JP2017210464A - 含窒素化合物及び含窒素化合物を含む有機電界発光素子 - Google Patents
含窒素化合物及び含窒素化合物を含む有機電界発光素子 Download PDFInfo
- Publication number
- JP2017210464A JP2017210464A JP2016112197A JP2016112197A JP2017210464A JP 2017210464 A JP2017210464 A JP 2017210464A JP 2016112197 A JP2016112197 A JP 2016112197A JP 2016112197 A JP2016112197 A JP 2016112197A JP 2017210464 A JP2017210464 A JP 2017210464A
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- chemical formula
- 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.)
- Withdrawn
Links
- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 141
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 108
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 230000005525 hole transport Effects 0.000 claims description 43
- 238000002347 injection Methods 0.000 claims description 29
- 239000007924 injection Substances 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 17
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052732 germanium Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004431 deuterium atom Chemical group 0.000 claims 12
- 239000010410 layer Substances 0.000 description 128
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000000463 material Substances 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 125000001424 substituent group Chemical group 0.000 description 24
- 239000007787 solid Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 16
- 239000012046 mixed solvent Substances 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002356 single layer Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 8
- 239000011787 zinc oxide Substances 0.000 description 8
- 0 *c1ccccc1N(*)c(cccc1)c1[S+](c1ccccc1)c1ccccc1 Chemical compound *c1ccccc1N(*)c(cccc1)c1[S+](c1ccccc1)c1ccccc1 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229920000767 polyaniline Polymers 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 150000001975 deuterium Chemical group 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 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 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003613 toluenes Chemical class 0.000 description 3
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-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
- 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
- HNWFFTUWRIGBNM-UHFFFAOYSA-N 2-methyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C)=CC=C21 HNWFFTUWRIGBNM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
- JTWMOWRMSZZHDR-UHFFFAOYSA-N 7-(5-hydroxy-2-methylphenyl)-6-(2-methoxyphenyl)-4-methylpurino[7,8-a]imidazole-1,3-dione Chemical compound COC1=CC=CC=C1N(C(=CN12)C=3C(=CC=C(O)C=3)C)C2=NC2=C1C(=O)NC(=O)N2C JTWMOWRMSZZHDR-UHFFFAOYSA-N 0.000 description 2
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound 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
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000006267 biphenyl group Chemical group 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
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 229940126545 compound 53 Drugs 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound 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 2
- 230000000694 effects Effects 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 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
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 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
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 150000003216 pyrazines Chemical class 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 150000004059 quinone derivatives Chemical class 0.000 description 2
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- TYHJXGDMRRJCRY-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) tin(4+) Chemical compound [O-2].[Zn+2].[Sn+4].[In+3] TYHJXGDMRRJCRY-UHFFFAOYSA-N 0.000 description 2
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-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
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- ZLGVZKQXZYQJSM-UHFFFAOYSA-N 1,2-diphenylbenzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 ZLGVZKQXZYQJSM-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 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 1
- 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 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- VSIKJPJINIDELZ-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octakis-phenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VSIKJPJINIDELZ-UHFFFAOYSA-N 0.000 description 1
- VCYDUTCMKSROID-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VCYDUTCMKSROID-UHFFFAOYSA-N 0.000 description 1
- FUGJJMVGGAWCAU-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound C1=CC=CC=C1P1(C=2C=CC=CC=2)=NP(C=2C=CC=CC=2)(C=2C=CC=CC=2)=NP(C=2C=CC=CC=2)(C=2C=CC=CC=2)=N1 FUGJJMVGGAWCAU-UHFFFAOYSA-N 0.000 description 1
- AIAJGVRFXREWPK-UHFFFAOYSA-N 2,8-bis(diphenylphosphoryl)dibenzofuran Chemical compound C=1C=CC=CC=1P(C=1C=C2C3=CC(=CC=C3OC2=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 AIAJGVRFXREWPK-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
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- IYKBMPHOPLFHAQ-UHFFFAOYSA-N 2-phenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=2C3=NC=CC=2)C3=N1 IYKBMPHOPLFHAQ-UHFFFAOYSA-N 0.000 description 1
- BRFOFYXSADOBSU-UHFFFAOYSA-N 3,3-diethylcyclopentene Chemical compound C(C)C1(C=CCC1)CC BRFOFYXSADOBSU-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- PMVRHMKYOMJWSD-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-diphenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PMVRHMKYOMJWSD-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- QYNTUCBQEHUHCS-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n-[4-[4-(n-[4-(n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QYNTUCBQEHUHCS-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IWLQAROWFLFUIM-UHFFFAOYSA-N C(C1)C=Cc2c1c(cccc1)c1[n]2-c(cc1c2c3ccc(N(C4C=CC=CC44)c5c4cccc5)c2)ccc1[n]3-c(cc1)ccc1-c1c(-c2ccccc2)nccn1 Chemical compound C(C1)C=Cc2c1c(cccc1)c1[n]2-c(cc1c2c3ccc(N(C4C=CC=CC44)c5c4cccc5)c2)ccc1[n]3-c(cc1)ccc1-c1c(-c2ccccc2)nccn1 IWLQAROWFLFUIM-UHFFFAOYSA-N 0.000 description 1
- RKXSXFWJUZYRGM-UHFFFAOYSA-N C(c(cc1)ccc1N1c(cccc2)c2[Si]2(c3ccccc3C3C=CC=CC23)c2c1cccc2)[n+]1ccc[n-]1 Chemical compound C(c(cc1)ccc1N1c(cccc2)c2[Si]2(c3ccccc3C3C=CC=CC23)c2c1cccc2)[n+]1ccc[n-]1 RKXSXFWJUZYRGM-UHFFFAOYSA-N 0.000 description 1
- KESRRRLHHXXBRW-UHFFFAOYSA-N C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 Chemical compound C1=CC=NC2=C3C(O)=CC=CC3=CC=C21 KESRRRLHHXXBRW-UHFFFAOYSA-N 0.000 description 1
- ZGISNGRLPQCTNB-UHFFFAOYSA-N C1C=CC=CC1c1nccnc1-c(cc1)ccc1-[n]1c(ccc(-[n]2c3ccccc3c3c2cccc3)c2)c2c2c1cccc2 Chemical compound C1C=CC=CC1c1nccnc1-c(cc1)ccc1-[n]1c(ccc(-[n]2c3ccccc3c3c2cccc3)c2)c2c2c1cccc2 ZGISNGRLPQCTNB-UHFFFAOYSA-N 0.000 description 1
- ARIJAQCWYMUBCD-UHFFFAOYSA-N CC(C1C=C2)(C=C2[n]2c3ccccc3c3c2cccc3)c2cc(N3c4ccccc4C4C=CC=CC34)ccc2N1c(cc1)ccc1C1=NC(c2ccccc2)=CC(c2ccccc2)N1 Chemical compound CC(C1C=C2)(C=C2[n]2c3ccccc3c3c2cccc3)c2cc(N3c4ccccc4C4C=CC=CC34)ccc2N1c(cc1)ccc1C1=NC(c2ccccc2)=CC(c2ccccc2)N1 ARIJAQCWYMUBCD-UHFFFAOYSA-N 0.000 description 1
- NGWLKUFKGWHPGD-UHFFFAOYSA-N CC(C1C=C2)(C=C2[n]2c3ccccc3c3c2cccc3)c2ccccc2N1c(cc1)ccc1C(NC(c1ccccc1)N=C1)=C1c1ccccc1 Chemical compound CC(C1C=C2)(C=C2[n]2c3ccccc3c3c2cccc3)c2ccccc2N1c(cc1)ccc1C(NC(c1ccccc1)N=C1)=C1c1ccccc1 NGWLKUFKGWHPGD-UHFFFAOYSA-N 0.000 description 1
- GHMDLEHOUKZSHG-UHFFFAOYSA-N CCN(c1c2cccc1)c1ccccc1P2(c1ccccc1)=O Chemical compound CCN(c1c2cccc1)c1ccccc1P2(c1ccccc1)=O GHMDLEHOUKZSHG-UHFFFAOYSA-N 0.000 description 1
- PCFGXCCLQIDTIK-UHFFFAOYSA-N Cc(cc1)cc2c1N(c(cc1)ccc1-c1nc(C)nc(-c3ccccc3)c1C)c1ccc(C)cc1C21c2ccccc2-c2ccccc12 Chemical compound Cc(cc1)cc2c1N(c(cc1)ccc1-c1nc(C)nc(-c3ccccc3)c1C)c1ccc(C)cc1C21c2ccccc2-c2ccccc12 PCFGXCCLQIDTIK-UHFFFAOYSA-N 0.000 description 1
- YAWLLONKIJLMAM-UHFFFAOYSA-N Cc(cc1C23c4ccccc4-c4ccccc24)ccc1N(c(cc1)ccc1-c1nc(-c2ccccc2)cc(-c2ccccc2)n1)c1c3cc(C)cc1 Chemical compound Cc(cc1C23c4ccccc4-c4ccccc24)ccc1N(c(cc1)ccc1-c1nc(-c2ccccc2)cc(-c2ccccc2)n1)c1c3cc(C)cc1 YAWLLONKIJLMAM-UHFFFAOYSA-N 0.000 description 1
- IPENWGJTDZZEPV-UHFFFAOYSA-N Cc(cc1C23c4ccccc4Oc4c2cccc4)ccc1N(c(cc1)ccc1-c1ncccn1)c1c3cc(C)cc1 Chemical compound Cc(cc1C23c4ccccc4Oc4c2cccc4)ccc1N(c(cc1)ccc1-c1ncccn1)c1c3cc(C)cc1 IPENWGJTDZZEPV-UHFFFAOYSA-N 0.000 description 1
- OPONZGFBEJUKHY-UHFFFAOYSA-N Cc1c(-c(cc2)ccc2-[n]2c(ccc(-[n]3c(C=CCC4)c4c4c3cccc4)c3)c3c3ccccc23)ncnc1-c1ccccc1 Chemical compound Cc1c(-c(cc2)ccc2-[n]2c(ccc(-[n]3c(C=CCC4)c4c4c3cccc4)c3)c3c3ccccc23)ncnc1-c1ccccc1 OPONZGFBEJUKHY-UHFFFAOYSA-N 0.000 description 1
- CQIJTQBDRMJXEG-UHFFFAOYSA-N Cc1c(-c(cc2)ccc2-[n]2c(ccc(-[n]3c4ccccc4c4c3cccc4)c3)c3c3cc(-[n]4c5ccccc5c5c4cccc5)ccc23)nccn1 Chemical compound Cc1c(-c(cc2)ccc2-[n]2c(ccc(-[n]3c4ccccc4c4c3cccc4)c3)c3c3cc(-[n]4c5ccccc5c5c4cccc5)ccc23)nccn1 CQIJTQBDRMJXEG-UHFFFAOYSA-N 0.000 description 1
- CAAZXJUVZYJXSE-DTSDQNDWSA-N Cc1c(-c(cc2)ccc2N(c2c(C3(c4ccccc4)c4ccccc4)cccc2)c2c3cccc2)nc(C)nc1-c(cc1)ccc1N1c2ccccc2C([C@H]2C=CC=CC2)(C2=CC=CCC2)c2ccccc12 Chemical compound Cc1c(-c(cc2)ccc2N(c2c(C3(c4ccccc4)c4ccccc4)cccc2)c2c3cccc2)nc(C)nc1-c(cc1)ccc1N1c2ccccc2C([C@H]2C=CC=CC2)(C2=CC=CCC2)c2ccccc12 CAAZXJUVZYJXSE-DTSDQNDWSA-N 0.000 description 1
- CASHWXLGBSEHKQ-UHFFFAOYSA-N Cc1c(-c(cc2)ccc2N2c3ccccc3C3(c(cccc4)c4-c4c3cccc4)c3ccccc23)nc(C)nc1-c(cc1)ccc1N(c1c(C23c4ccccc4-c4c2cccc4)cccc1)c1c3cccc1 Chemical compound Cc1c(-c(cc2)ccc2N2c3ccccc3C3(c(cccc4)c4-c4c3cccc4)c3ccccc23)nc(C)nc1-c(cc1)ccc1N(c1c(C23c4ccccc4-c4c2cccc4)cccc1)c1c3cccc1 CASHWXLGBSEHKQ-UHFFFAOYSA-N 0.000 description 1
- MPACWCQNQVHDEY-UHFFFAOYSA-N Cc1cc(C)nc(-c(cc2)ccc2-[n]2c(ccc(-[n]3c4ccccc4c4c3cccc4)c3)c3c3cc(-[n]4c5ccccc5c5c4cccc5)ccc23)n1 Chemical compound Cc1cc(C)nc(-c(cc2)ccc2-[n]2c(ccc(-[n]3c4ccccc4c4c3cccc4)c3)c3c3cc(-[n]4c5ccccc5c5c4cccc5)ccc23)n1 MPACWCQNQVHDEY-UHFFFAOYSA-N 0.000 description 1
- NSWVVOXMJZYHSG-UHFFFAOYSA-N Cc1cnc(C)nc1-c(cc1)ccc1-[n]1c(ccc(-[n]2c3ccccc3c3c2cccc3)c2)c2c2ccccc12 Chemical compound Cc1cnc(C)nc1-c(cc1)ccc1-[n]1c(ccc(-[n]2c3ccccc3c3c2cccc3)c2)c2c2ccccc12 NSWVVOXMJZYHSG-UHFFFAOYSA-N 0.000 description 1
- RSUUGFVARVOIRZ-UHFFFAOYSA-N Cc1nc(-c(cc2)ccc2N(c2c(C3(c4ccccc4)c4ccccc4)cccc2)c2c3cccc2)cc(-c(cc2)ccc2N(c2c(C3(c4ccccc4)c4ccccc4)cccc2)c2c3cccc2)n1 Chemical compound Cc1nc(-c(cc2)ccc2N(c2c(C3(c4ccccc4)c4ccccc4)cccc2)c2c3cccc2)cc(-c(cc2)ccc2N(c2c(C3(c4ccccc4)c4ccccc4)cccc2)c2c3cccc2)n1 RSUUGFVARVOIRZ-UHFFFAOYSA-N 0.000 description 1
- FIMUTBLUWQGTIJ-UHFFFAOYSA-N Cc1nc(Cl)cc(Cl)n1 Chemical compound Cc1nc(Cl)cc(Cl)n1 FIMUTBLUWQGTIJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- XIRXXTIWLFDPLU-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3ccc(-[n]4c5ccccc5c5c4cccc5)c2)c1[n]3-c(cc1)ccc1-c1ncccn1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1)cc(c2c3ccc(-[n]4c5ccccc5c5c4cccc5)c2)c1[n]3-c(cc1)ccc1-c1ncccn1 XIRXXTIWLFDPLU-UHFFFAOYSA-N 0.000 description 1
- ADPDPQNGSGRUGS-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c(cc1c2c3ccc(-[n]4c5ccccc5c5c4cccc5)c2)ccc1[n]3-c(cc1)ccc1-c1nccnc1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c(cc1c2c3ccc(-[n]4c5ccccc5c5c4cccc5)c2)ccc1[n]3-c(cc1)ccc1-c1nccnc1 ADPDPQNGSGRUGS-UHFFFAOYSA-N 0.000 description 1
- VKFWHTYHLBFBPG-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-[n]2c(ccc(-[n]3c4ccccc4c4c3cccc4)c3)c3c3ccccc23)c1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-[n]2c(ccc(-[n]3c4ccccc4c4c3cccc4)c3)c3c3ccccc23)c1 VKFWHTYHLBFBPG-UHFFFAOYSA-N 0.000 description 1
- GLGZTYOXLVUTHH-UHFFFAOYSA-N c(cc1)ccc1[Ge]1(c2ccccc2)c(cccc2)c2N(c(cc2)ccc2-c2ncccn2)c2ccccc12 Chemical compound c(cc1)ccc1[Ge]1(c2ccccc2)c(cccc2)c2N(c(cc2)ccc2-c2ncccn2)c2ccccc12 GLGZTYOXLVUTHH-UHFFFAOYSA-N 0.000 description 1
- YVVVSJAMVJMZRF-UHFFFAOYSA-N c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 Chemical compound c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 YVVVSJAMVJMZRF-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 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 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- UCLOAJGCFQIQQW-UHFFFAOYSA-N diphenylboron Chemical group C=1C=CC=CC=1[B]C1=CC=CC=C1 UCLOAJGCFQIQQW-UHFFFAOYSA-N 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)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
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical group S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-O tritert-butylphosphanium Chemical compound CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-O 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- 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
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
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)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
直接結合(direct linkage)は、例えば、単結合である。
Yは、直接結合又はCR2R3であってもよく、R2及びR3は、前述と同様である。
EL1:第1電極
HTR:正孔輸送領域
EML:発光層
ETR:電子輸送領域
EL2:第2電極
Claims (20)
- 下記の化学式(1)で示されることを特徴とする含窒素化合物。
X1〜X6は、各々独立的にCR1又はNであり、
X1〜X6の中でNは、1個又は2個であり、
R1は、水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上30以下のアルキル基、置換若しくは無置換のフルオレニル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
複数のR1は、互いに同一であるか、或いは異なり、
Lは、置換若しくは無置換の環形成炭素数6以上30以下のアリーレン基であり、
nは、1又は2であり、
Duは、下記の化学式(2)で示され、
Yは、直接結合、O、S、CR2R3、Si、Ge、P又はP=Oであり、
R2〜R11は、各々独立的に水素原子、重水素原子、置換若しくは無置換の炭素数1以上30以下のアルキル基、置換若しくは無置換のフルオレニル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であるか、或いは隣接する基と互いに結合して環を形成する。 - 前記Lは、置換若しくは無置換のフェニレン基であることを特徴とする請求項1に記載の含窒素化合物。
- Yは、直接結合又はCR2R3であり、
R2及びR3は各々独立的に水素原子、重水素原子、置換若しくは無置換の炭素数1以上30以下のアルキル基、置換若しくは無置換のフルオレニル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であるか、或いは隣接する基と互いに結合して環を形成することを特徴とする請求項1に記載の含窒素化合物。 - 第1の電極と、
前記第1の電極上に形成された正孔輸送領域と、
前記正孔輸送領域上に形成された発光層と、
前記発光層上に形成された電子輸送領域と、
前記電子輸送層上に提供された第2の電極と、を含み、
前記発光層は、下記の化学式(1)で示される含窒素化合物を含むことを特徴とする有機電界発光素子。
X1〜X6は、各々独立的にCR1又はNであり、
X1〜X6の中でNは、1個又は2個であり、
R1は、水素原子、重水素原子、ハロゲン基、置換若しくは無置換の炭素数1以上30以下のアルキル基、置換若しくは無置換のフルオレニル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
複数のR1は、互いに同一であるか、或いは異なり、
Lは、置換若しくは無置換の環形成炭素数6以上30以下のアリーレン基であり、
nは、1又は2であり、
Duは、下記の化学式(2)で示され、
Yは、直接結合、O、S、CR2R3、Si、Ge、P又はP=Oであり、
R2〜R11は、各々独立的に水素原子、重水素原子、置換若しくは無置換の炭素数1以上30以下のアルキル基、置換若しくは無置換のフルオレニル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であるか、或いは隣接する基と互いに結合して環を形成する。 - 前記化学式(1)で示される含窒素化合物は、
一重項のエネルギー準位及び三重項のエネルギー準位の差の絶対値が0.2eV以下であることを特徴とする請求項10に記載の有機電界発光素子。 - 前記Lは、置換若しくは無置換のフェニレン基であることを特徴とする請求項10に記載の有機電界発光素子。
- 前記Yは、直接結合又はCR2R3であり、
R2及びR3は各々独立的に水素原子、重水素原子、置換若しくは無置換の炭素数1以上30以下のアルキル基、置換若しくは無置換のフルオレニル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であるか、或いは隣接する基と互いに結合して環を形成することを特徴とする請求項10に記載の有機電界発光素子。 - 前記正孔輸送領域は、
正孔注入層及び正孔輸送層を含み、
前記電子輸送領域は、
電子注入層及び電子輸送層を含むことを特徴とする請求項10に記載の有機電界発光素子。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2016-0065045 | 2016-05-26 | ||
KR1020160065045A KR102651014B1 (ko) | 2016-05-26 | 2016-05-26 | 함질소 화합물 및 이를 포함하는 유기 전계 발광 소자 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020140484A Division JP7078961B2 (ja) | 2016-05-26 | 2020-08-21 | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2017210464A true JP2017210464A (ja) | 2017-11-30 |
Family
ID=60420571
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016112197A Withdrawn JP2017210464A (ja) | 2016-05-26 | 2016-06-03 | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 |
JP2020140484A Active JP7078961B2 (ja) | 2016-05-26 | 2020-08-21 | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020140484A Active JP7078961B2 (ja) | 2016-05-26 | 2020-08-21 | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 |
Country Status (3)
Country | Link |
---|---|
US (1) | US10686139B2 (ja) |
JP (2) | JP2017210464A (ja) |
KR (1) | KR102651014B1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111233906A (zh) * | 2018-11-29 | 2020-06-05 | 三星显示有限公司 | 有机电致发光器件和用于有机电致发光器件的多环化合物 |
US11309511B2 (en) | 2018-07-06 | 2022-04-19 | Samsung Display Co., Ltd. | Organic electroluminescence device and nitrogen-containing compound for organic electroluminescence device |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20180095760A (ko) * | 2017-02-17 | 2018-08-28 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 |
KR102472171B1 (ko) * | 2017-08-29 | 2022-11-30 | 삼성디스플레이 주식회사 | 다환 화합물 및 이를 포함하는 유기 전계 발광 소자 |
CN111247128B (zh) * | 2018-03-22 | 2023-05-23 | 株式会社Lg化学 | 化合物和包含其的有机发光二极管 |
CN109627233A (zh) * | 2018-07-27 | 2019-04-16 | 华南理工大学 | 一种基于咔唑衍生物取代的氮杂环分子的有机光电材料及其制备方法和应用 |
US11485706B2 (en) * | 2018-09-11 | 2022-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
TW202110808A (zh) * | 2019-06-27 | 2021-03-16 | 日商關東化學股份有限公司 | 螺環二氫吖啶系化合物、含有該化合物之電洞傳輸材料、及在電洞傳輸層中包含該化合物之有機電子裝置 |
CN110862817A (zh) * | 2019-09-30 | 2020-03-06 | 常州强力昱镭光电材料有限公司 | 热激活延迟荧光材料、热激活延迟荧光组合物及有机电致发光器件 |
CN111072677A (zh) * | 2019-12-27 | 2020-04-28 | 烟台显华化工科技有限公司 | 一类有机化合物及其应用 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011049511A (ja) * | 2009-07-31 | 2011-03-10 | Fujifilm Corp | 有機電界発光素子 |
WO2012048266A1 (en) * | 2010-10-08 | 2012-04-12 | Universal Display Corporation | Novel 3, 9-linked oligocarbazole-based hosts, containing dbt and dbr fragments, separated by aromatic spacers |
WO2012099219A1 (ja) * | 2011-01-20 | 2012-07-26 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US20130292659A1 (en) * | 2010-12-08 | 2013-11-07 | Hyung-Sun Kim | Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode |
WO2015016200A1 (ja) * | 2013-08-01 | 2015-02-05 | 国立大学法人九州大学 | 化合物、発光材料および有機発光素子 |
WO2015020217A1 (ja) * | 2013-08-09 | 2015-02-12 | 出光興産株式会社 | 有機エレクトロルミネッセンス用組成物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用材料溶液及び有機エレクトロルミネッセンス素子 |
WO2015033894A1 (ja) * | 2013-09-04 | 2015-03-12 | 出光興産株式会社 | カルバゾール誘導体、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器 |
US20150126736A1 (en) * | 2012-05-02 | 2015-05-07 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
WO2015093551A1 (ja) * | 2013-12-18 | 2015-06-25 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、インク組成物、有機エレクトロルミネッセンス素子、電子機器、及び化合物の製造方法 |
WO2015175678A1 (en) * | 2014-05-14 | 2015-11-19 | President And Fellows Of Harvard College | Organic light-emitting diode materials |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102386330B (zh) * | 2003-04-18 | 2014-10-22 | 株式会社半导体能源研究所 | 喹喔啉衍生物以及使用它的有机半导体元件、电致发光元件以及电子仪器 |
JP4810669B2 (ja) * | 2004-11-25 | 2011-11-09 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
TWI304441B (en) * | 2005-01-07 | 2008-12-21 | Ind Tech Res Inst | Micro power-assembly device driven by molecular motors |
US20100295444A1 (en) | 2009-05-22 | 2010-11-25 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US8335303B2 (en) * | 2009-11-11 | 2012-12-18 | Centurylink Intellectual Property Llc | System and method for telephone call control |
KR20110102055A (ko) * | 2010-03-10 | 2011-09-16 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR101779913B1 (ko) * | 2010-04-01 | 2017-09-20 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
KR101432599B1 (ko) * | 2010-08-04 | 2014-08-21 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
EP2667688A1 (en) * | 2011-01-20 | 2013-11-27 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
US10177312B2 (en) * | 2011-05-05 | 2019-01-08 | Merck Patent Gmbh | Compounds for electronic devices |
KR20140106631A (ko) | 2011-12-02 | 2014-09-03 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 유기 발광 소자 그리고 그것에 사용하는 지연 형광 재료 및 화합물 |
JP5594750B2 (ja) | 2012-05-17 | 2014-09-24 | 国立大学法人九州大学 | 化合物、発光材料および有機発光素子 |
KR102191778B1 (ko) | 2012-06-20 | 2020-12-16 | 에스에프씨 주식회사 | 이형고리 화합물 및 이를 포함하는 유기전계발광소자 |
KR102086544B1 (ko) * | 2012-07-31 | 2020-03-10 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR101636864B1 (ko) | 2012-10-08 | 2016-07-06 | 제일모직 주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
JP2016122672A (ja) * | 2013-03-18 | 2016-07-07 | 出光興産株式会社 | 発光装置 |
JP6567499B2 (ja) | 2013-04-08 | 2019-08-28 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセント素子 |
EP2984152B2 (de) | 2013-04-08 | 2022-01-05 | Merck Patent GmbH | Organische elektrolumineszenzvorrichtung |
JP6367189B2 (ja) | 2013-06-05 | 2018-08-01 | 株式会社Kyulux | 発光材料、有機発光素子および化合物 |
JP6627508B2 (ja) | 2013-08-14 | 2020-01-08 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置、表示装置及び蛍光発光性化合物 |
KR102140018B1 (ko) | 2013-12-17 | 2020-07-31 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
DE102014106987A1 (de) * | 2014-02-14 | 2015-08-20 | Hartmut Yersin | Organische TADF-Moleküle mit sterischer Behinderung am Donator und am Akzeptor für opto-elektronische Vorrichtungen |
US20160372683A1 (en) * | 2014-03-07 | 2016-12-22 | Konica Minolta, Inc. | Organic electroluminescence element, display device, illumination device, and light-emitting composition |
JP6017498B2 (ja) | 2014-06-13 | 2016-11-02 | リンナイ株式会社 | 温度検出装置 |
US9957280B2 (en) * | 2014-12-15 | 2018-05-01 | Samsung Electronics Co., Ltd. | Luminescent compound and electroluminescent device exhibiting thermally activated delayed fluorescence |
KR101769764B1 (ko) * | 2014-12-17 | 2017-08-22 | 경상대학교산학협력단 | 신규한 유기반도체 화합물 및 이를 이용한 유기전계발광소자 |
JP6580392B2 (ja) | 2015-01-08 | 2019-09-25 | 国立大学法人九州大学 | 化合物、混合物、発光層、有機発光素子およびアシストドーパント |
KR102633852B1 (ko) * | 2016-01-25 | 2024-02-07 | 삼성디스플레이 주식회사 | 카바졸계 화합물 및 이를 포함한 유기 발광 소자 |
-
2016
- 2016-05-26 KR KR1020160065045A patent/KR102651014B1/ko active IP Right Grant
- 2016-06-03 JP JP2016112197A patent/JP2017210464A/ja not_active Withdrawn
- 2016-12-14 US US15/378,084 patent/US10686139B2/en active Active
-
2020
- 2020-08-21 JP JP2020140484A patent/JP7078961B2/ja active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011049511A (ja) * | 2009-07-31 | 2011-03-10 | Fujifilm Corp | 有機電界発光素子 |
WO2012048266A1 (en) * | 2010-10-08 | 2012-04-12 | Universal Display Corporation | Novel 3, 9-linked oligocarbazole-based hosts, containing dbt and dbr fragments, separated by aromatic spacers |
US20130292659A1 (en) * | 2010-12-08 | 2013-11-07 | Hyung-Sun Kim | Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode |
WO2012099219A1 (ja) * | 2011-01-20 | 2012-07-26 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
US20150126736A1 (en) * | 2012-05-02 | 2015-05-07 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
WO2015016200A1 (ja) * | 2013-08-01 | 2015-02-05 | 国立大学法人九州大学 | 化合物、発光材料および有機発光素子 |
WO2015020217A1 (ja) * | 2013-08-09 | 2015-02-12 | 出光興産株式会社 | 有機エレクトロルミネッセンス用組成物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用材料溶液及び有機エレクトロルミネッセンス素子 |
WO2015033894A1 (ja) * | 2013-09-04 | 2015-03-12 | 出光興産株式会社 | カルバゾール誘導体、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器 |
WO2015093551A1 (ja) * | 2013-12-18 | 2015-06-25 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、インク組成物、有機エレクトロルミネッセンス素子、電子機器、及び化合物の製造方法 |
WO2015175678A1 (en) * | 2014-05-14 | 2015-11-19 | President And Fellows Of Harvard College | Organic light-emitting diode materials |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11309511B2 (en) | 2018-07-06 | 2022-04-19 | Samsung Display Co., Ltd. | Organic electroluminescence device and nitrogen-containing compound for organic electroluminescence device |
CN111233906A (zh) * | 2018-11-29 | 2020-06-05 | 三星显示有限公司 | 有机电致发光器件和用于有机电致发光器件的多环化合物 |
Also Published As
Publication number | Publication date |
---|---|
JP7078961B2 (ja) | 2022-06-01 |
US10686139B2 (en) | 2020-06-16 |
US20170346017A1 (en) | 2017-11-30 |
JP2021001175A (ja) | 2021-01-07 |
KR102651014B1 (ko) | 2024-03-26 |
KR20170134841A (ko) | 2017-12-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7078961B2 (ja) | 含窒素化合物及び含窒素化合物を含む有機電界発光素子 | |
KR102331777B1 (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 모노아민 화합물 | |
JP6965070B2 (ja) | アミン化合物及びそれを含む有機電界発光素子 | |
KR102585186B1 (ko) | 아민 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
JP2017203026A (ja) | 多環化合物及びこれを含む有機電界発光素子 | |
JP7481119B2 (ja) | 有機電界発光素子及び有機電界発光素子用多環化合物 | |
JP7264626B2 (ja) | アミン化合物及び有機電界発光素子 | |
JP2019127487A (ja) | 有機電界発光素子及び有機電界発光素子用モノアミン化合物 | |
KR20200087906A (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
JP2019182843A (ja) | 有機電界発光素子及び有機電界発光素子用多環化合物 | |
JP7479134B2 (ja) | 有機電界発光素子及び有機電界発光素子用多環化合物 | |
JP7349842B2 (ja) | 縮合環化合物、及びそれを含む有機電界発光素子 | |
JP2020143054A (ja) | 有機電界発光素子及び有機電界発光素子用多環化合物 | |
CN112625046A (zh) | 发光装置和用于发光装置的多环化合物 | |
CN113196511A (zh) | 有机电致发光器件和用于有机电致发光器件的螺环化合物 | |
JP2023123511A (ja) | 含窒素化合物及びそれを含む有機el素子 | |
CN111196780A (zh) | 有机电致发光装置及用于有机电致发光装置的化合物 | |
EP3428173B1 (en) | Dibenzo[b,e][1,4]oxasiline compounds and organic electroluminescence devices including the same | |
EP3483159B1 (en) | Nitrogen-containing compound and organic electroluminescence device including the same | |
US11165026B2 (en) | Heterocyclic compound and organic electroluminescence device including the same | |
JP7186037B2 (ja) | 含窒素化合物及びそれを含む有機電界発光素子 | |
KR102668795B1 (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
KR102545509B1 (ko) | 다환 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
JP2020090489A (ja) | 有機電界発光素子及び有機電界発光素子用多環化合物 | |
CN113024608A (zh) | 有机电致发光装置及用于有机电致发光装置的有机金属化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD01 | Notification of change of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7426 Effective date: 20160817 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20160817 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20180810 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20181102 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20181127 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20181127 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20181228 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190416 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200227 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200324 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200624 |
|
A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20200902 |