KR102084906B1

KR102084906B1 - 화합물, 유기 발광 소자 및 표시 장치

화합물, 유기 발광 소자 및 표시 장치 Download PDF

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Publication number: KR102084906B1
Authority: KR; South Korea
Prior art keywords: mmol; group; water; compound; layer
Prior art date: 2018-03-23

Application number

KR1020197025269A

Other languages

English (en)

Korean (ko)

Other versions

KR20190112083A (ko

Inventor

김정미

이종호

박기선

김미정

Original Assignee

에스케이머티리얼즈 주식회사

Priority date

2018-03-23

Filing date

2019-03-20

Publication date

2020-03-04

2019-03-20 Application filed by 에스케이머티리얼즈 주식회사 filed Critical 에스케이머티리얼즈 주식회사

2019-10-02 Publication of KR20190112083A publication Critical patent/KR20190112083A/ko

2020-03-04 Application granted granted Critical

2020-03-04 Publication of KR102084906B1 publication Critical patent/KR102084906B1/ko

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150000001875 compounds Chemical class 0.000 title claims abstract description 212
239000012044 organic layer Substances 0.000 claims description 139
239000010410 layer Substances 0.000 claims description 120
238000002347 injection Methods 0.000 claims description 34
239000007924 injection Substances 0.000 claims description 34
125000003118 aryl group Chemical group 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 21
238000000034 method Methods 0.000 claims description 20
230000005525 hole transport Effects 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
230000000903 blocking effect Effects 0.000 claims description 10
125000000732 arylene group Chemical group 0.000 claims description 8
229910052805 deuterium Inorganic materials 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000005549 heteroarylene group Chemical group 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 4
239000010409 thin film Substances 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 2
125000002993 cycloalkylene 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 217
238000006243 chemical reaction Methods 0.000 description 132
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 130
239000000741 silica gel Substances 0.000 description 130
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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
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239000000126 substance Substances 0.000 description 66
239000012467 final product Substances 0.000 description 55
238000010992 reflux Methods 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
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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 35
239000000463 material Substances 0.000 description 28
230000032258 transport Effects 0.000 description 28
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 24
238000001953 recrystallisation Methods 0.000 description 23
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 22
239000013067 intermediate product Substances 0.000 description 20
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
0 C/C(/*(C1)C1N*=C)=I(/C1)\C1*=C* Chemical compound C/C(/*(C1)C1N*=C)=I(/C1)\C1*=C* 0.000 description 19
238000003756 stirring 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
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239000000047 product Substances 0.000 description 13
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125000001424 substituent group Chemical group 0.000 description 9
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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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 7
239000004305 biphenyl Substances 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
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 6
125000003545 alkoxy group Chemical group 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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
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
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
238000000151 deposition Methods 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
125000006753 (C1-C60) heteroaryl group Chemical group 0.000 description 4
125000006749 (C6-C60) aryl group Chemical group 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 4
CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 4
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 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
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
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
125000005605 benzo group Chemical group 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000002019 doping agent Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
125000003367 polycyclic group Chemical group 0.000 description 4
239000000758 substrate Substances 0.000 description 4
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
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
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 3
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 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-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
125000003282 alkyl amino group Chemical group 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
125000003277 amino group Chemical group 0.000 description 3
125000003710 aryl alkyl group Chemical group 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
125000002560 nitrile group Chemical group 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000005416 organic matter Substances 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
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
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125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
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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
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 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
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
GAAYPTPSHXSMEM-UHFFFAOYSA-N 5h-thiochromeno[2,3-b]pyridine Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=N1 GAAYPTPSHXSMEM-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
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
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
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
UTHQKZPGYPTYOP-UHFFFAOYSA-N C(Cc1ccn2)c(cccc3)c3-c3c1c2ccc3-c1cc(-c(cc2)ccc2-c2nc(-c(cc3)ccc3-c3ccccc3)nc(-c3ccccc3)n2)ccc1 Chemical compound C(Cc1ccn2)c(cccc3)c3-c3c1c2ccc3-c1cc(-c(cc2)ccc2-c2nc(-c(cc3)ccc3-c3ccccc3)nc(-c3ccccc3)n2)ccc1 UTHQKZPGYPTYOP-UHFFFAOYSA-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
OPAASYYNUMTQIP-UHFFFAOYSA-N C1C(c2ccccc2)=NC(c(cc2)ccc2-c2ccccc2)=NC1c1cccc(-c2cc(-c(cc3-c(cccc4)c4S4)nc5c3c4ccc5)ccc2)c1 Chemical compound C1C(c2ccccc2)=NC(c(cc2)ccc2-c2ccccc2)=NC1c1cccc(-c2cc(-c(cc3-c(cccc4)c4S4)nc5c3c4ccc5)ccc2)c1 OPAASYYNUMTQIP-UHFFFAOYSA-N 0.000 description 1
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125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
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LBYWZGYNSFRXKJ-UHFFFAOYSA-N CC(C)(c1c-2cccc1)c1cccc3c1c-2cc(C(CC1)=CC=C1c1cc(-c2nc(-c4ccccc4)nc(-c4ccccc4)n2)ccc1)n3 Chemical compound CC(C)(c1c-2cccc1)c1cccc3c1c-2cc(C(CC1)=CC=C1c1cc(-c2nc(-c4ccccc4)nc(-c4ccccc4)n2)ccc1)n3 LBYWZGYNSFRXKJ-UHFFFAOYSA-N 0.000 description 1
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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
VEJYHTXRGLVPAP-UHFFFAOYSA-N CC1(C)OC(C2c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)C2OC1(C)C Chemical compound CC1(C)OC(C2c(cc3)c4c5c3-c(cccc3)c3Sc5ccc4)C2OC1(C)C VEJYHTXRGLVPAP-UHFFFAOYSA-N 0.000 description 1
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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
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
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
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
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
NOGGNYPXJHIXNU-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1cc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c2cnc3c4c2-c(cccc2)c2Sc4ccc3)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1cc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c2cnc3c4c2-c(cccc2)c2Sc4ccc3)n1 NOGGNYPXJHIXNU-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
XKVMNIAGQKFLDP-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c(ccc2ccn3)c-4c2c3Sc2c-4cccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c(cc2)ccc2-c(cc2)ccc2-c(ccc2ccn3)c-4c2c3Sc2c-4cccc2)n1 XKVMNIAGQKFLDP-UHFFFAOYSA-N 0.000 description 1
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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