CN116964063A - 多环芳香族化合物 - Google Patents

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Publication number

CN116964063A

CN116964063A CN202280020465.6A CN202280020465A CN116964063A CN 116964063 A CN116964063 A CN 116964063A CN 202280020465 A CN202280020465 A CN 202280020465A CN 116964063 A CN116964063 A CN 116964063A

Authority

CN

China

Prior art keywords

substituted

group

unsubstituted

formula

aryl

Prior art date

2021-03-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• -1 Polycyclic aromatic compounds Chemical class 0.000 title claims abstract description 426
• 125000003118 aryl group Chemical group 0.000 claims abstract description 283
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 236
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 174
• 239000001257 hydrogen Substances 0.000 claims abstract description 174
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 164
• 239000000463 material Substances 0.000 claims abstract description 156
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 112
• 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 43
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 35
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
• 150000002367 halogens Chemical group 0.000 claims abstract description 29
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
• 125000000732 arylene group Chemical group 0.000 claims abstract description 20
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
• 150000001875 compounds Chemical class 0.000 claims description 682
• 125000000217 alkyl group Chemical group 0.000 claims description 196
• 239000000126 substance Substances 0.000 claims description 147
• 239000002019 doping agent Substances 0.000 claims description 97
• 125000005647 linker group Chemical group 0.000 claims description 97
• 125000004986 diarylamino group Chemical group 0.000 claims description 95
• 125000003545 alkoxy group Chemical group 0.000 claims description 67
• 150000002431 hydrogen Chemical class 0.000 claims description 59
• 125000003342 alkenyl group Chemical group 0.000 claims description 58
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 46
• 125000004104 aryloxy group Chemical group 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 229910052799 carbon Inorganic materials 0.000 claims description 43
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
• 125000005240 diheteroarylamino group Chemical group 0.000 claims description 39
• 125000005110 aryl thio group Chemical group 0.000 claims description 37
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 22
• 125000003277 amino group Chemical group 0.000 claims description 17
• 125000005549 heteroarylene group Chemical group 0.000 claims description 17
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 229910052698 phosphorus Inorganic materials 0.000 claims description 13
• 229910052796 boron Inorganic materials 0.000 claims description 11
• 125000002947 alkylene group Chemical group 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
• 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
• 125000005241 heteroarylamino group Chemical group 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 abstract description 130
• 229910052727 yttrium Inorganic materials 0.000 abstract description 4
• 230000015572 biosynthetic process Effects 0.000 description 301
• 238000003786 synthesis reaction Methods 0.000 description 299
• 239000010410 layer Substances 0.000 description 238
• 125000004432 carbon atom Chemical group C* 0.000 description 177
• 238000000034 method Methods 0.000 description 136
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 70
• 238000002347 injection Methods 0.000 description 59
• 239000007924 injection Substances 0.000 description 59
• 238000006243 chemical reaction Methods 0.000 description 56
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 50
• 230000032258 transport Effects 0.000 description 48
• 239000010408 film Substances 0.000 description 42
• 239000000758 substrate Substances 0.000 description 40
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 34
• 125000001624 naphthyl group Chemical group 0.000 description 33
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 31
• 230000003111 delayed effect Effects 0.000 description 30
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 28
• 235000010290 biphenyl Nutrition 0.000 description 25
• 230000005525 hole transport Effects 0.000 description 24
• 229910052751 metal Inorganic materials 0.000 description 24
• 239000002184 metal Substances 0.000 description 24
• 238000007740 vapor deposition Methods 0.000 description 24
• 239000004305 biphenyl Substances 0.000 description 23
• 230000006870 function Effects 0.000 description 23
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 22
• 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 20
• 239000010409 thin film Substances 0.000 description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 239000000370 acceptor Substances 0.000 description 18
• 238000004519 manufacturing process Methods 0.000 description 18
• 125000005561 phenanthryl group Chemical group 0.000 description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
• 238000006467 substitution reaction Methods 0.000 description 16
• 239000011521 glass Substances 0.000 description 15
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 230000005284 excitation Effects 0.000 description 14
• 229920000642 polymer Polymers 0.000 description 14
• 239000004065 semiconductor Substances 0.000 description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
• 239000011159 matrix material Substances 0.000 description 13
• 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 12
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 12
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
• 238000011156 evaluation Methods 0.000 description 11
• 125000001725 pyrenyl group Chemical group 0.000 description 11
• 125000005580 triphenylene group Chemical group 0.000 description 11
• 239000000203 mixture Substances 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 229910052783 alkali metal Inorganic materials 0.000 description 9
• 150000001340 alkali metals Chemical class 0.000 description 9
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
• 239000004973 liquid crystal related substance Substances 0.000 description 9
• 125000004957 naphthylene group Chemical group 0.000 description 9
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
• 229920005989 resin Polymers 0.000 description 9
• 239000011347 resin Substances 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
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 229940045799 anthracyclines and related substance Drugs 0.000 description 8
• 238000000576 coating method Methods 0.000 description 8
• 230000005669 field effect Effects 0.000 description 8
• 238000002189 fluorescence spectrum Methods 0.000 description 8
• 229910052731 fluorine Inorganic materials 0.000 description 8
• 239000011737 fluorine Substances 0.000 description 8
• 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 8
• 239000012044 organic layer Substances 0.000 description 8
• 238000001296 phosphorescence spectrum Methods 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 125000003107 substituted aryl group Chemical group 0.000 description 8
• 229910052782 aluminium Inorganic materials 0.000 description 7
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
• 230000004888 barrier function Effects 0.000 description 7
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 7
• 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 7
• 229910052792 caesium Inorganic materials 0.000 description 7
• 230000000052 comparative effect Effects 0.000 description 7
• 238000004770 highest occupied molecular orbital Methods 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 238000004020 luminiscence type Methods 0.000 description 7
• 238000005259 measurement Methods 0.000 description 7
• 150000002739 metals Chemical class 0.000 description 7
• 238000006862 quantum yield reaction Methods 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
• 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
• 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
• 150000001454 anthracenes Chemical class 0.000 description 6
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 239000011248 coating agent Substances 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
• 230000000694 effects Effects 0.000 description 6
• 238000005286 illumination Methods 0.000 description 6
• PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
• 238000004768 lowest unoccupied molecular orbital Methods 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
• 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
• 239000000243 solution Substances 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 5
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
• 101710162371 Dihydroxy-acid dehydratase 1 Proteins 0.000 description 5
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-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
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
• 150000001342 alkaline earth metals Chemical class 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 5
• WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 5
• 230000000903 blocking effect Effects 0.000 description 5
• 238000005859 coupling reaction Methods 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
• 239000000539 dimer Substances 0.000 description 5
• 238000000295 emission spectrum Methods 0.000 description 5
• 238000001704 evaporation Methods 0.000 description 5
• 230000008020 evaporation Effects 0.000 description 5
• 230000005283 ground state Effects 0.000 description 5
• 150000004820 halides Chemical class 0.000 description 5
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 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
• 229910052744 lithium Inorganic materials 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 239000001301 oxygen Substances 0.000 description 5
• 238000005424 photoluminescence Methods 0.000 description 5
• 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
• 239000004926 polymethyl methacrylate Substances 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000011734 sodium Substances 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
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• 239000003341 Bronsted base Substances 0.000 description 4
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
• 101710162370 Dihydroxy-acid dehydratase 2 Proteins 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
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-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
• 238000005481 NMR spectroscopy Methods 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 4
• 125000004653 anthracenylene group Chemical group 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• 239000011230 binding agent Substances 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
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 238000009833 condensation Methods 0.000 description 4
• 230000005494 condensation Effects 0.000 description 4
• 230000008878 coupling Effects 0.000 description 4
• 238000010168 coupling process Methods 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
• 238000007336 electrophilic substitution reaction Methods 0.000 description 4
• 230000005281 excited state 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
• 239000011777 magnesium Substances 0.000 description 4
• 230000007246 mechanism Effects 0.000 description 4
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
• 229910052750 molybdenum Inorganic materials 0.000 description 4
• 239000011733 molybdenum Substances 0.000 description 4
• 125000002950 monocyclic group Chemical group 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
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 229910052761 rare earth metal Inorganic materials 0.000 description 4
• 150000002910 rare earth metals Chemical class 0.000 description 4
• 239000002994 raw material Substances 0.000 description 4
• 230000001603 reducing effect Effects 0.000 description 4
• 230000009467 reduction Effects 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 125000003003 spiro group Chemical group 0.000 description 4
• 125000000547 substituted alkyl group Chemical group 0.000 description 4
• 239000011593 sulfur Chemical group 0.000 description 4
• YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
• 150000003852 triazoles Chemical group 0.000 description 4
• MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 4
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
• MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 3
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
• 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 3
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