KR20220086224A - 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 - Google Patents
유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 Download PDFInfo
- Publication number
- KR20220086224A KR20220086224A KR1020200176480A KR20200176480A KR20220086224A KR 20220086224 A KR20220086224 A KR 20220086224A KR 1020200176480 A KR1020200176480 A KR 1020200176480A KR 20200176480 A KR20200176480 A KR 20200176480A KR 20220086224 A KR20220086224 A KR 20220086224A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- synthesis
- substituted
- preparation example
- unsubstituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 213
- 239000011368 organic material Substances 0.000 claims abstract description 11
- 230000005525 hole transport Effects 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000002347 injection Methods 0.000 claims description 36
- 239000007924 injection Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 230000003111 delayed effect Effects 0.000 claims description 22
- 239000002019 doping agent Substances 0.000 claims description 18
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005264 aryl amine group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 8
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000005067 haloformyl group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 58
- 230000015572 biosynthetic process Effects 0.000 description 347
- 238000003786 synthesis reaction Methods 0.000 description 345
- 238000002360 preparation method Methods 0.000 description 246
- 239000000376 reactant Substances 0.000 description 161
- 239000010410 layer Substances 0.000 description 151
- -1 3, 3-dimethylbutyl group Chemical group 0.000 description 74
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 26
- 150000002894 organic compounds Chemical class 0.000 description 23
- ROEOVWIEALGNLM-UHFFFAOYSA-N 5h-benzo[b]carbazole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4NC3=CC2=C1 ROEOVWIEALGNLM-UHFFFAOYSA-N 0.000 description 20
- UGFOTZLGPPWNPY-UHFFFAOYSA-N 7h-benzo[c]carbazole Chemical compound C1=CC=CC2=C3C4=CC=CC=C4NC3=CC=C21 UGFOTZLGPPWNPY-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 14
- 230000000903 blocking effect Effects 0.000 description 14
- RTTZJSBAKFDMEA-UHFFFAOYSA-N ctk8h5249 Chemical compound C1=CC=CC2=C3C4=CC5=CC=CC=C5C=C4NC3=CC=C21 RTTZJSBAKFDMEA-UHFFFAOYSA-N 0.000 description 13
- 239000002356 single layer Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- NIGIYSVQNPJEPT-UHFFFAOYSA-N C1=CC=CC=2C1=C1NC3=CC4=C(C=C3C1=CC=2)C=CC=C4 Chemical compound C1=CC=CC=2C1=C1NC3=CC4=C(C=C3C1=CC=2)C=CC=C4 NIGIYSVQNPJEPT-UHFFFAOYSA-N 0.000 description 8
- SBMXAWJSNIAHFR-UHFFFAOYSA-N n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NC=3C=C4C=CC=CC4=CC=3)=CC=C21 SBMXAWJSNIAHFR-UHFFFAOYSA-N 0.000 description 8
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 6
- 229920000767 polyaniline Polymers 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- NRZXZFVGTNEKPS-UHFFFAOYSA-N 1,2,5,6-dibenzcarbazole Chemical compound C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)N3)C3=CC=C21 NRZXZFVGTNEKPS-UHFFFAOYSA-N 0.000 description 5
- KEGHTUZLRZXPFU-UHFFFAOYSA-N C(C)(C)(C)C=1C=C2C=3C=C4C(=CC3NC2=CC1)C=CC=C4 Chemical compound C(C)(C)(C)C=1C=C2C=3C=C4C(=CC3NC2=CC1)C=CC=C4 KEGHTUZLRZXPFU-UHFFFAOYSA-N 0.000 description 5
- KFFBJKBEKNUMSL-UHFFFAOYSA-N C1=CC=CC2=C(C=3C(=CC=C(C=3)C(C)(C)C)N3)C3=CC=C21 Chemical compound C1=CC=CC2=C(C=3C(=CC=C(C=3)C(C)(C)C)N3)C3=CC=C21 KFFBJKBEKNUMSL-UHFFFAOYSA-N 0.000 description 5
- SPZXFXMHHCPNET-UHFFFAOYSA-M [Na+].ClCCl.CC([O-])=O Chemical compound [Na+].ClCCl.CC([O-])=O SPZXFXMHHCPNET-UHFFFAOYSA-M 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 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 4
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 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 4
- UNJZLNFHHINVOB-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-2-amine Chemical compound C1=CC=C2C(NC=3C=C4C=CC=CC4=CC=3)=CC=CC2=C1 UNJZLNFHHINVOB-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 4
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 4
- XIRDNVIBVXIQDO-UHFFFAOYSA-N 2-bromo-1,3-difluoro-5-methylbenzene Chemical compound CC1=CC(F)=C(Br)C(F)=C1 XIRDNVIBVXIQDO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- IOUYVXLOTZEOET-UHFFFAOYSA-N 8-tert-butyl-11H-benzo[a]carbazole Chemical compound CC(C)(C)C1=CC=C2NC3=C(C=CC=C4)C4=CC=C3C2=C1 IOUYVXLOTZEOET-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- GUYWPLAQEGZMME-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-12-yl)-2-bromophenyl]-N-naphthalen-1-ylnaphthalen-2-amine Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC=CC2=CC=CC=C12 GUYWPLAQEGZMME-UHFFFAOYSA-N 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- VMVGVGMRBKYIGN-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 VMVGVGMRBKYIGN-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000001931 thermography Methods 0.000 description 3
- 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 3
- YMLSHHJBHLOGTH-UHFFFAOYSA-N (4-bromo-3,5-difluorophenyl)-trimethylsilane Chemical compound C[Si](C)(C)C(C=C1F)=CC(F)=C1Br YMLSHHJBHLOGTH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 2
- FMHYVHRJVBVPFC-UHFFFAOYSA-N 12-(3-benzo[b]carbazol-5-yl-2-bromophenyl)-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 FMHYVHRJVBVPFC-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
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- 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
- YFGGXVUIBOZCBO-UHFFFAOYSA-N 2-bromo-1,3-difluoro-5-[3-(trifluoromethyl)phenyl]benzene Chemical group FC(C1=CC=CC(C(C=C2F)=CC(F)=C2Br)=C1)(F)F YFGGXVUIBOZCBO-UHFFFAOYSA-N 0.000 description 2
- RIADPSDLEHBSKU-UHFFFAOYSA-N 2-bromo-1,3-difluoro-5-phenylbenzene Chemical group FC(C=C(C=C1F)C2=CC=CC=C2)=C1Br RIADPSDLEHBSKU-UHFFFAOYSA-N 0.000 description 2
- HRZTZLCMURHWFY-UHFFFAOYSA-N 2-bromo-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Br HRZTZLCMURHWFY-UHFFFAOYSA-N 0.000 description 2
- ZBXUHDFWSOVTKA-UHFFFAOYSA-N 2-bromo-5-tert-butyl-1,3-difluorobenzene Chemical compound CC(C)(C)C1=CC(F)=C(Br)C(F)=C1 ZBXUHDFWSOVTKA-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
- RAGQYFJDOGDWHS-UHFFFAOYSA-N 3-(4-bromo-3,5-difluorophenyl)pyridine Chemical compound FC(C=C(C=C1F)C2=CC=CN=C2)=C1Br RAGQYFJDOGDWHS-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
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 2
- ZNJRONVKWRHYBF-VOTSOKGWSA-N 4-(dicyanomethylene)-2-methyl-6-julolidyl-9-enyl-4h-pyran Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-VOTSOKGWSA-N 0.000 description 2
- 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
- AHMZOXUVWPGHHH-UHFFFAOYSA-N 5-[2-bromo-3-(2-tert-butylbenzo[b]carbazol-5-yl)phenyl]-2-tert-butylbenzo[b]carbazole Chemical compound CC(C)(C)C(C=C1C2=C3C=C(C=CC=C4)C4=C2)=CC=C1N3C1=CC=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=CC(C(C)(C)C)=CC=C23)=C1Br AHMZOXUVWPGHHH-UHFFFAOYSA-N 0.000 description 2
- VWYJRLCUBVCRPR-UHFFFAOYSA-N 6h-dibenzo(b,h)carbazole Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4NC3=CC2=C1 VWYJRLCUBVCRPR-UHFFFAOYSA-N 0.000 description 2
- OSLJIQZYFZGVQP-UHFFFAOYSA-N 7-[2-bromo-3-(10-tert-butylbenzo[c]carbazol-7-yl)phenyl]-10-tert-butylbenzo[c]carbazole Chemical compound CC(C)(C)C(C=C1)=CC(C2=C3C=CC4=C2C=CC=C4)=C1N3C1=CC=CC(N(C2=C3C=C(C(C)(C)C)C=C2)C2=C3C(C=CC=C3)=C3C=C2)=C1Br OSLJIQZYFZGVQP-UHFFFAOYSA-N 0.000 description 2
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-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
- 101100495270 Caenorhabditis elegans cdc-26 gene Proteins 0.000 description 2
- 101100491335 Caenorhabditis elegans mat-2 gene Proteins 0.000 description 2
- 101100495256 Caenorhabditis elegans mat-3 gene Proteins 0.000 description 2
- 102100040428 Chitobiosyldiphosphodolichol beta-mannosyltransferase Human genes 0.000 description 2
- VXGUSDGCLNSENL-UHFFFAOYSA-N N-isoquinolin-6-ylisoquinolin-6-amine Chemical compound C1=C(C=NC=C2)C2=CC(NC2=CC=C(C=NC=C3)C3=C2)=C1 VXGUSDGCLNSENL-UHFFFAOYSA-N 0.000 description 2
- GLPKUFSLOUOUSW-UHFFFAOYSA-N N-quinolin-5-ylquinolin-5-amine Chemical compound C1=CC(NC2=C(C=CC=N3)C3=CC=C2)=C(C=CC=N2)C2=C1 GLPKUFSLOUOUSW-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- WGCXSIWGFOQDEG-UHFFFAOYSA-N [Zn].[Sn].[In] Chemical compound [Zn].[Sn].[In] WGCXSIWGFOQDEG-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 238000005266 casting Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 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
- 230000002349 favourable effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 238000007648 laser printing Methods 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- UCBRXEPLQQYGJM-UHFFFAOYSA-N n-(4-tert-butylphenyl)naphthalen-1-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=CC2=CC=CC=C12 UCBRXEPLQQYGJM-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000004059 quinone derivatives Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 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
- 229910052719 titanium Inorganic materials 0.000 description 2
- 150000003852 triazoles Chemical group 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
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000005406 washing 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
- 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- IJJYNFWMKNYNEW-UHFFFAOYSA-N 1-(4-pyren-1-ylphenyl)pyrene Chemical compound C1=CC(C=2C=CC(=CC=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)=C2C=CC3=CC=CC4=CC=C1C2=C43 IJJYNFWMKNYNEW-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- JXKQGMUHBKZPCD-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetraphenylpyrene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC=C4C=C(C(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 JXKQGMUHBKZPCD-UHFFFAOYSA-N 0.000 description 1
- ZNMQGESKMIQLFJ-UHFFFAOYSA-N 11-(2-bromo-3-carbazol-9-ylphenyl)benzo[a]carbazole Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12 ZNMQGESKMIQLFJ-UHFFFAOYSA-N 0.000 description 1
- RIYBDGZNYMSKNH-UHFFFAOYSA-N 11-(3-benzo[a]carbazol-11-yl-2-bromophenyl)benzo[a]carbazole Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12)=CC=C1)=C1N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12 RIYBDGZNYMSKNH-UHFFFAOYSA-N 0.000 description 1
- FVRDGOLOKYPUNK-UHFFFAOYSA-N 11-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)phenyl]benzo[a]carbazole Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC=CC(N2C3=C(C=CC=C4)C4=CC=C3C3=CC=CC=C23)=C1Br FVRDGOLOKYPUNK-UHFFFAOYSA-N 0.000 description 1
- YKAULFNNMORBIG-UHFFFAOYSA-N 11-[2-bromo-3-(8-tert-butylbenzo[a]carbazol-11-yl)phenyl]-8-tert-butylbenzo[a]carbazole Chemical compound CC(C)(C)C(C=C1C2=CC=C(C=CC=C3)C3=C22)=CC=C1N2C1=CC=CC(N2C3=C(C=CC=C4)C4=CC=C3C3=CC(C(C)(C)C)=CC=C23)=C1Br YKAULFNNMORBIG-UHFFFAOYSA-N 0.000 description 1
- ZCBWTJDCJVVOSP-UHFFFAOYSA-N 12-(2-bromo-3-carbazol-9-yl-5-methylphenyl)-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound CC(C=C1N2C3=CC=CC=C3C3=C2C=CC=C3)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br ZCBWTJDCJVVOSP-UHFFFAOYSA-N 0.000 description 1
- AGSMMMXJHNMUPC-UHFFFAOYSA-N 12-(2-bromo-3-carbazol-9-ylphenyl)-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 AGSMMMXJHNMUPC-UHFFFAOYSA-N 0.000 description 1
- NCEFBYZUKZOSDZ-UHFFFAOYSA-N 12-(2-bromo-3-carbazol-9-ylphenyl)-12-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaene Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N1C2=C(C=CC=C3)C3=CC=C2C2=CC(C=CC=C3)=C3C=C12 NCEFBYZUKZOSDZ-UHFFFAOYSA-N 0.000 description 1
- XFFUDBVJWIABGV-UHFFFAOYSA-N 12-(3-benzo[a]carbazol-11-yl-2-bromophenyl)-12-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaene Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12)=CC=C1)=C1N1C2=C(C=CC=C3)C3=CC=C2C2=CC(C=CC=C3)=C3C=C12 XFFUDBVJWIABGV-UHFFFAOYSA-N 0.000 description 1
- DOSVDKNOTUFWFD-UHFFFAOYSA-N 12-(3-benzo[b]carbazol-5-yl-2-bromophenyl)-12-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaene Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12)=CC=C1)=C1N1C2=C(C=CC=C3)C3=CC=C2C2=CC(C=CC=C3)=C3C=C12 DOSVDKNOTUFWFD-UHFFFAOYSA-N 0.000 description 1
- DMZJHLYETHTTKD-UHFFFAOYSA-N 12-(3-benzo[c]carbazol-7-yl-2-bromophenyl)-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 DMZJHLYETHTTKD-UHFFFAOYSA-N 0.000 description 1
- CWSSNXSDJHJTKL-UHFFFAOYSA-N 12-(3-benzo[c]carbazol-7-yl-2-bromophenyl)-12-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaene Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N1C2=C(C=CC=C3)C3=CC=C2C2=CC(C=CC=C3)=C3C=C12 CWSSNXSDJHJTKL-UHFFFAOYSA-N 0.000 description 1
- ZAAVGIPGJJOUBZ-UHFFFAOYSA-N 12-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)-5-methylphenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC(C)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br ZAAVGIPGJJOUBZ-UHFFFAOYSA-N 0.000 description 1
- GZTFYMVMOLWVOR-UHFFFAOYSA-N 12-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)-5-pyridin-3-ylphenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC(C2=CC=CN=C2)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br GZTFYMVMOLWVOR-UHFFFAOYSA-N 0.000 description 1
- IIHDMDHYSOITBE-UHFFFAOYSA-N 12-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)phenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br IIHDMDHYSOITBE-UHFFFAOYSA-N 0.000 description 1
- FGEVARNJWUOKFM-UHFFFAOYSA-N 12-[2-bromo-3-(6,12,18-triazapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3(8),4,6,9,14(19),15,17,20-decaen-12-yl)phenyl]-6,12,18-triazapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3(8),4,6,9,14(19),15,17,20-decaene Chemical compound BrC(C(N1C2=C(C=CC=N3)C3=CC=C2C2=C(C=CN=C3)C3=CC=C12)=CC=C1)=C1N1C2=C(C=CC=N3)C3=CC=C2C2=C(C=CN=C3)C3=CC=C12 FGEVARNJWUOKFM-UHFFFAOYSA-N 0.000 description 1
- HELQABNURPKSLI-UHFFFAOYSA-N 12-[2-bromo-5-tert-butyl-3-(3,6-ditert-butylcarbazol-9-yl)phenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC(C(C)(C)C)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br HELQABNURPKSLI-UHFFFAOYSA-N 0.000 description 1
- ZTKKMEHKPAMGQP-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-12-yl)-2-bromophenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 ZTKKMEHKPAMGQP-UHFFFAOYSA-N 0.000 description 1
- KXUQJLKWARLAES-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-12-yl)-2-bromophenyl]-12-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,13,15,17,19-decaene Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C1C=C(C=CC=C1)C1=C2 KXUQJLKWARLAES-UHFFFAOYSA-N 0.000 description 1
- JGVIOOPJJCUILW-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromo-5-[3-(trifluoromethyl)phenyl]phenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound FC(C1=CC=CC(C(C=C2N3C(C=C(C=CC=C4)C4=C4)=C4C4=C(C=CC=C5)C5=CC=C34)=CC(N3C(C=C(C=CC=C4)C4=C4)=C4C4=C(C=CC=C5)C5=CC=C34)=C2Br)=C1)(F)F JGVIOOPJJCUILW-UHFFFAOYSA-N 0.000 description 1
- BBQOZWQOOSWPSX-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromo-5-methylphenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound CC(C=C1N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br BBQOZWQOOSWPSX-UHFFFAOYSA-N 0.000 description 1
- FZMOCNIOCBLPDO-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromo-5-phenylphenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12)=CC(C1=CC=CC=C1)=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 FZMOCNIOCBLPDO-UHFFFAOYSA-N 0.000 description 1
- RGXBADLWEILEJN-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromo-5-propan-2-ylphenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound CC(C)C(C=C1N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br RGXBADLWEILEJN-UHFFFAOYSA-N 0.000 description 1
- RZFJTPIJLQVPHK-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromo-5-pyridin-3-ylphenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12)=CC(C1=CC=CN=C1)=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 RZFJTPIJLQVPHK-UHFFFAOYSA-N 0.000 description 1
- VTQXTJJLJVERDR-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromophenyl]-12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 VTQXTJJLJVERDR-UHFFFAOYSA-N 0.000 description 1
- ZLINFKUNWYRAQQ-UHFFFAOYSA-N 12-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromophenyl]-12-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaene Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC(C=CC=C3)=C3C=C12)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12 ZLINFKUNWYRAQQ-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AELZBFQHFNMGJS-UHFFFAOYSA-N 1h-1-benzosilole Chemical group C1=CC=C2[SiH2]C=CC2=C1 AELZBFQHFNMGJS-UHFFFAOYSA-N 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
- 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
- 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
- ZJBNFQDMUISUEF-UHFFFAOYSA-N 2-bromo-3-N,3-N-di(isoquinolin-6-yl)-1-N,1-N-dinaphthalen-2-ylbenzene-1,3-diamine Chemical compound BrC(C(N(C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1)=CC=C1)=C1N(C1=CC=C(C=NC=C2)C2=C1)C1=CC=C(C=NC=C2)C2=C1 ZJBNFQDMUISUEF-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
- JRKQMYYMKHPAHJ-DQPVQCHKSA-N 2-phenyl-N-[4-[(E)-2-[6-[(E)-2-[4-(N-phenylanilino)phenyl]ethenyl]naphthalen-2-yl]ethenyl]phenyl]aniline Chemical compound C(\C(C=C1)=CC=C1NC(C=CC=C1)=C1C1=CC=CC=C1)=C/C1=CC2=CC=C(/C=C/C(C=C3)=CC=C3N(C3=CC=CC=C3)C3=CC=CC=C3)C=C2C=C1 JRKQMYYMKHPAHJ-DQPVQCHKSA-N 0.000 description 1
- ZIRKGNPYKIBBID-UHFFFAOYSA-N 21-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)phenyl]-21-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15,17,19-decaene Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC=CC(N2C3=C(C=CC=C4)C4=C(C=CC=C4)C4=C3C3=C2C=CC=C3)=C1Br ZIRKGNPYKIBBID-UHFFFAOYSA-N 0.000 description 1
- BTROAEBZCFSKEI-UHFFFAOYSA-N 21-[3-(21-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15,17,19-decaen-21-yl)-2-bromophenyl]-21-azapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2,4,6,8,10,12,15,17,19-decaene Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=C(C=CC=C3)C3=C2C2=C1C=CC=C2)=CC=C1)=C1N1C2=C(C=CC=C3)C3=C(C=CC=C3)C3=C2C2=C1C=CC=C2 BTROAEBZCFSKEI-UHFFFAOYSA-N 0.000 description 1
- XETWNZRXQQQTTO-UHFFFAOYSA-N 25-azahexacyclo[12.11.0.02,7.08,13.015,24.016,21]pentacosa-1(25),2,5,7,9,11,13,15(24),16,18,20,22-dodecaene Chemical compound C1C=CC2=C3C=CC=CC3=C4C5=C(C=CC6=CC=CC=C65)N=C4C2=C1 XETWNZRXQQQTTO-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- LNQIJIDRNGJPKY-UHFFFAOYSA-N 4-[3-(25-azahexacyclo[12.11.0.02,7.08,13.015,24.016,21]pentacosa-1(25),2,5,7,9,11,13,15(24),16,18,20,22-dodecaen-4-yl)-2-bromophenyl]-25-azahexacyclo[12.11.0.02,7.08,13.015,24.016,21]pentacosa-1(25),2,5,7,9,11,13,15(24),16,18,20,22-dodecaene Chemical compound BrC1=C(C(C=C2)C=C3C2=C(C=CC=C2)C2=C2C3=NC3=C2C(C=CC=C2)=C2C=C3)C=CC=C1C(C=C1)C=C2C1=C(C=CC=C1)C1=C1C2=NC2=C1C(C=CC=C1)=C1C=C2 LNQIJIDRNGJPKY-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 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
- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 1
- OWIPJJNWWPNHPC-UHFFFAOYSA-N 5-(2-bromo-3-carbazol-9-ylphenyl)benzo[b]carbazole Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12 OWIPJJNWWPNHPC-UHFFFAOYSA-N 0.000 description 1
- QSPPNJPVMBBTNQ-UHFFFAOYSA-N 5-(3-benzo[a]carbazol-11-yl-2-bromophenyl)benzo[b]carbazole Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12 QSPPNJPVMBBTNQ-UHFFFAOYSA-N 0.000 description 1
- VUNKOABQTCIBQL-UHFFFAOYSA-N 5-(3-benzo[b]carbazol-5-yl-2-bromophenyl)benzo[b]carbazole Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12 VUNKOABQTCIBQL-UHFFFAOYSA-N 0.000 description 1
- YNPXZIJVNFJEEI-UHFFFAOYSA-N 5-(3-benzo[c]carbazol-7-yl-2-bromophenyl)benzo[b]carbazole Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12 YNPXZIJVNFJEEI-UHFFFAOYSA-N 0.000 description 1
- ASNFMNNLDGICLE-UHFFFAOYSA-N 5-[2-bromo-3-(10-tert-butylbenzo[c]carbazol-7-yl)phenyl]-2-tert-butylbenzo[b]carbazole Chemical compound CC(C)(C)C(C=C1C2=C3C=C(C=CC=C4)C4=C2)=CC=C1N3C(C=CC=C1N(C2=C3C=C(C(C)(C)C)C=C2)C2=C3C(C=CC=C3)=C3C=C2)=C1Br ASNFMNNLDGICLE-UHFFFAOYSA-N 0.000 description 1
- BWYSQHYUZUHELF-UHFFFAOYSA-N 5-[2-bromo-3-(8-tert-butylbenzo[a]carbazol-11-yl)phenyl]-2-tert-butylbenzo[b]carbazole Chemical compound CC(C)(C)C(C=C1C2=CC=C(C=CC=C3)C3=C22)=CC=C1N2C1=CC=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=CC(C(C)(C)C)=CC=C23)=C1Br BWYSQHYUZUHELF-UHFFFAOYSA-N 0.000 description 1
- ZDLIZBYRHMEIDB-UHFFFAOYSA-N 6,12,18-triazapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3(8),4,6,9,14(19),15,17,20-decaene Chemical compound C1=CC2=C3NC4=CC=C(C=NC=C5)C5=C4C3=CC=C2N=C1 ZDLIZBYRHMEIDB-UHFFFAOYSA-N 0.000 description 1
- SNCCSWJFEDJBLC-UHFFFAOYSA-N 6,12,18-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene Chemical compound C(C1=C2)=CN=CC1=CC1=C2NC2=C1C=C(C=NC=C1)C1=C2 SNCCSWJFEDJBLC-UHFFFAOYSA-N 0.000 description 1
- NEAMEOJVHSPMQT-UHFFFAOYSA-N 7-(2-bromo-3-carbazol-9-ylphenyl)benzo[c]carbazole Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1 NEAMEOJVHSPMQT-UHFFFAOYSA-N 0.000 description 1
- AFEWGBFCCQFENK-UHFFFAOYSA-N 7-(3-benzo[a]carbazol-11-yl-2-bromophenyl)benzo[c]carbazole Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12)=CC=C1)=C1N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1 AFEWGBFCCQFENK-UHFFFAOYSA-N 0.000 description 1
- BYNPGKBDRQFDPW-UHFFFAOYSA-N 7-(3-benzo[c]carbazol-7-yl-2-bromophenyl)benzo[c]carbazole Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1 BYNPGKBDRQFDPW-UHFFFAOYSA-N 0.000 description 1
- OVMWEVOZFPORDW-UHFFFAOYSA-N 7-[2-bromo-3-(8-tert-butylbenzo[a]carbazol-11-yl)phenyl]-10-tert-butylbenzo[c]carbazole Chemical compound CC(C)(C)C(C=C1C2=CC=C(C=CC=C3)C3=C22)=CC=C1N2C1=CC=CC(N(C2=C3C=C(C(C)(C)C)C=C2)C2=C3C(C=CC=C3)=C3C=C2)=C1Br OVMWEVOZFPORDW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CQLOSTJLLKKUQN-UHFFFAOYSA-N 9-(2-bromo-3-fluorophenyl)carbazole Chemical compound BrC1=C(C=CC=C1F)N1C2=CC=CC=C2C=2C=CC=CC1=2 CQLOSTJLLKKUQN-UHFFFAOYSA-N 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-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
- WEXXGZNCUPTRFZ-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1(=CC=CC=C1)N1C2=CC=CC=C2C=2C=CC=CC12.C1(=CC=CC=C1)N1C2=CC=CC=C2C=2C=CC=CC12 WEXXGZNCUPTRFZ-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 group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UDGCZJLRDGHPOI-UHFFFAOYSA-N C1=C2NC(C=C(C=CN=C3)C3=C3)=C3C2=C(C=CN=C2)C2=C1 Chemical compound C1=C2NC(C=C(C=CN=C3)C3=C3)=C3C2=C(C=CN=C2)C2=C1 UDGCZJLRDGHPOI-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HCAFDWVFTNVAHT-UHFFFAOYSA-N N-(2-bromo-3-carbazol-9-yl-5-methylphenyl)-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound CC(C=C1N2C3=CC=CC=C3C3=C2C=CC=C3)=CC(N(C2=CC3=CC=CC=C3C=C2)C2=CC3=CC=CC=C3C=C2)=C1Br HCAFDWVFTNVAHT-UHFFFAOYSA-N 0.000 description 1
- JEZSTXYEFCTDBI-UHFFFAOYSA-N N-(2-bromo-3-carbazol-9-ylphenyl)-N-isoquinolin-6-ylisoquinolin-6-amine Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N(C1=CC=C(C=NC=C2)C2=C1)C1=CC=C(C=NC=C2)C2=C1 JEZSTXYEFCTDBI-UHFFFAOYSA-N 0.000 description 1
- SWPWPUNWALZCEC-UHFFFAOYSA-N N-(2-bromo-3-carbazol-9-ylphenyl)-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 SWPWPUNWALZCEC-UHFFFAOYSA-N 0.000 description 1
- BDKFDZMVOMUXKV-UHFFFAOYSA-N N-(2-bromo-3-carbazol-9-ylphenyl)-N-phenylnaphthalen-1-amine Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N(C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 BDKFDZMVOMUXKV-UHFFFAOYSA-N 0.000 description 1
- KLVDHYJBCVHELX-UHFFFAOYSA-N N-(2-bromo-3-carbazol-9-ylphenyl)-N-quinolin-5-ylquinolin-5-amine Chemical compound BrC(C(N1C2=CC=CC=C2C2=C1C=CC=C2)=CC=C1)=C1N(C1=CC=CC2=C1C=CC=N2)C1=C(C=CC=N2)C2=CC=C1 KLVDHYJBCVHELX-UHFFFAOYSA-N 0.000 description 1
- RHRHZSFVXAXPID-UHFFFAOYSA-N N-(3-benzo[a]carbazol-11-yl-2-bromophenyl)-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 RHRHZSFVXAXPID-UHFFFAOYSA-N 0.000 description 1
- GJGVOZHVAUDHME-UHFFFAOYSA-N N-(3-benzo[a]carbazol-11-yl-2-bromophenyl)-N-phenylnaphthalen-1-amine Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC=CC=C12)=CC=C1)=C1N(C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 GJGVOZHVAUDHME-UHFFFAOYSA-N 0.000 description 1
- NLEQWHNJDOYOEE-UHFFFAOYSA-N N-(3-benzo[b]carbazol-5-yl-2-bromophenyl)-N-naphthalen-1-ylnaphthalen-1-amine Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12)=CC=C1)=C1N(C1=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 NLEQWHNJDOYOEE-UHFFFAOYSA-N 0.000 description 1
- LIFFSBYYROTIKX-UHFFFAOYSA-N N-(3-benzo[b]carbazol-5-yl-2-bromophenyl)-N-phenylnaphthalen-1-amine Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=CC=CC=C12)=CC=C1)=C1N(C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 LIFFSBYYROTIKX-UHFFFAOYSA-N 0.000 description 1
- HYLCLZRILQVSOQ-UHFFFAOYSA-N N-(3-benzo[c]carbazol-7-yl-2-bromophenyl)-N-naphthalen-1-ylnaphthalen-1-amine Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N(C1=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 HYLCLZRILQVSOQ-UHFFFAOYSA-N 0.000 description 1
- YPZDPJDNWDKPHT-UHFFFAOYSA-N N-(3-benzo[c]carbazol-7-yl-2-bromophenyl)-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 YPZDPJDNWDKPHT-UHFFFAOYSA-N 0.000 description 1
- AOTPLMCOWXSJBM-UHFFFAOYSA-N N-(3-benzo[c]carbazol-7-yl-2-bromophenyl)-N-phenylnaphthalen-1-amine Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N(C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 AOTPLMCOWXSJBM-UHFFFAOYSA-N 0.000 description 1
- ZEGBWYJGKPXWQX-UHFFFAOYSA-N N-(3-benzo[c]carbazol-7-yl-2-bromophenyl)-N-phenylnaphthalen-2-amine Chemical compound BrC(C(N(C1=C2C=CC=C1)C1=C2C(C=CC=C2)=C2C=C1)=CC=C1)=C1N(C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C1 ZEGBWYJGKPXWQX-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- CPBRBAXCOGUNJZ-UHFFFAOYSA-N N-[2-bromo-3-(10-tert-butylbenzo[c]carbazol-7-yl)phenyl]-N-(4-tert-butylphenyl)naphthalen-1-amine Chemical compound CC(C)(C)C(C=C1)=CC=C1N(C1=CC=CC2=CC=CC=C12)C(C=CC=C1N(C2=C3C=C(C(C)(C)C)C=C2)C2=C3C(C=CC=C3)=C3C=C2)=C1Br CPBRBAXCOGUNJZ-UHFFFAOYSA-N 0.000 description 1
- GQAYHMZUGASQBQ-UHFFFAOYSA-N N-[2-bromo-3-(2-tert-butylbenzo[b]carbazol-5-yl)phenyl]-N-(4-tert-butylphenyl)naphthalen-1-amine Chemical compound CC(C)(C)C(C=C1)=CC=C1N(C1=CC=CC2=CC=CC=C12)C(C=CC=C1N2C(C=C(C=CC=C3)C3=C3)=C3C3=CC(C(C)(C)C)=CC=C23)=C1Br GQAYHMZUGASQBQ-UHFFFAOYSA-N 0.000 description 1
- LYVWZCRCMPMCPN-UHFFFAOYSA-N N-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)-5-methylphenyl]-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC(C)=CC(N(C2=CC3=CC=CC=C3C=C2)C2=CC3=CC=CC=C3C=C2)=C1Br LYVWZCRCMPMCPN-UHFFFAOYSA-N 0.000 description 1
- TYZQJEKVRWZGQE-UHFFFAOYSA-N N-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)phenyl]-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC=CC(N(C2=CC3=CC=CC=C3C=C2)C2=CC3=CC=CC=C3C=C2)=C1Br TYZQJEKVRWZGQE-UHFFFAOYSA-N 0.000 description 1
- IOANRWPMBFHUDV-UHFFFAOYSA-N N-[2-bromo-3-(3,6-ditert-butylcarbazol-9-yl)phenyl]-N-phenylnaphthalen-1-amine Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC=CC(N(C2=CC=CC=C2)C2=CC=CC3=CC=CC=C23)=C1Br IOANRWPMBFHUDV-UHFFFAOYSA-N 0.000 description 1
- ZZAHROSEPZEIMW-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromophenyl]-N-naphthalen-1-ylnaphthalen-1-amine Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N(C1=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZZAHROSEPZEIMW-UHFFFAOYSA-N 0.000 description 1
- BGKSNGGQQUMGMQ-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromophenyl]-N-naphthalen-1-ylnaphthalen-2-amine Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC=CC2=CC=CC=C12 BGKSNGGQQUMGMQ-UHFFFAOYSA-N 0.000 description 1
- RUOUYNSJTLRURJ-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromophenyl]-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 RUOUYNSJTLRURJ-UHFFFAOYSA-N 0.000 description 1
- FPJMTRIIXRSJMD-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-2-bromophenyl]-N-phenylnaphthalen-1-amine Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C(C=CC=C3)C3=CC=C12)=CC=C1)=C1N(C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 FPJMTRIIXRSJMD-UHFFFAOYSA-N 0.000 description 1
- GQJGFUDYSPDCET-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaen-12-yl)-2-bromophenyl]-N-naphthalen-2-ylnaphthalen-2-amine Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC(C=CC=C3)=C3C=C12)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 GQJGFUDYSPDCET-UHFFFAOYSA-N 0.000 description 1
- ZEJTYNWJYBLSSS-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-1(13),2,4,6,8,10,14,16,18,20-decaen-12-yl)-2-bromophenyl]-N-phenylnaphthalen-1-amine Chemical compound BrC(C(N1C2=C(C=CC=C3)C3=CC=C2C2=CC(C=CC=C3)=C3C=C12)=CC=C1)=C1N(C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 ZEJTYNWJYBLSSS-UHFFFAOYSA-N 0.000 description 1
- GJXQGHHHNXBLOR-UHFFFAOYSA-N N-[3-(12-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,13,15,17,19-decaen-12-yl)-2-bromophenyl]-N-naphthalen-1-ylnaphthalen-2-amine Chemical compound BrC(C(N1C(C=C(C=CC=C2)C2=C2)=C2C2=C1C=C(C=CC=C1)C1=C2)=CC=C1)=C1N(C1=CC2=CC=CC=C2C=C1)C1=CC=CC2=CC=CC=C12 GJXQGHHHNXBLOR-UHFFFAOYSA-N 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- HSUJOVKXDRRJBC-UHFFFAOYSA-N [3,5-bis(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-4-bromophenyl]-trimethylsilane Chemical compound C[Si](C)(C)C(C=C1N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br HSUJOVKXDRRJBC-UHFFFAOYSA-N 0.000 description 1
- VUFFABKIDAVRPT-UHFFFAOYSA-N [3-(12-azapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaen-12-yl)-4-bromo-5-(3,6-ditert-butylcarbazol-9-yl)phenyl]-trimethylsilane Chemical compound CC(C)(C)C(C=C1)=CC(C2=CC(C(C)(C)C)=CC=C22)=C1N2C1=CC([Si](C)(C)C)=CC(N2C(C=C(C=CC=C3)C3=C3)=C3C3=C(C=CC=C4)C4=CC=C23)=C1Br VUFFABKIDAVRPT-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 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
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 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
- 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
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 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
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000005283 ground state 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- 125000001624 naphthyl group Chemical group 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
- 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
- 125000000962 organic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 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
- 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 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 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 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
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000003003 spiro group Chemical group 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
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical group S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical group S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- H10K85/658—Organoboranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
-
- H01L51/008—
-
- H01L51/5024—
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
-
- 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
- H10K2101/20—Delayed fluorescence 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020200176480A KR20220086224A (ko) | 2020-12-16 | 2020-12-16 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
| PCT/KR2021/019044 WO2022131780A1 (fr) | 2020-12-16 | 2021-12-15 | Composé électroluminescent organique et élément électroluminescent organique l'utilisant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020200176480A KR20220086224A (ko) | 2020-12-16 | 2020-12-16 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20220086224A true KR20220086224A (ko) | 2022-06-23 |
Family
ID=82057945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020200176480A KR20220086224A (ko) | 2020-12-16 | 2020-12-16 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR20220086224A (fr) |
| WO (1) | WO2022131780A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023190159A1 (fr) * | 2022-04-01 | 2023-10-05 | 東レ株式会社 | Composé, matériau d'élément électroluminescent et élément électroluminescent obtenu à l'aide de celui-ci, matériau d'élément de conversion photoélectrique, composition de conversion de couleur, feuille de conversion de couleur, unité de source de lumière, dispositif d'affichage et dispositif d'éclairage |
| CN117683055A (zh) * | 2022-08-26 | 2024-03-12 | 江苏三月科技股份有限公司 | 一种含有二苯基取代萘并吡咯结构的含硼有机化合物及其有机电致发光器件 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150033082A (ko) | 2013-09-23 | 2015-04-01 | 에스케이케미칼주식회사 | 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI636056B (zh) * | 2014-02-18 | 2018-09-21 | 學校法人關西學院 | 多環芳香族化合物及其製造方法、有機元件用材料及其應用 |
| US11502261B2 (en) * | 2017-05-02 | 2022-11-15 | Lg Chem Ltd. | Compound and organic light emitting device using the same |
| CN111684615B (zh) * | 2018-06-11 | 2023-10-17 | 株式会社Lg化学 | 有机发光器件 |
| CN111029477B (zh) * | 2019-12-10 | 2022-10-18 | 昆山国显光电有限公司 | 一种有机电致发光器件、显示面板及显示装置 |
| KR20210125621A (ko) * | 2020-04-07 | 2021-10-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함한 장치 |
-
2020
- 2020-12-16 KR KR1020200176480A patent/KR20220086224A/ko unknown
-
2021
- 2021-12-15 WO PCT/KR2021/019044 patent/WO2022131780A1/fr active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150033082A (ko) | 2013-09-23 | 2015-04-01 | 에스케이케미칼주식회사 | 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2022131780A1 (fr) | 2022-06-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3680244A1 (fr) | Dispositif électroluminescent organique et composé polycyclique pour dispositif électroluminescent organique | |
| KR102599981B1 (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
| KR102651014B1 (ko) | 함질소 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| KR102567881B1 (ko) | 함질소 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| EP3608320B1 (fr) | Dispositif électroluminescent organique et composé cyclique condensé pour dispositif électroluminescent organique | |
| US11276836B2 (en) | Organic electroluminescence device and polycyclic compound for organic electroluminescence device | |
| EP3882997A1 (fr) | Élément électroluminescent organique et composé spiro pour élément électroluminescent organique | |
| KR102639784B1 (ko) | 모노아민 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| KR20200107028A (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
| KR20210006554A (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 축합 다환 화합물 | |
| KR20200052513A (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
| KR20200120822A (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
| KR102400585B1 (ko) | 함질소 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| EP3653606A1 (fr) | Dispositif électroluminescent organique et composé pour dispositif électroluminescent organique | |
| EP3428173B1 (fr) | Composés dibenzo[b,e][1,4]oxasiline et dispositifs électroluminescents organiques les comprenant | |
| KR20220086224A (ko) | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 | |
| KR102428159B1 (ko) | 다환 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| KR20220086223A (ko) | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 | |
| KR102623053B1 (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
| KR102405134B1 (ko) | 함질소 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| KR20210070453A (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 축합다환 화합물 | |
| KR102485831B1 (ko) | 함질소 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| KR20200007111A (ko) | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 | |
| KR20220084871A (ko) | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 | |
| US20210226126A1 (en) | Organic electroluminescence device and fused polycyclic compound for organic electroluminescence device |