JP7354100B2 - 有機化合物、発光素子、発光装置、電子機器、および照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器、および照明装置 Download PDFInfo
- Publication number
- JP7354100B2 JP7354100B2 JP2020521634A JP2020521634A JP7354100B2 JP 7354100 B2 JP7354100 B2 JP 7354100B2 JP 2020521634 A JP2020521634 A JP 2020521634A JP 2020521634 A JP2020521634 A JP 2020521634A JP 7354100 B2 JP7354100 B2 JP 7354100B2
- Authority
- JP
- Japan
- Prior art keywords
- light emitting
- light
- abbreviation
- emitting element
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000002894 organic compounds Chemical class 0.000 title claims description 133
- 239000000463 material Substances 0.000 claims description 153
- 239000000758 substrate Substances 0.000 claims description 102
- 125000004432 carbon atom Chemical group C* 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003367 polycyclic group Chemical group 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- 125000002950 monocyclic group Chemical group 0.000 claims description 18
- 229910052717 sulfur Chemical group 0.000 claims description 18
- 239000011593 sulfur Chemical group 0.000 claims description 18
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 290
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
- -1 1-methylcyclohexyl group Chemical group 0.000 description 66
- 230000000052 comparative effect Effects 0.000 description 66
- 239000000126 substance Substances 0.000 description 66
- 239000007787 solid Substances 0.000 description 56
- 239000000203 mixture Substances 0.000 description 50
- 238000002347 injection Methods 0.000 description 48
- 239000007924 injection Substances 0.000 description 48
- 238000000034 method Methods 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 38
- 230000032258 transport Effects 0.000 description 37
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 33
- ITOKSWHFPQBNSE-UHFFFAOYSA-N [1]benzofuro[3,2-d]pyrimidine Chemical class N1=CN=C2C3=CC=CC=C3OC2=C1 ITOKSWHFPQBNSE-UHFFFAOYSA-N 0.000 description 31
- 238000010586 diagram Methods 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 238000000295 emission spectrum Methods 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000010408 film Substances 0.000 description 25
- 230000005525 hole transport Effects 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000007983 Tris buffer Substances 0.000 description 21
- OICJTSLHQGDCTQ-UHFFFAOYSA-N [1]benzothiolo[3,2-d]pyrimidine Chemical class N1=CN=C2C3=CC=CC=C3SC2=C1 OICJTSLHQGDCTQ-UHFFFAOYSA-N 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000000859 sublimation Methods 0.000 description 18
- 230000008022 sublimation Effects 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000004065 semiconductor Substances 0.000 description 17
- 230000005281 excited state Effects 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 14
- 239000010409 thin film Substances 0.000 description 14
- 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 14
- 125000005595 acetylacetonate group Chemical group 0.000 description 13
- HXITXNWTGFUOAU-UHFFFAOYSA-N dihydroxy-phenylborane Natural products OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 13
- 239000011159 matrix material Substances 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 12
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 12
- 230000005284 excitation Effects 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 11
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[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.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 10
- 239000000370 acceptor Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000007789 sealing Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- 230000006866 deterioration Effects 0.000 description 9
- ZQASITYRQOCACA-UHFFFAOYSA-N dicyclohexyl-[2-(2-methyl-1,3-dioxolan-2-yl)phenyl]phosphane Chemical compound C=1C=CC=C(P(C2CCCCC2)C2CCCCC2)C=1C1(C)OCCO1 ZQASITYRQOCACA-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 9
- 239000000565 sealant Substances 0.000 description 9
- 238000007740 vapor deposition Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 150000004982 aromatic amines Chemical class 0.000 description 8
- 238000004891 communication Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 125000002524 organometallic group Chemical class 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 8
- 238000007738 vacuum evaporation Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- 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 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 229910052741 iridium Inorganic materials 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 125000005580 triphenylene group Chemical group 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910008449 SnF 2 Inorganic materials 0.000 description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 6
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 6
- 239000002096 quantum dot Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000003566 sealing material Substances 0.000 description 6
- 238000005092 sublimation method Methods 0.000 description 6
- 125000006617 triphenylamine group Chemical group 0.000 description 6
- 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 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 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 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000012212 insulator Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000003252 quinoxalines Chemical class 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 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 4
- 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 4
- 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 4
- 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 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 4
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 150000002366 halogen compounds Chemical class 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 150000003220 pyrenes Chemical class 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 4
- 150000003230 pyrimidines Chemical class 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- 239000010937 tungsten Substances 0.000 description 4
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 4
- 239000011701 zinc Substances 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
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 3
- QVSJCRDHNCCXFC-UHFFFAOYSA-N 3-[9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]carbazol-3-yl]-9-phenylcarbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC(=CC=2)N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)=N1 QVSJCRDHNCCXFC-UHFFFAOYSA-N 0.000 description 3
- JGFSUSSEDMCHLG-UHFFFAOYSA-N 4-chloro-8-phenyl-[1]benzofuro[3,2-d]pyrimidine Chemical compound ClC=1C2=C(N=CN=1)C1=C(O2)C=CC(=C1)C1=CC=CC=C1 JGFSUSSEDMCHLG-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052769 Ytterbium Inorganic materials 0.000 description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 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
- 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
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001556 benzimidazoles Chemical class 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
- 238000010549 co-Evaporation Methods 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002390 heteroarenes Chemical class 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 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 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 150000005041 phenanthrolines Chemical class 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 229920002620 polyvinyl fluoride Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 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
- 238000004544 sputter deposition Methods 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical class ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Chemical class 0.000 description 3
- 229910001930 tungsten oxide Inorganic materials 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
- 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 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
- NYPMWIHVZGWERR-UHFFFAOYSA-N 10-(3-dibenzothiophen-4-ylphenyl)phenanthro[9,10-b]pyrazine Chemical compound C1=C2C3=CC=CC=C3C3=NC=CN=C3C2=CC=C1C1=CC(C2=C3SC=4C(C3=CC=C2)=CC=CC=4)=CC=C1 NYPMWIHVZGWERR-UHFFFAOYSA-N 0.000 description 2
- ZABORCXHTNWZRV-UHFFFAOYSA-N 10-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]phenoxazine Chemical compound O1C2=CC=CC=C2N(C2=CC=C(C=C2)C2=NC(=NC(=N2)C2=CC=CC=C2)C2=CC=CC=C2)C2=C1C=CC=C2 ZABORCXHTNWZRV-UHFFFAOYSA-N 0.000 description 2
- ASXSTQHYXCIZRV-UHFFFAOYSA-N 10-phenylspiro[acridine-9,10'-anthracene]-9'-one Chemical group C12=CC=CC=C2C(=O)C2=CC=CC=C2C1(C1=CC=CC=C11)C2=CC=CC=C2N1C1=CC=CC=C1 ASXSTQHYXCIZRV-UHFFFAOYSA-N 0.000 description 2
- HLHAHILPKRWJRV-UHFFFAOYSA-N 2,4,8-trichloro-[1]benzofuro[3,2-d]pyrimidine Chemical compound N1=C(Cl)N=C2C3=CC(Cl)=CC=C3OC2=C1Cl HLHAHILPKRWJRV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- XANIFASCQKHXRC-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2s1.Oc1ccccc1-c1nc2ccccc2s1 XANIFASCQKHXRC-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
- VCZWXBZWLXSLOZ-UHFFFAOYSA-N 2-hydroxy-5-phenylbenzonitrile Chemical compound C1=C(C#N)C(O)=CC=C1C1=CC=CC=C1 VCZWXBZWLXSLOZ-UHFFFAOYSA-N 0.000 description 2
- MKAQNAJLIITRHR-UHFFFAOYSA-N 3-(3-dibenzothiophen-4-ylphenyl)phenanthro[9,10-b]pyrazine Chemical compound C1=CC=C2C3=NC(C=4C=CC=C(C=4)C4=C5SC=6C(C5=CC=C4)=CC=CC=6)=CN=C3C3=CC=CC=C3C2=C1 MKAQNAJLIITRHR-UHFFFAOYSA-N 0.000 description 2
- WAJDLGKOJABKAN-UHFFFAOYSA-N 3-(4-naphthalen-1-ylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 WAJDLGKOJABKAN-UHFFFAOYSA-N 0.000 description 2
- FTZXDZQJFKXEGW-UHFFFAOYSA-N 3-(9,9-dimethylacridin-10-yl)xanthen-9-one Chemical compound C12=CC=CC=C2C(C)(C)C2=CC=CC=C2N1C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 FTZXDZQJFKXEGW-UHFFFAOYSA-N 0.000 description 2
- PUMOFXXLEABBTC-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9h-carbazole Chemical class C1=CC=C2C3=CC(C4=CC=C5NC=6C(C5=C4)=CC=CC=6)=CC=C3NC2=C1 PUMOFXXLEABBTC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PCUTZMWETFJZDZ-UHFFFAOYSA-N 3-[3-(3-carbazol-9-ylphenyl)phenyl]phenanthro[9,10-b]pyrazine Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)C=2N=C3C4=CC=CC=C4C4=CC=CC=C4C3=NC=2)=CC=C1 PCUTZMWETFJZDZ-UHFFFAOYSA-N 0.000 description 2
- MFWOWURWNZHYLA-UHFFFAOYSA-N 3-[3-(3-dibenzothiophen-4-ylphenyl)phenyl]phenanthro[9,10-b]pyrazine Chemical compound C1=CC=C2C3=NC(C=4C=CC=C(C=4)C=4C=CC=C(C=4)C4=C5SC=6C(C5=CC=C4)=CC=CC=6)=CN=C3C3=CC=CC=C3C2=C1 MFWOWURWNZHYLA-UHFFFAOYSA-N 0.000 description 2
- IHPRFEGMZFFUMH-UHFFFAOYSA-N 3-[4-(3,6-diphenylcarbazol-9-yl)phenyl]phenanthro[9,10-b]pyrazine Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2N=C3C4=CC=CC=C4C4=CC=CC=C4C3=NC=2)C=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 IHPRFEGMZFFUMH-UHFFFAOYSA-N 0.000 description 2
- ALEAISKRDWWJRK-UHFFFAOYSA-N 4,6-bis(3-dibenzothiophen-4-ylphenyl)pyrimidine Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC(C=2C=C(N=CN=2)C=2C=CC=C(C=2)C2=C3SC=4C(C3=CC=C2)=CC=CC=4)=CC=C1 ALEAISKRDWWJRK-UHFFFAOYSA-N 0.000 description 2
- DGVHCUNJUVMAKG-UHFFFAOYSA-N 4,6-bis(3-phenanthren-9-ylphenyl)pyrimidine Chemical compound C1=CC=C2C(C=3C=CC=C(C=3)C=3C=C(N=CN=3)C=3C=CC=C(C=3)C=3C4=CC=CC=C4C4=CC=CC=C4C=3)=CC3=CC=CC=C3C2=C1 DGVHCUNJUVMAKG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MBWBBPGBJFUUMC-UHFFFAOYSA-N 4-(3-dibenzothiophen-4-ylphenyl)-8-phenyl-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C(C=2SC3=C(C21)C=CC=C3)C=3C=C(C=CC3)C=3C2=C(N=CN3)C3=C(O2)C=CC(=C3)C3=CC=CC=C3 MBWBBPGBJFUUMC-UHFFFAOYSA-N 0.000 description 2
- SMAJQIMJGFHCCR-UHFFFAOYSA-N 4-[3,5-di(dibenzothiophen-4-yl)phenyl]dibenzothiophene Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=CC(C2=C3SC=4C(C3=CC=C2)=CC=CC=4)=C1 SMAJQIMJGFHCCR-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- CRHRWHRNQKPUPO-UHFFFAOYSA-N 4-n-naphthalen-1-yl-1-n,1-n-bis[4-(n-naphthalen-1-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 CRHRWHRNQKPUPO-UHFFFAOYSA-N 0.000 description 2
- UZNZNHYEKOEABY-UHFFFAOYSA-N 8-chloro-2,4-di(dibenzofuran-4-yl)-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C(C=2OC3=C(C=21)C=CC=C3)C=1N=C(C2=C(N=1)C1=C(O2)C=CC(=C1)Cl)C1=CC=CC2=C1OC1=C2C=CC=C1 UZNZNHYEKOEABY-UHFFFAOYSA-N 0.000 description 2
- PPSSWKFADZFOAK-UHFFFAOYSA-N 8-chloro-4-[3-(3-dibenzothiophen-4-ylphenyl)phenyl]-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=C2SC3=C(C4=CC(C5=CC(C6=NC=NC7=C6OC6=C7C=C(Cl)C=C6)=CC=C5)=CC=C4)C=CC=C3C2=CC=C1 PPSSWKFADZFOAK-UHFFFAOYSA-N 0.000 description 2
- GFILKYYGHIQJSF-UHFFFAOYSA-N 8-dibenzothiophen-4-yl-4-[3-(3-dibenzothiophen-4-ylphenyl)phenyl]-[1]benzofuro[3,2-d]pyrimidine Chemical compound O1C2=CC=C(C=C2C2=C1C(=NC=N2)C1=CC=CC(=C1)C1=CC=CC(=C1)C1=CC=CC2=C1SC1=C2C=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 GFILKYYGHIQJSF-UHFFFAOYSA-N 0.000 description 2
- NQSPKOIKJXTLOP-UHFFFAOYSA-N 8-phenyl-3H-[1]benzofuro[3,2-d]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C=1C=CC2=C(C=1)C=1N=CNC(C=1O2)=O NQSPKOIKJXTLOP-UHFFFAOYSA-N 0.000 description 2
- VDHOGVHFPFGPIP-UHFFFAOYSA-N 9-[3-[5-(3-carbazol-9-ylphenyl)pyridin-3-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=NC=C(C=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 VDHOGVHFPFGPIP-UHFFFAOYSA-N 0.000 description 2
- LNNMKLNCLINVKV-UHFFFAOYSA-N 9-[3-[6-(3-carbazol-9-ylphenyl)pyrimidin-4-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=C(N=CN=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 LNNMKLNCLINVKV-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- 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 group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HTJWUNNIRKDDIV-UHFFFAOYSA-N bis(1-adamantyl)-butylphosphane Chemical compound C1C(C2)CC(C3)CC2CC13P(CCCC)C1(C2)CC(C3)CC2CC3C1 HTJWUNNIRKDDIV-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
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- YMKWUIWQLPMOHF-UHFFFAOYSA-N ethyl 3-amino-5-phenyl-1-benzofuran-2-carboxylate Chemical compound NC=1C2=C(OC=1C(=O)OCC)C=CC(=C2)C1=CC=CC=C1 YMKWUIWQLPMOHF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 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
- 230000005389 magnetism Effects 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 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 2
- 229910000484 niobium oxide Inorganic materials 0.000 description 2
- 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 2
- 125000002971 oxazolyl group Chemical class 0.000 description 2
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 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 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 150000002987 phenanthrenes Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 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
- 230000000704 physical effect Effects 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 2
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910003449 rhenium oxide Inorganic materials 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 229910001936 tantalum oxide Inorganic materials 0.000 description 2
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000012546 transfer Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- UPWZWQGQRNPKTE-UHFFFAOYSA-N 1,2,3-trimethylidenecyclopropane Chemical class C=C1C(=C)C1=C UPWZWQGQRNPKTE-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
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- VRHPTNPRFKGMEH-UHFFFAOYSA-N 1-N,3-N,5-N-triphenyl-1-N,3-N,5-N-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC(N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)=CC(N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)=C1 VRHPTNPRFKGMEH-UHFFFAOYSA-N 0.000 description 1
- XFDYBCQHRPMIGD-UHFFFAOYSA-N 1-N,6-N-bis(3-methylphenyl)-1-N,6-N-bis[3-(9-phenylfluoren-9-yl)phenyl]pyrene-1,6-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=2C3=CC=C4C=CC(=C5C=CC(C3=C54)=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)=C1 XFDYBCQHRPMIGD-UHFFFAOYSA-N 0.000 description 1
- IPNLBJDLLBQZDZ-UHFFFAOYSA-N 1-N,6-N-diphenyl-1-N,6-N-bis[4-(9-phenylfluoren-9-yl)phenyl]pyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC=CC=1)C1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=C1 IPNLBJDLLBQZDZ-UHFFFAOYSA-N 0.000 description 1
- NXVCHTPHKWNQBW-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-(9,9'-spirobi[fluorene]-2-yl)benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 NXVCHTPHKWNQBW-UHFFFAOYSA-N 0.000 description 1
- QXPAPGDQRWESTP-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-(9-phenylcarbazol-3-yl)benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=CC=C1 QXPAPGDQRWESTP-UHFFFAOYSA-N 0.000 description 1
- JYLIWIHHHFIIJG-UHFFFAOYSA-N 1-n,3-n-diphenyl-1-n,3-n-bis(9-phenylcarbazol-3-yl)benzene-1,3-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=CC(N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)=C1 JYLIWIHHHFIIJG-UHFFFAOYSA-N 0.000 description 1
- FQNVFRPAQRVHKO-UHFFFAOYSA-N 1-n,4-n-bis(4-methylphenyl)-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(C)=CC=1)C1=CC=CC=C1 FQNVFRPAQRVHKO-UHFFFAOYSA-N 0.000 description 1
- JMOPQSRRTXUCQF-UHFFFAOYSA-N 1-n,6-n-di(dibenzofuran-2-yl)-1-n,6-n-diphenylpyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3=CC=CC=C3OC2=CC=1)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 JMOPQSRRTXUCQF-UHFFFAOYSA-N 0.000 description 1
- LFDCLPOBNOSPME-UHFFFAOYSA-N 1-n,6-n-di(dibenzothiophen-2-yl)-1-n,6-n-diphenylpyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3=CC=CC=C3SC2=CC=1)C1=CC=C(SC=2C3=CC=CC=2)C3=C1 LFDCLPOBNOSPME-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- CYPVTICNYNXTQP-UHFFFAOYSA-N 10-[4-[4-(9,9-dimethylacridin-10-yl)phenyl]sulfonylphenyl]-9,9-dimethylacridine Chemical compound C12=CC=CC=C2C(C)(C)C2=CC=CC=C2N1C1=CC=C(S(=O)(=O)C=2C=CC(=CC=2)N2C3=CC=CC=C3C(C)(C)C3=CC=CC=C32)C=C1 CYPVTICNYNXTQP-UHFFFAOYSA-N 0.000 description 1
- WAZCYXLGIFUKPS-UHFFFAOYSA-N 11-phenyl-12-[4-(11-phenylindolo[2,3-a]carbazol-12-yl)-6-(4-phenylphenyl)-1,3,5-triazin-2-yl]indolo[2,3-a]carbazole Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=C(N=C(N=2)N2C3=C4N(C=5C=CC=CC=5)C5=CC=CC=C5C4=CC=C3C3=CC=CC=C32)N2C3=C4N(C=5C=CC=CC=5)C5=CC=CC=C5C4=CC=C3C3=CC=CC=C32)C=C1 WAZCYXLGIFUKPS-UHFFFAOYSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical class [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- HQYLCTWBSBBHPN-UHFFFAOYSA-N 2,3-bis[4-(10-phenylanthracen-9-yl)phenyl]-6-pyridin-2-ylpyridine Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C(=NC(=CC=2)C=2N=CC=CC=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 HQYLCTWBSBBHPN-UHFFFAOYSA-N 0.000 description 1
- XXPNWFWBNCOYIN-UHFFFAOYSA-N 2,4-di(dibenzofuran-4-yl)-8-phenyl-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C(C=2OC3=C(C=21)C=CC=C3)C=1N=C(C2=C(N=1)C1=C(O2)C=CC(=C1)C1=CC=CC=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 XXPNWFWBNCOYIN-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- KGEXHQQDTHHXQA-UHFFFAOYSA-N 2,8-dichloro-4-[3-(3-dibenzothiophen-4-ylphenyl)phenyl]-[1]benzofuro[3,2-d]pyrimidine Chemical compound ClC=1N=C(C2=C(N=1)C1=C(O2)C=CC(=C1)Cl)C=1C=C(C=CC=1)C1=CC(=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 KGEXHQQDTHHXQA-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
- YDNOJUAQBFXZCR-UHFFFAOYSA-N 2-(2,3,4,5,6-pentafluorophenyl)acetonitrile Chemical compound FC1=C(F)C(F)=C(CC#N)C(F)=C1F YDNOJUAQBFXZCR-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
- UWANKHHZZKHIMI-UHFFFAOYSA-N 2-(3-dibenzothiophen-4-ylphenyl)-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C(C=2SC3=C(C21)C=CC=C3)C=3C=C(C=CC3)C=3N=CC2=C(N3)C3=C(O2)C=CC=C3 UWANKHHZZKHIMI-UHFFFAOYSA-N 0.000 description 1
- IZJOTDOLRQTPHC-UHFFFAOYSA-N 2-(4-carbazol-9-ylphenyl)-5-phenyl-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)O1 IZJOTDOLRQTPHC-UHFFFAOYSA-N 0.000 description 1
- PJEQASXKXVZLEK-UHFFFAOYSA-N 2-N',7-N'-diphenyl-2-N',7-N'-bis[4-(N-phenylanilino)phenyl]-9,9'-spirobi[fluorene]-2',7'-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC(=CC=C3C2=CC=1)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 PJEQASXKXVZLEK-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- TUMRGNWURXLFBN-UHFFFAOYSA-N 2-n,7-n-bis(4-carbazol-9-ylphenyl)-9,9-dimethyl-2-n,7-n-diphenylfluorene-2,7-diamine Chemical compound C1=C2C(C)(C)C3=CC(N(C=4C=CC=CC=4)C=4C=CC(=CC=4)N4C5=CC=CC=C5C5=CC=CC=C54)=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 TUMRGNWURXLFBN-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- GWHSOUPRKHXZPK-UHFFFAOYSA-N 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=C3C4=CC(=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=2C=C(C=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GWHSOUPRKHXZPK-UHFFFAOYSA-N 0.000 description 1
- 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
- WQRYZOAFWABMBD-UHFFFAOYSA-N 3-(4-phenanthren-9-ylphenyl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C4=CC=CC=C4C=3)C=C2C2=CC=CC=C21 WQRYZOAFWABMBD-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
- NRELWBPPAKVJAI-UHFFFAOYSA-N 3-(9-naphthalen-2-ylcarbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5N(C=5C=C6C=CC=CC6=CC=5)C4=CC=3)C=C2C2=CC=CC=C21 NRELWBPPAKVJAI-UHFFFAOYSA-N 0.000 description 1
- QIEWTACDLJLBTE-UHFFFAOYSA-N 3-N,6-N,9-triphenyl-3-N,6-N-bis[4-(N-phenylanilino)phenyl]carbazole-3,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C3=CC(=CC=C3N(C=3C=CC=CC=3)C2=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 QIEWTACDLJLBTE-UHFFFAOYSA-N 0.000 description 1
- DPECCMXOGAHFKQ-UHFFFAOYSA-N 3-N,6-N-dinaphthalen-1-yl-9-phenyl-3-N,6-N-bis[4-(N-phenylanilino)phenyl]carbazole-3,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=C2C3=CC(=CC=C3N(C=3C=CC=CC=3)C2=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 DPECCMXOGAHFKQ-UHFFFAOYSA-N 0.000 description 1
- LLDZJTIZVZFNCM-UHFFFAOYSA-J 3-[18-(2-carboxyethyl)-8,13-diethyl-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid;dichlorotin(2+) Chemical compound [H+].[H+].[Cl-].[Cl-].[Sn+4].[N-]1C(C=C2C(=C(C)C(=CC=3C(=C(C)C(=C4)N=3)CC)[N-]2)CCC([O-])=O)=C(CCC([O-])=O)C(C)=C1C=C1C(C)=C(CC)C4=N1 LLDZJTIZVZFNCM-UHFFFAOYSA-J 0.000 description 1
- MYTPBXDNSPHTLI-UHFFFAOYSA-N 3-[9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]carbazol-2-yl]-9-phenylcarbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=C(C=CC=2)N2C3=CC(=CC=C3C3=CC=CC=C32)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)=N1 MYTPBXDNSPHTLI-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
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- CSPHHXDZKRMFMK-UHFFFAOYSA-N 4-(3-phenylphenyl)dibenzothiophene Chemical group C1=CC=C(C=2SC3=C(C=21)C=CC=C3)C=1C=C(C=CC=1)C1=CC=CC=C1 CSPHHXDZKRMFMK-UHFFFAOYSA-N 0.000 description 1
- SRVJOVJZRDHXLX-UHFFFAOYSA-N 4-[3-(3-dibenzothiophen-4-ylphenyl)phenyl]-2,8-diphenyl-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C(C=2SC3=C(C=21)C=CC=C3)C=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C2=C(N=C(N=1)C1=CC=CC=C1)C1=C(O2)C=CC(=C1)C1=CC=CC=C1 SRVJOVJZRDHXLX-UHFFFAOYSA-N 0.000 description 1
- PXJJGOFCOSJEQL-UHFFFAOYSA-N 4-[3-(3-dibenzothiophen-4-ylphenyl)phenyl]-8-phenyl-[1]benzofuro[3,2-d]pyrimidine Chemical compound C1=CC=C(C=2SC3=C(C=21)C=CC=C3)C=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C2=C(N=CN=1)C1=C(O2)C=CC(=C1)C1=CC=CC=C1 PXJJGOFCOSJEQL-UHFFFAOYSA-N 0.000 description 1
- RVTNHUBWDWSZKX-UHFFFAOYSA-N 4-[3-[3-(9-phenylfluoren-9-yl)phenyl]phenyl]dibenzofuran Chemical compound C1=CC=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(C=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RVTNHUBWDWSZKX-UHFFFAOYSA-N 0.000 description 1
- LGDCSNDMFFFSHY-UHFFFAOYSA-N 4-butyl-n,n-diphenylaniline Polymers C1=CC(CCCC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 LGDCSNDMFFFSHY-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- IJVFZXJHZBXCJC-UHFFFAOYSA-N 4-n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-1-n,1-n,4-n-triphenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=CC=C1 IJVFZXJHZBXCJC-UHFFFAOYSA-N 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
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- AEJARLYXNFRVLK-UHFFFAOYSA-N 4H-1,2,3-triazole Chemical class C1C=NN=N1 AEJARLYXNFRVLK-UHFFFAOYSA-N 0.000 description 1
- FADIAMGIKWXGRY-UHFFFAOYSA-N 5,12-bis(2-phenylphenyl)tetracene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C(C1=CC2=CC=CC=C2C=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1C1=CC=CC=C1 FADIAMGIKWXGRY-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
- PVCONXMDUZOPJH-UHFFFAOYSA-N 5-bromo-2-hydroxybenzonitrile Chemical compound OC1=CC=C(Br)C=C1C#N PVCONXMDUZOPJH-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
- MWQDBYKWEGXSJW-UHFFFAOYSA-N 6,12-dimethoxy-5,11-diphenylchrysene Chemical compound C12=C3C=CC=CC3=C(OC)C(C=3C=CC=CC=3)=C2C2=CC=CC=C2C(OC)=C1C1=CC=CC=C1 MWQDBYKWEGXSJW-UHFFFAOYSA-N 0.000 description 1
- WTHBTUVMXUWUNO-UHFFFAOYSA-N 6-[3-(9,10-diphenylanthracen-2-yl)phenyl]naphtho[2,1-b][1]benzofuran Chemical compound C1=CC=CC=C1C(C1=CC=C(C=C11)C=2C=C(C=CC=2)C=2C=3OC4=CC=CC=C4C=3C3=CC=CC=C3C=2)=C(C=CC=C2)C2=C1C1=CC=CC=C1 WTHBTUVMXUWUNO-UHFFFAOYSA-N 0.000 description 1
- JFHIIYSJKXQYIJ-UHFFFAOYSA-N 7-[4-(10-phenyl-9-anthryl)phenyl]-7h-dibenzo[c,g]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=C(C4=CC=CC=C4C=C3)C3=C4C=CC=CC4=CC=C32)C=C1 JFHIIYSJKXQYIJ-UHFFFAOYSA-N 0.000 description 1
- XJJZDHLZRNRKHD-UHFFFAOYSA-N 8-chloro-4-(3-dibenzothiophen-4-ylphenyl)-[1]benzofuro[3,2-d]pyrimidine Chemical compound ClC=1C=CC2=C(C=1)C=1N=CN=C(C=1O2)C1=CC(=CC=C1)C1=CC=CC2=C1SC1=C2C=CC=C1 XJJZDHLZRNRKHD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- OAXLYKRMEWDQGS-UHFFFAOYSA-N 9,9-dimethyl-2-n,2-n,7-n,7-n-tetraphenylfluorene-2,7-diamine Chemical compound C1=C2C(C)(C)C3=CC(N(C=4C=CC=CC=4)C=4C=CC=CC=4)=CC=C3C2=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 OAXLYKRMEWDQGS-UHFFFAOYSA-N 0.000 description 1
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)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)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-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
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- RQTORZWIAZFXNZ-UHFFFAOYSA-N 9-(3-phenylphenyl)-3-[9-(3-phenylphenyl)carbazol-3-yl]carbazole Chemical compound C1=CC=CC=C1C1=CC=CC(N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=C3C4=CC=CC=C4N(C=4C=C(C=CC=4)C=4C=CC=CC=4)C3=CC=2)=C1 RQTORZWIAZFXNZ-UHFFFAOYSA-N 0.000 description 1
- ZAYDYNVXBIQORO-UHFFFAOYSA-N 9-(3-phenylphenyl)-3-[9-(4-phenylphenyl)carbazol-3-yl]carbazole Chemical compound C1=CC=CC=C1C1=CC=C(C=C1)N1C2=C(C3=CC(=CC=C13)C1=CC=C3N(C4=CC=CC=C4C3=C1)C1=CC=CC(C3=CC=CC=C3)=C1)C=CC=C2 ZAYDYNVXBIQORO-UHFFFAOYSA-N 0.000 description 1
- GVEOOAAZBOGDSN-UHFFFAOYSA-N 9-(4-phenylphenyl)-3-[9-(4-phenylphenyl)carbazol-3-yl]carbazole Chemical compound C1=CC=CC=C1C1=CC=C(N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=C3C4=CC=CC=C4N(C=4C=CC(=CC=4)C=4C=CC=CC=4)C3=CC=2)C=C1 GVEOOAAZBOGDSN-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
- 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 1
- HOGUGXVETSOMRE-UHFFFAOYSA-N 9-[4-[2-(4-phenanthren-9-ylphenyl)ethenyl]phenyl]phenanthrene Chemical compound C1=CC=C2C(C3=CC=C(C=C3)C=CC=3C=CC(=CC=3)C=3C4=CC=CC=C4C4=CC=CC=C4C=3)=CC3=CC=CC=C3C2=C1 HOGUGXVETSOMRE-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
- SXGIRTCIFPJUEQ-UHFFFAOYSA-N 9-anthracen-9-ylanthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C(C=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C21 SXGIRTCIFPJUEQ-UHFFFAOYSA-N 0.000 description 1
- BHMSJRYEKYBHTN-UHFFFAOYSA-N 9-phenyl-10-[4-[4-(9-phenylfluoren-9-yl)phenyl]phenyl]anthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=CC(=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=C1 BHMSJRYEKYBHTN-UHFFFAOYSA-N 0.000 description 1
- DDCOSPFEMPUOFY-UHFFFAOYSA-N 9-phenyl-3-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 DDCOSPFEMPUOFY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 102100025982 BMP/retinoic acid-inducible neural-specific protein 1 Human genes 0.000 description 1
- GMQFEFKWWXUCIF-UHFFFAOYSA-N C1(=CC=CC=C1)C1(C2=CC=CC=C2C=2C=CC=CC1=2)C=1C=C(C=CC=1)C=1C=C(C=CC=1)C1=CC=CC=2OC3=C(C=21)C=CC=C3 Chemical compound C1(=CC=CC=C1)C1(C2=CC=CC=C2C=2C=CC=CC1=2)C=1C=C(C=CC=1)C=1C=C(C=CC=1)C1=CC=CC=2OC3=C(C=21)C=CC=C3 GMQFEFKWWXUCIF-UHFFFAOYSA-N 0.000 description 1
- ZYNFGMXIAPFYDQ-UHFFFAOYSA-N C1=CC=C(C=C1)N1C(=NN=C1C1=CC=C(C=C1)N1C2=CC=CC=C2N(C2=CC=CC=C2)C2=CC=CC=C12)C1=CC=CC=C1 Chemical compound C1=CC=C(C=C1)N1C(=NN=C1C1=CC=C(C=C1)N1C2=CC=CC=C2N(C2=CC=CC=C2)C2=CC=CC=C12)C1=CC=CC=C1 ZYNFGMXIAPFYDQ-UHFFFAOYSA-N 0.000 description 1
- SZLZVPNMBKWFIT-UHFFFAOYSA-N C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=CC(=CC=2)C=2C(=NC(=CC=2)C=2N=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=CC(=CC=2)C=2C(=NC(=CC=2)C=2N=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 SZLZVPNMBKWFIT-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 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
- 229920000742 Cotton Polymers 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 101000933342 Homo sapiens BMP/retinoic acid-inducible neural-specific protein 1 Proteins 0.000 description 1
- 101000715194 Homo sapiens Cell cycle and apoptosis regulator protein 2 Proteins 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 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
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- OTCYVTOIHSKZAJ-UHFFFAOYSA-N OB(O)C1=CC(=CC=C1)N1C2=C(C=CC=C2)C2=C1C=CC1=C2SC2=C1C=CC=C2 Chemical compound OB(O)C1=CC(=CC=C1)N1C2=C(C=CC=C2)C2=C1C=CC1=C2SC2=C1C=CC=C2 OTCYVTOIHSKZAJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WDVSHHCDHLJJJR-UHFFFAOYSA-N Proflavine Chemical compound C1=CC(N)=CC2=NC3=CC(N)=CC=C3C=C21 WDVSHHCDHLJJJR-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- WRNUGYVROIIUTC-UHFFFAOYSA-L [Ir+3].N1=C(C=CC2=CC=C3C(=C12)C=CC=C3)C(=O)[O-].N3=C(C=CC1=CC=C2C(=C31)C=CC=C2)C(=O)[O-] Chemical compound [Ir+3].N1=C(C=CC2=CC=C3C(=C12)C=CC=C3)C(=O)[O-].N3=C(C=CC1=CC=C2C(=C31)C=CC=C2)C(=O)[O-] WRNUGYVROIIUTC-UHFFFAOYSA-L 0.000 description 1
- OEEBMHFZRDUQFW-UHFFFAOYSA-L [Pt](Cl)Cl.C(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC Chemical compound [Pt](Cl)Cl.C(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC OEEBMHFZRDUQFW-UHFFFAOYSA-L 0.000 description 1
- FYNZMQVSXQQRNQ-UHFFFAOYSA-J [Sn](F)(F)(F)F.C(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC Chemical compound [Sn](F)(F)(F)F.C(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC FYNZMQVSXQQRNQ-UHFFFAOYSA-J 0.000 description 1
- 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 1
- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- HXFVOUUOTHJFPX-UHFFFAOYSA-N alumane;zinc Chemical compound [AlH3].[Zn] HXFVOUUOTHJFPX-UHFFFAOYSA-N 0.000 description 1
- 239000005407 aluminoborosilicate glass Substances 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-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
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000005388 borosilicate glass Substances 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
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052804 chromium 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
- 230000000295 complement effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 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
- 239000011258 core-shell material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 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
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical compound [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 1
- ADHNFLCTOCFIFV-UHFFFAOYSA-N europium(3+) 1,10-phenanthroline Chemical compound [Eu+3].c1cnc2c(c1)ccc1cccnc21 ADHNFLCTOCFIFV-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 229910052733 gallium Inorganic materials 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
- 230000005484 gravity Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 238000010884 ion-beam technique Methods 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
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000001459 lithography Methods 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 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
- 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 1
- LNFOMBWFZZDRKO-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(10-phenylanthracen-9-yl)phenyl]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=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 LNFOMBWFZZDRKO-UHFFFAOYSA-N 0.000 description 1
- FERQQMSWHMDPNT-UHFFFAOYSA-N n,n,4,9-tetraphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C(=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FERQQMSWHMDPNT-UHFFFAOYSA-N 0.000 description 1
- MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 description 1
- XAWQWMLNBYNXJX-UHFFFAOYSA-N n,n-diphenyl-9-[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)C=3C4=CC=CC=C4C(C=4C=CC=CC=4)=C4C=CC=CC4=3)C2=CC=1)C1=CC=CC=C1 XAWQWMLNBYNXJX-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
- AJNJGJDDJIBTBP-UHFFFAOYSA-N n-(9,10-diphenylanthracen-2-yl)-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AJNJGJDDJIBTBP-UHFFFAOYSA-N 0.000 description 1
- RVHDEFQSXAYURV-UHFFFAOYSA-N n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)C=C1 RVHDEFQSXAYURV-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
- 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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 229960000286 proflavine Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000005060 rubber Substances 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 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
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- DKWSBNMUWZBREO-UHFFFAOYSA-N terbium Chemical compound [Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb] DKWSBNMUWZBREO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 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
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
-
- 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
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
-
- 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
- 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
- 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
- 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
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
-
- 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
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
本実施の形態では、本発明の一態様である有機化合物について説明する。なお、本発明の一態様である有機化合物は、下記一般式(G1)で表される、ベンゾフロピリミジン誘導体またはベンゾチエノピリミジン誘導体である。なお、本発明の一態様である有機化合物は、下記一般式(G1)で表されるようにベンゾフロピリミジン骨格またはベンゾチエノピリミジン骨格の8位に無置換のフェニル基を有する構造である。
上記一般式(G1)で表される有機化合物の合成には、種々の反応を適用することができ、例えば、以下の合成スキームに示す簡便な方法により、一般式(G1)で表される有機化合物を合成することができる。
本実施の形態では、実施の形態1で示した有機化合物を用いた発光素子について図1を用いて説明する。
まず、発光素子の基本的な構造について説明する。図1(A)には、一対の電極間に発光層を含むEL層を有する発光素子の一例を示す。具体的には、第1の電極101と第2の電極102との間にEL層103が挟まれた構造を有する。
次に、本発明の一態様であり、図1に示す発光素子の具体的な構造および作製方法について説明する。なお、ここでは、図1(A)や図1(C)に示すようにEL層103が単層構造である発光素子だけでなく、図1(B)、図1(D)及び図1(E)に示すタンデム構造の発光素子についても、まとめて説明する。なお、図1に示す各発光素子がマイクロキャビティ構造を有する場合、例えば、第1の電極101を反射電極として形成し、第2の電極102を半透過・半反射電極として形成すればよい。また、所望の電極材料を単数または複数用い、単層または積層して形成することができる。また、第2の電極102は、EL層(103、103b)を形成した後、上記と同様に材料を選択して形成する。また、これらの電極の作製には、スパッタ法や真空蒸着法を用いることができる。
第1の電極101および第2の電極102を形成する材料としては、上述した両電極の機能が満たせるのであれば、以下に示す材料を適宜組み合わせて用いることができる。例えば、金属、合金、電気伝導性化合物、およびこれらの混合物などを適宜用いることができる。具体的には、In-Sn酸化物(ITOともいう)、In-Si-Sn酸化物(ITSOともいう)、In-Zn酸化物、In-W-Zn酸化物が挙げられる。その他、アルミニウム(Al)、チタン(Ti)、クロム(Cr)、マンガン(Mn)、鉄(Fe)、コバルト(Co)、ニッケル(Ni)、銅(Cu)、ガリウム(Ga)、亜鉛(Zn)、インジウム(In)、スズ(Sn)、モリブデン(Mo)、タンタル(Ta)、タングステン(W)、パラジウム(Pd)、金(Au)、白金(Pt)、銀(Ag)、イットリウム(Y)、ネオジム(Nd)などの金属、およびこれらを適宜組み合わせて含む合金を用いることもできる。その他、上記例示のない元素周期表の第1族または第2族に属する元素(例えば、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、ストロンチウム(Sr))、ユウロピウム(Eu)、イッテルビウム(Yb)などの希土類金属およびこれらを適宜組み合わせて含む合金、その他グラフェン等を用いることができる。
正孔注入層(111、111a、111b)は、陽極である第1の電極101や電荷発生層(104)からEL層(103、103a、103b)に正孔(ホール)を注入する層であり、正孔注入性の高い材料を含む層である。
発光層(113、113a、113b、113c)は、発光物質を含む層である。なお、発光物質としては、青色、紫色、青紫色、緑色、黄緑色、黄色、橙色、赤色などの発光色を呈する物質を適宜用いる。また、複数の発光層(113a、113b、113c)に異なる発光物質を用いることにより異なる発光色を呈する構成(例えば、補色の関係にある発光色を組み合わせて得られる白色発光)とすることができる。さらに、一つの発光層が異なる発光物質を有する積層構造であっても良い。
電子輸送層(114、114a、114b)は、電子注入層(115、115a、115b)によって、第2の電極102から注入された電子を発光層(113、113a、113b)に輸送する層である。なお、電子輸送層(114、114a、114b)は、電子輸送性材料を含む層である。電子輸送層(114、114a、114b)に用いる電子輸送性材料は、1×10-6cm2/Vs以上の電子移動度を有する物質が好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、これら以外のものを用いることができる。また、実施の形態1で示した本発明の一態様である有機化合物は電子輸送性に優れているため、電子輸送層としても利用可能である。
電子注入層(115、115a、115b)は、電子注入性の高い物質を含む層である。電子注入層(115、115a、115b)には、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。また、電子注入層(115、115a、115b)にエレクトライドを用いてもよい。エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。なお、上述した電子輸送層(114、114a、114b)を構成する物質を用いることもできる。
図1(D)に示す発光素子において、電荷発生層104は、第1の電極(陽極)101と第2の電極(陰極)102との間に電圧を印加したときに、EL層103aに電子を注入し、EL層103bに正孔を注入する機能を有する。なお、電荷発生層104は、正孔輸送性材料に電子受容体(アクセプター)が添加された構成であっても、電子輸送性材料に電子供与体(ドナー)が添加された構成であってもよい。また、これらの両方の構成が積層されていても良い。なお、上述した材料を用いて電荷発生層104を形成することにより、EL層が積層された場合における駆動電圧の上昇を抑制することができる。
本実施の形態で示した発光素子は、様々な基板上に形成することができる。なお、基板の種類は、特定のものに限定されることはない。基板の一例としては、半導体基板(例えば単結晶基板又はシリコン基板)、SOI基板、ガラス基板、石英基板、プラスチック基板、金属基板、ステンレス・スチル基板、ステンレス・スチル・ホイルを有する基板、タングステン基板、タングステン・ホイルを有する基板、可撓性基板、貼り合わせフィルム、繊維状の材料を含む紙、又は基材フィルムなどが挙げられる。
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。なお、図2(A)に示す発光装置は、第1の基板201上のトランジスタ(FET)202と発光素子(203R、203G、203B、203W)が電気的に接続されてなるアクティブマトリクス型の発光装置であり、複数の発光素子(203R、203G、203B、203W)は、共通のEL層204を有し、また、各発光素子の発光色に応じて、各発光素子の電極間の光学距離が調整されたマイクロキャビティ構造を有する。また、EL層204から得られた発光が第2の基板205に形成されたカラーフィルタ(206R、206G、206B)を介して射出されるトップエミッション型の発光装置である。
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、本発明の一態様である発光素子を有する発光装置を適用して完成させた様々な電子機器や自動車の一例について、説明する。なお、発光装置は、本実施の形態で説明する電子機器において、主に表示部に適用することができる。
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光素子を適用して作製される照明装置の構成について図7を用いて説明する。
本実施例では、実施の形態1の構造式(100)で表される本発明の一態様である有機化合物、4-[3-(ジベンゾチオフェン-4-イル)フェニル]-8-フェニル-[1]ベンゾフロ[3,2-d]ピリミジン(略称:8Ph-4mDBtPBfpm)の合成方法について説明する。なお、8Ph-4mDBtPBfpmの構造を以下に示す。
8-クロロ-4-[3-(ジベンゾチオフェン-4-イル)フェニル]-[1]ベンゾフロ[3,2-d]ピリミジン3.00g、フェニルボロン酸0.95g、リン酸三カリウム4.12g、ジグリム65mL、t-ブタノール1.44gを三口フラスコに入れ、フラスコ内を減圧下攪拌することで脱気し、窒素置換した。この混合物に酢酸パラジウム(II)42.7mg、ジ(1-アダマンチル)-n-ブチルホスフィン140mgを加え、120℃で15.5時間攪拌した。
次に、8Ph-4mDBtPBfpmのトルエン溶液および固体薄膜の紫外可視吸収スペクトル(以下、単に「吸収スペクトル」という)及び発光スペクトルを測定した。
本実施例では、実施の形態1の構造式(101)で表される本発明の一態様である有機化合物、4-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]-8-フェニル-[1]ベンゾフロ[3,2-d]ピリミジン(略称:8Ph-4mDBtBPBfpm)の合成方法について説明する。なお、8Ph-4mDBtBPBfpmの構造を以下に示す。
フェニルボロン酸1.57g、5-ブロモ-2-ヒドロキシベンゾニトリル2.30g、炭酸カリウム3.21g、トルエン43.5mL、エタノール14.5mL及び水11.6mLを三口フラスコに加え、減圧下で攪拌することにより脱気して窒素置換した。
次に上記ステップ1で得られた目的物である2-ヒドロキシ-5-フェニルベンゾニトリル1.86g、炭酸カリウム2.65gを三口フラスコに入れて窒素置換した。この混合物にブロモ酢酸エチル1.91g、N,N-ジメチルホルムアミド12mLを加え、100℃で14時間攪拌した。得られた反応物を氷水に入れて1時間攪拌し、吸引ろ過により得られたろ物を水で洗浄し、目的物の茶色固体を収量2.13g、収率80%で得た。この合成スキームを下記式(b-2)に示す。
次に上記ステップ2で得られた目的物である3-アミノ-5-フェニルベンゾ[b]フラン-2-カルボン酸エチル2.13g、ホルムアミド11mLをナスフラスコに入れて150℃で加熱した。この混合物にホルムアミジン酢酸塩1.59gを加え、160℃で14.5時間攪拌した。得られた反応物に水を加えて吸引ろ過し、ろ物をトルエン、ヘキサンで洗浄し、目的物である薄茶色固体を収量1.86g、収率94%で得た。この合成スキームを下記式(b-3)に示す。
次に上記ステップ3で得られた目的物である8-フェニル[1]ベンゾフロ[3,2-d]ピリミジン-4(3H)-オン1.86g、N,N-ジメチルホルムアミド0.05mLを三口フラスコへ入れ、攪拌した。この混合物へ塩化ホスホリル10.7gを加え、90℃で17時間攪拌した。得られた反応物を氷水へ入れて、水酸化ナトリウムおよび飽和重曹水を用いて中和し、1時間攪拌した。この混合物を吸引ろ過し、ろ物をエタノールで洗浄し、目的物である黄土色固体を収量1.84g、収率92%で得た。この合成スキームを下記式(b-4)に示す。
次に上記ステップ4で得られた4-クロロ-8-フェニル[1]ベンゾフロ[3,2-d]ピリミジン1.00g、3’-(ジベンゾチオフェン-4-イル)-1,1’-ビフェニル-3-イルボロン酸1.52g、炭酸カリウム0.997g、トルエン13.5mL、エタノール4.5mL及び水3.6mLを三口フラスコへ入れ、減圧下で攪拌することにより脱気して窒素置換した。
次に、8Ph-4mDBtBPBfpmのトルエン溶液および固体薄膜の紫外可視吸収スペクトル(以下、単に「吸収スペクトル」という)及び発光スペクトルを測定した。
本実施例では、実施の形態1の構造式(102)で表される本発明の一態様である有機化合物、4-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]-2,8-ジフェニル[1]ベンゾフロ[3,2-d]ピリミジン(略称:2,8Ph-4mDBtBPBfpm)の合成方法について説明する。なお、2,8Ph-4mDBtBPBfpmの構造を以下に示す。
2,4,8-トリクロロ[1]ベンゾフロ[3,2-d]ピリミジン1.22g、3’-(ジベンゾチオフェン-4-イル)-1,1’-ビフェニル-3-イルボロン酸1.67g、炭酸カリウム1.02g、トルエン13.7mL、エタノール4.6mL、水3.7mLを三口フラスコに入れ、減圧下攪拌することで脱気し、窒素置換した。
次に、ステップ1で得られた目的物である2,8-ジクロロ-4-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]-[1]ベンゾフロ[3,2-d]ピリミジン2.06g、フェニルボロン酸0.968g、フッ化セシウム1.09g、メシチレン36mLを三口フラスコに入れ、減圧下攪拌することで脱気し、窒素置換した。
本実施例では、実施の形態1の構造式(200)で表される本発明の一態様である有機化合物、2,4-ビス(ジベンゾフラン-4-イル)-8-フェニル-[1]ベンゾフロ[3,2-d]ピリミジン(略称:8Ph-2,4DBf2Bfpm)の合成方法について説明する。なお、8Ph-2,4DBf2Bfpmの構造を以下に示す。
2,4,8-トリクロロ[1]ベンゾフロ[3,2-d]ピリミジン1.56g、ジベンゾフラン-4-ボロン酸2.42g、炭酸カリウム1.58g、トルエン22mL、エタノール7mL、水5.7mLを三口フラスコに入れ、フラスコ内を減圧下攪拌することで脱気し、窒素置換した。
次に、ステップ1の目的物である2,4-ビス(ジベンゾフラン-4-イル)-8-クロロ-[1]ベンゾフロ[3,2-d]ピリミジン2.84g、フェニルボロン酸0.78g、フッ化セシウム1.62g、メシチレン53mLを三口フラスコに入れ、フラスコ内を減圧下攪拌することで脱気し、窒素置換した。
本実施例で示す発光素子は、図14に示すように基板900上に形成された第1の電極901上に正孔注入層911、正孔輸送層912、発光層913、電子輸送層914、電子注入層915が順次積層され、電子注入層915上に第2の電極903が積層された構造を有する。
作製した各発光素子の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。また、各発光素子の動作特性の結果として電流密度-輝度特性を図15、電圧-輝度特性を図16、輝度-電流効率特性を図17、電圧-電流特性を図18にそれぞれ示す。
作製した発光素子4および比較発光素子5の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
作製した発光素子6、比較発光素子7、および比較発光素子8の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
本参考合成例では、本実施例における比較発光素子7に用いた下記構造式で表される有機化合物、8-(ジベンゾチオフェン-4-イル)-4-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]-[1]ベンゾフロ[3,2-d]ピリミジン(略称:8DBt-4mDBtBPBfpm)(構造式(300))の合成例を具体的に例示する。
本参考合成例では、本実施例における比較発光素子8に用いた下記構造式で表される有機化合物、4-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]-8-[3-(ジベンゾチオフェン-4-イル)フェニル]-[1]ベンゾフロ[3,2-d]ピリミジン(略称:8mDBtP-4mDBtBPBfpm)(構造式(301))の合成例を具体的に例示する。
本実施例では、実施の形態1の構造式(117)で表される本発明の一態様である有機化合物、5-[3-(8-フェニル[1]ベンゾフロ[3,2-d]ピリミジン-4-イル)フェニル]-5H-[1]ベンゾチエノ[3,2-c]カルバゾール(略称:8Ph-4mBTczPBfpm)の合成方法について説明する。なお、8Ph-4mBTczPBfpmの構造を以下に示す。
4-クロロ-8-フェニル[1]ベンゾフロ[3,2-d]ピリミジン0.85g、3-(5H-ベンゾチエノ[3,2-c]カルバゾール-5-イル)フェニルボロン酸1.31g、炭酸カリウム0.83g、トルエン11.2mL、エタノール3.8mL、水3mLを三口フラスコに加え、フラスコ内を減圧下攪拌することで脱気し、窒素置換した。この混合物にテトラキストリフェニルホスフィンパラジウム(0)105mgを加え、100℃で15時間攪拌した。この反応物に水を加えて吸引ろ過し、得られたろ物を水、エタノールおよびトルエンで洗浄した。得られたろ物を熱したトルエンで溶解し、セライト、アルミナ、セライトの順に充填したろ過補助剤に通した。得られた溶液を濃縮、乾固し、トルエンにて再結晶することにより、目的物である黄色固体を収量1.35g、収率75%で得た。
作製した発光素子9の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
Claims (12)
- 一般式(G3)で表される有機化合物。
(式中、Qは酸素または硫黄を表す。また、Htuniは下記一般式(Ht-1)~(Ht-26)のいずれか一を表す。また、R1は、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数5乃至7の単環式飽和炭化水素、置換もしくは無置換の炭素数7乃至10の多環式飽和炭化水素、置換もしくは無置換の炭素数6乃至13のアリール基、または置換もしくは無置換の炭素数3乃至12のヘテロアリール基を表す。)
(式中、Qは酸素または硫黄を表す。また、R2~R71はそれぞれ1乃至4の置換基を表し、かつそれぞれ独立に水素、炭素数1~6のアルキル基、置換もしくは無置換のフェニル基のいずれか一を表す。また、Ar1は、置換もしくは無置換の炭素数6乃至13のアリール基を表す。) - 一般式(G4)で表される有機化合物。
(式中、Qは酸素または硫黄を表す。また、Htuniは下記一般式(Ht-1)~(Ht-26)のいずれか一を表す。また、R1は、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数5乃至7の単環式飽和炭化水素、置換もしくは無置換の炭素数7乃至10の多環式飽和炭化水素、置換もしくは無置換の炭素数6乃至13のアリール基、または置換もしくは無置換の炭素数3乃至12のヘテロアリール基を表す。)
(式中、Qは酸素または硫黄を表す。また、R2~R71はそれぞれ1乃至4の置換基を表し、かつそれぞれ独立に水素、炭素数1~6のアルキル基、置換もしくは無置換のフェニル基のいずれか一を表す。また、Ar1は、置換もしくは無置換の炭素数6乃至13のアリール基を表す。) - 請求項1または請求項2において、
前記R1の置換もしくは無置換の炭素数5乃至7の単環式飽和炭化水素、置換もしくは無置換の炭素数7乃至10の多環式飽和炭化水素、置換もしくは無置換の炭素数6乃至13のアリール基、または置換もしくは無置換の炭素数3乃至12のヘテロアリール基が置換基を有する場合、前記置換基は、炭素数1乃至7のアルキル基、炭素数5乃至7のシクロアルキル基、炭素数6乃至12のアリール基のいずれかである有機化合物。 - 構造式(100)、(101)、(102)、(117)、または(200)のいずれか一で表される有機化合物。
- 請求項1乃至請求項4のいずれか一に記載の有機化合物を用いた発光素子。
- 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4のいずれか一に記載の有機化合物を有する発光素子。 - 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4のいずれか一に記載の有機化合物と、燐光材料と、を有する発光素子。 - 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4のいずれか一に記載の有機化合物と、燐光材料と、カルバゾール誘導体と、を有する発光素子。 - 請求項8において、
前記カルバゾール誘導体は、ビカルバゾール誘導体である発光素子。 - 請求項5乃至請求項9のいずれか一に記載の発光素子と、
トランジスタ、または基板の少なくとも一と、を有する発光装置。 - 請求項10に記載の発光装置と、
マイク、カメラ、操作用ボタン、外部接続部、または、スピーカの少なくとも一と、を有する電子機器。 - 請求項5乃至請求項9のいずれか一に記載の発光素子と、
筐体、カバー、または、支持台の少なくとも一と、を有する照明装置。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018104892 | 2018-05-31 | ||
JP2018104892 | 2018-05-31 | ||
PCT/IB2019/054167 WO2019229584A1 (ja) | 2018-05-31 | 2019-05-21 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
Publications (3)
Publication Number | Publication Date |
---|---|
JPWO2019229584A1 JPWO2019229584A1 (ja) | 2021-07-26 |
JPWO2019229584A5 JPWO2019229584A5 (ja) | 2022-05-17 |
JP7354100B2 true JP7354100B2 (ja) | 2023-10-02 |
Family
ID=68697461
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020521634A Active JP7354100B2 (ja) | 2018-05-31 | 2019-05-21 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20210206775A1 (ja) |
JP (1) | JP7354100B2 (ja) |
KR (1) | KR20210015846A (ja) |
CN (1) | CN112218870A (ja) |
WO (1) | WO2019229584A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20230389344A1 (en) | 2020-09-24 | 2023-11-30 | Merck Patent Gmbh | Organic electroluminescent device |
TW202231838A (zh) | 2020-10-27 | 2022-08-16 | 德商麥克專利有限公司 | 有機電致發光裝置 |
WO2023052377A1 (de) | 2021-09-30 | 2023-04-06 | Merck Patent Gmbh | Organische elektrolumineszierende vorrichtung |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150207082A1 (en) | 2014-01-23 | 2015-07-23 | Universal Display Corporation | Organic materials for oleds |
JP2017119682A (ja) | 2015-12-25 | 2017-07-06 | 株式会社半導体エネルギー研究所 | 化合物、発光素子、表示装置、電子機器、及び照明装置 |
US20170200903A1 (en) | 2014-05-28 | 2017-07-13 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, and organic electronic element and electronic device using same |
JP2018510148A (ja) | 2015-03-03 | 2018-04-12 | ドク サン ネオルクス カンパニー リミテッド | 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 |
WO2019017741A1 (ko) | 2017-07-20 | 2019-01-24 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200541401A (en) | 2004-02-13 | 2005-12-16 | Idemitsu Kosan Co | Organic electroluminescent device |
CN109608473B (zh) * | 2013-03-26 | 2021-05-11 | 株式会社半导体能源研究所 | 用于发光元件的化合物及其合成方法 |
KR101941154B1 (ko) * | 2016-08-23 | 2019-01-23 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
-
2019
- 2019-05-21 JP JP2020521634A patent/JP7354100B2/ja active Active
- 2019-05-21 CN CN201980036561.8A patent/CN112218870A/zh active Pending
- 2019-05-21 US US17/056,625 patent/US20210206775A1/en active Pending
- 2019-05-21 WO PCT/IB2019/054167 patent/WO2019229584A1/ja active Application Filing
- 2019-05-21 KR KR1020207035441A patent/KR20210015846A/ko unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150207082A1 (en) | 2014-01-23 | 2015-07-23 | Universal Display Corporation | Organic materials for oleds |
US20170200903A1 (en) | 2014-05-28 | 2017-07-13 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, and organic electronic element and electronic device using same |
JP2018510148A (ja) | 2015-03-03 | 2018-04-12 | ドク サン ネオルクス カンパニー リミテッド | 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 |
JP2017119682A (ja) | 2015-12-25 | 2017-07-06 | 株式会社半導体エネルギー研究所 | 化合物、発光素子、表示装置、電子機器、及び照明装置 |
WO2019017741A1 (ko) | 2017-07-20 | 2019-01-24 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Also Published As
Publication number | Publication date |
---|---|
KR20210015846A (ko) | 2021-02-10 |
WO2019229584A1 (ja) | 2019-12-05 |
JPWO2019229584A1 (ja) | 2021-07-26 |
CN112218870A (zh) | 2021-01-12 |
US20210206775A1 (en) | 2021-07-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7358552B2 (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 | |
JP7377315B2 (ja) | 発光素子、混合材料および発光素子用材料 | |
JP7458452B2 (ja) | 発光素子 | |
JP7441297B2 (ja) | 混合材料 | |
JP2023002574A (ja) | 発光素子 | |
JP7170930B1 (ja) | 発光デバイス、発光装置、電子機器、および照明装置 | |
JP7354100B2 (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 | |
JP2023025011A (ja) | 発光素子 | |
JP2022166086A (ja) | 化合物 | |
JP2019189540A (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 | |
JP7297758B2 (ja) | 発光素子、発光装置、電子機器、および照明装置 | |
JP2023113638A (ja) | 発光素子 | |
JP2021024863A (ja) | 有機化合物、発光デバイス、発光装置、電子機器、および照明装置 | |
JP7287953B2 (ja) | 有機金属錯体、発光デバイス、発光装置、電子機器、および照明装置 | |
WO2020058811A1 (ja) | 有機化合物、発光デバイス、発光装置、電子機器、および照明装置 | |
JP2023179530A (ja) | 蒸着用組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220509 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220509 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230509 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230703 |
|
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: 20230829 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230920 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7354100 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |