JP2014033195A - 有機化合物、発光素子、発光装置、電子機器及び照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器及び照明装置 Download PDFInfo
- Publication number
- JP2014033195A JP2014033195A JP2013145971A JP2013145971A JP2014033195A JP 2014033195 A JP2014033195 A JP 2014033195A JP 2013145971 A JP2013145971 A JP 2013145971A JP 2013145971 A JP2013145971 A JP 2013145971A JP 2014033195 A JP2014033195 A JP 2014033195A
- Authority
- JP
- Japan
- Prior art keywords
- light
- organic compound
- emitting element
- skeleton
- layer
- 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.)
- Withdrawn
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 184
- 125000000732 arylene group Chemical group 0.000 claims abstract description 24
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 23
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims abstract description 21
- SHWNDUJCIYUZRF-UHFFFAOYSA-N imidazo[1,2-f]phenanthridine Chemical group C1=CC=C2N3C=CN=C3C3=CC=CC=C3C2=C1 SHWNDUJCIYUZRF-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims description 112
- 230000005525 hole transport Effects 0.000 claims description 34
- -1 biphenyldiyl group Chemical group 0.000 claims description 33
- 229910052741 iridium Inorganic materials 0.000 claims description 29
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000002524 organometallic group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 2
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 288
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 238000005401 electroluminescence Methods 0.000 description 59
- 239000000758 substrate Substances 0.000 description 41
- 239000000126 substance Substances 0.000 description 39
- 238000002347 injection Methods 0.000 description 33
- 239000007924 injection Substances 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 28
- 238000000862 absorption spectrum Methods 0.000 description 24
- 230000005284 excitation Effects 0.000 description 23
- 230000003287 optical effect Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000007983 Tris buffer Substances 0.000 description 15
- 238000000295 emission spectrum Methods 0.000 description 15
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000005281 excited state Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000001308 synthesis method Methods 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical group 0.000 description 11
- 239000012046 mixed solvent Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 125000005595 acetylacetonate group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 230000006870 function Effects 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 9
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 9
- 238000012546 transfer Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 238000007789 sealing Methods 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000010453 quartz Substances 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 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 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- HEZMWWAKWCSUCB-PHDIDXHHSA-N (3R,4R)-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylic acid Chemical compound O[C@@H]1C=CC(C(O)=O)=C[C@H]1O HEZMWWAKWCSUCB-PHDIDXHHSA-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
- 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 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 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 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
- PMWOFIVNSBKMRQ-UHFFFAOYSA-N 3h-imidazo[4,5-k]phenanthridine Chemical group C1=CC=C2C3=C(NC=N4)C4=CC=C3C=NC2=C1 PMWOFIVNSBKMRQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QWHJQWGKQJFIFQ-UHFFFAOYSA-N 7-(3-dibenzothiophen-4-ylphenyl)imidazo[1,2-f]phenanthridine Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC(C=2C=C3C4=CC=CC=C4C=4N(C3=CC=2)C=CN=4)=CC=C1 QWHJQWGKQJFIFQ-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 4
- 229910001947 lithium oxide Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 4
- 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 4
- 239000011701 zinc Substances 0.000 description 4
- 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 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910052769 Ytterbium Inorganic materials 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920002620 polyvinyl fluoride Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 3
- 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UOCMXZLNHQBBOS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2o1.Oc1ccccc1-c1nc2ccccc2o1 UOCMXZLNHQBBOS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- AEJARLYXNFRVLK-UHFFFAOYSA-N 4H-1,2,3-triazole Chemical group C1C=NN=N1 AEJARLYXNFRVLK-UHFFFAOYSA-N 0.000 description 2
- WZVQDEHBOSPVCZ-UHFFFAOYSA-N 7-bromoimidazo[1,2-f]phenanthridine Chemical compound C1=CC=C2C3=NC=CN3C3=CC=C(Br)C=C3C2=C1 WZVQDEHBOSPVCZ-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-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
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 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
- 239000002253 acid Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 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
- 229910052796 boron Inorganic materials 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- ADHNFLCTOCFIFV-UHFFFAOYSA-N europium(3+) 1,10-phenanthroline Chemical compound [Eu+3].c1cnc2c(c1)ccc1cccnc21 ADHNFLCTOCFIFV-UHFFFAOYSA-N 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 238000001296 phosphorescence spectrum Methods 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010248 power generation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000002310 reflectometry Methods 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005092 sublimation method Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 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 2
- 229910001930 tungsten oxide Inorganic materials 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005019 vapor deposition process Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- NLOHUARANQHPPJ-UHFFFAOYSA-N (3-dibenzothiophen-4-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C1 NLOHUARANQHPPJ-UHFFFAOYSA-N 0.000 description 1
- AZFHXIBNMPIGOD-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;iridium Chemical compound [Ir].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O AZFHXIBNMPIGOD-LNTINUHCSA-N 0.000 description 1
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- CNSRBJWFPJMRFB-UHFFFAOYSA-N 2,8-diphenyl-4-[4-(9-phenylfluoren-9-yl)phenyl]dibenzothiophene Chemical compound C1=CC=CC=C1C1=CC=C(SC=2C3=CC(=CC=2C=2C=CC(=CC=2)C2(C4=CC=CC=C4C4=CC=CC=C42)C=2C=CC=CC=2)C=2C=CC=CC=2)C3=C1 CNSRBJWFPJMRFB-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
- GJLCPQHEVZERAU-UHFFFAOYSA-N 2-(3-dibenzothiophen-4-ylphenyl)-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C1 GJLCPQHEVZERAU-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
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- WMAXWOOEPJQXEB-UHFFFAOYSA-N 2-phenyl-5-(4-phenylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 WMAXWOOEPJQXEB-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
- 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 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- CUZCTQFIEMXSQG-UHFFFAOYSA-N 4-(2,6-dimethylphenyl)-3-(2-methylphenyl)-5-phenyl-1,2,4-triazole Chemical compound CC1=CC=CC=C1C(N1C=2C(=CC=CC=2C)C)=NN=C1C1=CC=CC=C1 CUZCTQFIEMXSQG-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- OPYUBDQDQKABTN-UHFFFAOYSA-N 4-phenyl-6-[4-(9-phenylfluoren-9-yl)phenyl]dibenzothiophene Chemical compound C1=CC=CC=C1C1=CC=CC2=C1SC1=C(C=3C=CC(=CC=3)C3(C4=CC=CC=C4C4=CC=CC=C43)C=3C=CC=CC=3)C=CC=C12 OPYUBDQDQKABTN-UHFFFAOYSA-N 0.000 description 1
- OKEZAUMKBWTTCR-AATRIKPKSA-N 5-methyl-2-[4-[(e)-2-[4-(5-methyl-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound CC1=CC=C2OC(C3=CC=C(C=C3)/C=C/C3=CC=C(C=C3)C=3OC4=CC=C(C=C4N=3)C)=NC2=C1 OKEZAUMKBWTTCR-AATRIKPKSA-N 0.000 description 1
- ALRSFKVXPVILBX-UHFFFAOYSA-N 7-[3-(3-dibenzothiophen-4-ylphenyl)phenyl]imidazo[1,2-f]phenanthridine Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC(C=2C=CC=C(C=2)C=2C=C3C4=CC=CC=C4C=4N(C3=CC=2)C=CN=4)=CC=C1 ALRSFKVXPVILBX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QUSBGJQBCNEPES-UHFFFAOYSA-N 9,9-dimethyl-n-phenyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=CC=C1 QUSBGJQBCNEPES-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- VUMVABVDHWICAZ-UHFFFAOYSA-N N-phenyl-N-[4-[4-[N-(9,9'-spirobi[fluorene]-2-yl)anilino]phenyl]phenyl]-9,9'-spirobi[fluorene]-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4(C5=CC=CC=C5C5=CC=CC=C54)C4=CC=CC=C4C3=CC=2)C=C1 VUMVABVDHWICAZ-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- YEOIALCFGKWUBD-UHFFFAOYSA-N [3-(3-dibenzothiophen-4-ylphenyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=C(C=CC=2)C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C1 YEOIALCFGKWUBD-UHFFFAOYSA-N 0.000 description 1
- UQTFIXNHFSUCBI-UHFFFAOYSA-K [Ir+3].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-] Chemical compound [Ir+3].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-].CC1(NN(C(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)C)C(=O)[O-] UQTFIXNHFSUCBI-UHFFFAOYSA-K 0.000 description 1
- UUZNAHMBDODUEY-UHFFFAOYSA-K [Ir+3].CC=1N(C(NN1)(C(=O)[O-])C1=CC=CC=C1)C1=CC=CC=C1.CC=1N(C(NN1)(C(=O)[O-])C1=CC=CC=C1)C1=CC=CC=C1.CC=1N(C(NN1)(C(=O)[O-])C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Ir+3].CC=1N(C(NN1)(C(=O)[O-])C1=CC=CC=C1)C1=CC=CC=C1.CC=1N(C(NN1)(C(=O)[O-])C1=CC=CC=C1)C1=CC=CC=C1.CC=1N(C(NN1)(C(=O)[O-])C1=CC=CC=C1)C1=CC=CC=C1 UUZNAHMBDODUEY-UHFFFAOYSA-K 0.000 description 1
- 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 1
- SUFKFXIFMLKZTD-UHFFFAOYSA-N [Tb+3].N1=CC=CC2=CC=C3C=CC=NC3=C12 Chemical compound [Tb+3].N1=CC=CC2=CC=C3C=CC=NC3=C12 SUFKFXIFMLKZTD-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- 150000001543 aryl boronic acids 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
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-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
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical class CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical class C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000012905 input function Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 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
- RLJFAIXYJNBEDX-UHFFFAOYSA-N n-[chloro(phenyl)methylidene]-2-methylbenzenecarbohydrazonoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=NN=C(Cl)C1=CC=CC=C1 RLJFAIXYJNBEDX-UHFFFAOYSA-N 0.000 description 1
- MSCLVLGBAGCXEC-UHFFFAOYSA-N n-phenyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-9,9'-spirobi[fluorene]-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MSCLVLGBAGCXEC-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
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 1
- 150000007530 organic bases 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
- QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000012827 research and development 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
- 239000002356 single layer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 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
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 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 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910001935 vanadium oxide 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
- 239000011787 zinc oxide Substances 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—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
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Abstract
【解決手段】陰極と陽極の間に挟持された発光層を含む発光素子において、発光層は、有機化合物を含み、有機化合物が、イミダゾ[1,2−f]フェナントリジン骨格と、ジベンゾチオフェン骨格またはジベンゾフラン骨格とがアリーレン基を介して結合する。
【選択図】図1
Description
本実施の形態では、陰極と陽極の間に挟持された発光層を含む発光素子について、図1を用いて説明する。
合成スキーム(A−1)に示すように、イミダゾ[1,2−f]フェナントリジン誘導体のハロゲン化物(化合物1)と、ジベンゾチオフェン骨格、又はジベンゾフラン骨格を有するアリールボロン酸エステル、又はアリールボロン酸(化合物2)を、鈴木・宮浦反応によりカップリングさせることで、目的化合物を得ることができる。
本実施の形態では、本発明の一態様である有機化合物と、三重項励起エネルギーを発光に変える発光性材料と、正孔輸送性材料とを発光層に用いた発光素子について、図2(A)及び図2(B)を用いて説明する。
本実施の形態では、本発明の一態様として、電荷発生層を挟んでEL層を複数有する構造の発光素子(以下、タンデム型発光素子という)について説明する。
本実施の形態では、本発明の一態様である発光装置について説明する。
本実施の形態では、本発明の一態様である発光素子を有する発光装置について説明する。
本実施の形態では、上記実施の形態に示す本発明の一態様の発光装置をその一部に含む電子機器について説明する。電子機器としては、ビデオカメラ、デジタルカメラ等のカメラ、ゴーグル型ディスプレイ、ナビゲーションシステム、音響再生装置(カーオーディオ、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、スマートフォン、携帯型ゲーム機、電子書籍、またはタブレット型端末等)、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表示装置を備えた装置)などが挙げられる。これらの電子機器の具体例について、図6、及び図7を用いて説明する。
まず、下記構造式(101)で示す7mDBTPIPt−IIの合成法の一例について説明する。
まず、下記構造式(107)で示す7mDBtBPIPtの合成法の一例について説明する。
まず、基板1100上に、珪素または酸化珪素を含有した酸化インジウム−酸化スズ(ITO−SiO2、以下ITSOと略記する。)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、用いたターゲットの組成は、In2O3:SnO2:SiO2=85:10:5[重量%]とした。また、第1の電極1101の膜厚は、110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極1101は、発光素子の陽極として機能する電極である。
まず、基板1100上に、ITO−SiO2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、用いたターゲットの組成は、In2O3:SnO2:SiO2=85:10:5[重量%]とした。また、第1の電極1101の膜厚は、110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極1101は、発光素子の陽極として機能する電極である。
発光素子3は、発光素子2と同様に作製した。発光素子2の作製と異なる点は、第1の発光層1113aと第2の発光層1113b、および第1の電子輸送層1114aに発光素子2とは異なる化合物を用いた点である。
上記実施例4及び実施例5で用いたIr(mpptz−dmp)3の合成方法について説明する。なお、Ir(mpptz−dmp)3の構造を以下に示す。
まず、N−[1−クロロ−1−(2−メチルフェニル)メチリデン]−N’−[1−クロロ−(1−フェニル)メチリデン]ヒドラジン12.6g(43.3mmol)、2,6−ジメチルアニリン15.7g(134.5mmol)、N,N−ジメチルアニリン100mlを500mlナスフラスコに入れ、120℃で20時間加熱攪拌した。所定時間反応後、この反応溶液を1N塩酸200mlにゆっくり加えた。この溶液にジクロロメタンを加え有機層に目的物を抽出した。得られた有機層を水、炭酸水素ナトリウム水溶液で洗浄し、硫酸マグネシウムで乾燥させた。自然ろ過により硫酸マグネシウムを除去し、得られたろ液を濃縮し、黒色の液体を得た。この液体をシリカゲルカラムクロマトグラフィーにより精製した。展開溶媒は酢酸エチル:ヘキサン=1:5とした。得られたフラクションを濃縮し、白色固体を得た。この固体を酢酸エチルにより再結晶を行い、Hmpptz−dmpの白色固体を4.5g、収率31%で得た。ステップ1の合成スキームを以下に示す。
上記ステップ1で得た配位子Hmpptz−dmp2.5g(7.4mmol)、トリス(アセチルアセトナト)イリジウム(III)0.7g(1.5mmol)を高温加熱容器に入れ、脱気した。この反応容器を、内部をArフローしながら250℃で48時間加熱攪拌した。所定時間反応後、得られた固体をジクロロメタンで洗浄し、不溶物の緑色固体を吸引ろ過により得た。この固体をトルエンに溶解させ、アルミナとセライトの積層を通してろ過した。得られたフラクションを濃縮し、緑色固体を得た。この固体をトルエンで再結晶を行い、燐光性有機金属イリジウム錯体Ir(mpptz−dmp)3の緑色粉末を0.8g、収率45%で得た。ステップ2の合成スキームを以下に示す。
101 第1の電極
102 EL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
115 電子注入層
201 第1の電極
203 第2の電極
210 EL層
213 第1の有機化合物
214 第2の有機化合物
215 第3の有機化合物
221 正孔注入層
222 正孔輸送層
223 発光層
224 電子輸送層
225 電子注入層
301 第1の電極
303 第2の電極
311 第1のEL層
312 第2のEL層
313 電荷発生層
450B 第1の発光素子
450G 第2の発光素子
450R 第3の発光素子
451 反射電極
452 半透過・半反射電極
453a 第1の透明導電層
453b 第2の透明導電層
454 発光層
454B 第1の発光層
454G 第2の発光層
454R 第3の発光層
455 EL層
501 素子基板
502 画素部
503 駆動回路部
504 駆動回路部
505 シール材
506 封止基板
507 配線
508 FPC
509 nチャネル型TFT
510 pチャネル型TFT
511 スイッチング用TFT
512 電流制御用TFT
513 第1の電極
514 絶縁物
515 EL層
516 第2の電極
517 発光素子
518 空間
611 筐体
612 支持台
613 表示部
614 スピーカー部
615 ビデオ入力端子
621 本体
622 筐体
623 表示部
624 キーボード
625 外部接続ポート
626 ポインティングデバイス
631 本体
632 筐体
633 表示部
634 音声入力部
635 音声出力部
636 操作キー
637 外部接続ポート
638 アンテナ
641 本体
642 表示部
643 筐体
644 外部接続ポート
645 リモコン受信部
646 受像部
647 バッテリー
648 音声入力部
649 操作キー
650 接眼部
701 筐体
702 液晶パネル
703 バックライト
704 筐体
705 ドライバIC
706 端子
801 筐体
802 光源
901 照明装置
902 テレビ装置
1100 基板
1101 第1の電極
1103 第2の電極
1111 正孔注入層
1112 正孔輸送層
1113a 第1の発光層
1113b 第2の発光層
1114a 第1の電子輸送層
1114b 第2の電子輸送層
1115 電子注入層
9033 留め具
9034 スイッチ
9035 電源スイッチ
9036 スイッチ
9038 操作スイッチ
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a 領域
9632b 領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9637 コンバータ
9638 操作キー
9639 ボタン
Claims (19)
- 陰極と陽極の間に挟持された発光層を含む発光素子において、
前記発光層は、有機化合物を含み、
前記有機化合物が、イミダゾ[1,2−f]フェナントリジン骨格と、ジベンゾチオフェン骨格またはジベンゾフラン骨格とがアリーレン基を介して結合する
ことを特徴とする発光素子。 - 陰極と陽極の間に挟持された発光層を含む発光素子において、
前記発光層は、第1の有機化合物と、第2の有機化合物とを含み、
前記第1の有機化合物が、イミダゾ[1,2−f]フェナントリジン骨格と、ジベンゾチオフェン骨格またはジベンゾフラン骨格とがアリーレン基を介して結合し、
前記第2の有機化合物が、有機金属イリジウム錯体である
ことを特徴とする発光素子。 - 陰極と陽極の間に挟持された発光層を含む発光素子において、
前記発光層は、第1の有機化合物と、第2の有機化合物と、第3の有機化合物とを含み、
前記第1の有機化合物が、イミダゾ[1,2−f]フェナントリジン骨格と、ジベンゾチオフェン骨格またはジベンゾフラン骨格とがアリーレン基を介して結合し、
前記第2の有機化合物が、有機金属イリジウム錯体であり、
前記第3の有機化合物が、アミン骨格を含まない正孔輸送性材料である
ことを特徴とする発光素子。 - 請求項1乃至請求項3のいずれか一において、
前記陰極側の前記発光層に接して電子輸送層を、含み、
前記電子輸送層が、前記有機化合物または前記第1の有機化合物を含む
ことを特徴とする発光素子。 - 請求項1乃至請求項3のいずれか一において、
前記陽極側の前記発光層に接して正孔輸送層を、含み、
前記正孔輸送層が、アミン骨格を含まない正孔輸送性材料である
ことを特徴とする発光素子。 - 請求項5において、
前記正孔輸送層が、カルバゾール骨格を含む
ことを特徴とする発光素子。 - 請求項1乃至請求項6のずれか一において、
前記ジベンゾチオフェン骨格または前記ジベンゾフラン骨格の4位が前記アリーレン基に結合する
ことを特徴とする発光素子。 - 前記請求項1乃至請求項7のいずれか一において、
前記イミダゾ[1,2−f]フェナントリジン骨格の7位が前記アリーレン基に結合する
ことを特徴とする発光素子。 - 陰極と陽極の間に挟持された発光層を含む発光素子において、
前記発光層は、有機化合物を含み、
前記有機化合物が、一般式(G1)で表される
ことを特徴とする発光素子。
(式中、R1〜R9及びR21〜R27は、それぞれ独立に、水素、炭素数1〜4のアルキル基、または炭素数6〜13の置換もしくは無置換のアリール基を表す。また、Arは、炭素数6〜13の置換または無置換のアリーレン基を表す。また、Zは硫黄原子または酸素原子を表す。) - 請求項9において、
前記Arが、置換または無置換のフェニレン基、あるいは置換または無置換のビフェニルジイル基である
ことを特徴とする発光素子。 - 請求項9または請求項10において、
前記Arが、置換または無置換のm−フェニレン基である
ことを特徴とする発光素子。 - 陰極と陽極の間に挟持された発光層を含む発光素子において、
前記発光層は、有機化合物を含み、
前記有機化合物が、一般式(G2)で表される
ことを特徴とする発光素子。
(式中、R1〜R9、R11〜R14及びR21〜R27は、それぞれ独立に、水素、炭素数1〜4のアルキル基、または炭素数6〜13の置換もしくは無置換のアリール基を表す。また、Zは硫黄原子または酸素原子を表す。) - 請求項1乃至請求項12のいずれか一に記載の発光素子を用いた発光装置。
- 請求項13に記載の発光装置を用いた電子機器。
- 請求項13に記載の発光装置を用いた照明装置。
- 一般式(G1)で表されることを特徴とする有機化合物。
(式中、R1〜R9及びR21〜R27は、それぞれ独立に、水素、炭素数1〜4のアルキル基、または炭素数6〜13の置換もしくは無置換のアリール基を表す。また、Arは、炭素数6〜13の置換または無置換のアリーレン基を表す。また、Zは硫黄原子または酸素原子を表す。) - 請求項16において、前記Arが、置換または無置換のフェニレン基、あるいは置換または無置換のビフェニルジイル基である
ことを特徴とする有機化合物。 - 請求項16または請求項17において、
前記Arが、置換または無置換のm−フェニレン基である
ことを特徴とする有機化合物。 - 一般式(G2)で表されることを特徴とする有機化合物。
(式中、R1〜R9、R11〜R14及びR21〜R27は、それぞれ独立に、水素、炭素数1〜4のアルキル基、または炭素数6〜13の置換もしくは無置換のアリール基を表す。また、Zは硫黄原子または酸素原子を表す。)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013145971A JP2014033195A (ja) | 2012-07-13 | 2013-07-12 | 有機化合物、発光素子、発光装置、電子機器及び照明装置 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012157602 | 2012-07-13 | ||
JP2012157602 | 2012-07-13 | ||
JP2013145971A JP2014033195A (ja) | 2012-07-13 | 2013-07-12 | 有機化合物、発光素子、発光装置、電子機器及び照明装置 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018033458A Division JP6547021B2 (ja) | 2012-07-13 | 2018-02-27 | 有機化合物、発光素子、発光装置、電子機器及び照明装置 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2014033195A true JP2014033195A (ja) | 2014-02-20 |
Family
ID=49913204
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013145971A Withdrawn JP2014033195A (ja) | 2012-07-13 | 2013-07-12 | 有機化合物、発光素子、発光装置、電子機器及び照明装置 |
JP2018033458A Active JP6547021B2 (ja) | 2012-07-13 | 2018-02-27 | 有機化合物、発光素子、発光装置、電子機器及び照明装置 |
JP2019116327A Active JP6817376B2 (ja) | 2012-07-13 | 2019-06-24 | 発光素子、発光装置、電子機器および照明装置 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018033458A Active JP6547021B2 (ja) | 2012-07-13 | 2018-02-27 | 有機化合物、発光素子、発光装置、電子機器及び照明装置 |
JP2019116327A Active JP6817376B2 (ja) | 2012-07-13 | 2019-06-24 | 発光素子、発光装置、電子機器および照明装置 |
Country Status (2)
Country | Link |
---|---|
US (2) | US20140014930A1 (ja) |
JP (3) | JP2014033195A (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020009536A (ja) * | 2018-07-03 | 2020-01-16 | キヤノン株式会社 | 白色有機発光素子 |
KR20230098192A (ko) | 2020-10-30 | 2023-07-03 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 캐리어 수송용 재료, 호스트용 재료, 발광 디바이스, 발광 장치, 전자 기기, 및 조명 장치 |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140014930A1 (en) | 2012-07-13 | 2014-01-16 | Semiconductor Energy Laboratory Co., Ltd. | Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
TWI638472B (zh) | 2012-08-03 | 2018-10-11 | 日商半導體能源研究所股份有限公司 | 發光元件 |
US20140316841A1 (en) * | 2013-04-23 | 2014-10-23 | Kofax, Inc. | Location-based workflows and services |
US10043982B2 (en) | 2013-04-26 | 2018-08-07 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, display device, electronic device, and lighting device |
US9231217B2 (en) | 2013-11-28 | 2016-01-05 | Semiconductor Energy Laboratory Co., Ltd. | Synthesis method of organometallic complex, synthesis method of pyrazine derivative, 5,6-diaryl-2-pyrazyl triflate, light-emitting element, light-emitting device, electronic device, and lighting device |
KR102523989B1 (ko) | 2013-12-02 | 2023-04-21 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
US10403830B2 (en) | 2014-05-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10301338B2 (en) | 2014-05-08 | 2019-05-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10636983B2 (en) | 2014-05-08 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3140871B1 (en) | 2014-05-08 | 2018-12-26 | Universal Display Corporation | Stabilized imidazophenanthridine materials |
US20160104855A1 (en) | 2014-10-10 | 2016-04-14 | Semiconductor Energy Laboratory Co., Ltd. | Light-Emitting Element, Display Device, Electronic Device, and Lighting Device |
US10635907B2 (en) * | 2015-01-13 | 2020-04-28 | Vivint, Inc. | Enhanced doorbell camera interactions |
KR101706752B1 (ko) * | 2015-02-17 | 2017-02-27 | 서울대학교산학협력단 | 호스트, 인광 도펀트 및 형광 도펀트를 포함하는 유기발광소자 |
TWI737594B (zh) * | 2015-03-09 | 2021-09-01 | 日商半導體能源研究所股份有限公司 | 發光元件,顯示裝置,電子裝置,與照明裝置 |
TWI704706B (zh) | 2015-03-09 | 2020-09-11 | 日商半導體能源研究所股份有限公司 | 發光元件、顯示裝置、電子裝置及照明設置 |
EP3680948A3 (en) * | 2015-08-21 | 2020-10-21 | Samsung Display Co., Ltd. | Organic light-emitting device |
WO2019171197A1 (ja) | 2018-03-07 | 2019-09-12 | 株式会社半導体エネルギー研究所 | 発光素子、表示装置、電子機器、有機化合物及び照明装置 |
CN113412508A (zh) | 2019-02-06 | 2021-09-17 | 株式会社半导体能源研究所 | 发光器件、发光设备、显示装置、电子设备及照明装置 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010215759A (ja) * | 2009-03-16 | 2010-09-30 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料 |
JP2010267847A (ja) * | 2009-05-15 | 2010-11-25 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
US20120025697A1 (en) * | 2010-08-02 | 2012-02-02 | Semiconductor Energy Laboratory Co., Ltd. | Triazole Derivative, Heterocyclic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device and Lighting Device |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6939624B2 (en) * | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
CN101355141B (zh) * | 2001-06-15 | 2012-02-29 | 佳能株式会社 | 有机电致发光元件 |
US6869695B2 (en) * | 2001-12-28 | 2005-03-22 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
ITBO20020165A1 (it) * | 2002-03-29 | 2003-09-29 | Consiglio Nazionale Ricerche | Dispositivo elettroluminescente organico con droganti cromofori |
KR100713989B1 (ko) * | 2005-07-15 | 2007-05-04 | 삼성에스디아이 주식회사 | 백색 유기 발광 소자 및 그의 제조방법 |
KR102103062B1 (ko) * | 2006-02-10 | 2020-04-22 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-f]페난트리딘 및 디이미다조[1,2-a:1',2'-c]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
JP6009144B2 (ja) * | 2007-08-08 | 2016-10-19 | ユニバーサル ディスプレイ コーポレイション | トリフェニレン基を含むベンゾ縮合チオフェンまたはベンゾ縮合フラン化合物 |
US8815411B2 (en) * | 2007-11-09 | 2014-08-26 | The Regents Of The University Of Michigan | Stable blue phosphorescent organic light emitting devices |
JP2009267255A (ja) * | 2008-04-28 | 2009-11-12 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
EP2570412B1 (en) | 2008-11-03 | 2017-01-04 | LG Chem, Ltd. | Novel nitrogen-containing heterocyclic compound and organic electronic device using the same |
TWI620747B (zh) * | 2010-03-01 | 2018-04-11 | 半導體能源研究所股份有限公司 | 雜環化合物及發光裝置 |
WO2012111680A1 (en) | 2011-02-16 | 2012-08-23 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting body, light-emitting layer, and light-emitting device |
KR102136426B1 (ko) | 2011-02-16 | 2020-07-21 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 엘리먼트 |
KR102345510B1 (ko) | 2011-02-16 | 2021-12-31 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자 |
KR102112967B1 (ko) | 2011-03-23 | 2020-05-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자 |
KR102479832B1 (ko) | 2011-04-07 | 2022-12-22 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자 |
EP2730634B1 (en) | 2011-07-08 | 2019-10-09 | LG Chem, Ltd. | Novel compound and organic electronic device using same |
US20140014930A1 (en) * | 2012-07-13 | 2014-01-16 | Semiconductor Energy Laboratory Co., Ltd. | Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
-
2013
- 2013-07-11 US US13/939,768 patent/US20140014930A1/en not_active Abandoned
- 2013-07-12 JP JP2013145971A patent/JP2014033195A/ja not_active Withdrawn
-
2018
- 2018-02-27 JP JP2018033458A patent/JP6547021B2/ja active Active
-
2019
- 2019-06-24 JP JP2019116327A patent/JP6817376B2/ja active Active
- 2019-09-17 US US16/573,475 patent/US11910710B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010215759A (ja) * | 2009-03-16 | 2010-09-30 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料 |
JP2010267847A (ja) * | 2009-05-15 | 2010-11-25 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
US20120025697A1 (en) * | 2010-08-02 | 2012-02-02 | Semiconductor Energy Laboratory Co., Ltd. | Triazole Derivative, Heterocyclic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device and Lighting Device |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020009536A (ja) * | 2018-07-03 | 2020-01-16 | キヤノン株式会社 | 白色有機発光素子 |
JP7224796B2 (ja) | 2018-07-03 | 2023-02-20 | キヤノン株式会社 | 白色有機発光素子 |
KR20230098192A (ko) | 2020-10-30 | 2023-07-03 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 캐리어 수송용 재료, 호스트용 재료, 발광 디바이스, 발광 장치, 전자 기기, 및 조명 장치 |
Also Published As
Publication number | Publication date |
---|---|
US11910710B2 (en) | 2024-02-20 |
US20140014930A1 (en) | 2014-01-16 |
US20200013966A1 (en) | 2020-01-09 |
JP6817376B2 (ja) | 2021-01-20 |
JP2018129517A (ja) | 2018-08-16 |
JP2019176179A (ja) | 2019-10-10 |
JP6547021B2 (ja) | 2019-07-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6817376B2 (ja) | 発光素子、発光装置、電子機器および照明装置 | |
JP6266822B2 (ja) | 発光素子 | |
JP6598906B2 (ja) | 有機化合物 | |
TWI490211B (zh) | 有機金屬錯合物,發光元件,發光裝置,電子裝置及照明裝置 | |
JP5982321B2 (ja) | 発光素子、発光装置、電子機器、および照明装置 | |
TWI667818B (zh) | 發光元件、發光裝置、電子裝置以及照明設備 | |
JP6017368B2 (ja) | 発光素子、発光装置、電子機器、および照明装置 | |
JP6312368B2 (ja) | 有機化合物、発光素子、発光装置、電子機器及び照明装置 | |
JP6147993B2 (ja) | 発光素子、発光装置、電子機器、照明装置、及び有機化合物 | |
JP6407561B2 (ja) | 有機金属錯体、発光素子、発光装置、電子機器、及び照明装置 | |
JP6189090B2 (ja) | 有機材料の製造方法、発光素子の製造方法、発光装置の製造方法及び照明装置の製造方法 | |
WO2019097361A1 (ja) | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160623 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20170518 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170530 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170713 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20171205 |
|
A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20180228 |