JP5019837B2 - スピロフルオレン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 - Google Patents
スピロフルオレン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 Download PDFInfo
- Publication number
- JP5019837B2 JP5019837B2 JP2006265047A JP2006265047A JP5019837B2 JP 5019837 B2 JP5019837 B2 JP 5019837B2 JP 2006265047 A JP2006265047 A JP 2006265047A JP 2006265047 A JP2006265047 A JP 2006265047A JP 5019837 B2 JP5019837 B2 JP 5019837B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- light
- hydrogen
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims description 121
- 125000004432 carbon atom Chemical group C* 0.000 claims description 209
- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 229910052739 hydrogen Inorganic materials 0.000 claims description 137
- 239000001257 hydrogen Substances 0.000 claims description 136
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 150000002431 hydrogen Chemical class 0.000 claims description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
- 239000010410 layer Substances 0.000 description 300
- 239000010408 film Substances 0.000 description 98
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- 238000005481 NMR spectroscopy Methods 0.000 description 66
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 65
- 239000000758 substrate Substances 0.000 description 64
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 230000005525 hole transport Effects 0.000 description 53
- 238000002347 injection Methods 0.000 description 48
- 239000007924 injection Substances 0.000 description 48
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 45
- -1 fluoren-2-yl group Chemical group 0.000 description 43
- 150000002894 organic compounds Chemical class 0.000 description 43
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 40
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 40
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 40
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 40
- 239000010409 thin film Substances 0.000 description 40
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 230000009477 glass transition Effects 0.000 description 33
- 238000000034 method Methods 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- 239000007787 solid Substances 0.000 description 27
- 238000000862 absorption spectrum Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000004065 semiconductor Substances 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 22
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000002484 cyclic voltammetry Methods 0.000 description 19
- 230000006870 function Effects 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 19
- 125000001624 naphthyl group Chemical group 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 18
- 229910052782 aluminium Inorganic materials 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 0 Cc(cc1)cc2c1-c1ccc(*)cc1C21c2cc(N(c3ccccc3)c(cc3)ccc3N(c3ccccc3)c3ccccc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound Cc(cc1)cc2c1-c1ccc(*)cc1C21c2cc(N(c3ccccc3)c(cc3)ccc3N(c3ccccc3)c3ccccc3)ccc2-c(cc2)c1cc2N(c1ccccc1)c(cc1)ccc1N(c1ccccc1)c1ccccc1 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000011521 glass Substances 0.000 description 16
- 239000011229 interlayer Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 229910052697 platinum Inorganic materials 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 12
- 238000005259 measurement Methods 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 238000005192 partition Methods 0.000 description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 description 12
- 229910052710 silicon Inorganic materials 0.000 description 12
- 239000010703 silicon Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 239000000956 alloy Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- 230000002194 synthesizing effect Effects 0.000 description 11
- ONCCVJKFWKAZAE-UHFFFAOYSA-N 2-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(Br)C=C12 ONCCVJKFWKAZAE-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 229910045601 alloy Inorganic materials 0.000 description 10
- 229910052814 silicon oxide Inorganic materials 0.000 description 10
- 238000012546 transfer Methods 0.000 description 10
- 229910052581 Si3N4 Inorganic materials 0.000 description 9
- 238000000295 emission spectrum Methods 0.000 description 9
- 238000005530 etching Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 9
- 238000004544 sputter deposition Methods 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 8
- 239000003990 capacitor Substances 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 230000001681 protective effect Effects 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 7
- LDFCHUHQZQRSHF-UHFFFAOYSA-N 9-(4-bromophenyl)-10-phenylanthracene Chemical compound C1=CC(Br)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 LDFCHUHQZQRSHF-UHFFFAOYSA-N 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910044991 metal oxide Inorganic materials 0.000 description 7
- 150000004706 metal oxides Chemical class 0.000 description 7
- 229910052750 molybdenum Inorganic materials 0.000 description 7
- 239000011733 molybdenum Substances 0.000 description 7
- UPJLZKCEPFAKSH-UHFFFAOYSA-N 2',7'-dibromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC(Br)=CC=C1C1=CC=C(Br)C=C12 UPJLZKCEPFAKSH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 239000004677 Nylon Substances 0.000 description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 229910021417 amorphous silicon Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 230000001747 exhibiting effect Effects 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229920001778 nylon Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- 239000003566 sealing material Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 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 5
- 230000000694 effects Effects 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 239000002346 layers by function Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 5
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 4
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 4
- LUBXLGUQZVKOFP-UHFFFAOYSA-N 9-phenylanthracene Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 LUBXLGUQZVKOFP-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- DZRDATNLTUIPAY-UHFFFAOYSA-N n,9-diphenylcarbazol-3-amine Chemical compound C=1C=C2N(C=3C=CC=CC=3)C3=CC=CC=C3C2=CC=1NC1=CC=CC=C1 DZRDATNLTUIPAY-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 238000001420 photoelectron spectroscopy Methods 0.000 description 4
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000003115 supporting electrolyte Substances 0.000 description 4
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- 239000010937 tungsten Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UVFHVMMGEWRPFP-UHFFFAOYSA-N 2,7-dibromo-9-(2-phenylphenyl)fluoren-9-ol Chemical compound C12=CC(Br)=CC=C2C2=CC=C(Br)C=C2C1(O)C1=CC=CC=C1C1=CC=CC=C1 UVFHVMMGEWRPFP-UHFFFAOYSA-N 0.000 description 3
- CWGRCRZFJOXQFV-UHFFFAOYSA-N 2,7-dibromofluoren-9-one Chemical compound C1=C(Br)C=C2C(=O)C3=CC(Br)=CC=C3C2=C1 CWGRCRZFJOXQFV-UHFFFAOYSA-N 0.000 description 3
- MPECBEYAWUTHRZ-UHFFFAOYSA-N 2-bromo-9-(2-phenylphenyl)fluoren-9-ol Chemical compound C12=CC=CC=C2C2=CC=C(Br)C=C2C1(O)C1=CC=CC=C1C1=CC=CC=C1 MPECBEYAWUTHRZ-UHFFFAOYSA-N 0.000 description 3
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 3
- WHGGVVHVBFMGSG-UHFFFAOYSA-N 9-bromo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 3
- QNZJXQPLZAOZLQ-UHFFFAOYSA-N 9-iodo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(I)=C2C=CC=CC2=C1C1=CC=CC=C1 QNZJXQPLZAOZLQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229910021419 crystalline silicon Inorganic materials 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 238000005499 laser crystallization Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 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 3
- 239000011701 zinc Substances 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 2
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 2
- NXVCHTPHKWNQBW-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-(9,9'-spirobi[fluorene]-2-yl)benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 NXVCHTPHKWNQBW-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(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)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- OCQFHFNWMCLWKC-UHFFFAOYSA-N 1-n,4-n,4-n-triphenylbenzene-1,4-diamine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 OCQFHFNWMCLWKC-UHFFFAOYSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC(=CC=2)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=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group 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 2
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 2
- LEVVHYCKPQWKOP-UHFFFAOYSA-N [Si].[Ge] Chemical compound [Si].[Ge] LEVVHYCKPQWKOP-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 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 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 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 2
- 230000006872 improvement Effects 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 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 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 description 2
- 238000001039 wet etching Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-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
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-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
- OBMPIWRNYHXYBC-UHFFFAOYSA-N 1-n,1-n,3-n,3-n,5-n,5-n-hexakis(3-methylphenyl)benzene-1,3,5-triamine Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C=C(C=C(C=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 OBMPIWRNYHXYBC-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
- OXMLYOWNIHJUJX-UHFFFAOYSA-N 1-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C=3C4=CC=CC=C4C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=C(C=34)C(C)(C)C)=CC=C21 OXMLYOWNIHJUJX-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-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
- UOCMXZLNHQBBOS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2o1.Oc1ccccc1-c1nc2ccccc2o1 UOCMXZLNHQBBOS-UHFFFAOYSA-N 0.000 description 1
- MTCARZDHUIEYMB-UHFFFAOYSA-N 2-bromofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C2=C1 MTCARZDHUIEYMB-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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-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
- PZLZJGZGJHZQAU-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(CC)=CC=C1N1C(C=2C=CC(=CC=2)C(C)(C)C)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 PZLZJGZGJHZQAU-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
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-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
- RTVGVLGMPQMGNB-UHFFFAOYSA-N 4-carbazol-9-yl-n-phenylaniline Chemical compound C=1C=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1NC1=CC=CC=C1 RTVGVLGMPQMGNB-UHFFFAOYSA-N 0.000 description 1
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UOOBIWAELCOCHK-BQYQJAHWSA-N 870075-87-9 Chemical compound O1C(C(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 UOOBIWAELCOCHK-BQYQJAHWSA-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
- SXGIRTCIFPJUEQ-UHFFFAOYSA-N 9-anthracen-9-ylanthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C(C=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C21 SXGIRTCIFPJUEQ-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910017073 AlLi Inorganic materials 0.000 description 1
- HOMUFCLOFCQYHS-UHFFFAOYSA-N Bc1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 Chemical compound Bc1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 HOMUFCLOFCQYHS-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OLWNZTWGGKZODP-UHFFFAOYSA-N C(C(C=C1)N(c(cc2)ccc2-[n]2c(cccc3)c3c3c2cccc3)c2cc3ccccc3cc2)C(C23c4ccccc4-c4ccccc24)=C1c1c3cccc1 Chemical compound C(C(C=C1)N(c(cc2)ccc2-[n]2c(cccc3)c3c3c2cccc3)c2cc3ccccc3cc2)C(C23c4ccccc4-c4ccccc24)=C1c1c3cccc1 OLWNZTWGGKZODP-UHFFFAOYSA-N 0.000 description 1
- BUSXWOQNZUTYLY-UHFFFAOYSA-N C(C1)C=C(C=CC=C2)C2=C1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2c1cccc2 Chemical compound C(C1)C=C(C=CC=C2)C2=C1N(c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2c1cccc2 BUSXWOQNZUTYLY-UHFFFAOYSA-N 0.000 description 1
- OISVIGAIEDIRNI-UHFFFAOYSA-N C(C12)=CC=CC1Nc1c2cccc1 Chemical compound C(C12)=CC=CC1Nc1c2cccc1 OISVIGAIEDIRNI-UHFFFAOYSA-N 0.000 description 1
- FGSIODVXEPJHKN-UHFFFAOYSA-N C(C1c2ccccc22)=CC(N(c3ccccc3)c(cc3)cc4c3[nH]c3ccccc43)=CC1C21c2ccccc2-c2c1cccc2 Chemical compound C(C1c2ccccc22)=CC(N(c3ccccc3)c(cc3)cc4c3[nH]c3ccccc43)=CC1C21c2ccccc2-c2c1cccc2 FGSIODVXEPJHKN-UHFFFAOYSA-N 0.000 description 1
- HNULEGKIKFHNES-UHFFFAOYSA-N C(C1c2ccccc22)=CC(N(c3ccccc3)c(cc3c4c5cccc4)ccc3[n]5-c3c(cccc4)c4ccc3)=CC1C21c2ccccc2-c2ccccc12 Chemical compound C(C1c2ccccc22)=CC(N(c3ccccc3)c(cc3c4c5cccc4)ccc3[n]5-c3c(cccc4)c4ccc3)=CC1C21c2ccccc2-c2ccccc12 HNULEGKIKFHNES-UHFFFAOYSA-N 0.000 description 1
- ARXBOQPHJYNTKD-UHFFFAOYSA-N C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1C1=CC=CC=C13 Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=C(C=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1C1=CC=CC=C13 ARXBOQPHJYNTKD-UHFFFAOYSA-N 0.000 description 1
- WQCSIEAAHBYSLW-UHFFFAOYSA-N C1C=CC(N(c2ccccc2)c(cc2)ccc2N(c(cc2)cc3c2-c2ccccc2C32c3ccccc3-c3c2cccc3)c2cc3ccccc3cc2)=CC1 Chemical compound C1C=CC(N(c2ccccc2)c(cc2)ccc2N(c(cc2)cc3c2-c2ccccc2C32c3ccccc3-c3c2cccc3)c2cc3ccccc3cc2)=CC1 WQCSIEAAHBYSLW-UHFFFAOYSA-N 0.000 description 1
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 1
- XJVMJQMZJBUXRT-UHFFFAOYSA-N CC(C1)C=CC(c2ccccc22)=C1C21c(cc(cc2)N(c(cc3)cc(c4ccccc44)c3[n]4-c3ccccc3)c3c(cccc4)c4ccc3)c2-c2ccccc12 Chemical compound CC(C1)C=CC(c2ccccc22)=C1C21c(cc(cc2)N(c(cc3)cc(c4ccccc44)c3[n]4-c3ccccc3)c3c(cccc4)c4ccc3)c2-c2ccccc12 XJVMJQMZJBUXRT-UHFFFAOYSA-N 0.000 description 1
- LWQMRYKPRWKTFR-UHFFFAOYSA-N CC1(C=CC=CC11)c2ccccc2C11c2ccccc2C2C=CC(N(C3=CC=CCC3)c(cc3)cc4c3[n](C)c3c4cccc3)=CC12 Chemical compound CC1(C=CC=CC11)c2ccccc2C11c2ccccc2C2C=CC(N(C3=CC=CCC3)c(cc3)cc4c3[n](C)c3c4cccc3)=CC12 LWQMRYKPRWKTFR-UHFFFAOYSA-N 0.000 description 1
- MKDUVNJKMWDPIG-UHFFFAOYSA-N CCCC(c(cc1)cc(c2c3CCC(C)=C2)c1[n]3-c(cc1)ccc1N(C1=CC=CCC1)c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12)S Chemical compound CCCC(c(cc1)cc(c2c3CCC(C)=C2)c1[n]3-c(cc1)ccc1N(C1=CC=CCC1)c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12)S MKDUVNJKMWDPIG-UHFFFAOYSA-N 0.000 description 1
- ZJMGIHJPJUKNGS-UHFFFAOYSA-N CCCCNc(cc1)cc(C2=CC(C(CCC)N)=CCC22)c1N2c(cc1)ccc1N(c1ccccc1)c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12 Chemical compound CCCCNc(cc1)cc(C2=CC(C(CCC)N)=CCC22)c1N2c(cc1)ccc1N(c1ccccc1)c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12 ZJMGIHJPJUKNGS-UHFFFAOYSA-N 0.000 description 1
- GCXHLKVHACPBOR-UHFFFAOYSA-N Cc1cc(cccc2)c2cc1-[n](c1ccccc1c1c2)c1ccc2N(c1ccccc1)C(C=CC1c2ccccc22)=CC1C21c2ccccc2-c2c1cccc2 Chemical compound Cc1cc(cccc2)c2cc1-[n](c1ccccc1c1c2)c1ccc2N(c1ccccc1)C(C=CC1c2ccccc22)=CC1C21c2ccccc2-c2c1cccc2 GCXHLKVHACPBOR-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910018594 Si-Cu Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910008465 Si—Cu Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 1
- XODPZXALWLGDCE-UHFFFAOYSA-N acetic acid;acetylene;ethene Chemical compound C=C.C#C.CC(O)=O XODPZXALWLGDCE-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
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IDRLMTGDSZBTPT-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12)c(cc1)cc2c1[n-]c1c2cccc1 Chemical compound c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12)c(cc1)cc2c1[n-]c1c2cccc1 IDRLMTGDSZBTPT-UHFFFAOYSA-N 0.000 description 1
- KIOATLUXQRCWLR-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12)c1c(cccc2)c2ccc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2ccccc12)c1c(cccc2)c2ccc1 KIOATLUXQRCWLR-UHFFFAOYSA-N 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 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
- 230000002349 favourable effect Effects 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
- CMLCVSPDRZVSRT-UHFFFAOYSA-N n,9-diphenyl-n-(9,9'-spirobi[fluorene]-2-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 CMLCVSPDRZVSRT-UHFFFAOYSA-N 0.000 description 1
- AGBXQLCOXANMQO-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-n-phenyl-4-(10-phenylanthracen-9-yl)aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=C(C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 AGBXQLCOXANMQO-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- VZYZZKOUCVXTOJ-UHFFFAOYSA-N n-[4-[4-(n-(9,9-dimethylfluoren-2-yl)anilino)phenyl]phenyl]-9,9-dimethyl-n-phenylfluoren-2-amine Chemical group C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C(C)(C)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 VZYZZKOUCVXTOJ-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- OFIYHXOOOISSDN-UHFFFAOYSA-N tellanylidenegallium Chemical compound [Te]=[Ga] OFIYHXOOOISSDN-UHFFFAOYSA-N 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
Images
Landscapes
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
S.A.Van Slyke,C.H.Chen,and C.W.Tang,"Organic electroluminescent devices with improved stability",Appl.Phys.Lett. 69 (15),7 October 1996
本実施の形態では本発明のスピロフルオレン誘導体について説明する。
(実施の形態2)
本実施の形態では、本発明の発光装置について図2、図3を参照し、作製方法を示しながら説明する。なお、本実施の形態ではアクティブマトリクス型の発光装置を作成する例を示したが、本発明はパッシブ型の発光装置についてももちろん適用することが可能である。
本実施の形態では、本発明の発光装置であるパネルの外観について図5を用いて説明する。図5(A)は基板上に形成されたトランジスタおよび発光素子を対向基板4006との間に形成したシール材によって封止したパネルの上面図であり、図5(B)は図5(A)の断面図に相応する。また、このパネルに搭載されている発光素子の有する構成は、実施の形態2に示したような構成である。
本実施の形態では、実施の形態4で示したパネル、モジュールが有する画素回路、保護回路及びそれらの動作について説明する。なお、図2、図3に示してきた断面図は駆動用TFT1403と発光素子1405の断面図模式図となっている。
図8(A)に本発明の発光装置の構成の一例を示す。図8(A)は順テーパー構造を有するパッシブマトリクス型の発光装置の画素部における断面図の一部である。図8(A)に示した本発明の発光装置は基板200、発光素子の第1の電極201、隔壁202、有機化合物を含む層203、発光素子の第2の電極204、対向基板207の構成を含む。
本発明の電子機器の代表例を図9を参照して説明する。本発明に係る電子機器は、少なくとも実施の形態1に記載のスピロフルオレン誘導体を含む発光素子もしくは実施の形態2で示した発光素子と、当該発光素子を制御する制御回路とを備えている。本発明の電子機器としては、例えば、ビデオカメラ、デジタルカメラ、ゴーグル型ディスプレイ(ヘッドマウントディスプレイ)、ナビゲーションシステム、音響再生装置(カーオーディオコンポ等)、コンピュータ、ゲーム機器、携帯情報端末(モバイルコンピュータ、携帯電話、携帯型ゲーム機または電子書籍等)、記録媒体を備えた画像再生装置(具体的にはDigital Versatile Disc(DVD)等の記録媒体を再生し、その画像を表示しうるディスプレイを備えた装置)などが挙げられる。
2−ブロモースピロ−9,9’−ビフルオレンの合成方法について説明する。
1H NMR(300MHz、CDCl3) δppm:7.86−7.79(m,3H),7.70(d,1H,J=8.4Hz),7.50−7.47(m,1H),7.41−7.34(m,3H),7.12(t,3H,J=7.7Hz),6.85(d,1H,J=2.1Hz),6.74−6.76(m、3H)
DPAの合成方法について説明する。
1H NMR(300MHz,CDCl3) δppm: 7.32(d,2H,J=8.7Hz),7.29−7.23(m,4H),7.08−7.00(m,6H),6.94(d,2H,J=8.7Hz)
DPASFの合成方法について説明する。
1H NMR(300MHz、DMSO−d6);δ=7.95(d,J=7.80Hz、2H),7.90(d,J=7.80Hz,2H),7.40−7.77(m,26H),6.67(d,J=7.20Hz,2H),6.55(d,J=7.20Hz,1H),6.16(d,J=2.33Hz,1H)
PCAの合成方法について説明する。
1H NMR(300MHz、CDCl3);δ=6.84(t、J=6.9Hz、1H)、6.97(d、J=7.8Hz、2H)、7.20−7.61(m、13H)、7.90(s、1H)、8.04(d、7.8Hz、1H)。
この化合物の1H NMRを次に示す。また、1H NMRチャートを図50(A)、(B)に示す。なお、図50(B)は、図50(A)における6.5ppm〜8.5ppmの範囲を拡大して表したチャートである。
1H NMR(300MHz、DMSO−d6);δ=6.73(t、J=7.5Hz、1H)、7.02(d、J=8.1Hz、2H)、7.16−7.70(m、12H)、7.95(s、1H)、8.06(s、1H)、8.17(d、J=7.8Hz)。
さらに、13C NMRを次に示す。また、13C NMRチャートを図51(A)、(B)に示す。なお、図51(B)は、図51(A)における100ppm〜150ppmの範囲を拡大して表したチャートである。
13C NMR(75.5MHz、DMSO−d6);δ=109.55、110.30、110.49、114.71、118.22、119.70、120.14、120.61、122.58、123.35、126.18、126.48、127.37、129.15、130.14、135.71、136.27、137.11、140.41、145.61。
PCASFの合成方法について説明する。
1H NMR(300MHz、DMSO−d6);δ=8.04(d,J=7.21Hz,1H),7.89−7.85(m,5H),7.69−7.50(m,5H),7.43−7.31(m,5H),7.27−7.10(m,6H),7.07−7.01(m,2H),6.95−6.86(m,4H),6.73(d,J=7.80Hz,2H),6.52(d,J=7.80Hz,1H),6.31(d,J=2.4Hz,1H)
YGAの合成方法について説明する。
1H NMR(300MHz,DMSO−d6)δppm:8.14(d,J= 7.8 Hz,2H),7.73(d,J= 8.7Hz,2H),7.46(d,J= 8.4 Hz,2H),7.42−7.26(m,6H)
1H NMR(300MHz,DMSO−d6)δppm:8.47(s,1H),8.22(d,J=7.8Hz,2H),7.44−7.16(m,14H),6.92−6.87(m,1H)
YGASFの合成。
1H NMR(300MHz、DMSO−d6);δ=8.19(d,J=7.80Hz,2H),7.97−7.91(m,4H),7.43−7.01(m,22H),6.71(d,J=7.80Hz,2H),6.71(d,J=7.80Hz,2H),6.58(d,J=6.9Hz,1H) 6.32(d,J=2.10Hz,1H)。
2,7−ジブロモ−スピロ−9,9’−ビフルオレンの合成。
DPA2SFの合成。
1H NMR(300MHz,DMSO−d6);δ=7.84(d,J=7.21Hz,2H),7.77(d,J=7.80Hz,2H),7.32−7.79(m,40H),6.73(d,J=7.80Hz,2H),6.16(d,J=2.10Hz,2H)
実施例10で使用したYGAPA、CzPAは新規物質であるため、以下に合成方法を記載する。
(i) 9−フェニルアントラセンの合成。
9−ブロモアントラセンを5.4g(21.1mmol)、フェニルボロン酸を2.6g (21.1mmol)、Pd(OAc)2を60mg(0.21mmol)、2mol/lの炭酸カリウム(K2CO3)水溶液を10ml(20mmol)、トリ(オルトトリル)ホスフィン(P(o−tolyl)3)を263mg(0.84mmol)、1,2−ジメトキシエタン(略称:DME)を20ml混合し、80℃、9時間撹拌した。反応後、析出した固体を吸引ろ過で回収してから、トルエンに溶かしフロリジール、セライト、アルミナを通してろ過をした。ろ液を水、飽和食塩水で洗浄後、硫酸マグネシウムで乾燥した。自然ろ過後、ろ液を濃縮したところ目的物である9−フェニルアントラセンの淡褐色固体を21.5g収率85%で得た(合成スキーム(j−3))。
9−フェニルアントラセン6.0g(23.7mmol)を四塩化炭素80mlに溶かし、その反応溶液へ、滴下ロートにより、臭素3.80g(21.1mmol)を四塩化炭素10mlに溶かした溶液を滴下した。滴下終了後室温で1時間攪拌した。反応後チオ硫酸ナトリウム水溶液を加えて反応をストップさせた。有機層をNaOH水溶液、飽和食塩水で洗浄し硫酸マグネシウムで乾燥した。自然ろ過後、濃縮しトルエンに溶かしフロリジール、セライト、アルミナを通してろ過を行った。ろ液を濃縮し、ジクロロメタン、ヘキサンにより再結晶を行ったところ、目的物である9−ブロモ−10−フェニルアントラセンの淡黄色個体を7.0g、収率89%で得た(合成スキーム(j−4))。
9−ブロモ−10−フェニルアントラセン3.33g(10mmol)をテトラヒドロフラン(略称:THF)80mlに溶かし、−78℃にしてから、その反応溶液へ滴下ロートにより、n−BuLi(1.6M)7.5ml(12.0mmol)を滴下し1時間攪拌した。ヨウ素5g(20.0mmol)をTHF20mlに溶かした溶液を滴下し−78℃でさらに2時間攪拌した。反応後チオ硫酸ナトリウム水溶液を加えて反応をストップした。有機層をチオ硫酸ナトリウム水溶液、飽和食塩水で洗浄し硫酸マグネシウムで乾燥した。自然濾過後ろ液を濃縮して、得られた固体をエタノールにより再結晶したところ目的物である9−ヨード−10−フェニルアントラセンの淡黄色固体を3.1g、収率83%で得た(合成スキーム(j−5))。
9−ヨード−10−フェニルアントラセン1.0g (2.63 mmol)、p−ブロモフェニルボロン酸542 mg (2.70mmol)、Pd(PPh3)4 46mg(0.03mmol)、2mol/Lの炭酸カリウム(K2CO3)水溶液3ml(6mmol)、トルエン 10mlを80℃、9時間撹拌した。反応後、トルエンを加えてからフロリジール、セライト、アルミナを通してろ過をした。ろ液を水、飽和食塩水で洗浄後、硫酸マグネシウムで乾燥した。自然ろ過後、ろ液を濃縮し、クロロホルム、ヘキサンにより再結晶したところ目的物である9−(4−ブロモフェニル)−10−フェニルアントラセンの淡褐色固体を562mg、収率45%で得た(合成スキーム(j−6))。
9−(4−ブロモフェニル)−10−フェニルアントラセン409mg(1.0mmol)、実施例3のステップ1でその作製方法を示した、YGA 339mg(1.0mmol)、Pd(dba)2 6mg(0.01mmol)、tert−BuONa 500mg(5.2mol)、P(tert−Bu)3(10wt%ヘキサン溶液)0.1ml、トルエン10ml、80℃で4時間攪拌した。反応後、溶液を水で洗浄し、水層をトルエンで抽出し、有機層と併せて飽和食塩水で洗浄後、硫酸マグネシウムで乾燥した。自然ろ過後、濃縮し得られた油状物をシリカゲルカラムクロマトグラフィー(ヘキサン:トルエン=7:3)により精製し、ジクロロメタン、ヘキサンにより再結晶したところ目的物であるYGAPAの黄色粉末状固体を534mg収率81%で得た(合成スキーム(j−7))。この化合物を核磁気共鳴法(1H NMR)によって測定したところ、YGAPAであることが確認できた。図49に得られた化合物の1H NMRチャートを示す。
18 外部入力端子部
19 外部入力端子部
23 画素部
25 フレキシブルプリント配線基板
28 ドライバIC
29 外部回路基板
50 基板
51a 第1の下地絶縁層
51b 第2の下地絶縁層
52 半導体層
53 ゲート絶縁層
54 ゲート電極
59 絶縁膜(水素化膜)
60 第1の層間絶縁層
61a 接続部
61b 配線
63 第2の層間絶縁層
64 第1の電極
65 隔壁
66 有機化合物を含む層
67 第2の電極
70 薄膜トランジスタ
88 樹脂
89 乾燥剤
90 偏光板
91 保護フィルム
93 発光素子
94 対向基板
101 第1の電極
102 有機化合物を含む層
103 第2の電極
200 基板
201 第1の電極
202 隔壁
203 有機化合物を含む層
204 第2の電極
207 対向基板
210 保護膜
211 シール用の接着剤
212 異方性導電膜
213 フレキシブルプリント配線基板
1401 スイッチング用TFT
1402 容量素子
1403 駆動用TFT
1404 電流制御用TFT
1405 発光素子
1406 TFT
1410 信号線
1411 電源線
1412 電源線
1414 走査線
1415 走査線
1500 画素部
1554 共通電位線
1555 共通電位線
1561 ダイオード
1562 ダイオード
2001 筐体
2003 表示部
2004 スピーカー部
2101 本体
2102 筐体
2103 表示部
2104 音声入力部
2105 音声出力部
2106 操作キー
2108 アンテナ
2201 本体
2202 筐体
2203 表示部
2204 キーボード
2205 外部接続ポート
2206 ポインティングマウス
2301 本体
2302 表示部
2303 スイッチ
2304 操作キー
2305 赤外線ポート
2401 筐体
2402 表示部
2403 スピーカー部
2404 操作キー
2405 記録媒体挿入部
4001 基板
4002 画素部
4003 信号線駆動回路
4004 走査線駆動回路
4005 シール材
4006 対向基板
4007 充填材
4008 薄膜トランジスタ
4010 薄膜トランジスタ
4011 発光素子
4014 走査線
4015 走査線
4016 接続端子
4018 FPC
4019 異方性導電膜
Claims (25)
- 請求項1乃至請求項21いずれか1項に記載のスピロフルオレン誘導体を含む発光素子用材料。
- 請求項1乃至請求項21いずれか1項に記載のスピロフルオレン誘導体を含む発光素子。
- 請求項23に記載の発光素子と、
前記発光素子の発光を制御する制御回路を有する発光装置。 - 請求項23に記載の発光素子を用いた表示部を有し、
前記発光素子の発光を制御する制御回路を備えた電子機器。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006265047A JP5019837B2 (ja) | 2005-09-30 | 2006-09-28 | スピロフルオレン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005289418 | 2005-09-30 | ||
JP2005289418 | 2005-09-30 | ||
JP2006265047A JP5019837B2 (ja) | 2005-09-30 | 2006-09-28 | スピロフルオレン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007119457A JP2007119457A (ja) | 2007-05-17 |
JP5019837B2 true JP5019837B2 (ja) | 2012-09-05 |
Family
ID=38143674
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006265047A Active JP5019837B2 (ja) | 2005-09-30 | 2006-09-28 | スピロフルオレン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5019837B2 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI638583B (zh) * | 2007-09-27 | 2018-10-11 | 半導體能源研究所股份有限公司 | 發光元件,發光裝置,與電子設備 |
KR20130058086A (ko) * | 2007-12-03 | 2013-06-03 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 카바졸 유도체, 및 카바졸 유도체를 사용하는 발광 소자, 발광 장치 및 전자 기기 |
KR20100097180A (ko) * | 2007-12-28 | 2010-09-02 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그들을 이용한 유기 전기발광 소자 |
US20110253991A1 (en) * | 2008-12-26 | 2011-10-20 | Nippon Steel Chemical Co., Ltd. | Organic electroluminescence device |
KR101245243B1 (ko) | 2009-12-16 | 2013-03-19 | 덕산하이메탈(주) | 스피로 카바졸 화합물 및 이를 이용한 유기전기소자, 그 단말 |
DE202012013737U1 (de) | 2011-03-23 | 2020-09-30 | Semiconductor Energy Laboratory Co., Ltd. | Lichtemittierendes Element |
CN103518270B (zh) * | 2011-04-07 | 2016-04-06 | 株式会社半导体能源研究所 | 使用磷光化合物和由其形成激基复合物的有机化合物的发光元件 |
EP3101088B1 (en) * | 2012-02-14 | 2017-11-29 | Merck Patent GmbH | Materials for organic electroluminescent devices |
DE102013214661B4 (de) * | 2012-08-03 | 2023-01-05 | Semiconductor Energy Laboratory Co., Ltd. | Licht emittierendes Element, Licht emittierende Vorrichtung und Beleuchtungsvorrichtung |
WO2014021441A1 (en) | 2012-08-03 | 2014-02-06 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, electronic device, and lighting device |
US20150228899A1 (en) * | 2012-08-31 | 2015-08-13 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
JP7257952B2 (ja) | 2017-05-19 | 2023-04-14 | 株式会社半導体エネルギー研究所 | 電子デバイス、表示装置、電子機器、及び照明装置 |
JP7325731B2 (ja) | 2018-08-23 | 2023-08-15 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
JP2018199722A (ja) * | 2018-09-14 | 2018-12-20 | 株式会社半導体エネルギー研究所 | 有機化合物及び発光装置 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4122901B2 (ja) * | 2002-08-28 | 2008-07-23 | 富士ゼロックス株式会社 | 有機電界発光素子 |
-
2006
- 2006-09-28 JP JP2006265047A patent/JP5019837B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2007119457A (ja) | 2007-05-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10056559B2 (en) | Spirofluorene derivative, material for light-emitting element, light-emitting element, light-emitting device, and electronic device | |
JP5019837B2 (ja) | スピロフルオレン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 | |
JP6378378B2 (ja) | 物質、発光素子、発光装置、電子機器、有機デバイス | |
KR101540037B1 (ko) | 퀴녹살린 유도체, 및 퀴녹살린 유도체를 사용한 발광소자, 발광장치, 전자 기기 | |
JP5439550B2 (ja) | スチルベン誘導体、発光素子、および発光装置 | |
KR101359412B1 (ko) | 카르바졸 유도체, 발광소자용 재료, 발광소자, 발광 장치 및 전자기기 | |
JP5041752B2 (ja) | アントラセン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 | |
JP2007039431A (ja) | アントラセン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 | |
JP2007045809A (ja) | アントラセン誘導体とそれを用いた発光素子、発光装置、電子機器 | |
JP5838232B2 (ja) | 芳香族アミン化合物、発光素子、発光装置、電子機器、および芳香族アミン化合物の合成方法 | |
US20070037011A1 (en) | Arylamine compound and synthetic method thereof | |
JP5041767B2 (ja) | カルバゾール誘導体、発光素子用材料、発光素子、発光装置及び電子機器 | |
JP5401007B2 (ja) | 芳香族アミン化合物、発光素子、発光装置、電子機器 | |
JP4963214B2 (ja) | スチルベン誘導体、発光素子用材料、発光素子、発光装置及び電子機器 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090918 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120529 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120612 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5019837 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150622 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150622 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |