WO2019182360A1 - 화합물, 유기 발광 소자 및 표시 장치 - Google Patents
화합물, 유기 발광 소자 및 표시 장치 Download PDFInfo
- Publication number
- WO2019182360A1 WO2019182360A1 PCT/KR2019/003261 KR2019003261W WO2019182360A1 WO 2019182360 A1 WO2019182360 A1 WO 2019182360A1 KR 2019003261 W KR2019003261 W KR 2019003261W WO 2019182360 A1 WO2019182360 A1 WO 2019182360A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substituted
- unsubstituted
- mmol
- water
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 211
- 239000012044 organic layer Substances 0.000 claims description 141
- 239000010410 layer Substances 0.000 claims description 118
- -1 sulfoxy group Chemical group 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000002347 injection Methods 0.000 claims description 34
- 239000007924 injection Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 125000006753 (C1-C60) heteroaryl group Chemical group 0.000 claims description 6
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000003974 aralkylamines Chemical group 0.000 claims description 3
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005462 imide group Chemical group 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 258
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 218
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 132
- 238000006243 chemical reaction Methods 0.000 description 132
- 239000000741 silica gel Substances 0.000 description 132
- 229910002027 silica gel Inorganic materials 0.000 description 132
- 239000000203 mixture Substances 0.000 description 110
- 239000000460 chlorine Substances 0.000 description 91
- 230000015572 biosynthetic process Effects 0.000 description 88
- 238000003786 synthesis reaction Methods 0.000 description 86
- 0 *1NC(c2ccccc2)=NC(c(cc2)ccc2-c2ccccc2)=NC1c1cccc(-c(cc2)ccc2-c2cc(-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)ccc2)c1 Chemical compound *1NC(c2ccccc2)=NC(c(cc2)ccc2-c2ccccc2)=NC1c1cccc(-c(cc2)ccc2-c2cc(-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)ccc2)c1 0.000 description 63
- 239000012467 final product Substances 0.000 description 55
- 239000000126 substance Substances 0.000 description 53
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 46
- 238000010992 reflux Methods 0.000 description 46
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 45
- 238000004821 distillation Methods 0.000 description 45
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 45
- 239000011368 organic material Substances 0.000 description 43
- 239000000463 material Substances 0.000 description 28
- 230000032258 transport Effects 0.000 description 28
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 24
- 239000013067 intermediate product Substances 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- ZPJDYVCZIGHJTB-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaen-14-yl)-1,3,2-dioxaborolane Chemical compound C1=CC(=C2C=CC=C3SC=4C=CC=CC=4C1=C23)B1OC(C(O1)(C)C)(C)C ZPJDYVCZIGHJTB-UHFFFAOYSA-N 0.000 description 19
- 238000001953 recrystallisation Methods 0.000 description 19
- SRYWUYQMWQYKHH-UHFFFAOYSA-N 12-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C2C3=C(C=NC=C13)C=1C=CC=CC=1S2)C SRYWUYQMWQYKHH-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- VSSFGRBIDNAUHK-UHFFFAOYSA-N BrC1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 Chemical compound BrC1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 VSSFGRBIDNAUHK-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 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 5
- LPLLWKZDMKTEMV-UHFFFAOYSA-N 1-bromo-3-(3-bromophenyl)benzene Chemical group BrC1=CC=CC(C=2C=C(Br)C=CC=2)=C1 LPLLWKZDMKTEMV-UHFFFAOYSA-N 0.000 description 5
- VLRGDAXVXZAYKJ-UHFFFAOYSA-N 8-oxa-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound C1=C2C=3C(=CC=NC=3C=C1)OC1=C2C=CC=C1 VLRGDAXVXZAYKJ-UHFFFAOYSA-N 0.000 description 5
- HZRJGFDDRAJJEI-UHFFFAOYSA-N 8-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound C1=NC(C2=CC=CC=C2O2)=C3C2=CC=CC3=C1 HZRJGFDDRAJJEI-UHFFFAOYSA-N 0.000 description 5
- JKHCVYDYGWHIFJ-UHFFFAOYSA-N Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 Chemical compound Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 JKHCVYDYGWHIFJ-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 4
- FVQBRDRAILXTMJ-UHFFFAOYSA-N 2-chloro-4,6-bis(4-phenylphenyl)-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1C(C=C1)=CC=C1C1=CC=CC=C1 FVQBRDRAILXTMJ-UHFFFAOYSA-N 0.000 description 4
- JUUFZAFYUIVYRW-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-5-yl)-1,3,2-dioxaborolane Chemical compound C1=CC=C2C=CC=C3SC=4C=C(C=CC=4C1=C23)B1OC(C(O1)(C)C)(C)C JUUFZAFYUIVYRW-UHFFFAOYSA-N 0.000 description 4
- NUFVIQZVVRFGKR-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-oxa-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound CC1(OB(OC1(C)C)C=1C=CC2=C(C=1)OC1=CC=NC=3C=CC=C2C1=3)C NUFVIQZVVRFGKR-UHFFFAOYSA-N 0.000 description 4
- WTQTYSCZJIMZKB-UHFFFAOYSA-N 8,8-diphenyl-15-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound C1(=CC=CC=C1)C1(C2=CC=CC=C2C=2C=C(N=C3C=CC=C1C=23)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 WTQTYSCZJIMZKB-UHFFFAOYSA-N 0.000 description 4
- OSHMXRLGBXUQOF-UHFFFAOYSA-N 8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound C1=CC=C2C(=C1)C3=CC=CC4=C3C(=NC=C4)S2 OSHMXRLGBXUQOF-UHFFFAOYSA-N 0.000 description 4
- UCVLBDDILYCEDZ-UHFFFAOYSA-N 8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound C1=CC2=C3C(=C1)C4=C(N=CC=C4)SC3=CC=C2 UCVLBDDILYCEDZ-UHFFFAOYSA-N 0.000 description 4
- BKYGVUDAWIQUCI-UHFFFAOYSA-N 8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound C1=CC(C2=CC=CC=C2S2)=C3C2=CC=CC3=C1 BKYGVUDAWIQUCI-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 3
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 3
- OQNBMNMAAARXJU-UHFFFAOYSA-N 10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-14,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound B1(OC(C(O1)(C)C)(C)C)C2=C3C4=C(C=C2)N=CN=C4C5=CC=CC=C5S3 OQNBMNMAAARXJU-UHFFFAOYSA-N 0.000 description 3
- RVIPXARZFHBILZ-UHFFFAOYSA-N 16-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2)C RVIPXARZFHBILZ-UHFFFAOYSA-N 0.000 description 3
- DGRRKZULOFLYST-UHFFFAOYSA-N 2-[4-(3-bromophenyl)phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 DGRRKZULOFLYST-UHFFFAOYSA-N 0.000 description 3
- AMYQFFDJUSYNOE-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C=1C=CC2=C(C=1)OC=1C=CC=C3C=CN=C2C=13)C AMYQFFDJUSYNOE-UHFFFAOYSA-N 0.000 description 3
- GAAYPTPSHXSMEM-UHFFFAOYSA-N 5h-thiochromeno[2,3-b]pyridine Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=N1 GAAYPTPSHXSMEM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- VAIPJQIPFPRJKJ-UHFFFAOYSA-N 1,4-bis(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 VAIPJQIPFPRJKJ-UHFFFAOYSA-N 0.000 description 2
- LIGABBLKQSAQMD-UHFFFAOYSA-N 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrole Chemical group CC1(OB(OC1(C)C)C1=CC=C(C=C1)N1C=CC=C1)C LIGABBLKQSAQMD-UHFFFAOYSA-N 0.000 description 2
- GWOAJJWBCSUGHH-UHFFFAOYSA-N 1-bromo-4-(4-iodophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(I)C=C1 GWOAJJWBCSUGHH-UHFFFAOYSA-N 0.000 description 2
- DGVJYJILIIHQCL-UHFFFAOYSA-N 10-(4-bromophenyl)-8-thia-14,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound BrC1=CC=C(C=C1)C1=C2C3=C(N=CN=C3C=C1)C=1C=CC=CC=1S2 DGVJYJILIIHQCL-UHFFFAOYSA-N 0.000 description 2
- OFCSWAFQNUTUQH-UHFFFAOYSA-N 10-[4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]-8-thia-14,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=C2C3=C(N=CN=C3C=C1)C=1C=CC=CC=1S2)C OFCSWAFQNUTUQH-UHFFFAOYSA-N 0.000 description 2
- FDBVMALKHLUESZ-UHFFFAOYSA-N 14-[3-(3-bromophenyl)phenyl]-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C=CC2=C3C=1C=CC=C3SC=1C=CC=CC2=1 FDBVMALKHLUESZ-UHFFFAOYSA-N 0.000 description 2
- GIUBPXDWZZIRJT-UHFFFAOYSA-N 14-[3-[3-(4-bromophenyl)phenyl]phenyl]-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound BrC1=CC=C(C=C1)C=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C=CC2=C3C=1C=CC=C3SC=1C=CC=CC2=1 GIUBPXDWZZIRJT-UHFFFAOYSA-N 0.000 description 2
- SOAKZYAHZZHMRW-UHFFFAOYSA-N 15-(3-bromophenyl)-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound BrC=1C=C(C=CC=1)C=1N=C2C=CC=C3C2=C(C=1)C=1C=CC=CC=1S3 SOAKZYAHZZHMRW-UHFFFAOYSA-N 0.000 description 2
- SBXOXFIAUFPUDM-UHFFFAOYSA-N 15-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound CC1(OB(OC1(C)C)C=1N=C2C=CC=C3C2=C(C=1)C=1C=CC=CC=1S3)C SBXOXFIAUFPUDM-UHFFFAOYSA-N 0.000 description 2
- UNIYSHHMRVZKKO-UHFFFAOYSA-N 15-[3-[4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]phenyl]-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1N=C2C=CC=C3C2=C(C=1)C=1C=CC=CC=1S3)C UNIYSHHMRVZKKO-UHFFFAOYSA-N 0.000 description 2
- OQRMGDZPGOSRCY-UHFFFAOYSA-N 16-(3-bromophenyl)-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC=C2C=CN=C3C2=C1C=1C=CC=CC=1S3 OQRMGDZPGOSRCY-UHFFFAOYSA-N 0.000 description 2
- XKFSITVJCNSLET-UHFFFAOYSA-N 16-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C2C=CN=C3C2=C1C=1C=CC=CC=1S3)C XKFSITVJCNSLET-UHFFFAOYSA-N 0.000 description 2
- MWKZMEYDHDQXHL-UHFFFAOYSA-N 16-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound CC1(OB(OC1(C)C)C1=C2C=3C(=CC=NC=3C=C1)SC=1C=CC=CC=12)C MWKZMEYDHDQXHL-UHFFFAOYSA-N 0.000 description 2
- AUAHUYMDLQTNCV-UHFFFAOYSA-N 16-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound CC1(OB(OC1(C)C)C1=CN=C2C=CC=C3C2=C1C=1C=CC=CC=1S3)C AUAHUYMDLQTNCV-UHFFFAOYSA-N 0.000 description 2
- JCKFUKRCRBPXPT-UHFFFAOYSA-N 16-(4-bromophenyl)-8-thia-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC1=CC=C(C=C1)C1=C2C=3C(=CC=NC=3C=C1)SC=1C=CC=CC=12 JCKFUKRCRBPXPT-UHFFFAOYSA-N 0.000 description 2
- SLUUQIZRVLHMBS-UHFFFAOYSA-N 16-(4-bromophenyl)-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound BrC1=CC=C(C=C1)C1=CN=C2C=CC=C3C2=C1C=1C=CC=CC=1S3 SLUUQIZRVLHMBS-UHFFFAOYSA-N 0.000 description 2
- JOCFJRLHKWFSJS-UHFFFAOYSA-N 16-(4-bromophenyl)-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C(C=C1)C1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2 JOCFJRLHKWFSJS-UHFFFAOYSA-N 0.000 description 2
- UVNGUPHXIZHHEF-UHFFFAOYSA-N 16-[3-(3-bromophenyl)phenyl]-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC(=CC=C1)C1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2 UVNGUPHXIZHHEF-UHFFFAOYSA-N 0.000 description 2
- YMHKVKYTHNJBMO-UHFFFAOYSA-N 16-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C=1C=C(C=CC=1)C1=CC=C2C=CN=C3C2=C1C=1C=CC=CC=1S3)C YMHKVKYTHNJBMO-UHFFFAOYSA-N 0.000 description 2
- JLZMHRSWSHDSND-UHFFFAOYSA-N 16-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=CN=C2C=CC=C3C2=C1C=1C=CC=CC=1S3)C JLZMHRSWSHDSND-UHFFFAOYSA-N 0.000 description 2
- ZKSQIXNEFHHQBJ-UHFFFAOYSA-N 2-(3-bromophenyl)-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 ZKSQIXNEFHHQBJ-UHFFFAOYSA-N 0.000 description 2
- XTSYSYAUVJMZOP-UHFFFAOYSA-N 2-(4-bromophenyl)-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 XTSYSYAUVJMZOP-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical group 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
- ZCCPIXWQNBPVDR-UHFFFAOYSA-N 2-[3-(4-bromophenyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 ZCCPIXWQNBPVDR-UHFFFAOYSA-N 0.000 description 2
- GQKJVGJMCSBODN-UHFFFAOYSA-N 2-[3-[3-(3-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C=1C=C(C=CC=1)C1=CC(=CC=C1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 GQKJVGJMCSBODN-UHFFFAOYSA-N 0.000 description 2
- JITVBXMXBQQFLA-UHFFFAOYSA-N 2-[3-[3-(4-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C=1C=C(C=CC=1)C1=CC(=CC=C1)C1=CC=C(C=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 JITVBXMXBQQFLA-UHFFFAOYSA-N 0.000 description 2
- HAVWLIPEEKFTPI-UHFFFAOYSA-N 2-[3-[4-(3-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 HAVWLIPEEKFTPI-UHFFFAOYSA-N 0.000 description 2
- AIEQLAVNCQIGSJ-UHFFFAOYSA-N 2-[3-[4-(4-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=CC=C(C=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 AIEQLAVNCQIGSJ-UHFFFAOYSA-N 0.000 description 2
- NSSJUFRITKZZTL-UHFFFAOYSA-N 2-[4-(4-bromophenyl)phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C1=CC=C(C=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 NSSJUFRITKZZTL-UHFFFAOYSA-N 0.000 description 2
- CPPGVPJEFODCKN-UHFFFAOYSA-N 2-[4-[3-(3-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C1=CC(=CC=C1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 CPPGVPJEFODCKN-UHFFFAOYSA-N 0.000 description 2
- SUMVDNPCUMNPMZ-UHFFFAOYSA-N 2-[4-[3-(4-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C1=CC(=CC=C1)C1=CC=C(C=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 SUMVDNPCUMNPMZ-UHFFFAOYSA-N 0.000 description 2
- ISFPYXSEFLODIS-UHFFFAOYSA-N 2-[4-[4-(3-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 ISFPYXSEFLODIS-UHFFFAOYSA-N 0.000 description 2
- KCSDRKFHIIEYKL-UHFFFAOYSA-N 2-[4-[4-(4-bromophenyl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 KCSDRKFHIIEYKL-UHFFFAOYSA-N 0.000 description 2
- RWGKBMCEENXUQK-UHFFFAOYSA-N 2-[4-[4-(4-bromophenyl)phenyl]phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 RWGKBMCEENXUQK-UHFFFAOYSA-N 0.000 description 2
- KZBGTTBBPWIMOT-UHFFFAOYSA-N 2-chloro-4-(4-phenylphenyl)-[1]benzothiolo[3,2-d]pyrimidine Chemical compound C1=CC=CC(=C1)C1=CC=C(C2=NC(=NC3=C2SC2=C3C=CC=C2)Cl)C=C1 KZBGTTBBPWIMOT-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 2
- YPIGZIQGXMGRQO-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-4-yl)-1,3,2-dioxaborolane Chemical compound C1=CC=C2C=CC=C3SC=4C=CC(=CC=4C1=C23)B1OC(C(O1)(C)C)(C)C YPIGZIQGXMGRQO-UHFFFAOYSA-N 0.000 description 2
- DJQLZRJEDQBYLD-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[3-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-5-yl)phenyl]-1,3,2-dioxaborolane Chemical compound C1=CC=C2C=CC=C3SC=4C=C(C=CC=4C1=C23)C=1C=C(C=CC=1)B1OC(C(O1)(C)C)(C)C DJQLZRJEDQBYLD-UHFFFAOYSA-N 0.000 description 2
- KDNVPSHTQUFQHF-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[3-[3-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaen-14-yl)phenyl]phenyl]-1,3,2-dioxaborolane Chemical compound C1=CC(=C2C=CC=C3SC=4C=CC=CC=4C1=C23)C=1C=C(C=CC=1)C1=CC(=CC=C1)B1OC(C(O1)(C)C)(C)C KDNVPSHTQUFQHF-UHFFFAOYSA-N 0.000 description 2
- PJUXHAZHKYASAU-UHFFFAOYSA-N 4-(3-bromophenyl)-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC(=CC=C1)C1=CC=C2SC3=CC=CC4=C3C(=CC=C4)C2=C1 PJUXHAZHKYASAU-UHFFFAOYSA-N 0.000 description 2
- RCOJLKXEQACLKA-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC2=C(C=C1)SC1=NC=CC3=CC=CC2=C13)C RCOJLKXEQACLKA-UHFFFAOYSA-N 0.000 description 2
- LLLIQCGQCJHHIU-UHFFFAOYSA-N 5-(3-bromophenyl)-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC=1C=C(C=CC=1)C=1C=CC=2C3=C4C(C=CC=C4SC=2C=1)=CC=C3 LLLIQCGQCJHHIU-UHFFFAOYSA-N 0.000 description 2
- HDLPONLLJOSAIM-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4h-cyclopenta[c]pyrazol-3-yl]-n-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(CCC2)=C2C(C=2N=C(NC=3C=CN=CC=3)C(OCCN(C)C)=CN=2)=N1 HDLPONLLJOSAIM-UHFFFAOYSA-N 0.000 description 2
- FTJXKYHUGKOOCQ-UHFFFAOYSA-N 5-[3-(3-bromophenyl)phenyl]-8-oxa-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C=CC2=C(C=1)OC1=CC=NC=3C=CC=C2C1=3 FTJXKYHUGKOOCQ-UHFFFAOYSA-N 0.000 description 2
- LGFMCZYVZHZJFK-UHFFFAOYSA-N 5-[4-(4-bromophenyl)phenyl]-8-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)C=1C=CC2=C(C=1)OC=1C=CC=C3C=CN=C2C=13 LGFMCZYVZHZJFK-UHFFFAOYSA-N 0.000 description 2
- UGMQPXUYVGQCSR-UHFFFAOYSA-N 5-bromo-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C2C(SC3=CC=CC4=C3C2=CC=C4)=C1 UGMQPXUYVGQCSR-UHFFFAOYSA-N 0.000 description 2
- JVGBTWHMFWOTFU-UHFFFAOYSA-N 8,8-dimethyl-15-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound CC1(C2=CC=CC=C2C=2C=C(N=C3C=CC=C1C=23)B1OC(C(O1)(C)C)(C)C)C JVGBTWHMFWOTFU-UHFFFAOYSA-N 0.000 description 2
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 2
- GMKXBEHWRYBYAC-UHFFFAOYSA-N C(C(C=C1)c(cc2)c-3c4c2ccnc4Sc2ccccc-32)C=C1c1cc(-c2nc(cccc3)c3c(-c(cc3)ccc3-c3ccccc3)c2)ccc1 Chemical compound C(C(C=C1)c(cc2)c-3c4c2ccnc4Sc2ccccc-32)C=C1c1cc(-c2nc(cccc3)c3c(-c(cc3)ccc3-c3ccccc3)c2)ccc1 GMKXBEHWRYBYAC-UHFFFAOYSA-N 0.000 description 2
- SNZKHXDSUMUFCP-UHFFFAOYSA-N C1(=CC=C(C=C1)C1=NC(=NC(=N1)C=1C=C(C=CC=1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C=1C=C(C=CC=1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 SNZKHXDSUMUFCP-UHFFFAOYSA-N 0.000 description 2
- ZZKQZQPJDGXLKD-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C4C(=CC=C3)N=CC=C4S2 Chemical compound C1=CC=C2C(=C1)C3=C4C(=CC=C3)N=CC=C4S2 ZZKQZQPJDGXLKD-UHFFFAOYSA-N 0.000 description 2
- PFTJHXLMKVDJKK-UHFFFAOYSA-N CC1C(c2ccccc2)=C(C=CC=C2)C2=NC1c1cc(-c(cc2)ccc2-c(cc2)c-3c4c2nccc4Sc2ccccc-32)ccc1 Chemical compound CC1C(c2ccccc2)=C(C=CC=C2)C2=NC1c1cc(-c(cc2)ccc2-c(cc2)c-3c4c2nccc4Sc2ccccc-32)ccc1 PFTJHXLMKVDJKK-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UHUMDPHLHZIWIM-UHFFFAOYSA-N N1=CC(C2=CC=CC=C2S2)=C3C2=CC=CC3=C1 Chemical compound N1=CC(C2=CC=CC=C2S2)=C3C2=CC=CC3=C1 UHUMDPHLHZIWIM-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- WHPHHWBSZVPMIJ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2ccccc2)nc(-c(cc2)ccc2-c2ccc3c4c2-c(cccn2)c2Sc4ccc3)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2ccccc2)nc(-c(cc2)ccc2-c2ccc3c4c2-c(cccn2)c2Sc4ccc3)n1 WHPHHWBSZVPMIJ-UHFFFAOYSA-N 0.000 description 2
- ZRIHIHLEDOQMHC-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c(cc3-4)ccc3Sc3c5c-4cccc5ccn3)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c(cc3-4)ccc3Sc3c5c-4cccc5ccn3)c2)n1 ZRIHIHLEDOQMHC-UHFFFAOYSA-N 0.000 description 2
- CXHDLBMDVBBUNF-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2cccc(-c3c(-c4cccnc4Sc4ccc5)c4c5cc3)c2)nc2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2cccc(-c3c(-c4cccnc4Sc4ccc5)c4c5cc3)c2)nc2c1cccc2 CXHDLBMDVBBUNF-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 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
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003413 spiro compounds Chemical group 0.000 description 2
- 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 2
- NDVOVQWJSVNZIW-UHFFFAOYSA-N thiochromeno[4,3,2-de]quinoline Chemical compound C1=CC(C2=CC=CC=C2S2)=C3C2=CC=CC3=N1 NDVOVQWJSVNZIW-UHFFFAOYSA-N 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- WXJYWBIOPQQQOY-UHFFFAOYSA-N 10-[4-(3-bromophenyl)phenyl]-8-thia-14,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC=C(C=C1)C1=C2C3=C(N=CN=C3C=C1)C=1C=CC=CC=1S2 WXJYWBIOPQQQOY-UHFFFAOYSA-N 0.000 description 1
- YYCNEPNUQMCWQM-UHFFFAOYSA-N 10-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-8-thia-14,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=C2C3=C(N=CN=C3C=C1)C=1C=CC=CC=1S2)C YYCNEPNUQMCWQM-UHFFFAOYSA-N 0.000 description 1
- RGQCPCAAEKDUGO-UHFFFAOYSA-N 10-bromo-8-thia-14,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound BrC1=C2C3=C(N=CN=C3C=C1)C=1C=CC=CC=1S2 RGQCPCAAEKDUGO-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- RHQQLWLDPFMKPJ-UHFFFAOYSA-N 12-[4-(4-bromophenyl)phenyl]-8-thia-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound C1=CC=C2C(=C1)C3=CN=CC4=C(C=CC(=C34)S2)C5=CC=C(C=C5)C6=CC=C(C=C6)Br RHQQLWLDPFMKPJ-UHFFFAOYSA-N 0.000 description 1
- SIOPHWXBQANFFC-UHFFFAOYSA-N 12-[4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]-8-thia-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C2C3=C(C=NC=C13)C=1C=CC=CC=1S2)C SIOPHWXBQANFFC-UHFFFAOYSA-N 0.000 description 1
- NQKXICWXHGXUOL-UHFFFAOYSA-N 12-bromo-8-thia-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC1=CC=C2C3=C(C=NC=C13)C=1C=CC=CC=1S2 NQKXICWXHGXUOL-UHFFFAOYSA-N 0.000 description 1
- JMRNZSPITCBQMI-UHFFFAOYSA-N 14-bromo-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound BrC=1C=CC2=C3C=1C=CC=C3SC=1C=CC=CC2=1 JMRNZSPITCBQMI-UHFFFAOYSA-N 0.000 description 1
- KRNXVYLJYSGYDP-UHFFFAOYSA-N 15-[3-(3-bromophenyl)phenyl]-8,8-diphenyl-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC(=CC=C1)C=1N=C2C=CC=C3C2=C(C=1)C1=CC=CC=C1C3(C1=CC=CC=C1)C1=CC=CC=C1 KRNXVYLJYSGYDP-UHFFFAOYSA-N 0.000 description 1
- PEHICFIFQXQSQB-UHFFFAOYSA-N 15-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C=1C=C(C=CC=1)C=1N=C2C=CC=C3C2=C(C=1)C=1C=CC=CC=1S3)C PEHICFIFQXQSQB-UHFFFAOYSA-N 0.000 description 1
- ZWZPZKYGVKYMSR-UHFFFAOYSA-N 15-[3-[4-(4-bromophenyl)phenyl]phenyl]-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=CC=C1)C=1N=C2C=CC=C3C2=C(C=1)C=1C=CC=CC=1S3 ZWZPZKYGVKYMSR-UHFFFAOYSA-N 0.000 description 1
- UZKHQQIFHPSQRD-UHFFFAOYSA-N 15-[4-(4-bromophenyl)phenyl]-8,8-diphenyl-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)C=1N=C2C=CC=C3C2=C(C=1)C1=CC=CC=C1C3(C1=CC=CC=C1)C1=CC=CC=C1 UZKHQQIFHPSQRD-UHFFFAOYSA-N 0.000 description 1
- SYDRPBTVOXGSEM-UHFFFAOYSA-N 15-[4-[4-(3-bromophenyl)phenyl]phenyl]-8,8-diphenyl-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1N=C2C=CC=C3C2=C(C=1)C1=CC=CC=C1C3(C1=CC=CC=C1)C1=CC=CC=C1 SYDRPBTVOXGSEM-UHFFFAOYSA-N 0.000 description 1
- AUEDANVBOKBLSY-UHFFFAOYSA-N 15-bromo-8,8-dimethyl-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC=1N=C2C=CC=C3C2=C(C=1)C1=CC=CC=C1C3(C)C AUEDANVBOKBLSY-UHFFFAOYSA-N 0.000 description 1
- GQXQJKTWAKJRSS-UHFFFAOYSA-N 15-bromo-8,8-diphenyl-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC=1N=C2C=CC=C3C2=C(C=1)C1=CC=CC=C1C3(C1=CC=CC=C1)C1=CC=CC=C1 GQXQJKTWAKJRSS-UHFFFAOYSA-N 0.000 description 1
- UYGXEDSSCWAPKQ-UHFFFAOYSA-N 16-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-8-thia-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=C2C=3C(=CC=NC=3C=C1)SC=1C=CC=CC=12)C UYGXEDSSCWAPKQ-UHFFFAOYSA-N 0.000 description 1
- NUJZBLQCPZMYLB-UHFFFAOYSA-N 16-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2)C NUJZBLQCPZMYLB-UHFFFAOYSA-N 0.000 description 1
- BQJMWALPQWHZRC-UHFFFAOYSA-N 16-[4-[3-(3-bromophenyl)phenyl]phenyl]-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC=1C=C(C=CC=1)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2 BQJMWALPQWHZRC-UHFFFAOYSA-N 0.000 description 1
- PUJJMIFRCRJAKZ-UHFFFAOYSA-N 16-[4-[3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]phenyl]-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C=1C=C(C=CC=1)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2)C PUJJMIFRCRJAKZ-UHFFFAOYSA-N 0.000 description 1
- LBHBXPURFOSCBE-UHFFFAOYSA-N 16-[4-[3-[3-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]phenyl]phenyl]phenyl]-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C1=CC=CC=C1)C=1C=C(C=CC=1)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2)C1=CC=CC=C1 LBHBXPURFOSCBE-UHFFFAOYSA-N 0.000 description 1
- GISQNXQORXWPMS-UHFFFAOYSA-N 16-bromo-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound BrC1=CC=C2C=CN=C3C2=C1C=1C=CC=CC=1S3 GISQNXQORXWPMS-UHFFFAOYSA-N 0.000 description 1
- OXQZSJVVMGWUGX-UHFFFAOYSA-N 16-bromo-8-thia-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound BrC1=C2C=3C(=CC=NC=3C=C1)SC=1C=CC=CC=12 OXQZSJVVMGWUGX-UHFFFAOYSA-N 0.000 description 1
- IPACAXRYKBBZFZ-UHFFFAOYSA-N 16-bromo-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene Chemical compound BrC1=CN=C2C=CC=C3C2=C1C=1C=CC=CC=1S3 IPACAXRYKBBZFZ-UHFFFAOYSA-N 0.000 description 1
- JLHKXFRALYBWEC-UHFFFAOYSA-N 16-bromo-8-thia-6-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C2C3=C1C=1C(=NC=CC=1)SC3=CC=C2 JLHKXFRALYBWEC-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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- UJORPFQWUKFXIE-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4h-cyclopenta[c]pyrazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(CCC2)=C2C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 UJORPFQWUKFXIE-UHFFFAOYSA-N 0.000 description 1
- PLXPMZVMTNSXBA-UHFFFAOYSA-N 2-[3-(3-bromophenyl)phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2C=C(C=CC=2)C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 PLXPMZVMTNSXBA-UHFFFAOYSA-N 0.000 description 1
- UBRHFQOOIGNSRM-UHFFFAOYSA-N 2-[3-(4-bromophenyl)phenyl]-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C=1C=C(C=CC=1)C1=CC=C(C=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 UBRHFQOOIGNSRM-UHFFFAOYSA-N 0.000 description 1
- WVEAUBVQXFADEO-UHFFFAOYSA-N 2-[4-[4-(3-bromophenyl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound BrC=1C=C(C=CC=1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 WVEAUBVQXFADEO-UHFFFAOYSA-N 0.000 description 1
- QPICKCJCTMRVCS-UHFFFAOYSA-N 2-bromo-1-phenylbenzimidazole Chemical compound BrC1=NC2=CC=CC=C2N1C1=CC=CC=C1 QPICKCJCTMRVCS-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- VSMPNDGQPFFGPG-UHFFFAOYSA-N 2-chloro-4-(4-phenylphenyl)quinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C(C=C1)=CC=C1C1=CC=CC=C1 VSMPNDGQPFFGPG-UHFFFAOYSA-N 0.000 description 1
- ICQFFYYMWOOREK-UHFFFAOYSA-N 2-chloro-4-phenyl-[1]benzothiolo[3,2-d]pyrimidine Chemical compound S1C2=C(C3=C1C(C1=CC=CC=C1)=NC(=N3)Cl)C=CC=C2 ICQFFYYMWOOREK-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
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- KWSZETYDTRJUML-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[3-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-4-yl)phenyl]-1,3,2-dioxaborolane Chemical compound C1=CC=C2C=CC=C3SC=4C=CC(=CC=4C1=C23)C=1C=C(C=CC=1)B1OC(C(O1)(C)C)(C)C KWSZETYDTRJUML-UHFFFAOYSA-N 0.000 description 1
- POKQNZPMVVRGTB-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[4-(4-phenylphenyl)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 POKQNZPMVVRGTB-UHFFFAOYSA-N 0.000 description 1
- TYOXPRXCLLOJPM-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[4-[3-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-4-yl)phenyl]phenyl]-1,3,2-dioxaborolane Chemical compound C1=CC=C2C=CC=C3SC=4C=CC(=CC=4C1=C23)C=1C=C(C=CC=1)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C TYOXPRXCLLOJPM-UHFFFAOYSA-N 0.000 description 1
- ZNWOKTPLTABXSM-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)SC4=CC=CC5=NC=CC3=C54 ZNWOKTPLTABXSM-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- NCRYPUYIGROSND-UHFFFAOYSA-N 4-(4-phenylphenyl)-2-[4-[3-[3-(8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaen-14-yl)phenyl]phenyl]phenyl]-[1]benzothiolo[3,2-d]pyrimidine Chemical compound C1(=CC=C(C=C1)C=1C2=C(N=C(N=1)C1=CC=C(C=C1)C1=CC(=CC=C1)C1=CC(=CC=C1)C=1C=CC3=C4C=1C=CC=C4SC=1C=CC=CC3=1)C1=C(S2)C=CC=C1)C1=CC=CC=C1 NCRYPUYIGROSND-UHFFFAOYSA-N 0.000 description 1
- GVIJZEHCDKCVOR-UHFFFAOYSA-N 4-[3-(4-bromophenyl)phenyl]-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C(C=C1)C1=CC(=CC=C1)C1=CC=C2SC3=CC=CC4=C3C(=CC=C4)C2=C1 GVIJZEHCDKCVOR-UHFFFAOYSA-N 0.000 description 1
- CLYOZGKVDXJYEN-UHFFFAOYSA-N 4-[4-[4-(4-bromophenyl)phenyl]phenyl]-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC2=C(C=C1)SC1=NC=CC3=CC=CC2=C13 CLYOZGKVDXJYEN-UHFFFAOYSA-N 0.000 description 1
- WYBDNFSIINMVHF-UHFFFAOYSA-N 4-bromo-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC2=C(C=C1)SC1=NC=CC3=CC=CC2=C13 WYBDNFSIINMVHF-UHFFFAOYSA-N 0.000 description 1
- VNZUEIIRFLBJKG-UHFFFAOYSA-N 4-bromo-8-thia-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound BrC1=CC2=C(C=C1)SC=1C3=C2C=CN=C3C=CC=1 VNZUEIIRFLBJKG-UHFFFAOYSA-N 0.000 description 1
- ILGJHIYRJPAUQV-UHFFFAOYSA-N 4-bromo-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC1=CC=C2SC3=CC=CC4=C3C(=CC=C4)C2=C1 ILGJHIYRJPAUQV-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- UNBUTVWNUNPSGC-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)C4=CC=CC5=C4C(=NC=C5)S3 UNBUTVWNUNPSGC-UHFFFAOYSA-N 0.000 description 1
- WWQXEGUOJADSMG-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-thia-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)C4=NC=CC5=C4C(=CC=C5)S3 WWQXEGUOJADSMG-UHFFFAOYSA-N 0.000 description 1
- XPEOONVZFMHIII-UHFFFAOYSA-N 5-[3-(3-bromophenyl)phenyl]-8-thiatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C=CC=2C3=C4C(C=CC=C4SC=2C=1)=CC=C3 XPEOONVZFMHIII-UHFFFAOYSA-N 0.000 description 1
- HJXZBKCYEBKXMV-UHFFFAOYSA-N 5-[3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]-8-oxa-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound CC1(OB(OC1(C)C)C=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C=CC2=C(C=1)OC1=CC=NC=3C=CC=C2C1=3)C HJXZBKCYEBKXMV-UHFFFAOYSA-N 0.000 description 1
- RIFYYMKWFMJHJZ-UHFFFAOYSA-N 5-[4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]-8-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1C=CC2=C(C=1)OC=1C=CC=C3C=CN=C2C=13)C RIFYYMKWFMJHJZ-UHFFFAOYSA-N 0.000 description 1
- VZLBVCXFIMBLFU-UHFFFAOYSA-N 5-[4-[4-(4-bromophenyl)phenyl]phenyl]-8-oxa-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1C=CC2=C(C=1)OC1=CC=NC=3C=CC=C2C1=3 VZLBVCXFIMBLFU-UHFFFAOYSA-N 0.000 description 1
- GLCCMXHZUHNCGT-UHFFFAOYSA-N 5-[4-[4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]phenyl]-8-oxa-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1C=CC2=C(C=1)OC1=CC=NC=3C=CC=C2C1=3)C GLCCMXHZUHNCGT-UHFFFAOYSA-N 0.000 description 1
- AJMDYOVRRWSCBF-UHFFFAOYSA-N 5-bromo-8-oxa-12-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,9,11,13,15-octaene Chemical compound BrC=1C=CC2=C(C=1)OC1=CC=NC=3C=CC=C2C1=3 AJMDYOVRRWSCBF-UHFFFAOYSA-N 0.000 description 1
- QIIBSJDZRGIYHO-UHFFFAOYSA-N 5-bromo-8-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC=1C=CC2=C(C=1)OC=1C=CC=C3C=CN=C2C=13 QIIBSJDZRGIYHO-UHFFFAOYSA-N 0.000 description 1
- LUMZQUYJLHDIMP-UHFFFAOYSA-N 5-bromo-8-thia-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC=1C=CC2=C(C=1)SC1=NC=CC3=CC=CC2=C13 LUMZQUYJLHDIMP-UHFFFAOYSA-N 0.000 description 1
- MYLBACZRGBUTPC-UHFFFAOYSA-N 5-bromo-8-thia-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaene Chemical compound BrC=1C=CC2=C(C=1)SC=1C=CC=C3C=CN=C2C=13 MYLBACZRGBUTPC-UHFFFAOYSA-N 0.000 description 1
- OLGIKDIOPLMRCF-UHFFFAOYSA-N 8,8-diphenyl-15-[4-[4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]phenyl]-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12,14-octaene Chemical compound C1(=CC=CC=C1)C1(C2=CC=CC=C2C=2C=C(N=C3C=CC=C1C=23)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=CC=C1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 OLGIKDIOPLMRCF-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- KHBQSXGEPIJGMT-UHFFFAOYSA-N 8-thia-14,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaene Chemical compound C1=NC(C2=CC=CC=C2S2)=C3C2=CC=CC3=N1 KHBQSXGEPIJGMT-UHFFFAOYSA-N 0.000 description 1
- FRYRJNHMRVINIZ-UHFFFAOYSA-N B1CCOO1 Chemical compound B1CCOO1 FRYRJNHMRVINIZ-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- YFFCQNLYLJGRLC-UHFFFAOYSA-N BrC(C1)(C1C=C1)C=C1c1cc(Br)ccc1 Chemical compound BrC(C1)(C1C=C1)C=C1c1cc(Br)ccc1 YFFCQNLYLJGRLC-UHFFFAOYSA-N 0.000 description 1
- CBLUKCZQHSWPIV-UHFFFAOYSA-N Brc1nc2ccccc2nc1C1=CCCC=C1 Chemical compound Brc1nc2ccccc2nc1C1=CCCC=C1 CBLUKCZQHSWPIV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KMEBGICJZGWZIQ-UHFFFAOYSA-N C(C(C(C1)=C2)c3cccc4ccnc1c34)C=C2c1cc(-c(cc2)ccc2-c(cc2)ccc2-c2nc(-c(cc3)ccc3-c3ccccc3)nc(-c3ccccc3)n2)ccc1 Chemical compound C(C(C(C1)=C2)c3cccc4ccnc1c34)C=C2c1cc(-c(cc2)ccc2-c(cc2)ccc2-c2nc(-c(cc3)ccc3-c3ccccc3)nc(-c3ccccc3)n2)ccc1 KMEBGICJZGWZIQ-UHFFFAOYSA-N 0.000 description 1
- SGOPSNIBQZTMPT-UHFFFAOYSA-N C(C(C=C1)c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)C=C1c1cccc(-c(cc2)c3c4c2-c(cccc2)c2Sc4ccc3)c1 Chemical compound C(C(C=C1)c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)C=C1c1cccc(-c(cc2)c3c4c2-c(cccc2)c2Sc4ccc3)c1 SGOPSNIBQZTMPT-UHFFFAOYSA-N 0.000 description 1
- GOBDTOYFOVDLDU-UHFFFAOYSA-N C(C1)C=CC=C1c1nc(-c(cc2)ccc2-c2cccc(-c3cc(-c(cc4)cc-5c4Sc4cccc6c4c-5ccc6)ccc3)c2)nc(-c(cc2)ccc2-c2ccccc2)n1 Chemical compound C(C1)C=CC=C1c1nc(-c(cc2)ccc2-c2cccc(-c3cc(-c(cc4)cc-5c4Sc4cccc6c4c-5ccc6)ccc3)c2)nc(-c(cc2)ccc2-c2ccccc2)n1 GOBDTOYFOVDLDU-UHFFFAOYSA-N 0.000 description 1
- XPSAENZDNGLHKE-UHFFFAOYSA-N C(C1)C=CC=C1c1nc(-c2cccc(-c(cc3)ccc3-c3cc(-c4ccc5c6c4-c(cccn4)c4Sc6ccc5)ccc3)c2)nc(-c2ccccc2)n1 Chemical compound C(C1)C=CC=C1c1nc(-c2cccc(-c(cc3)ccc3-c3cc(-c4ccc5c6c4-c(cccn4)c4Sc6ccc5)ccc3)c2)nc(-c2ccccc2)n1 XPSAENZDNGLHKE-UHFFFAOYSA-N 0.000 description 1
- LBMXUCCFNLMLRK-UHFFFAOYSA-N C(C1C2=CC=CCC2C2C(C=C3)c4cccc(-c5nc(cccc6)c6nc5-c5ccccc5)c4)C1c1c2c3ncc1 Chemical compound C(C1C2=CC=CCC2C2C(C=C3)c4cccc(-c5nc(cccc6)c6nc5-c5ccccc5)c4)C1c1c2c3ncc1 LBMXUCCFNLMLRK-UHFFFAOYSA-N 0.000 description 1
- HKWLZLWKARGBLG-UHFFFAOYSA-N C(C1CC1)SC(C1)C1c1ccc-2c3c1cccc3Cc(cc1)c-2cc1-c1cc(-c(cc2)ccc2-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 Chemical compound C(C1CC1)SC(C1)C1c1ccc-2c3c1cccc3Cc(cc1)c-2cc1-c1cc(-c(cc2)ccc2-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)ccc1 HKWLZLWKARGBLG-UHFFFAOYSA-N 0.000 description 1
- SFFNWSXVKCEAOS-UHFFFAOYSA-N C(C=CC=C1)C=C1c1nc(-c2ccncc2)cc(-c2cc(-c3cc(-c4cc(-c(cc5)cc-6c5Sc5nccc7c5c-6ccc7)ccc4)ccc3)ccc2)c1 Chemical compound C(C=CC=C1)C=C1c1nc(-c2ccncc2)cc(-c2cc(-c3cc(-c4cc(-c(cc5)cc-6c5Sc5nccc7c5c-6ccc7)ccc4)ccc3)ccc2)c1 SFFNWSXVKCEAOS-UHFFFAOYSA-N 0.000 description 1
- BFOIVEWUMOHYML-UHFFFAOYSA-N C(CC(c(cc1)ccc1-c1cc(-c2nc(cccc3)c3nc2-c2ccccc2)ccc1)=C1)C=C1c1cnc2c3c1-c(cccc1)c1Sc3ccc2 Chemical compound C(CC(c(cc1)ccc1-c1cc(-c2nc(cccc3)c3nc2-c2ccccc2)ccc1)=C1)C=C1c1cnc2c3c1-c(cccc1)c1Sc3ccc2 BFOIVEWUMOHYML-UHFFFAOYSA-N 0.000 description 1
- PXKXVMIVCZARPJ-UHFFFAOYSA-N C(COc1cc(-c(cc2)ccc2-c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)ccc1-1)c2cccc3c2c-1ncc3 Chemical compound C(COc1cc(-c(cc2)ccc2-c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)ccc1-1)c2cccc3c2c-1ncc3 PXKXVMIVCZARPJ-UHFFFAOYSA-N 0.000 description 1
- JBTLFCCMZOQMOR-UHFFFAOYSA-N C(Cc1ncc2)c(ccc(-c3cc(-c(cc4)ccc4-c(cc4)ccc4-c4nc(-c(cc5)ccc5-c5ccccc5)nc(-c5ccccc5)n4)ccc3)c3)c3-c3c1c2ccc3 Chemical compound C(Cc1ncc2)c(ccc(-c3cc(-c(cc4)ccc4-c(cc4)ccc4-c4nc(-c(cc5)ccc5-c5ccccc5)nc(-c5ccccc5)n4)ccc3)c3)c3-c3c1c2ccc3 JBTLFCCMZOQMOR-UHFFFAOYSA-N 0.000 description 1
- HYZQWJOZIUYWFW-UHFFFAOYSA-N C(c(cccc1)c1-c1ncnc(cc2)c11)c1c2-c1cc(-c2cc(-c3ccncc3)nc(-c3ccncc3)c2)ccc1 Chemical compound C(c(cccc1)c1-c1ncnc(cc2)c11)c1c2-c1cc(-c2cc(-c3ccncc3)nc(-c3ccncc3)c2)ccc1 HYZQWJOZIUYWFW-UHFFFAOYSA-N 0.000 description 1
- YIBYKMNXVKAOMQ-UHFFFAOYSA-N C(c1c-2cccc1)c1cccc3ncc(-c(cc4)ccc4-c(cc4)ccc4-c4cc(-c5nc(-c6ccccc6)nc(-c6ccccc6)n5)ccc4)c-2c13 Chemical compound C(c1c-2cccc1)c1cccc3ncc(-c(cc4)ccc4-c(cc4)ccc4-c4cc(-c5nc(-c6ccccc6)nc(-c6ccccc6)n5)ccc4)c-2c13 YIBYKMNXVKAOMQ-UHFFFAOYSA-N 0.000 description 1
- WKZQXFMHNDGDIV-BGRWSDHPSA-N C/C=C\C=C/Cc1nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3)cc-4c3Sc3cccc5c3c-4ccn5)c2)nc(-c(cc2)ccc2-c2ccccc2)n1 Chemical compound C/C=C\C=C/Cc1nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3)cc-4c3Sc3cccc5c3c-4ccn5)c2)nc(-c(cc2)ccc2-c2ccccc2)n1 WKZQXFMHNDGDIV-BGRWSDHPSA-N 0.000 description 1
- HRNLBAMJUFNOBB-UHFFFAOYSA-N C1=CC2=NC(Br)=CC(C=3C(=CC=CC=3)S3)=C2C3=C1 Chemical compound C1=CC2=NC(Br)=CC(C=3C(=CC=CC=3)S3)=C2C3=C1 HRNLBAMJUFNOBB-UHFFFAOYSA-N 0.000 description 1
- SHGYRZNGRPRONQ-UHFFFAOYSA-N C1C=CC=CC1c1nc(cccc2)c2nc1-c(cc1)ccc1-c(cc1)ccc1-c1ccc2Sc(cccc3)c3-c3cncc1c23 Chemical compound C1C=CC=CC1c1nc(cccc2)c2nc1-c(cc1)ccc1-c(cc1)ccc1-c1ccc2Sc(cccc3)c3-c3cncc1c23 SHGYRZNGRPRONQ-UHFFFAOYSA-N 0.000 description 1
- WXERADHZCUKPOP-UHFFFAOYSA-N C1Sc(cc(cc2)-c(cc3)ccc3-c(cc3)ccc3-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)c2-c2cccc3cccc1c23 Chemical compound C1Sc(cc(cc2)-c(cc3)ccc3-c(cc3)ccc3-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)c2-c2cccc3cccc1c23 WXERADHZCUKPOP-UHFFFAOYSA-N 0.000 description 1
- LZBCWQPPUDSNSP-UHFFFAOYSA-N C1c2cc(-c3cccc(-c4cc(-c5nc(-c(cc6)ccc6-c6ccccc6)nc(-c6ccccc6)n5)ccc4)c3)ccc2-c2cccc3cccc1c23 Chemical compound C1c2cc(-c3cccc(-c4cc(-c5nc(-c(cc6)ccc6-c6ccccc6)nc(-c6ccccc6)n5)ccc4)c3)ccc2-c2cccc3cccc1c23 LZBCWQPPUDSNSP-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- KEMMZONAHFHQLA-UHFFFAOYSA-N C=C(c(cc1)c-2cc1-c1cc(-c(cc3)ccc3-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)ccc1)c1cccc3cccc-2c13 Chemical compound C=C(c(cc1)c-2cc1-c1cc(-c(cc3)ccc3-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)ccc1)c1cccc3cccc-2c13 KEMMZONAHFHQLA-UHFFFAOYSA-N 0.000 description 1
- LXYHRLBTURQIJP-AAPHRLRXSA-N C=C/C=C1\C2=C(C=C)c(cccc3)c3SC2=CC=C1c1cccc(-c2nc(cccc3)c3nc2-c2ccccc2)c1 Chemical compound C=C/C=C1\C2=C(C=C)c(cccc3)c3SC2=CC=C1c1cccc(-c2nc(cccc3)c3nc2-c2ccccc2)c1 LXYHRLBTURQIJP-AAPHRLRXSA-N 0.000 description 1
- LBJBAAAGDLSUNS-UHFFFAOYSA-N C=S1c2cc(-c(cc3)ccc3-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)ccc2-c2cccc3cccc1c23 Chemical compound C=S1c2cc(-c(cc3)ccc3-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)ccc2-c2cccc3cccc1c23 LBJBAAAGDLSUNS-UHFFFAOYSA-N 0.000 description 1
- DOYAPHQCZAEMGN-UHFFFAOYSA-N C=[Br]c1nc2ccccc2nc1-c1ccccc1 Chemical compound C=[Br]c1nc2ccccc2nc1-c1ccccc1 DOYAPHQCZAEMGN-UHFFFAOYSA-N 0.000 description 1
- BFTLDZJYCVSISS-YTCTUYNNSA-N CC(C(/C(/c(cc1)ccc1-c(cc1)cc-2c1Sc1cccc3c1c-2ccn3)=N\c1c(C)cccc1)c1ccccc1)=C Chemical compound CC(C(/C(/c(cc1)ccc1-c(cc1)cc-2c1Sc1cccc3c1c-2ccn3)=N\c1c(C)cccc1)c1ccccc1)=C BFTLDZJYCVSISS-YTCTUYNNSA-N 0.000 description 1
- DINCYBRSNKCVSQ-DQRAZIAOSA-N CC(C(C1C2C3=CC=CC2)=C(/C=C\N)C=CC1c1cc(-c2nc(cccc4)c4nc2-c2ccccc2)ccc1)C3=C Chemical compound CC(C(C1C2C3=CC=CC2)=C(/C=C\N)C=CC1c1cc(-c2nc(cccc4)c4nc2-c2ccccc2)ccc1)C3=C DINCYBRSNKCVSQ-DQRAZIAOSA-N 0.000 description 1
- GMQJPRYCRZDRMJ-UHFFFAOYSA-N CC(C)(C(C)(C)OBB1OC(C)(C)C(C)(C)O1)O Chemical compound CC(C)(C(C)(C)OBB1OC(C)(C)C(C)(C)O1)O GMQJPRYCRZDRMJ-UHFFFAOYSA-N 0.000 description 1
- VNNGIQWWMNXPFM-UHFFFAOYSA-N CC(C)(c1c-2cccc1)c1cccc3c1c-2cc(-c1cc(-c(cc2)ccc2-c(cc2)ccc2-c2nc(cccc4)c4[n]2-c2ccccc2)ccc1)n3 Chemical compound CC(C)(c1c-2cccc1)c1cccc3c1c-2cc(-c1cc(-c(cc2)ccc2-c(cc2)ccc2-c2nc(cccc4)c4[n]2-c2ccccc2)ccc1)n3 VNNGIQWWMNXPFM-UHFFFAOYSA-N 0.000 description 1
- MRCQOXPTUUGQQH-UHFFFAOYSA-N CC(C1)(C2=CC=C1c1cc(-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)ccc1)Sc1c3c2cccc3ccc1 Chemical compound CC(C1)(C2=CC=C1c1cc(-c3nc(-c(cc4)ccc4-c4ccccc4)nc(-c4ccccc4)n3)ccc1)Sc1c3c2cccc3ccc1 MRCQOXPTUUGQQH-UHFFFAOYSA-N 0.000 description 1
- VYJYMEKZHYKTHB-UHFFFAOYSA-N CC(C1c2ccccc2)c(cccc2)c2N=C1c(cc1)ccc1-c1ccc2c3c1-c(cccc1)c1Sc3ncc2 Chemical compound CC(C1c2ccccc2)c(cccc2)c2N=C1c(cc1)ccc1-c1ccc2c3c1-c(cccc1)c1Sc3ncc2 VYJYMEKZHYKTHB-UHFFFAOYSA-N 0.000 description 1
- WJECYFAQWQBFCR-WDHDNBHHSA-N CC(c1cc(nc(cc2-c(cccc3)c3S3)-c4cc(/C(/C(c5ccccc5)=C)=N/c5c(C)cccc5)ccc4)c2c3c1)[IH]C Chemical compound CC(c1cc(nc(cc2-c(cccc3)c3S3)-c4cc(/C(/C(c5ccccc5)=C)=N/c5c(C)cccc5)ccc4)c2c3c1)[IH]C WJECYFAQWQBFCR-WDHDNBHHSA-N 0.000 description 1
- XFTKPKKNUXOQAS-UHFFFAOYSA-N CC1(C)OB([B](OC(C)(C)C2(C)C)=[O]2=C)OC1(C)C Chemical compound CC1(C)OB([B](OC(C)(C)C2(C)C)=[O]2=C)OC1(C)C XFTKPKKNUXOQAS-UHFFFAOYSA-N 0.000 description 1
- RYQUEJPNNQRQCN-UHFFFAOYSA-N CC1(C)OB(c(cc2)ccc2C(C=CC2)=CC2(C)C(C)(CC=C2)C=C2c2ccc-3c4c2cccc4Sc2ccccc-32)OC1(C)C Chemical compound CC1(C)OB(c(cc2)ccc2C(C=CC2)=CC2(C)C(C)(CC=C2)C=C2c2ccc-3c4c2cccc4Sc2ccccc-32)OC1(C)C RYQUEJPNNQRQCN-UHFFFAOYSA-N 0.000 description 1
- NOSNPUFKAFCLQC-UHFFFAOYSA-N CC1(C)OB(c2ccc3SC4=CC=CCC4c4cncc2c34)OC1(C)C Chemical compound CC1(C)OB(c2ccc3SC4=CC=CCC4c4cncc2c34)OC1(C)C NOSNPUFKAFCLQC-UHFFFAOYSA-N 0.000 description 1
- YKGUKWCLRMNMPE-UHFFFAOYSA-N CC1(C)OB(c2ccc3Sc4ccccc4C4=CN(C)Cc2c34)OC1(C)C Chemical compound CC1(C)OB(c2ccc3Sc4ccccc4C4=CN(C)Cc2c34)OC1(C)C YKGUKWCLRMNMPE-UHFFFAOYSA-N 0.000 description 1
- URKKBSZJZSVOHD-UHFFFAOYSA-N CC1(C)OB(c2cccc(-c3cccc(-c4ccc(-c5cccc6cccc(S7)c56)c7c4)c3)c2)OC1(C)C Chemical compound CC1(C)OB(c2cccc(-c3cccc(-c4ccc(-c5cccc6cccc(S7)c56)c7c4)c3)c2)OC1(C)C URKKBSZJZSVOHD-UHFFFAOYSA-N 0.000 description 1
- IBFAFEBFNHJIEF-UHFFFAOYSA-N CC1C(c(cc2)ccc2-c2ccc3Sc(cccc4)c4-c4cncc2c34)=CC=C(B2OC(C)(C)C(C)(C)O2)C1 Chemical compound CC1C(c(cc2)ccc2-c2ccc3Sc(cccc4)c4-c4cncc2c34)=CC=C(B2OC(C)(C)C(C)(C)O2)C1 IBFAFEBFNHJIEF-UHFFFAOYSA-N 0.000 description 1
- ZMSZKTJXKCUELS-UHFFFAOYSA-N CC1C=C(B2OC(C)(C)C(C)(C)O2)C=CC1c(cc1)ccc1-c1ccc2Sc(cccc3)c3-c3cncc1c23 Chemical compound CC1C=C(B2OC(C)(C)C(C)(C)O2)C=CC1c(cc1)ccc1-c1ccc2Sc(cccc3)c3-c3cncc1c23 ZMSZKTJXKCUELS-UHFFFAOYSA-N 0.000 description 1
- XWYATJYFPSVRTO-UHFFFAOYSA-N CCSS(C)(CC)c(cc1)cc(S2)c1-c(cc1)c3c2cccc3c1-c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound CCSS(C)(CC)c(cc1)cc(S2)c1-c(cc1)c3c2cccc3c1-c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 XWYATJYFPSVRTO-UHFFFAOYSA-N 0.000 description 1
- YCKSAKUKYKYGSD-UHFFFAOYSA-N CN1C(c(cc2)ccc2-c2cccc(-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)=NC(c2ccccc2)=NC1c(cc1)ccc1-c1ccccc1 Chemical compound CN1C(c(cc2)ccc2-c2cccc(-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)=NC(c2ccccc2)=NC1c(cc1)ccc1-c1ccccc1 YCKSAKUKYKYGSD-UHFFFAOYSA-N 0.000 description 1
- TWVIDYQABARFBL-ZETCQYMHSA-N C[C@@H](C=CC1=C)C1=C Chemical compound C[C@@H](C=CC1=C)C1=C TWVIDYQABARFBL-ZETCQYMHSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MVRBJJFGHMWBKQ-UHFFFAOYSA-N Cc(cc1)ccc1-c1cc(-c(ccc2ncc3)c-4c2c3Sc2c-4cccc2)cc(-c2ccccc2)n1 Chemical compound Cc(cc1)ccc1-c1cc(-c(ccc2ncc3)c-4c2c3Sc2c-4cccc2)cc(-c2ccccc2)n1 MVRBJJFGHMWBKQ-UHFFFAOYSA-N 0.000 description 1
- UNXDIUUPZIUYNK-UHFFFAOYSA-N Cc(cccc1)c1-c1c(c(C)ccc2)c2ncc1-c1cccc(-c(cc2)ccc2-c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)c1 Chemical compound Cc(cccc1)c1-c1c(c(C)ccc2)c2ncc1-c1cccc(-c(cc2)ccc2-c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)c1 UNXDIUUPZIUYNK-UHFFFAOYSA-N 0.000 description 1
- PTLBRGIBRDAARO-UHFFFAOYSA-N Cc1ccnc2c1c(-c(c(O)c1)ccc1-c1nc(-c3ccccc3)nc(-c3ccccc3)n1)ccc2 Chemical compound Cc1ccnc2c1c(-c(c(O)c1)ccc1-c1nc(-c3ccccc3)nc(-c3ccccc3)n1)ccc2 PTLBRGIBRDAARO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- UIMCAAQFCOSRFM-LDLOPFEMSA-N N[C@@H]1C=CC(c2cc(-c3cc(-c4cccc(-c5cc(-c(cc6)c7Sc8ccccc8-c8ncnc6c78)ccc5)c4)ccc3)cc(-c3ccncc3)n2)=CC1 Chemical compound N[C@@H]1C=CC(c2cc(-c3cc(-c4cccc(-c5cc(-c(cc6)c7Sc8ccccc8-c8ncnc6c78)ccc5)c4)ccc3)cc(-c3ccncc3)n2)=CC1 UIMCAAQFCOSRFM-LDLOPFEMSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 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 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical class 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
- FZKKMFQDNSNNAJ-UHFFFAOYSA-N c(cc1)cc2c1nc(-c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c(cc1)cc(O3)c1-c1c4c3ccnc4ccc1)[n]2-c1ccccc1 Chemical compound c(cc1)cc2c1nc(-c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c(cc1)cc(O3)c1-c1c4c3ccnc4ccc1)[n]2-c1ccccc1 FZKKMFQDNSNNAJ-UHFFFAOYSA-N 0.000 description 1
- XDVYSXBNNRAISP-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c2cc(-c(cc3)cc(O4)c3-c3c5c4ccnc5ccc3)ccc2)nc2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c2cc(-c(cc3)cc(O4)c3-c3c5c4ccnc5ccc3)ccc2)nc2c1cccc2 XDVYSXBNNRAISP-UHFFFAOYSA-N 0.000 description 1
- DRBLBPZKKYLCCF-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3)cc(O4)c3-c3c5c4cccc5ccn3)c2)nc2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3)cc(O4)c3-c3c5c4cccc5ccn3)c2)nc2c1cccc2 DRBLBPZKKYLCCF-UHFFFAOYSA-N 0.000 description 1
- HYWUVARNJHEZIQ-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(-c2cc(-c3cc(-c4cc(-c(cc5)cc(O6)c5-c5cccc7c5c6ccn7)ccc4)ccc3)ccc2)nc2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(-c2cc(-c3cc(-c4cc(-c(cc5)cc(O6)c5-c5cccc7c5c6ccn7)ccc4)ccc3)ccc2)nc2ccccc12 HYWUVARNJHEZIQ-UHFFFAOYSA-N 0.000 description 1
- TWMOOKYVFNUMLP-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1cc(cccc2)c2nc1-c(cc1)ccc1-c1cccc(-c(cc2)ccc2-c2nc3cccc(Sc4ccccc4-4)c3c-4c2)c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1cc(cccc2)c2nc1-c(cc1)ccc1-c1cccc(-c(cc2)ccc2-c2nc3cccc(Sc4ccccc4-4)c3c-4c2)c1 TWMOOKYVFNUMLP-UHFFFAOYSA-N 0.000 description 1
- BVOMNCWFXBYRKB-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)c-3c4c2nccc4Sc2ccccc-32)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)c-3c4c2nccc4Sc2ccccc-32)n1 BVOMNCWFXBYRKB-UHFFFAOYSA-N 0.000 description 1
- BZYDWYARYSLJBA-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)c3c4c2-c(cccc2)c2Sc4ccc3)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)c3c4c2-c(cccc2)c2Sc4ccc3)n1 BZYDWYARYSLJBA-UHFFFAOYSA-N 0.000 description 1
- IVECERAXOYJYQH-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)cc-3c2Sc2cccc4c2c-3ccc4)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)cc-3c2Sc2cccc4c2c-3ccc4)n1 IVECERAXOYJYQH-UHFFFAOYSA-N 0.000 description 1
- MIZRVZWXIMDCKW-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)cc-3c2Sc2cccc4c2c-3ccc4)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c(cc2)cc-3c2Sc2cccc4c2c-3ccc4)n1 MIZRVZWXIMDCKW-UHFFFAOYSA-N 0.000 description 1
- ULTSSWINMBSESA-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c2cccc(-c(cc3S4)ccc3-c3nccc5cccc4c35)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c2cccc(-c(cc3S4)ccc3-c3nccc5cccc4c35)c2)n1 ULTSSWINMBSESA-UHFFFAOYSA-N 0.000 description 1
- WMPSBWXXKZLDMS-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c2cccc(-c3ccc(-c4cccc5cccc(S6)c45)c6c3)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c2cccc(-c3ccc(-c4cccc5cccc(S6)c45)c6c3)c2)n1 WMPSBWXXKZLDMS-UHFFFAOYSA-N 0.000 description 1
- AJCGEKDXLCWADP-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3S4)ccc3-c3nccc5c3c4ccc5)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3S4)ccc3-c3nccc5c3c4ccc5)c2)n1 AJCGEKDXLCWADP-UHFFFAOYSA-N 0.000 description 1
- UNTQKUUKFPIQTG-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c3ccc4Sc(cccc5)c5-c5cncc3c45)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c3ccc4Sc(cccc5)c5-c5cncc3c45)c2)n1 UNTQKUUKFPIQTG-UHFFFAOYSA-N 0.000 description 1
- DSTRHUYSKPSAAK-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c3cc(-c(cc4)c5c6c4-c(cccc4)c4Sc6ccc5)ccc3)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c3cc(-c(cc4)c5c6c4-c(cccc4)c4Sc6ccc5)ccc3)c2)n1 DSTRHUYSKPSAAK-UHFFFAOYSA-N 0.000 description 1
- VRGWPHUZDKWBGH-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c3ccc(-c4cccc5cccc(S6)c45)c6c3)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c3ccc(-c4cccc5cccc(S6)c45)c6c3)c2)n1 VRGWPHUZDKWBGH-UHFFFAOYSA-N 0.000 description 1
- AEKVJNLIGDHBLV-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2c(-c3cccnc3Sc3ccc4)c3c4cc2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2c(-c3cccnc3Sc3ccc4)c3c4cc2)n1 AEKVJNLIGDHBLV-UHFFFAOYSA-N 0.000 description 1
- AICSCYRKVQQQLB-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2ccc(-c3cccc4cccc(S5)c34)c5c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2ccc(-c3cccc4cccc(S5)c34)c5c2)n1 AICSCYRKVQQQLB-UHFFFAOYSA-N 0.000 description 1
- ACGCLXGIGDSOFB-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)n1 ACGCLXGIGDSOFB-UHFFFAOYSA-N 0.000 description 1
- AXISJKXQAVUXHH-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)cc-4c3Sc3cccc5c3c-4ccc5)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)cc-4c3Sc3cccc5c3c-4ccc5)c2)n1 AXISJKXQAVUXHH-UHFFFAOYSA-N 0.000 description 1
- LBUAJFLVXIIWHS-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)n1 LBUAJFLVXIIWHS-UHFFFAOYSA-N 0.000 description 1
- VFJUEIYSROJOAL-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c3cc(-c(cc4)c5c6c4-c(cccc4)c4Sc6ccc5)ccc3)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c3cc(-c(cc4)c5c6c4-c(cccc4)c4Sc6ccc5)ccc3)c2)n1 VFJUEIYSROJOAL-UHFFFAOYSA-N 0.000 description 1
- TZHBUOKSVRJNBO-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c3cc(-c(cc4)cc-5c4Sc4cccc6c4c-5ccc6)ccc3)c2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c3cc(-c(cc4)cc-5c4Sc4cccc6c4c-5ccc6)ccc3)c2)n1 TZHBUOKSVRJNBO-UHFFFAOYSA-N 0.000 description 1
- STNQXIOMTTWGTE-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cnc3c4c2-c2ccccc2Sc4ccc3)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cnc3c4c2-c2ccccc2Sc4ccc3)n1 STNQXIOMTTWGTE-UHFFFAOYSA-N 0.000 description 1
- NRHCNAOKGLNYAZ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(C2=CC=C3Sc(cccc4)c4C4=C3C2=CC=C=C4)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(C2=CC=C3Sc(cccc4)c4C4=C3C2=CC=C=C4)n1 NRHCNAOKGLNYAZ-UHFFFAOYSA-N 0.000 description 1
- MLCKJXXKHVSBQL-UHFFFAOYSA-N c(cc1)ccc1-c1cc(cccc2)c2nc1-c(cc1)ccc1-c1cccc(-c(cc2)ccc2-c2ccc3Sc(cccc4)c4-c4cncc2c34)c1 Chemical compound c(cc1)ccc1-c1cc(cccc2)c2nc1-c(cc1)ccc1-c1cccc(-c(cc2)ccc2-c2ccc3Sc(cccc4)c4-c4cncc2c34)c1 MLCKJXXKHVSBQL-UHFFFAOYSA-N 0.000 description 1
- YQEWXSDNEODGDB-UHFFFAOYSA-N c(cc1)ccc1-c1cc(cccc2)c2nc1-c(cc1)ccc1-c1cnc2c3c1-c(cccc1)c1Sc3ccc2 Chemical compound c(cc1)ccc1-c1cc(cccc2)c2nc1-c(cc1)ccc1-c1cnc2c3c1-c(cccc1)c1Sc3ccc2 YQEWXSDNEODGDB-UHFFFAOYSA-N 0.000 description 1
- RVUJDHYXQHEMFB-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2cc(-c3cccc(-c4cc(-c(cc5)cc-6c5Sc5nccc7c5c-6ccc7)ccc4)c3)ccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2cc(-c3cccc(-c4cc(-c(cc5)cc-6c5Sc5nccc7c5c-6ccc7)ccc4)c3)ccc2)nc(-c2ccccc2)n1 RVUJDHYXQHEMFB-UHFFFAOYSA-N 0.000 description 1
- YIDPGRBNNUCDQK-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2O3)ccc2-c2nccc4cccc3c24)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2O3)ccc2-c2nccc4cccc3c24)n1 YIDPGRBNNUCDQK-UHFFFAOYSA-N 0.000 description 1
- NXPKDCHXLPUEQK-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)c2)n1 NXPKDCHXLPUEQK-UHFFFAOYSA-N 0.000 description 1
- PTFFWQLUSGJZNE-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c3ccc(-c4cccc5cccc(S6)c45)c6c3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3)ccc3-c3ccc(-c4cccc5cccc(S6)c45)c6c3)c2)n1 PTFFWQLUSGJZNE-UHFFFAOYSA-N 0.000 description 1
- RSGLDKNPHDIWAI-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3O4)ccc3-c3nccc5c3c4ccc5)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c(cc3O4)ccc3-c3nccc5c3c4ccc5)c2)n1 RSGLDKNPHDIWAI-UHFFFAOYSA-N 0.000 description 1
- JVHXSIWUKXUNPA-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c3ccc(-c4cccc5nccc(O6)c45)c6c3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c2cccc(-c3ccc(-c4cccc5nccc(O6)c45)c6c3)c2)n1 JVHXSIWUKXUNPA-UHFFFAOYSA-N 0.000 description 1
- WXNHVVPXHFMKDT-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3cc(-c(cc4)ccc4-c(cc4)cc-5c4Sc4cccc6cccc-5c46)ccc3)ccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3cc(-c(cc4)ccc4-c(cc4)cc-5c4Sc4cccc6cccc-5c46)ccc3)ccc2)n1 WXNHVVPXHFMKDT-UHFFFAOYSA-N 0.000 description 1
- FTVUCBJMUHFZGA-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3cc(-c(cc4)ccc4-c4ccc-5c6c4cccc6Sc4ccccc-54)ccc3)ccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3cc(-c(cc4)ccc4-c4ccc-5c6c4cccc6Sc4ccccc-54)ccc3)ccc2)n1 FTVUCBJMUHFZGA-UHFFFAOYSA-N 0.000 description 1
- RTDYLGHOAZUFHI-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3cc(-c4ccc(-c5cccc6nccc(O7)c56)c7c4)ccc3)ccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cc(-c3cc(-c4ccc(-c5cccc6nccc(O7)c56)c7c4)ccc3)ccc2)n1 RTDYLGHOAZUFHI-UHFFFAOYSA-N 0.000 description 1
- UJTNYJMXRCLNHC-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c3cc(-c(cc4-c(cccc5)c5S5)cc6c4c5ccc6)ccc3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c3cc(-c(cc4-c(cccc5)c5S5)cc6c4c5ccc6)ccc3)c2)n1 UJTNYJMXRCLNHC-UHFFFAOYSA-N 0.000 description 1
- JKLCVLGDEGNXAP-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c3cc(-c(ccc4ncc5)c-6c4c5Sc4c-6cccc4)ccc3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3)ccc3-c3cc(-c(ccc4ncc5)c-6c4c5Sc4c-6cccc4)ccc3)c2)n1 JKLCVLGDEGNXAP-UHFFFAOYSA-N 0.000 description 1
- OXINSQXDZPQXRM-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3O4)ccc3-c3nccc5c3c4ccc5)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c(cc3O4)ccc3-c3nccc5c3c4ccc5)c2)n1 OXINSQXDZPQXRM-UHFFFAOYSA-N 0.000 description 1
- KTGRKUOEXGLRHE-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c3ccc(-c4cccc5nccc(O6)c45)c6c3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2cccc(-c3ccc(-c4cccc5nccc(O6)c45)c6c3)c2)n1 KTGRKUOEXGLRHE-UHFFFAOYSA-N 0.000 description 1
- RMRSOBJJTVGIKI-UHFFFAOYSA-N c1ccc(C(c2ccccc2)(c2ccccc2-2)c3cccc4c3c-2cc(-c2nc(-c(cc3)ccc3-c3ccccc3)nc(-c3ccccc3)n2)n4)cc1 Chemical compound c1ccc(C(c2ccccc2)(c2ccccc2-2)c3cccc4c3c-2cc(-c2nc(-c(cc3)ccc3-c3ccccc3)nc(-c3ccccc3)n2)n4)cc1 RMRSOBJJTVGIKI-UHFFFAOYSA-N 0.000 description 1
- HPAKIRNUYYAYSX-UHFFFAOYSA-N c1ccc(C2Nc(cccc3)c3N=C2c2cc(-c3cccc(-c4cc(-c5ccc(-c6cccc7ccnc(S8)c67)c8c5)ccc4)c3)ccc2)cc1 Chemical compound c1ccc(C2Nc(cccc3)c3N=C2c2cc(-c3cccc(-c4cc(-c5ccc(-c6cccc7ccnc(S8)c67)c8c5)ccc4)c3)ccc2)cc1 HPAKIRNUYYAYSX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002212 flavone derivatives Chemical class 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
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 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 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- OCVXZQOKBHXGRU-UHFFFAOYSA-N iodine(1+) Chemical compound [I+] OCVXZQOKBHXGRU-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([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
- 239000011133 lead Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YPJRZWDWVBNDIW-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[4-[4-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-MBALSZOMSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 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
- 150000002987 phenanthrenes Chemical class 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
- 238000005424 photoluminescence Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 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
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 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
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010345 tape casting Methods 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
Definitions
- the present invention relates to a compound, an organic light emitting element, and an organic EL display device.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
- organic monomolecular substances include PBD (2-biphenyl-4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole) derivatives bound to Spiro compounds and TPBI (2, 2 ', 2 "-(benzene-1,3,5-triyl) -tris (1-phenyl-1H-benzimidazole) and the like are known.
- An object of the present invention is to provide an organic light emitting device having a high efficiency and a low driving voltage and a display device using the same through a compound having high electron mobility and excellent hole blocking ability.
- a 1 is a group represented by any one of the following structures
- Y1 is any one of S, O, or C
- X 4 to X 9 are the same as or different from each other, and each independently N or C,
- Ar 5 and Ar 6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, A substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,
- L is a direct bond; Substituted or unsubstituted arylene group; Substituted or unsubstituted hetero arylene group; Or a substituted or unsubstituted C 9 ⁇ C 60 condensed polycyclic group,
- a 2 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or un
- the compounds of the present invention have high electron mobility and are excellent in hole blocking ability.
- the organic light emitting device using the compound of the present invention as an organic layer has high efficiency and low driving voltage.
- FIG. 1 is an exemplary view of an organic light emitting device according to an embodiment of the present invention.
- halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
- alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise specified, and is a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, or an alkyl-substituted group.
- radicals of saturated aliphatic functional groups including cycloalkyl groups, cycloalkyl-substituted alkyl groups.
- alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
- heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
- alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
- cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
- alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
- alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
- aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
- aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
- an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
- the aryl group may include, but is not limited to, a single ring aryl group, a phenyl group, a biphenyl group, a terphenyl group, and as a multicyclic aryl group, a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, It may include, but is not limited to, a chrysenyl group, a fluorenyl group, and a spirofluorene group.
- the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
- the fluorenyl group When the fluorenyl group is substituted, it may have a structure as follows, but is not limited thereto.
- aryl or "ar” means a radical substituted with an aryl group.
- an arylalkyl group is an alkyl group substituted with an aryl group
- an arylalkenyl group is an alkenyl group substituted with an aryl group
- the radical substituted with an aryl group has the carbon number described herein.
- an arylalkoxy group means an alkoxy group substituted with an aryl group
- an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
- an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
- the arylcarbonyl group is a carbonyl group substituted with an aryl group.
- heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
- heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings are included. Adjacent functional groups may be formed in combination.
- Heteroatom refers to N, O, S, P or Si unless otherwise stated.
- Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
- heterocyclic group examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phen
- aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
- aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
- ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a hetero ring having 2 to 60 carbon atoms, or a combination thereof. Saturated or unsaturated rings.
- heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
- carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
- ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
- substituted in the term “substituted or unsubstituted” as used herein refers to deuterium, halogen, amino, nitrile, nitro, C 1 -C 20 alkyl, C 1 -C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of,
- the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
- FIG. 1 is an exemplary view of an organic light emitting device according to an embodiment of the present invention.
- the organic light emitting diode 100 includes the first electrode 120, the second electrode 180, the first electrode 110, and the second electrode 180 formed on the substrate 110.
- the organic material layer formed between the), the organic material layer comprises a compound according to the invention.
- the first electrode 120 may be an anode (anode)
- the second electrode 180 may be a cathode (cathode)
- the first electrode may be a cathode and the second electrode may be an anode.
- anode material a material having a large work function is preferable to facilitate the injection of holes into the organic material layer.
- anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
- the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
- the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. In this case, at least some of the remaining layers except for the emission layer 150 may not be formed.
- the layers formed between the first electrode 120 and the light emitting layer 150 constitute a hole transport region
- the layers formed on the second electrode 180 and the light emitting layer 150 constitute an electron transport region.
- the hole injection layer 130 is a layer that facilitates the injection of holes from the first electrode 120, and the hole injection material is preferably a compound having excellent hole injection effect from the anode and thin film formation ability.
- the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
- hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transport layer 140 is a layer that receives holes from the hole injection layer 130 and transports holes to the light emitting layer 150.
- a material having high mobility to holes is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
- the light emitting layer 150 emits light in the visible region by transporting and combining holes and electrons from the hole transport layer 140 and the electron transport layer 160, respectively, and the light emitting material has good quantum efficiency with respect to fluorescence or phosphorescence.
- the substance is preferred. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
- the light emitting layer 150 may include a host material and a dopant material.
- the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
- the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
- the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
- At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
- the electron transport layer 160 is a layer that receives electrons from the electron injection layer 170 and transports electrons to the emission layer 150, and a material having high mobility to electrons is suitable as the electron transport material. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport material of the present invention will be described later.
- the electron injection layer 170 is a layer that facilitates the injection of electrons from the second electrode 180, a compound having the ability to transport electrons and excellent in the electron injection effect and the thin film formation ability from the cathode electrode Do. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
- Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese and tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] qui Nolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o -Cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like It is not limited.
- the organic material layer is a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer in addition to the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, the electron injection layer 170. 141 may be further included, and the electron transport layer 160 may serve as a hole blocking layer.
- the organic light emitting diode according to the present invention may include a protective layer or a light efficiency improving layer formed on one surface of the first electrode 120 and the second electrode 180 opposite to the organic material layer. It may further include.
- the compound according to the present invention is used in an electron transport region such as an electron injection layer 170, an electron transport layer 160, a hole blocking layer, etc.
- an electron transport region such as an electron injection layer 170, an electron transport layer 160, a hole blocking layer, etc.
- the present invention is not limited thereto. It may also be used as a material for the hole transport region such as the layer 130, the hole transport layer 140, the host or the dopant of the light emitting layer 150, or the light efficiency improving layer.
- the organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method such as vacuum evaporation or sputtering.
- PVD physical vapor deposition
- the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and thereon, a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer ( After forming the organic layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.
- the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
- the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
- WOLED White Organic Light Emitting Device
- Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented.
- a side-by-side method in which R (Red), g (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, g, and B light emitting layers are stacked up and down.
- a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
- CCM color conversion material
- Another embodiment of the present invention may include a display device including the organic light-emitting device of the present invention described above, and an electronic device including a control unit for controlling the display device.
- the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
- a 1 is a group represented by any one of the following structures
- Y1 is any one of S, O, or C
- X 4 to X 9 are the same as or different from each other, and each independently N or C,
- Ar 5 and Ar 6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, A substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,
- L is a direct bond; Substituted or unsubstituted arylene group; Substituted or unsubstituted hetero arylene group; Or a substituted or unsubstituted C 9 ⁇ C 60 condensed polycyclic group,
- a 2 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or un
- L has the following structure, L1 ⁇ L3 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group; Or a substituted or unsubstituted C 9 to C 60 condensed polycyclic group.
- L is a direct bond, a substituted or unsubstituted C 9 ⁇ C 60 condensed polycyclic group, or a group having the following structure.
- l, m, and n are each independently 0 or 1.
- a 2 is any one selected from the following structures.
- X 1 to X 3 are each independently C or N, at least one of X 1 to X 3 is N, and Ar 1 and Ar 2 are each independently hydrogen, deuterium, halogen, cyano, substituted or Unsubstituted C 1 to C 60 alkyl group, substituted or unsubstituted C 3 to C 10 cycloalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, or substituted or unsubstituted C 1 to C 60 heteroaryl group to be.
- a 2 is represented by the following structural formula
- X1 to X3 are each independently C or N, at least one of X1 to X3 is N, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1
- Ar3 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1-C60 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, or substituted
- A2 is any one of the following groups.
- the compound of Formula 1 is any one of the following compounds.
- the first electrode A second electrode opposite the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the compound of Formula 1 described above.
- the first electrode is an anode
- the second electrode is a cathode
- the organic layer is i) a light emitting layer, ii) a hole injection layer interposed between the first electrode and the light emitting layer.
- a hole transport region including at least one of a hole transport layer and an electron blocking layer
- the electron transport region includes the compound of Formula 1.
- the electron transport layer includes the compound of formula (1).
- a display device including the organic light emitting element, wherein the first electrode of the organic light emitting element is electrically connected to a source electrode or a drain electrode of the thin film transistor.
- 10-bromothiochromeno [4,3,2-ij] isoquinoline (1 equiv) was dissolved in DMF in a round bottom flask, followed by bis (pinacolato) diboron (1.1 equiv), Pd (dppf) Cl 2 (0.03 equiv), KOAc ( 3 equivalents) was added and refluxed at 130 ° C. for 4 hours. Upon completion of the reaction, DMF was removed by distillation and extracted with CH 2 Cl 2 and water.
- 6-bromothiochromeno [4,3,2-de] quinazoline (1 equiv) was dissolved in DMF in a round bottom flask, followed by bis (pinacolato) diboron (1.1 equiv), Pd (dppf) Cl 2 (0.03 equiv), KOAc ( 3 equivalents) was added and refluxed at 130 ° C. for 4 hours. Upon completion of the reaction, DMF was removed by distillation and extracted with CH 2 Cl 2 and water.
- Compound 1-1-2 to 1-1-3 can be synthesized in the same manner as Compound 1-1-1, using cores 1-2 to 1-3.
- Compound 1-3-8 to 1-3-9 are Using cores 1-2 to 1-3, synthesis is possible in the same manner as for compounds 1-3-7.
- Compound 1-3-11 to 1-3-12 are Using cores 1-2 to 1-3, synthesis is possible in the same manner as for compounds 1-3-10.
- Compounds 2-1-2 to 2-1-10 can be synthesized in the same manner as for compounds 2-1-1, using cores 2-2 to 2-10.
- Compounds 2-2-2 to 2-2-10 can be synthesized in the same manner as for compounds 2-2-1, using cores 2-2 to 2-10.
- Compounds 2-2-12 to 2-2-20 can be synthesized in the same manner as for compounds 2-2-11, using cores 2-2 to 2-10.
- Compounds 2-3-2 to 2-3-10 can be synthesized in the same manner as Compound 2-3-1, using cores 2-2 to 2-10.
- Compounds 2-3-12 to 2-3-20 can be synthesized in the same manner as Compound 2-3-11, using Cores 2-2 to 2-10.
- Compound 2-3-22 to 2-3-30 can be synthesize
- Compounds 2-3-32 to 2-3-40 can be synthesized in the same manner as Compound 2-3-31, using cores 2-2 to 2-10.
- Compounds 2-4-2 to 2-4-10 can be synthesized in the same manner as for compounds 2-4-1, using cores 2-2 to 2-10.
- Compounds 2-4-12 to 2-4-20 can be synthesized in the same manner as for compounds 2-4-11, using cores 2-2 to 2-10.
- Compounds 2-4-22 to 2-4-20 can be synthesized in the same manner as for compounds 2-4-21, using cores 2-2 to 2-10.
- Compounds 2-4-32 to 2-4-40 can be synthesized in the same manner as for compounds 2-4-31, using cores 2-2 to 2-10.
- Compounds 2-4-42 to 2-4-50 can be synthesized in the same manner as for compounds 2-4-41, using cores 2-2 to 2-10.
- Compounds 2-4-52 to 2-4-60 can be synthesized in the same manner as for compounds 2-4-51, using cores 2-2 to 2-10.
- Compounds 2-4-62 to 2-4-70 can be synthesized in the same manner as for compounds 2-4-61, using cores 2-2 to 2-10.
- Compounds 2-4-72 to 2-4-80 can be synthesized in the same manner as for compounds 2-4-71, using cores 2-2 to 2-10.
- Compound 4-1-2 can be synthesized in the same manner as Compound 4-1-1 using Core 4-2.
- the remaining compounds 4-2-1 to 4-4-16 are the same as those in the corresponding synthesis examples in the synthesis examples of the compounds 2-1-1 to 2-4-80, using the core 4-1 or 4-2. Can be synthesized.
- Compound 5-1-2 can be synthesized in the same manner as Compound 5-1-1 using Core 5-2.
- the remaining compounds 5-2-1 to 5-4-16 are the same as those in the corresponding synthesis examples in the synthesis examples of the compounds 2-1-1 to 2-4-80, using the core 5-1 or 5-2 Can be synthesized.
- the intermediate product 1- (3-bromophenyl) thiochromeno [4,3,2-ij] isoquinoline (15 g, 38.4 mmol) was dissolved in DMF in a round bottom flask, followed by 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) (10.7 g, 42.3 mmol), Pd (dppf) Cl 2 (0.8 g, 1.2 mmol), KOAc (15.9 g, 115.3 mmol) was added and refluxed at 130 ° C. for 4 hours. Upon completion of the reaction, DMF was removed by distillation and extracted with CH 2 Cl 2 and water.
- the remaining compounds can be synthesized in the same manner.
- Example 1-38 Of the blue organic light emitting device To the electron transport layer Application example )
- 2-TNATA was vacuum deposited on the ITO anode layer to form a hole injection layer having a thickness of 60 nm, and a 4,4'-bis [N- (1-naphthyl) -N-phenylamino] ratio was formed on the hole injection layer.
- Phenyl hereinafter referred to as NPB was vacuum deposited to form a hole transport layer having a thickness of 30 nm.
- LiF is vacuum deposited on the electron transport layer to form an electron injection layer having a thickness of 1nm, and the electron injection
- An organic light-emitting device was manufactured by vacuum evaporating Al on the layer to form a 300 nm thick cathode.
- An organic light emitting diode was manufactured according to the same method as Experimental Example except for using the following ET1 instead of the compound represented by Formula 1 of the present invention as an electron transport layer material.
- An organic light emitting diode was manufactured according to the same method as Experimental Example except for using the following ET2 instead of the compound represented by Formula 1 of the present invention as an electron transport layer material.
- the compound of the present invention can be used in an organic light emitting device and an organic EL display device including the same.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201980011489.3A CN111683942A (zh) | 2018-03-23 | 2019-03-20 | 化合物、有机发光器件及显示装置 |
KR1020197025269A KR102084906B1 (ko) | 2018-03-23 | 2019-03-20 | 화합물, 유기 발광 소자 및 표시 장치 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20180034103 | 2018-03-23 | ||
KR10-2018-0034103 | 2018-03-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2019182360A1 true WO2019182360A1 (ko) | 2019-09-26 |
Family
ID=67986562
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2019/003261 WO2019182360A1 (ko) | 2018-03-23 | 2019-03-20 | 화합물, 유기 발광 소자 및 표시 장치 |
Country Status (3)
Country | Link |
---|---|
KR (1) | KR102084906B1 (zh) |
CN (1) | CN111683942A (zh) |
WO (1) | WO2019182360A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021244442A1 (zh) * | 2020-06-05 | 2021-12-09 | 陕西莱特光电材料股份有限公司 | 有机化合物以及使用其的电子元件和电子装置 |
WO2023096225A1 (ko) * | 2021-11-29 | 2023-06-01 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층 형성용 조성물 |
WO2023223855A1 (ja) * | 2022-05-20 | 2023-11-23 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20210075535A (ko) * | 2019-12-13 | 2021-06-23 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102560362B1 (ko) * | 2020-06-26 | 2023-07-27 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR20220039898A (ko) * | 2020-09-21 | 2022-03-30 | 솔루스첨단소재 주식회사 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR20220142919A (ko) | 2021-04-15 | 2022-10-24 | 에스케이머티리얼즈제이엔씨 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20230034917A (ko) | 2021-09-02 | 2023-03-10 | 에스케이머티리얼즈제이엔씨 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20230071062A (ko) | 2021-11-15 | 2023-05-23 | 에스케이머티리얼즈제이엔씨 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20230136054A (ko) | 2022-03-17 | 2023-09-26 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20230137826A (ko) | 2022-03-22 | 2023-10-05 | 에스케이머티리얼즈제이엔씨 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20230143926A (ko) | 2022-04-06 | 2023-10-13 | 에스케이머티리얼즈제이엔씨 주식회사 | 유기 전계 발광 소자 및 표시 장치 |
KR20230148106A (ko) | 2022-04-15 | 2023-10-24 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20230149689A (ko) | 2022-04-19 | 2023-10-27 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자용 조성물, 유기 전계 발광 소자 및 표시 장치 |
KR20230155355A (ko) | 2022-05-03 | 2023-11-10 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
WO2023228828A1 (ja) * | 2022-05-27 | 2023-11-30 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び電子機器 |
KR20230175107A (ko) | 2022-06-21 | 2023-12-29 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20240003993A (ko) | 2022-07-04 | 2024-01-11 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20240031694A (ko) | 2022-09-01 | 2024-03-08 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
KR20240045767A (ko) | 2022-09-30 | 2024-04-08 | 에스케이 주식회사 | 화합물, 유기 전계 발광 소자 및 표시 장치 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150096152A (ko) * | 2014-02-14 | 2015-08-24 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20160100136A (ko) * | 2015-02-13 | 2016-08-23 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR20170049398A (ko) * | 2015-10-27 | 2017-05-10 | 주식회사 엘지화학 | 고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR20170063411A (ko) * | 2015-11-30 | 2017-06-08 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
KR20170137976A (ko) * | 2016-06-03 | 2017-12-14 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101482829B1 (ko) * | 2010-11-22 | 2015-01-14 | 이데미쓰 고산 가부시키가이샤 | 유기 일렉트로루미네선스 소자 |
JP6016482B2 (ja) * | 2012-07-03 | 2016-10-26 | キヤノン株式会社 | ジベンゾキサンテン化合物、有機発光素子、表示装置、画像情報処理装置及び画像形成装置 |
KR102269131B1 (ko) * | 2013-07-01 | 2021-06-25 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
KR102184675B1 (ko) * | 2014-03-19 | 2020-12-01 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
WO2015178585A1 (ko) * | 2014-05-22 | 2015-11-26 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR101913628B1 (ko) * | 2014-07-08 | 2018-10-31 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
KR102498304B1 (ko) * | 2016-04-20 | 2023-02-10 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR102512628B1 (ko) * | 2016-05-11 | 2023-03-24 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN107266440A (zh) * | 2017-07-28 | 2017-10-20 | 长春海谱润斯科技有限公司 | 一种电子传输材料、合成方法及其有机发光器件 |
-
2019
- 2019-03-20 KR KR1020197025269A patent/KR102084906B1/ko active IP Right Grant
- 2019-03-20 WO PCT/KR2019/003261 patent/WO2019182360A1/ko active Application Filing
- 2019-03-20 CN CN201980011489.3A patent/CN111683942A/zh active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150096152A (ko) * | 2014-02-14 | 2015-08-24 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20160100136A (ko) * | 2015-02-13 | 2016-08-23 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR20170049398A (ko) * | 2015-10-27 | 2017-05-10 | 주식회사 엘지화학 | 고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR20170063411A (ko) * | 2015-11-30 | 2017-06-08 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
KR20170137976A (ko) * | 2016-06-03 | 2017-12-14 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021244442A1 (zh) * | 2020-06-05 | 2021-12-09 | 陕西莱特光电材料股份有限公司 | 有机化合物以及使用其的电子元件和电子装置 |
WO2023096225A1 (ko) * | 2021-11-29 | 2023-06-01 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층 형성용 조성물 |
WO2023223855A1 (ja) * | 2022-05-20 | 2023-11-23 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
Also Published As
Publication number | Publication date |
---|---|
CN111683942A (zh) | 2020-09-18 |
KR20190112083A (ko) | 2019-10-02 |
KR102084906B1 (ko) | 2020-03-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2019182360A1 (ko) | 화합물, 유기 발광 소자 및 표시 장치 | |
WO2021107737A1 (ko) | 유기 발광 소자 | |
WO2020004844A1 (ko) | 화합물, 유기 전계 발광 소자 및 표시 장치 | |
WO2019164327A1 (ko) | 유기 발광 소자 | |
WO2019139419A1 (ko) | 유기 발광 소자 | |
WO2017057976A1 (ko) | 스피로형 화합물 및 이를 포함하는 유기 발광 소자 | |
WO2019221545A1 (ko) | 유기발광소자 | |
WO2021112403A1 (ko) | 유기화합물을 포함하는 유기전기소자 및 이를 포함하는 전자 장치 | |
WO2019240464A1 (ko) | 유기 발광 소자 | |
WO2020009467A1 (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
WO2022015084A1 (ko) | 유기 발광 소자 | |
WO2020166875A1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
WO2019059611A1 (ko) | 유기 발광 소자 | |
WO2016140549A9 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
WO2016175624A1 (ko) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 | |
WO2018124588A1 (ko) | 유기 발광 소자 | |
WO2019135665A1 (ko) | 유기 발광 소자 | |
WO2017131483A1 (ko) | 스피로형 화합물 및 이를 포함하는 유기 전자 소자 | |
WO2011145876A2 (ko) | 신규 하이브리드 유기 화합물 및 이를 이용한 유기 전계 발광소자 | |
WO2020022768A1 (ko) | 유기 발광 소자 | |
WO2019168358A1 (ko) | 화합물, 유기 발광 소자 및 표시 장치 | |
WO2021020929A1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
WO2021020946A1 (ko) | 유기 발광 소자 | |
WO2014025209A1 (ko) | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
WO2021049843A1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
ENP | Entry into the national phase |
Ref document number: 20197025269 Country of ref document: KR Kind code of ref document: A |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 19771391 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 19771391 Country of ref document: EP Kind code of ref document: A1 |