KR102663374B1 - 치환된 1,3,5-트리아진계 화합물, 조성물 및 이의 용도 - Google Patents
치환된 1,3,5-트리아진계 화합물, 조성물 및 이의 용도 Download PDFInfo
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- KR102663374B1 KR102663374B1 KR1020217035151A KR20217035151A KR102663374B1 KR 102663374 B1 KR102663374 B1 KR 102663374B1 KR 1020217035151 A KR1020217035151 A KR 1020217035151A KR 20217035151 A KR20217035151 A KR 20217035151A KR 102663374 B1 KR102663374 B1 KR 102663374B1
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- 239000000203 mixture Chemical class 0.000 title claims abstract description 57
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 570
- 239000000463 material Substances 0.000 claims abstract description 246
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000010410 layer Substances 0.000 claims description 146
- 125000001072 heteroaryl group Chemical group 0.000 claims description 113
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 111
- 125000003118 aryl group Chemical group 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 74
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 150000002367 halogens Chemical group 0.000 claims description 61
- 125000005842 heteroatom Chemical group 0.000 claims description 46
- 150000002431 hydrogen Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 230000005525 hole transport Effects 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- -1 1,3,5-triazine compound Chemical class 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000011630 iodine Substances 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000012776 electronic material Substances 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 230000008901 benefit Effects 0.000 abstract description 7
- 150000000182 1,3,5-triazines Chemical class 0.000 abstract description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 928
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 928
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 928
- 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 370
- 238000003786 synthesis reaction Methods 0.000 description 202
- 230000015572 biosynthetic process Effects 0.000 description 200
- 238000000034 method Methods 0.000 description 184
- 230000008569 process Effects 0.000 description 178
- 238000004458 analytical method Methods 0.000 description 173
- 239000000047 product Substances 0.000 description 173
- 238000004949 mass spectrometry Methods 0.000 description 172
- 239000013076 target substance Substances 0.000 description 171
- 150000001793 charged compounds Chemical class 0.000 description 168
- 230000000052 comparative effect Effects 0.000 description 41
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 40
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- MLVNYXXTYFTPRK-UHFFFAOYSA-N 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine Chemical compound C1=CC(F)=CC=C1C1=NC(Cl)=NC(C=2C=CC(F)=CC=2)=N1 MLVNYXXTYFTPRK-UHFFFAOYSA-N 0.000 description 28
- 230000000694 effects Effects 0.000 description 23
- OTJZMNIBLUCUJZ-UHFFFAOYSA-N 2,4-diphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC(C=2C=CC=CC=2)=N1 OTJZMNIBLUCUJZ-UHFFFAOYSA-N 0.000 description 20
- 150000004985 diamines Chemical class 0.000 description 17
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 13
- LPSLMIOUKRPZDC-UHFFFAOYSA-N 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine Chemical compound C1=CC(C)=CC=C1C1=NC(Cl)=NC(C=2C=CC(C)=CC=2)=N1 LPSLMIOUKRPZDC-UHFFFAOYSA-N 0.000 description 13
- QELBFKBJJRWUNG-UHFFFAOYSA-N 2-chloro-4,6-bis(4-propan-2-ylphenyl)-1,3,5-triazine Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(Cl)=NC(C=2C=CC(=CC=2)C(C)C)=N1 QELBFKBJJRWUNG-UHFFFAOYSA-N 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 10
- 238000005401 electroluminescence Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 9
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 230000007246 mechanism Effects 0.000 description 8
- 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 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002131 composite material Substances 0.000 description 7
- LSZYULBSFXDTPV-UHFFFAOYSA-N 2,4-bis(4-fluorophenyl)-1,3,5-triazine Chemical compound Fc1ccc(cc1)-c1ncnc(n1)-c1ccc(F)cc1 LSZYULBSFXDTPV-UHFFFAOYSA-N 0.000 description 6
- SAHBFLYFJBLFIG-UHFFFAOYSA-N 2-chloro-4,6-bis[4-(trifluoromethyl)phenyl]-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=C(C=C1)C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F SAHBFLYFJBLFIG-UHFFFAOYSA-N 0.000 description 6
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 6
- ASOFZHSTJHGQDT-UHFFFAOYSA-N 3,5-difluorobenzaldehyde Chemical compound FC1=CC(F)=CC(C=O)=C1 ASOFZHSTJHGQDT-UHFFFAOYSA-N 0.000 description 6
- WTWBUQJHJGUZCY-UHFFFAOYSA-N 4-Isopropyl benzaldehyde Natural products CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- MTDFZPKKVXCFLS-UHFFFAOYSA-N 1-(3-propan-2-ylphenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound C(C)(C)C=1C=C(C=CC1)C1(C(C=CC=C1)N)N MTDFZPKKVXCFLS-UHFFFAOYSA-N 0.000 description 5
- VBUCTUDUHYMXKV-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound C(C)(C)C1=CC=C(C=C1)C1(C(C=CC=C1)N)N VBUCTUDUHYMXKV-UHFFFAOYSA-N 0.000 description 5
- HCGZTGWBSHYUBR-UHFFFAOYSA-N 2-n-(2-propan-2-ylphenyl)benzene-1,2-diamine Chemical compound CC(C)C1=CC=CC=C1NC1=CC=CC=C1N HCGZTGWBSHYUBR-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000010408 film Substances 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VNAHZHWURTWPAL-UHFFFAOYSA-N 1-(3-fluorophenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound FC=1C=C(C=CC1)C1(C(C=CC=C1)N)N VNAHZHWURTWPAL-UHFFFAOYSA-N 0.000 description 4
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
- VFEOWFKLGIXFND-UHFFFAOYSA-N 2-n-pyridin-3-ylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CN=C1 VFEOWFKLGIXFND-UHFFFAOYSA-N 0.000 description 4
- WDRQNOGGIOMQNA-UHFFFAOYSA-N 2-n-pyridin-4-ylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=NC=C1 WDRQNOGGIOMQNA-UHFFFAOYSA-N 0.000 description 4
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- JLXHGJHEUWPEKD-UHFFFAOYSA-N 1-(2-fluorophenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound FC1=C(C=CC=C1)C1(C(C=CC=C1)N)N JLXHGJHEUWPEKD-UHFFFAOYSA-N 0.000 description 3
- OAOKAISXSFKHME-UHFFFAOYSA-N 1-(2-phenylphenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound C1(=C(C=CC=C1)C1(C(C=CC=C1)N)N)C1=CC=CC=C1 OAOKAISXSFKHME-UHFFFAOYSA-N 0.000 description 3
- NXQFHIDPABMEQB-UHFFFAOYSA-N 1-(3,5-difluorophenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound FC=1C=C(C=C(C1)F)C1(C(C=CC=C1)N)N NXQFHIDPABMEQB-UHFFFAOYSA-N 0.000 description 3
- NLRJDDXKPOKRMM-UHFFFAOYSA-N 1-(3-phenylphenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound C1=CC=C(C=C1)C2=CC(=CC=C2)C3(C=CC=CC3N)N NLRJDDXKPOKRMM-UHFFFAOYSA-N 0.000 description 3
- PZWCYOMAPAAIKM-UHFFFAOYSA-N 1-(4-fluorophenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound FC1=CC=C(C=C1)C1(C(C=CC=C1)N)N PZWCYOMAPAAIKM-UHFFFAOYSA-N 0.000 description 3
- NXGISHNBTXEMBP-UHFFFAOYSA-N 1-(4-phenylphenyl)cyclohexa-3,5-diene-1,2-diamine Chemical compound C1=CC=C(C=C1)C2=CC=C(C=C2)C3(C=CC=CC3N)N NXGISHNBTXEMBP-UHFFFAOYSA-N 0.000 description 3
- JQEUBSXRRWBZLZ-UHFFFAOYSA-N 1-[3,5-di(propan-2-yl)phenyl]cyclohexa-3,5-diene-1,2-diamine Chemical compound C(C)(C)C=1C=C(C=C(C1)C(C)C)C1(C(C=CC=C1)N)N JQEUBSXRRWBZLZ-UHFFFAOYSA-N 0.000 description 3
- UNKHZTKLZVMGCA-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]cyclohexa-3,5-diene-1,2-diamine Chemical compound C1=CC(C(C=C1)(C2=CC(=CC=C2)C(F)(F)F)N)N UNKHZTKLZVMGCA-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- LCRCBXLHWTVPEQ-UHFFFAOYSA-N 2-phenylbenzaldehyde Chemical compound O=CC1=CC=CC=C1C1=CC=CC=C1 LCRCBXLHWTVPEQ-UHFFFAOYSA-N 0.000 description 3
- KFKSIUOALVIACE-UHFFFAOYSA-N 3-phenylbenzaldehyde Chemical compound O=CC1=CC=CC(C=2C=CC=CC=2)=C1 KFKSIUOALVIACE-UHFFFAOYSA-N 0.000 description 3
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-methyl-benzaldehyde Natural products CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 3
- FXLOVSHXALFLKQ-UHFFFAOYSA-N para-methylbenzaldehyde Natural products CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- PBPKTJQXZHKCJC-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]cyclohexa-3,5-diene-1,2-diamine Chemical compound C1=CC(C(C=C1)(C2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)N)N PBPKTJQXZHKCJC-UHFFFAOYSA-N 0.000 description 2
- CYKLTULAUWZNIU-UHFFFAOYSA-N 2-n-(2-methylphenyl)benzene-1,2-diamine Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1N CYKLTULAUWZNIU-UHFFFAOYSA-N 0.000 description 2
- MKWLGVQXOJRYGU-UHFFFAOYSA-N 2-n-(3-methylphenyl)benzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N)=C1 MKWLGVQXOJRYGU-UHFFFAOYSA-N 0.000 description 2
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- UUFIHEBXYDLWTO-UHFFFAOYSA-N N2-(4-methylphenyl)benzene-1,2-diamine Chemical compound C1=CC(C)=CC=C1NC1=CC=CC=C1N UUFIHEBXYDLWTO-UHFFFAOYSA-N 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
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- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical group C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D403/02—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 two hetero rings
- C07D403/10—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 two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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