KR20230010039A

KR20230010039A - 다환 방향족 화합물

다환 방향족 화합물 Download PDF

Info

Publication number: KR20230010039A
Authority: KR; South Korea
Prior art keywords: carbon atoms; ring; substituted; aryl; alkyl
Prior art date: 2020-05-13

Application number

KR1020227042152A

Other languages

English (en)

Korean (ko)

Inventor

타쿠지 하타케야마

야스유키 사사다

야스히로 콘도

료스케 카와스미

Original Assignee

가꼬우 호징 관세이 가쿠잉

에스케이머티리얼즈제이엔씨 주식회사

Priority date

2020-05-13

Filing date

2021-05-06

Publication date

2023-01-17

2021-05-06 Application filed by 가꼬우 호징 관세이 가쿠잉, 에스케이머티리얼즈제이엔씨 주식회사 filed Critical 가꼬우 호징 관세이 가쿠잉

2023-01-17 Publication of KR20230010039A publication Critical patent/KR20230010039A/ko

Links

-1 polycyclic aromatic compounds Chemical class 0.000 title claims abstract description 587
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 311
125000001424 substituent group Chemical group 0.000 claims abstract description 202
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 196
239000001257 hydrogen Substances 0.000 claims abstract description 196
239000000463 material Substances 0.000 claims abstract description 183
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 129
150000001924 cycloalkanes Chemical class 0.000 claims abstract description 48
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 32
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 22
229910052805 deuterium Inorganic materials 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 622
125000003118 aryl group Chemical group 0.000 claims description 479
125000000217 alkyl group Chemical group 0.000 claims description 323
150000001875 compounds Chemical class 0.000 claims description 313
125000000753 cycloalkyl group Chemical group 0.000 claims description 284
239000010410 layer Substances 0.000 claims description 281
229920000642 polymer Polymers 0.000 claims description 104
238000000034 method Methods 0.000 claims description 92
238000002347 injection Methods 0.000 claims description 83
239000007924 injection Substances 0.000 claims description 83
239000000203 mixture Substances 0.000 claims description 77
125000005647 linker group Chemical group 0.000 claims description 75
150000002431 hydrogen Chemical class 0.000 claims description 64
125000003545 alkoxy group Chemical group 0.000 claims description 56
125000003342 alkenyl group Chemical group 0.000 claims description 54
238000006243 chemical reaction Methods 0.000 claims description 53
229910052782 aluminium Inorganic materials 0.000 claims description 48
125000004986 diarylamino group Chemical group 0.000 claims description 45
125000000732 arylene group Chemical group 0.000 claims description 44
125000005549 heteroarylene group Chemical group 0.000 claims description 43
125000002993 cycloalkylene group Chemical group 0.000 claims description 41
239000012044 organic layer Substances 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
125000004104 aryloxy group Chemical group 0.000 claims description 37
125000000304 alkynyl group Chemical group 0.000 claims description 36
230000005525 hole transport Effects 0.000 claims description 36
229910052736 halogen Chemical group 0.000 claims description 33
150000002367 halogens Chemical group 0.000 claims description 33
239000002019 doping agent Substances 0.000 claims description 32
229910052799 carbon Inorganic materials 0.000 claims description 30
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 29
229910052751 metal Inorganic materials 0.000 claims description 29
239000002184 metal Substances 0.000 claims description 29
239000003960 organic solvent Substances 0.000 claims description 28
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 28
229910052717 sulfur Inorganic materials 0.000 claims description 28
125000005240 diheteroarylamino group Chemical group 0.000 claims description 27
125000004093 cyano group Chemical group *C#N 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
229910052698 phosphorus Inorganic materials 0.000 claims description 23
239000010409 thin film Substances 0.000 claims description 23
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 20
229910052796 boron Inorganic materials 0.000 claims description 20
239000000178 monomer Substances 0.000 claims description 19
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 17
125000005577 anthracene group Chemical group 0.000 claims description 16
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 15
125000004665 trialkylsilyl group Chemical group 0.000 claims description 14
150000001454 anthracenes Chemical class 0.000 claims description 13
HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 12
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 11
150000001340 alkali metals Chemical class 0.000 claims description 11
XPJUXTZYXPASRB-UHFFFAOYSA-N benzo[f]pentahelicene Chemical compound C1=CC=C2C3=C4C5=CC=CC=C5C=CC4=CC=C3C3=CC=CC=C3C2=C1 XPJUXTZYXPASRB-UHFFFAOYSA-N 0.000 claims description 11
238000004132 cross linking Methods 0.000 claims description 11
229910052761 rare earth metal Inorganic materials 0.000 claims description 11
150000002910 rare earth metals Chemical class 0.000 claims description 11
125000000547 substituted alkyl group Chemical group 0.000 claims description 11
230000005669 field effect Effects 0.000 claims description 10
229910052733 gallium Inorganic materials 0.000 claims description 10
125000005106 triarylsilyl group Chemical group 0.000 claims description 10
229910052785 arsenic Inorganic materials 0.000 claims description 9
150000004820 halides Chemical class 0.000 claims description 9
239000005267 main chain polymer Substances 0.000 claims description 9
230000000379 polymerizing effect Effects 0.000 claims description 9
150000003918 triazines Chemical class 0.000 claims description 8
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
150000001342 alkaline earth metals Chemical class 0.000 claims description 7
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 7
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
150000003222 pyridines Chemical class 0.000 claims description 7
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 7
150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
229920006037 cross link polymer Polymers 0.000 claims description 6
230000005684 electric field Effects 0.000 claims description 6
150000003230 pyrimidines Chemical class 0.000 claims description 6
150000003384 small molecules Chemical class 0.000 claims description 6
150000007979 thiazole derivatives Chemical class 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
150000002219 fluoranthenes Chemical class 0.000 claims description 5
125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims description 4
150000005041 phenanthrolines Chemical class 0.000 claims description 4
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
150000008045 alkali metal halides Chemical class 0.000 claims description 3
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 3
229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 3
150000007981 azolines Chemical class 0.000 claims description 2
150000003967 siloles Chemical class 0.000 claims description 2
150000001716 carbazoles Chemical class 0.000 claims 1
239000011243 crosslinked material Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 104
239000010408 film Substances 0.000 description 67
230000032258 transport Effects 0.000 description 67
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 65
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 50
230000015572 biosynthetic process Effects 0.000 description 42
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 38
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 36
239000000758 substrate Substances 0.000 description 36
125000001624 naphthyl group Chemical group 0.000 description 34
239000000047 product Substances 0.000 description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 description 26
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 23
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
238000003786 synthesis reaction Methods 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229910052760 oxygen Inorganic materials 0.000 description 18
239000000243 solution Substances 0.000 description 18
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
239000002994 raw material Substances 0.000 description 17
125000002619 bicyclic group Chemical group 0.000 description 16
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 16
238000000576 coating method Methods 0.000 description 15
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 15
125000005842 heteroatom Chemical group 0.000 description 15
239000000126 substance Substances 0.000 description 15
125000004429 atom Chemical group 0.000 description 14
239000004065 semiconductor Substances 0.000 description 14
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
230000006870 function Effects 0.000 description 13
125000000623 heterocyclic group Chemical group 0.000 description 13
239000001301 oxygen Substances 0.000 description 13
125000005561 phenanthryl group Chemical group 0.000 description 13
238000010189 synthetic method Methods 0.000 description 13
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000011248 coating agent Substances 0.000 description 12
239000011593 sulfur Substances 0.000 description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
239000011521 glass Substances 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
229920005989 resin Polymers 0.000 description 11
239000011347 resin Substances 0.000 description 11
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 10
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 10
238000001035 drying Methods 0.000 description 10
229910052731 fluorine Inorganic materials 0.000 description 10
239000011737 fluorine Substances 0.000 description 10
239000011159 matrix material Substances 0.000 description 10
125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 10
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 10
125000003277 amino group Chemical group 0.000 description 9
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 9
125000005110 aryl thio group Chemical group 0.000 description 9
239000011230 binding agent Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 9
239000010949 copper Substances 0.000 description 9
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 9
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 9
239000004094 surface-active agent Substances 0.000 description 9
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 8
125000001931 aliphatic group Chemical group 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
229910052792 caesium Inorganic materials 0.000 description 8
229910052802 copper Inorganic materials 0.000 description 8
230000000694 effects Effects 0.000 description 8
125000001041 indolyl group Chemical group 0.000 description 8
229910052744 lithium Inorganic materials 0.000 description 8
125000004957 naphthylene group Chemical group 0.000 description 8
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 8
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000003003 spiro group Chemical group 0.000 description 8
125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
IGDNJMOBPOHHRN-UHFFFAOYSA-N 5h-benzo[b]phosphindole Chemical group C1=CC=C2C3=CC=CC=C3PC2=C1 IGDNJMOBPOHHRN-UHFFFAOYSA-N 0.000 description 7
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 7
150000001491 aromatic compounds Chemical class 0.000 description 7
230000008859 change Effects 0.000 description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
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 7
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 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 7
125000002883 imidazolyl group Chemical group 0.000 description 7
150000002739 metals Chemical class 0.000 description 7
125000002971 oxazolyl group Chemical group 0.000 description 7
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 7
125000003373 pyrazinyl group Chemical group 0.000 description 7
125000000714 pyrimidinyl group Chemical group 0.000 description 7
230000001603 reducing effect Effects 0.000 description 7
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
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 6
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
239000003341 Bronsted base Substances 0.000 description 6
QYZOKWLTSOHTJI-UHFFFAOYSA-N C1=CC=C2P(=O)C=CC2=C1 Chemical group C1=CC=C2P(=O)C=CC2=C1 QYZOKWLTSOHTJI-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 6
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 6
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
239000012043 crude product Substances 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
230000003111 delayed effect Effects 0.000 description 6
238000005401 electroluminescence Methods 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
150000002430 hydrocarbons Chemical group 0.000 description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 6
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 6
125000000842 isoxazolyl group Chemical group 0.000 description 6
238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 6
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 6
125000003226 pyrazolyl group Chemical group 0.000 description 6
125000004076 pyridyl group Chemical group 0.000 description 6
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 6
239000011734 sodium Substances 0.000 description 6
125000003831 tetrazolyl group Chemical group 0.000 description 6
125000001544 thienyl group Chemical group 0.000 description 6
125000005580 triphenylene group Chemical group 0.000 description 6
238000001771 vacuum deposition Methods 0.000 description 6
125000005955 1H-indazolyl group Chemical group 0.000 description 5
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 5
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
239000002841 Lewis acid Substances 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
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