JP2010209059A - 有機化合物、アントラセン誘導体、およびアントラセン誘導体を用いた発光素子、発光装置、電子機器並びに照明装置 - Google Patents
有機化合物、アントラセン誘導体、およびアントラセン誘導体を用いた発光素子、発光装置、電子機器並びに照明装置 Download PDFInfo
- Publication number
- JP2010209059A JP2010209059A JP2009238048A JP2009238048A JP2010209059A JP 2010209059 A JP2010209059 A JP 2010209059A JP 2009238048 A JP2009238048 A JP 2009238048A JP 2009238048 A JP2009238048 A JP 2009238048A JP 2010209059 A JP2010209059 A JP 2010209059A
- Authority
- JP
- Japan
- Prior art keywords
- light
- layer
- emitting element
- emitting
- anthracene derivative
- 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.)
- Granted
Links
- 150000001454 anthracenes Chemical class 0.000 title claims abstract description 143
- 150000002894 organic compounds Chemical class 0.000 title claims description 114
- -1 biphenyl-4,4'-diyl Chemical group 0.000 claims abstract description 66
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 25
- 238000005286 illumination Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 310
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 208
- 239000000126 substance Substances 0.000 description 102
- 238000006243 chemical reaction Methods 0.000 description 87
- 238000000034 method Methods 0.000 description 81
- 239000000203 mixture Substances 0.000 description 66
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 44
- 239000012046 mixed solvent Substances 0.000 description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 40
- 239000007787 solid Substances 0.000 description 40
- 239000000463 material Substances 0.000 description 39
- 238000006722 reduction reaction Methods 0.000 description 39
- 238000007254 oxidation reaction Methods 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 37
- 229910052757 nitrogen Inorganic materials 0.000 description 37
- 239000000758 substrate Substances 0.000 description 37
- 230000000052 comparative effect Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 34
- 230000005525 hole transport Effects 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- 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 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 238000000862 absorption spectrum Methods 0.000 description 25
- 239000000706 filtrate Substances 0.000 description 25
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000010408 film Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 238000005259 measurement Methods 0.000 description 23
- 239000012044 organic layer Substances 0.000 description 23
- 239000002131 composite material Substances 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 229910052736 halogen Inorganic materials 0.000 description 20
- 230000003647 oxidation Effects 0.000 description 20
- 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 20
- 229910052763 palladium Inorganic materials 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
- 230000009467 reduction Effects 0.000 description 18
- 239000010409 thin film Substances 0.000 description 18
- 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 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000002484 cyclic voltammetry Methods 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 230000002194 synthesizing effect Effects 0.000 description 16
- 239000008096 xylene Substances 0.000 description 16
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 13
- 229910045601 alloy Inorganic materials 0.000 description 13
- 239000000956 alloy Substances 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 12
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 238000004544 sputter deposition Methods 0.000 description 12
- LUBXLGUQZVKOFP-UHFFFAOYSA-N 9-phenylanthracene Chemical class C1=CC=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 LUBXLGUQZVKOFP-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 230000006866 deterioration Effects 0.000 description 11
- 238000000295 emission spectrum Methods 0.000 description 11
- 238000004770 highest occupied molecular orbital Methods 0.000 description 11
- 239000011159 matrix material Substances 0.000 description 11
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 239000004973 liquid crystal related substance Substances 0.000 description 10
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 10
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 10
- 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 10
- 239000000047 product Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 150000001412 amines Chemical group 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 239000010453 quartz Substances 0.000 description 9
- 238000005215 recombination Methods 0.000 description 9
- 230000006798 recombination Effects 0.000 description 9
- 238000000859 sublimation Methods 0.000 description 9
- 230000008022 sublimation Effects 0.000 description 9
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 9
- 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 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 150000001342 alkaline earth metals Chemical class 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 150000001716 carbazoles Chemical class 0.000 description 8
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 150000007529 inorganic bases Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 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 7
- 238000001771 vacuum deposition Methods 0.000 description 7
- RDZHCKRAHUPIFK-UHFFFAOYSA-N 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(I)C(=O)N(I)C1=O RDZHCKRAHUPIFK-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000006887 Ullmann reaction Methods 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 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 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- JEYLGFCAZBGCMC-UHFFFAOYSA-N 3-(4-bromophenyl)-9-phenylcarbazole Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 JEYLGFCAZBGCMC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 5
- 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 5
- 239000005749 Copper compound Substances 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 150000001880 copper compounds Chemical class 0.000 description 5
- 230000005281 excited state Effects 0.000 description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 229910052814 silicon oxide Inorganic materials 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 229940125773 compound 10 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000412 dendrimer Substances 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 239000012336 iodinating agent Substances 0.000 description 4
- 230000026045 iodination Effects 0.000 description 4
- 238000006192 iodination reaction Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 4
- 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 compound 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 3
- RVCKCEDKBVEEHL-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzyl alcohol Chemical compound OCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl RVCKCEDKBVEEHL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CCIVUDMVXNBUCY-UHFFFAOYSA-N 4-bromo-n-phenylaniline Chemical compound C1=CC(Br)=CC=C1NC1=CC=CC=C1 CCIVUDMVXNBUCY-UHFFFAOYSA-N 0.000 description 3
- OGHOZWNRKYYYHY-UHFFFAOYSA-N 4-naphthalen-1-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=CC2=CC=CC=C12 OGHOZWNRKYYYHY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UQVFZEYHQJJGPD-UHFFFAOYSA-N 9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UQVFZEYHQJJGPD-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002253 acid Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 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 3
- 230000000737 periodic effect Effects 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 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 3
- 239000003566 sealing material Substances 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000005092 sublimation method Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- HAFQHNGZPQYKFF-UHFFFAOYSA-N 1,3,3a,4,6,6a-hexahydropentalene-2,5-dione Chemical compound C1C(=O)CC2CC(=O)CC21 HAFQHNGZPQYKFF-UHFFFAOYSA-N 0.000 description 2
- NOMFIHIZHACVDR-UHFFFAOYSA-N 1,3,4,6-tetraiodo-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound IN1C(=O)N(I)C2C1N(I)C(=O)N2I NOMFIHIZHACVDR-UHFFFAOYSA-N 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 group 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 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
- 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 2
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- DXEBPLKAEYRVTF-UHFFFAOYSA-N 4-(4-naphthalen-1-ylphenyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(C=2C3=CC=CC=C3C=CC=2)C=C1 DXEBPLKAEYRVTF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KOGDFDWINXIWHI-OWOJBTEDSA-N 4-[(e)-2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1 KOGDFDWINXIWHI-OWOJBTEDSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- USIXUMGAHVBSHQ-UHFFFAOYSA-N 9,10-bis(3,5-diphenylphenyl)anthracene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C3=CC=CC=C3C(C=3C=C(C=C(C=3)C=3C=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=2)=C1 USIXUMGAHVBSHQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229920003026 Acene Polymers 0.000 description 2
- 229910017073 AlLi Inorganic materials 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 2
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- BBNZOXKLBAWRSH-UHFFFAOYSA-N n,9-diphenyl-n-[4-(10-phenylanthracen-9-yl)phenyl]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=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 BBNZOXKLBAWRSH-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ATKDFNSBYLLHRS-UHFFFAOYSA-N n-phenyl-4-(9-phenylcarbazol-3-yl)aniline Chemical compound C=1C=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=CC=1NC1=CC=CC=C1 ATKDFNSBYLLHRS-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 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 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000001420 photoelectron spectroscopy Methods 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 239000003586 protic polar solvent 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
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000003980 solgel method Methods 0.000 description 2
- 238000001228 spectrum 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
- 239000003115 supporting electrolyte Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 150000003613 toluenes Chemical class 0.000 description 2
- 230000007704 transition Effects 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
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
- BPJXIDDLYYGLDN-UHFFFAOYSA-N 1,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC2=CC=CC=C22)=CC=CC1=C2C1=CC=CC=C1 BPJXIDDLYYGLDN-UHFFFAOYSA-N 0.000 description 1
- RTSZQXSYCGBHMO-UHFFFAOYSA-N 1,2,4-trichloro-3-prop-1-ynoxybenzene Chemical compound CC#COC1=C(Cl)C=CC(Cl)=C1Cl RTSZQXSYCGBHMO-UHFFFAOYSA-N 0.000 description 1
- SIJHJHYRYHIWFW-UHFFFAOYSA-N 1,3,6,8-tetraphenylpyrene Chemical compound C1=CC=CC=C1C(C1=CC=C23)=CC(C=4C=CC=CC=4)=C(C=C4)C1=C2C4=C(C=1C=CC=CC=1)C=C3C1=CC=CC=C1 SIJHJHYRYHIWFW-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
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- XEENEQWQRGXBJJ-UHFFFAOYSA-N 1-butylperylene Chemical group C1=CC(C=2C(CCCC)=CC=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 XEENEQWQRGXBJJ-UHFFFAOYSA-N 0.000 description 1
- XMFUWUVTKIEZJL-UHFFFAOYSA-N 1-n,4-n,2-tris(4-methylphenyl)-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(C(N(C=2C=CC=CC=2)C=2C=CC(C)=CC=2)=CC=1)C=1C=CC(C)=CC=1)C1=CC=CC=C1 XMFUWUVTKIEZJL-UHFFFAOYSA-N 0.000 description 1
- VOIVTTPPKHORBL-UHFFFAOYSA-N 1-naphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C=3C4=CC5=CC=CC=C5C=C4C=CC=3)=CC=CC2=C1 VOIVTTPPKHORBL-UHFFFAOYSA-N 0.000 description 1
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical class C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 description 1
- JEBPFDQAOYARIB-UHFFFAOYSA-N 2,3,6,7-tetramethyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C=3C4=CC(C)=C(C)C=C4C(C=4C=C5C=CC=CC5=CC=4)=C4C=C(C(=CC4=3)C)C)=CC=C21 JEBPFDQAOYARIB-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
- 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
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-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
- MNHPNCZSKTUPMB-UHFFFAOYSA-N 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene Chemical compound C=12C=CC=CC2=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C2=CC(C(C)(C)C)=CC=C2C=1C(C=C1)=CC=C1C1=CC=CC=C1 MNHPNCZSKTUPMB-UHFFFAOYSA-N 0.000 description 1
- WBPXZSIKOVBSAS-UHFFFAOYSA-N 2-tert-butylanthracene Chemical compound C1=CC=CC2=CC3=CC(C(C)(C)C)=CC=C3C=C21 WBPXZSIKOVBSAS-UHFFFAOYSA-N 0.000 description 1
- GRTDQSRHHHDWSQ-UHFFFAOYSA-N 3,6-diphenyl-9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 GRTDQSRHHHDWSQ-UHFFFAOYSA-N 0.000 description 1
- TVMBOHMLKCZFFW-UHFFFAOYSA-N 3-N,6-N,9-triphenyl-3-N,6-N-bis(9-phenylcarbazol-3-yl)carbazole-3,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC(=CC=C3N(C=3C=CC=CC=3)C2=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 TVMBOHMLKCZFFW-UHFFFAOYSA-N 0.000 description 1
- PJUAIXDOXUXBDR-UHFFFAOYSA-N 3-iodo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(I)=CC=C2N1C1=CC=CC=C1 PJUAIXDOXUXBDR-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
- PTDDLSWZPLQORQ-UHFFFAOYSA-N 4-[3-tert-butyl-10-[4-(N-(4-carbazol-9-ylphenyl)anilino)phenyl]anthracen-9-yl]-N-(4-carbazol-9-ylphenyl)-N-phenylaniline Chemical compound C=12C=CC=CC2=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C2=CC(C(C)(C)C)=CC=C2C=1C(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 PTDDLSWZPLQORQ-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- QYNTUCBQEHUHCS-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n-[4-[4-(n-[4-(n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-1-n,4-n-diphenylbenzene-1,4-diamine Chemical group 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)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QYNTUCBQEHUHCS-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
- DWSKWYAKBATHET-UHFFFAOYSA-N 5,12-diphenyltetracene Chemical compound C1=CC=CC=C1C(C1=CC2=CC=CC=C2C=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 DWSKWYAKBATHET-UHFFFAOYSA-N 0.000 description 1
- NKEZXXDRXPPROK-UHFFFAOYSA-N 9,10-bis(2-naphthalen-1-ylphenyl)anthracene Chemical compound C12=CC=CC=C2C(C2=CC=CC=C2C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 NKEZXXDRXPPROK-UHFFFAOYSA-N 0.000 description 1
- YTSGZCWSEMDTBC-UHFFFAOYSA-N 9,10-bis(4-methylnaphthalen-1-yl)anthracene Chemical compound C12=CC=CC=C2C(C)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C)C2=CC=CC=C12 YTSGZCWSEMDTBC-UHFFFAOYSA-N 0.000 description 1
- BITWULPDIGXQDL-UHFFFAOYSA-N 9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene Chemical compound C=1C=C(C=2C3=CC=CC=C3C(C=3C=CC(C=C(C=4C=CC=CC=4)C=4C=CC=CC=4)=CC=3)=C3C=CC=CC3=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 BITWULPDIGXQDL-UHFFFAOYSA-N 0.000 description 1
- OEYLQYLOSLLBTR-UHFFFAOYSA-N 9-(2-phenylphenyl)-10-[10-(2-phenylphenyl)anthracen-9-yl]anthracene Chemical group C1=CC=CC=C1C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1C1=CC=CC=C1 OEYLQYLOSLLBTR-UHFFFAOYSA-N 0.000 description 1
- DTGCMKMICLCAQU-UHFFFAOYSA-N 9-[3-[2-(3-phenanthren-9-ylphenyl)ethenyl]phenyl]phenanthrene Chemical compound C1=CC=C2C(C=3C=CC=C(C=3)C=CC=3C=C(C=CC=3)C=3C4=CC=CC=C4C4=CC=CC=C4C=3)=CC3=CC=CC=C3C2=C1 DTGCMKMICLCAQU-UHFFFAOYSA-N 0.000 description 1
- XCICDYGIJBPNPC-UHFFFAOYSA-N 9-[4-[3,5-bis(4-carbazol-9-ylphenyl)phenyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=C(C=C(C=2)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 XCICDYGIJBPNPC-UHFFFAOYSA-N 0.000 description 1
- ZWSVEGKGLOHGIQ-UHFFFAOYSA-N 9-[4-[4-(4-carbazol-9-ylphenyl)-2,3,5,6-tetraphenylphenyl]phenyl]carbazole Chemical compound C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(C=1C=CC=CC=1)=C1C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)=C1C1=CC=CC=C1 ZWSVEGKGLOHGIQ-UHFFFAOYSA-N 0.000 description 1
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 1
- NBYGJKGEGNTQBK-UHFFFAOYSA-N 9-phenyl-10-(10-phenylanthracen-9-yl)anthracene Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 NBYGJKGEGNTQBK-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
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910000789 Aluminium-silicon alloy Inorganic materials 0.000 description 1
- PWCVNBVFXSIXQM-UHFFFAOYSA-N C(CCC)C1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC(=CC12)C(C)(C)C)C1=C(C=CC=C1)CCCC Chemical compound C(CCC)C1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC(=CC12)C(C)(C)C)C1=C(C=CC=C1)CCCC PWCVNBVFXSIXQM-UHFFFAOYSA-N 0.000 description 1
- YOPFHMFSOLIIPC-UHFFFAOYSA-N C1(=CC=CC=C1)N(C=1C=CC=2N(C3=CC=CC=C3C2C1)C1=CC=CC=C1)C1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)N(C=1C=CC=2N(C3=CC=CC=C3C2C1)C1=CC=CC=C1)C1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=CC=C1 YOPFHMFSOLIIPC-UHFFFAOYSA-N 0.000 description 1
- ZKHISQHQYQCSJE-UHFFFAOYSA-N C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C=C(C=1)N(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)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C=C(C=1)N(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)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 ZKHISQHQYQCSJE-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
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MXZNUGFCDVAXLG-CHWSQXEVSA-N [(2S)-1-[(2R)-3-methyl-2-(pyridine-4-carbonylamino)butanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@@H](NC(=O)c1ccncc1)C(=O)N1CCC[C@@H]1B(O)O MXZNUGFCDVAXLG-CHWSQXEVSA-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
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-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
- 239000004305 biphenyl Substances 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
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 150000001846 chrysenes Chemical class 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
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 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 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
- BHQBDOOJEZXHPS-UHFFFAOYSA-N ctk3i0272 Chemical group C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(=C1C=2C=CC=CC=2)C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C(C=4C(=C(C=5C=CC=CC=5)C(C=5C=CC=CC=5)=C(C=5C=CC=CC=5)C=4C=4C=CC=CC=4)C=4C=CC=CC=4)=C4C=CC=CC4=3)=C3C=CC=CC3=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 BHQBDOOJEZXHPS-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GQDKQZAEQBGVBS-UHFFFAOYSA-N dibenzo[g,p]chrysene Chemical class C1=CC=CC2=C3C4=CC=CC=C4C4=CC=CC=C4C3=C(C=CC=C3)C3=C21 GQDKQZAEQBGVBS-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 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
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 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
- 238000009815 homocoupling reaction Methods 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-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(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
- CRWAGLGPZJUQQK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-[2-[4-(n-(4-carbazol-9-ylphenyl)anilino)phenyl]ethenyl]-n-phenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 CRWAGLGPZJUQQK-UHFFFAOYSA-N 0.000 description 1
- LONYJNZXYCLXDO-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-n-phenyl-4-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 LONYJNZXYCLXDO-UHFFFAOYSA-N 0.000 description 1
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 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
- 229910052760 oxygen Inorganic materials 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
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Abstract
【解決手段】一般式(G1)で表されるアントラセン誘導体等を提供する。一般式(G1)において、Ar2、Ar3、Ar4は、それぞれ独立に、フェニレン基、又は、ビフェニル−4,4’−ジイル基を表す。
【選択図】なし
Description
本実施の形態では、本発明一態様であるアントラセン誘導体、及び、前記アントラセン誘導体を合成する際に用いられる有機化合物について説明する。
本実施の形態では、実施の形態1で示したアントラセン誘導体を用いた発光素子の一態様について、図1(A)を用いて以下に説明する。
本実施の形態では、実施の形態2で示した構成と異なる構成の発光素子について説明する。
本実施の形態では、実施の形態2および実施の形態3で示した構成と異なる構成の発光素子について、図1(A)を用いて説明する。
本実施の形態では、実施の形態2乃至実施の形態4で示した構成と、異なる構成の発光素子について図1(B)を用いて説明する。
本実施の形態は、本発明の一態様に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の態様について、図2を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する発光素子である。発光ユニットとしては、実施の形態2で示した有機化合物を含む層102と同様な構成を用いることができる。つまり、実施の形態2で示した発光素子は、1つの発光ユニットを有する発光素子であり、本実施の形態では、複数の発光ユニットを有する発光素子について説明する。
本実施の形態では、実施の形態1で示したアントラセン誘導体を用いて作製された発光装置について説明する。
本実施の形態では、実施の形態7に示す発光装置をその一部に含む本発明の一態様の電子機器について説明する。本実施の形態で示す電子機器は、実施の形態1に示したアントラセン誘導体を含み、長寿命の表示部を有する。また、消費電力の低減された表示部を有する。
[ステップ4:3−(4−ブロモフェニル)−9−フェニル−9H−カルバゾールの合成]
発光素子1の構造を、図9(A)を用いて説明する。まず、ガラス基板1100上に、酸化珪素を含むインジウムスズ酸化物をスパッタリング法にて成膜し、第1の電極1101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
次に、発光素子1の比較として、比較発光素子1を作成した。比較発光素子1の素子構造を、図9(A)を用いて説明する。比較発光素子1は、発光層1104に、本発明の一態様であるアントラセン誘導体であるPCBNAPAの代わりに、4−(10−フェニル−9−アントリル)−4’−(9−フェニル−9H−カルバゾール−3−イル)トリフェニルアミン(略称:PCBAPA)を用いて作成した。ここで、CzPAとPCBAPAとの重量比は、1:0.10(=CzPA:PCBAPA)となるように調節した。比較発光素子1は、発光層1104以外の構成は全て発光素子1と同じ構成である。
まず、ガラス基板1100上に、酸化珪素を含むインジウムスズ酸化物をスパッタリング法にて成膜し、第1の電極1101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
次に、発光素子2の比較発光素子2を作成した。比較発光素子2の素子構造を、図9(B)を用いて説明する。比較発光素子2は、第1の発光層1200及び第2の発光層1201に、本発明の一態様であるアントラセン誘導体であるPCBNAPAの代わりに、構造式(v)で表されるPCBAPAを用いて作成した。ここで、第1の発光層1200はPCBAPAを用い、第2の発光層1201においてCzPAとPCBAPAの重量比は1:0.05(=CzPA:PCBAPA)となるように調節した。比較発光素子2は、第1の発光層1200及び第2の発光層1201以外の構成は、全て発光素子2と同じである。
101 第1の電極
102 有機化合物を含む層
103 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
121 第1の層
122 第2の層
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 有機化合物を含む層(EL層)
617 第2の電極
618 発光素子
623 nチャネル型TFT
624 pチャネル型TFT
901 筐体
902 液晶層
903 バックライト
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 有機化合物を含む層(EL層)
956 電極
1100 ガラス基板
1101 第1の電極
1102 複合材料を含む層
1103 正孔輸送層
1104 発光層
1105 電子輸送層
1106 電子注入層
1107 第2の電極
1200 第1の発光層
1201 第2の発光層
2001 筐体
2002 光源
3001 照明装置
3002 テレビ装置
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9401 本体
9402 筐体
9403 表示部
9404 音声入力部
9405 音声出力部
9406 操作キー
9407 外部接続ポート
9408 アンテナ
9501 本体
9502 表示部
9503 筐体
9504 外部接続ポート
9505 リモコン受信部
9506 受像部
9507 バッテリー
9508 音声入力部
9509 操作キー
9510 接眼部
Claims (14)
- 一般式(G1)で表されるアントラセン誘導体。
(一般式(G1)において、Ar2、Ar3、Ar4は、それぞれ独立に、フェニレン基、又は、ビフェニル−4,4’−ジイル基を表す。) - 一般式(G1−1)で表されるアントラセン誘導体。
(一般式(G1−1)において、Ar2、Ar3は、それぞれ独立に、フェニレン基、又は、ビフェニル−4,4’−ジイル基を表す。) - 一般式(G1−2)で表されるアントラセン誘導体。
(一般式(G1−2)において、Ar3は、フェニレン基、又は、ビフェニル−4,4’−ジイル基を表す。) - 構造式(101)で表されるアントラセン誘導体。
- 構造式(103)で表されるアントラセン誘導体。
- 一般式(G2)で表される有機化合物。
(一般式(G2)において、Ar3、Ar4は、それぞれ独立に、フェニレン基、又は、ビフェニル−4,4’−ジイル基を表す。) - 一般式(G2−1)で表される有機化合物。
(一般式(G2−1)において、Ar3は、フェニレン基、又は、ビフェニル−4,4’−ジイル基を表す。) - 構造式(301)で表される有機化合物。
- 構造式(302)で表される有機化合物。
- 一対の電極間に、請求項1乃至請求項5のいずれか一項に記載のアントラセン誘導体を含むことを特徴とする発光素子。
- 一対の電極間に発光層を有し、前記発光層は請求項1乃至請求項5のいずれか一項に記載のアントラセン誘導体を含むことを特徴とする発光素子。
- 請求項10または請求項11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とを有することを特徴とする発光装置。
- 表示部を有し、前記表示部は、請求項10または請求項11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とを備えたことを特徴とする電子機器。
- 請求項12の発光装置を用いて形成されたことを特徴とする照明装置。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009238048A JP5489632B2 (ja) | 2008-10-17 | 2009-10-15 | 有機化合物、アントラセン誘導体、およびアントラセン誘導体を用いた発光素子、発光装置 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008269097 | 2008-10-17 | ||
JP2008269097 | 2008-10-17 | ||
JP2009030140 | 2009-02-12 | ||
JP2009030140 | 2009-02-12 | ||
JP2009238048A JP5489632B2 (ja) | 2008-10-17 | 2009-10-15 | 有機化合物、アントラセン誘導体、およびアントラセン誘導体を用いた発光素子、発光装置 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010209059A true JP2010209059A (ja) | 2010-09-24 |
JP2010209059A5 JP2010209059A5 (ja) | 2012-11-08 |
JP5489632B2 JP5489632B2 (ja) | 2014-05-14 |
Family
ID=42109198
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009238048A Expired - Fee Related JP5489632B2 (ja) | 2008-10-17 | 2009-10-15 | 有機化合物、アントラセン誘導体、およびアントラセン誘導体を用いた発光素子、発光装置 |
Country Status (3)
Country | Link |
---|---|
US (1) | US7960566B2 (ja) |
JP (1) | JP5489632B2 (ja) |
CN (1) | CN101723876B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020039708A1 (ja) | 2018-08-23 | 2020-02-27 | 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 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101579918B1 (ko) | 2007-04-25 | 2015-12-24 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 안트라센 유도체, 및 안트라센 유도체를 사용한 발광소자, 발광장치, 및 전자 기기 |
JP2011088887A (ja) * | 2009-09-22 | 2011-05-06 | Semiconductor Energy Lab Co Ltd | ハロゲン化ジアリールアミン化合物、およびその合成方法 |
US8283855B2 (en) * | 2010-01-11 | 2012-10-09 | Semiconductor Energy Laboratory Co., Ltd. | Method for synthesis of anthracene derivative |
WO2012023989A2 (en) | 2010-08-20 | 2012-02-23 | Rhodia Operations | Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels, and foams |
EP2433929B1 (en) | 2010-09-27 | 2013-10-23 | Semiconductor Energy Laboratory Co, Ltd. | Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
KR101961613B1 (ko) | 2011-12-12 | 2019-03-25 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
CN102584678B (zh) * | 2012-01-16 | 2012-12-26 | 山东盛华电子新材料有限公司 | 一种n-苯基-3-(4-溴苯基)咔唑的合成方法 |
US10461260B2 (en) * | 2014-06-03 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN105237461A (zh) * | 2015-10-21 | 2016-01-13 | 山东盛华电子新材料有限公司 | 一种可再回收改性钯碳对卤代物格氏试剂直接偶联卤代物合成杂环化合物的方法 |
KR101837006B1 (ko) * | 2017-01-25 | 2018-03-09 | 한남대학교 산학협력단 | 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자 |
WO2018158659A1 (ja) * | 2017-03-03 | 2018-09-07 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
KR20200136115A (ko) * | 2019-05-27 | 2020-12-07 | 주식회사 동진쎄미켐 | 캡핑층용 유기 화합물 및 이를 포함하는 유기 발광 소자 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007045816A (ja) * | 2005-07-14 | 2007-02-22 | Semiconductor Energy Lab Co Ltd | カルバゾール誘導体、及びそれを用いて得られた発光素子用材料、発光素子、電子機器 |
JP2007056006A (ja) * | 2005-07-27 | 2007-03-08 | Semiconductor Energy Lab Co Ltd | 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 |
JP5133259B2 (ja) * | 2006-11-24 | 2013-01-30 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3649302B2 (ja) | 1996-05-23 | 2005-05-18 | 出光興産株式会社 | 有機電界発光素子 |
TWI327563B (en) * | 2004-05-24 | 2010-07-21 | Au Optronics Corp | Anthracene compound and organic electroluminescent device including the anthracene compound |
CN100521283C (zh) * | 2004-11-26 | 2009-07-29 | 株式会社半导体能源研究所 | 发光元件、发光器件和电子器件 |
WO2006070907A1 (en) * | 2004-12-28 | 2006-07-06 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, light emitting element using the same, and light emitting device using the same |
CN102629666B (zh) | 2005-03-28 | 2015-08-19 | 株式会社半导体能源研究所 | 蒽衍生物、发光元件用材料、发光元件、发光装置和电子器件 |
WO2007013537A1 (en) | 2005-07-27 | 2007-02-01 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, material for light emitting element, light emitting element, light emitting device, and electronic appliance |
CN101253150B (zh) * | 2005-09-02 | 2012-06-06 | 株式会社半导体能源研究所 | 蒽衍生物 |
KR101579918B1 (ko) * | 2007-04-25 | 2015-12-24 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 안트라센 유도체, 및 안트라센 유도체를 사용한 발광소자, 발광장치, 및 전자 기기 |
US8283055B2 (en) * | 2008-10-17 | 2012-10-09 | Semiconductor Energy Laboratory Co., Ltd. | Material for light-emitting element, light-emitting element, light-emitting device, electronic device, and lighting device |
-
2009
- 2009-10-08 US US12/576,016 patent/US7960566B2/en not_active Expired - Fee Related
- 2009-10-15 JP JP2009238048A patent/JP5489632B2/ja not_active Expired - Fee Related
- 2009-10-16 CN CN200910208039.1A patent/CN101723876B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007045816A (ja) * | 2005-07-14 | 2007-02-22 | Semiconductor Energy Lab Co Ltd | カルバゾール誘導体、及びそれを用いて得られた発光素子用材料、発光素子、電子機器 |
JP2007056006A (ja) * | 2005-07-27 | 2007-03-08 | Semiconductor Energy Lab Co Ltd | 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 |
JP5133259B2 (ja) * | 2006-11-24 | 2013-01-30 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020039708A1 (ja) | 2018-08-23 | 2020-02-27 | 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 |
Also Published As
Publication number | Publication date |
---|---|
US7960566B2 (en) | 2011-06-14 |
CN101723876A (zh) | 2010-06-09 |
CN101723876B (zh) | 2014-12-10 |
US20100099890A1 (en) | 2010-04-22 |
JP5489632B2 (ja) | 2014-05-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6522829B2 (ja) | 合成方法 | |
JP5489632B2 (ja) | 有機化合物、アントラセン誘導体、およびアントラセン誘導体を用いた発光素子、発光装置 | |
JP5738501B1 (ja) | 有機化合物 | |
JP6170203B2 (ja) | 化合物 | |
JP5489633B2 (ja) | 発光素子用材料、発光素子、発光装置 | |
JP5411424B2 (ja) | アントラセン誘導体、及びアントラセン誘導体を用いた発光素子、発光装置、電子機器 | |
JP5830139B2 (ja) | 有機化合物 | |
JP2008106063A (ja) | アントラセン誘導体、およびアントラセン誘導体を用いた発光素子、発光装置、電子機器 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120920 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120920 |
|
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: 20140204 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140225 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5489632 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
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 |
|
LAPS | Cancellation because of no payment of annual fees |