KR20230156725A - 다환 방향족 화합물 - Google Patents

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Publication number

KR20230156725A

KR20230156725A KR1020237032540A KR20237032540A KR20230156725A KR 20230156725 A KR20230156725 A KR 20230156725A KR 1020237032540 A KR1020237032540 A KR 1020237032540A KR 20237032540 A KR20237032540 A KR 20237032540A KR 20230156725 A KR20230156725 A KR 20230156725A

Authority

KR

South Korea

Prior art keywords

substituted

unsubstituted

bonded

compound

ring

Prior art date

2021-03-15

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• -1 polycyclic aromatic compounds Chemical class 0.000 title claims abstract description 482
• 125000003118 aryl group Chemical group 0.000 claims abstract description 293
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 245
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 169
• 239000001257 hydrogen Substances 0.000 claims abstract description 169
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 163
• 239000000463 material Substances 0.000 claims abstract description 130
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 105
• 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 54
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 45
• 229910052805 deuterium Chemical group 0.000 claims abstract description 44
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 31
• 150000002367 halogens Chemical group 0.000 claims abstract description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 23
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
• 150000001875 compounds Chemical class 0.000 claims description 662
• 125000000217 alkyl group Chemical group 0.000 claims description 199
• 125000005647 linker group Chemical group 0.000 claims description 136
• 239000002019 doping agent Substances 0.000 claims description 96
• 125000004986 diarylamino group Chemical group 0.000 claims description 89
• 125000003545 alkoxy group Chemical group 0.000 claims description 66
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 62
• 150000002431 hydrogen Chemical group 0.000 claims description 58
• 125000003342 alkenyl group Chemical group 0.000 claims description 56
• 125000005240 diheteroarylamino group Chemical group 0.000 claims description 55
• 238000005401 electroluminescence Methods 0.000 claims description 49
• 125000004104 aryloxy group Chemical group 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 43
• 125000005110 aryl thio group Chemical group 0.000 claims description 38
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 33
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 22
• 125000000732 arylene group Chemical group 0.000 claims description 17
• 125000005549 heteroarylene group Chemical group 0.000 claims description 15
• 229910052782 aluminium Inorganic materials 0.000 claims description 13
• 229910052796 boron Inorganic materials 0.000 claims description 10
• 229910052698 phosphorus Inorganic materials 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 229910052785 arsenic Inorganic materials 0.000 claims description 6
• 229910052733 gallium Inorganic materials 0.000 claims description 6
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
• 125000001769 aryl amino group Chemical group 0.000 claims description 5
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 abstract description 128
• 230000015572 biosynthetic process Effects 0.000 description 299
• 238000003786 synthesis reaction Methods 0.000 description 299
• 239000010410 layer Substances 0.000 description 254
• 125000004432 carbon atom Chemical group C* 0.000 description 195
• 238000002347 injection Methods 0.000 description 70
• 239000007924 injection Substances 0.000 description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 69
• 230000032258 transport Effects 0.000 description 60
• 238000006243 chemical reaction Methods 0.000 description 54
• 239000000758 substrate Substances 0.000 description 42
• 239000010408 film Substances 0.000 description 40
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 39
• 230000005284 excitation Effects 0.000 description 37
• 125000001624 naphthyl group Chemical group 0.000 description 31
• 230000003111 delayed effect Effects 0.000 description 30
• 230000005525 hole transport Effects 0.000 description 28
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 26
• 229910052751 metal Inorganic materials 0.000 description 25
• 239000002184 metal Substances 0.000 description 25
• 239000010409 thin film Substances 0.000 description 23
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 21
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 20
• 238000004519 manufacturing process Methods 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 239000000370 acceptor Substances 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
• 238000000151 deposition Methods 0.000 description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• 230000008021 deposition Effects 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 230000006870 function Effects 0.000 description 14
• 239000011521 glass Substances 0.000 description 14
• 239000011159 matrix material Substances 0.000 description 14
• 239000000203 mixture Substances 0.000 description 14
• 239000004065 semiconductor Substances 0.000 description 14
• 238000006467 substitution reaction Methods 0.000 description 14
• 125000005561 phenanthryl group Chemical group 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 12
• 125000003107 substituted aryl group Chemical group 0.000 description 12
• 230000036961 partial effect Effects 0.000 description 11
• 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 11
• 125000005577 anthracene group Chemical group 0.000 description 10
• 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 10
• 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 10
• 238000011156 evaluation Methods 0.000 description 10
• PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
• 229920005989 resin Polymers 0.000 description 10
• 239000011347 resin Substances 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 239000011737 fluorine Substances 0.000 description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
• 238000005259 measurement Methods 0.000 description 9
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
• 238000001296 phosphorescence spectrum Methods 0.000 description 9
• 229920000642 polymer Polymers 0.000 description 9
• 125000001725 pyrenyl group Chemical group 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 150000001340 alkali metals Chemical class 0.000 description 8
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
• 238000009833 condensation Methods 0.000 description 8
• 230000005494 condensation Effects 0.000 description 8
• 239000004973 liquid crystal related substance Substances 0.000 description 8
• 238000004020 luminiscence type Methods 0.000 description 8
• 125000004957 naphthylene group Chemical group 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 230000001603 reducing effect Effects 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
• 230000000903 blocking effect Effects 0.000 description 7
• 230000000052 comparative effect Effects 0.000 description 7
• 230000005669 field effect Effects 0.000 description 7
• 238000002189 fluorescence spectrum Methods 0.000 description 7
• 150000002739 metals Chemical class 0.000 description 7
• 229910052760 oxygen Inorganic materials 0.000 description 7
• 125000004665 trialkylsilyl group Chemical group 0.000 description 7
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
• 102100039104 Dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit DAD1 Human genes 0.000 description 6
• 101000884921 Homo sapiens Dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit DAD1 Proteins 0.000 description 6
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 230000004888 barrier function Effects 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
• 230000005281 excited state Effects 0.000 description 6
• 230000005283 ground state Effects 0.000 description 6
• 238000004770 highest occupied molecular orbital Methods 0.000 description 6
• 229910052744 lithium Inorganic materials 0.000 description 6
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• 229910052700 potassium Inorganic materials 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 125000000168 pyrrolyl group Chemical group 0.000 description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 6
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
• HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
• 238000010521 absorption reaction Methods 0.000 description 5
• 150000001454 anthracenes Chemical class 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 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 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 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 5
• 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
• 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 5
• ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
• 101150112582 dad2 gene Proteins 0.000 description 5
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 5
• 125000001041 indolyl group Chemical group 0.000 description 5
• 239000011777 magnesium Substances 0.000 description 5
• 239000001301 oxygen Substances 0.000 description 5
• 230000008569 process Effects 0.000 description 5
• 238000006862 quantum yield reaction Methods 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 125000003003 spiro group Chemical group 0.000 description 5
• 125000000547 substituted alkyl group Chemical group 0.000 description 5
• 238000007740 vapor deposition Methods 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
• 239000002841 Lewis acid Substances 0.000 description 4
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• 238000000862 absorption spectrum Methods 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• 150000001342 alkaline earth metals Chemical class 0.000 description 4
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 125000004653 anthracenylene group Chemical group 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• WZJYKHNJTSNBHV-UHFFFAOYSA-N benzoquinoline Natural products C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 238000000576 coating method Methods 0.000 description 4
• 239000010949 copper Substances 0.000 description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
• IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 4
• DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 4
• 230000005684 electric field Effects 0.000 description 4
• 239000007789 gas Substances 0.000 description 4
• 125000000623 heterocyclic group Chemical group 0.000 description 4
• 150000002430 hydrocarbons Chemical group 0.000 description 4
• 239000012212 insulator Substances 0.000 description 4
• 150000007517 lewis acids Chemical class 0.000 description 4
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
• 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
• 229910052749 magnesium Inorganic materials 0.000 description 4
• IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 4
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
• 150000002894 organic compounds Chemical class 0.000 description 4
• 239000011368 organic material Substances 0.000 description 4
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
• 239000004926 polymethyl methacrylate Substances 0.000 description 4
• 125000003226 pyrazolyl group Chemical group 0.000 description 4
• 239000002994 raw material Substances 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• 230000003595 spectral effect Effects 0.000 description 4
• 125000005415 substituted alkoxy group Chemical group 0.000 description 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
• 239000011593 sulfur Chemical group 0.000 description 4
• 150000003852 triazoles Chemical group 0.000 description 4
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
• 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 3
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