B1/ko active IP Right Grant
- 2014-10-08 US US15/028,239 patent/US10177315B2/en not_active Expired - Fee Related
- 2014-10-09 TW TW103135201A patent/TWI619696B/zh active
Patent Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002151272A (ja) | 2000-11-09 | 2002-05-24 | Nissan Chem Ind Ltd | 電界発光素子 |
WO2004043117A1 (ja) | 2002-11-07 | 2004-05-21 | Nissan Chemical Industries,Ltd. | 電荷輸送性ワニス |
WO2004105446A1 (ja) | 2003-05-20 | 2004-12-02 | Nissan Chemical Industries, Ltd. | 電荷輸送性ワニス |
WO2005000832A1 (ja) | 2003-06-25 | 2005-01-06 | Nissan Chemical Industries, Ltd. | 1,4-ベンゾジオキサンスルホン酸化合物及び電子受容性物質としての利用 |
WO2005042621A1 (ja) | 2003-10-30 | 2005-05-12 | Nissan Chemical Industries, Ltd. | 電荷輸送性化合物、電荷輸送性材料、電荷輸送性ワニス、電荷輸送性薄膜及び有機エレクトロルミネッセンス素子 |
WO2005043962A1 (ja) | 2003-10-31 | 2005-05-12 | Nissan Chemical Industries, Ltd. | 1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 |
WO2005107335A1 (ja) | 2004-04-30 | 2005-11-10 | Nissan Chemical Industries, Ltd. | 良溶媒及び貧溶媒を含有するワニス |
WO2006006459A1 (ja) | 2004-07-09 | 2006-01-19 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物の精製方法およびオリゴアニリン化合物 |
WO2006025342A1 (ja) | 2004-08-31 | 2006-03-09 | Nissan Chemical Industries, Ltd. | アリールスルホン酸化合物及び電子受容性物質としての利用 |
WO2006137473A1 (ja) | 2005-06-24 | 2006-12-28 | Nissan Chemical Industries, Ltd. | 芳香族スルホン酸化合物の製造法 |
WO2007049631A1 (ja) | 2005-10-28 | 2007-05-03 | Nissan Chemical Industries, Ltd. | スプレー又はインクジェット塗布用電荷輸送性ワニス |
WO2007099808A1 (ja) | 2006-02-23 | 2007-09-07 | Nissan Chemical Industries, Ltd. | スルホン酸エステル化合物およびその利用 |
WO2008010474A1 (fr) | 2006-07-18 | 2008-01-24 | Nissan Chemical Industries, Ltd. | Vernis contenant des charges |
WO2008032616A1 (en) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Oligoaniline compounds |
WO2008032617A1 (fr) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Composé d'oligoaniline et son utilisation |
WO2008129947A1 (ja) | 2007-04-12 | 2008-10-30 | Nissan Chemical Industries, Ltd. | オリゴアニリン化合物 |
WO2009096352A1 (ja) | 2008-01-29 | 2009-08-06 | Nissan Chemical Industries, Ltd. | アリールスルホン酸化合物および電子受容性物質としての利用 |
WO2010041701A1 (ja) | 2008-10-09 | 2010-04-15 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2010058777A1 (ja) | 2008-11-19 | 2010-05-27 | 日産化学工業株式会社 | 電荷輸送性材料および電荷輸送性ワニス |
WO2010058776A1 (ja) | 2008-11-19 | 2010-05-27 | 日産化学工業株式会社 | 電荷輸送性材料および電荷輸送性ワニス |
WO2013042623A1 (ja) | 2011-09-21 | 2013-03-28 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2013129249A1 (ja) | 2012-03-02 | 2013-09-06 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014115865A1 (ja) | 2013-01-28 | 2014-07-31 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014132834A1 (ja) | 2013-02-26 | 2014-09-04 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014132917A1 (ja) | 2013-02-28 | 2014-09-04 | 日産化学工業株式会社 | 電荷輸送性ワニス |
WO2014141998A1 (ja) | 2013-03-11 | 2014-09-18 | 日産化学工業株式会社 | 電荷輸送性ワニス |
Non-Patent Citations (2)
Title |
---|
BULLETIN OF CHEMICAL SOCIETY OF JAPAN, vol. 67, 1994, pages 1749 - 1752 |
See also references of EP3056484A4 |
Also Published As
Publication number | Publication date |
---|---|
EP3056484A1 (en) | 2016-08-17 |
US10177315B2 (en) | 2019-01-08 |
CN105612146B (zh) | 2017-10-27 |
TW201527265A (zh) | 2015-07-16 |
US20160248018A1 (en) | 2016-08-25 |
CN105612146A (zh) | 2016-05-25 |
KR20160067924A (ko) | 2016-06-14 |
KR102257239B1 (ko) | 2021-05-27 |
EP3056484A4 (en) | 2017-07-05 |
TWI619696B (zh) | 2018-04-01 |
JPWO2015053320A1 (ja) | 2017-03-09 |
JP6368943B2 (ja) | 2018-08-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6443588B2 (ja) | スルホン酸エステル化合物及びその利用 | |
JP6414213B2 (ja) | 有機エレクトロルミネッセンス素子の正孔注入層形成用ワニス | |
WO2017217455A1 (ja) | スルホン酸エステル化合物及びその利用 | |
JP7310609B2 (ja) | 電荷輸送性ワニス | |
WO2015146965A1 (ja) | トリアリールアミン誘導体及びその利用 | |
JP2019206591A (ja) | アニリン誘導体およびその製造方法 | |
JP6424835B2 (ja) | アリールスルホン酸化合物及びその利用 | |
WO2016204079A1 (ja) | 電荷輸送性ワニス及び有機エレクトロルミネッセンス素子 | |
WO2019124412A1 (ja) | スルホン酸エステル化合物及びその利用 | |
KR20160132440A (ko) | 아닐린 유도체 및 그 이용 | |
JP6551693B2 (ja) | 電荷輸送性ワニス、電荷輸送性薄膜及びその製造方法、並びに有機エレクトロルミネッセンス素子及びその製造方法 | |
WO2015146912A1 (ja) | フルオレン誘導体及びその利用 | |
JP6551411B2 (ja) | 電荷輸送性材料 | |
JP6432593B2 (ja) | 電荷輸送性ワニス | |
JP6368943B2 (ja) | アリールスルホン酸化合物及びその利用並びにアリールスルホン酸化合物の製造方法 | |
JP7161507B2 (ja) | 電荷輸送性ワニス | |
WO2016039360A1 (ja) | 電荷輸送性ワニス | |
JP6521270B2 (ja) | 電荷輸送性膜の製造方法、電荷輸送性膜、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法 | |
WO2016052252A1 (ja) | 電荷輸送性ワニス |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14853056 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2015541613 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15028239 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REEP | Request for entry into the european phase |
Ref document number: 2014853056 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2014853056 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 20167011796 Country of ref document: KR Kind code of ref document: A |