CN114026147A - 多环芳香族化合物 - Google Patents
多环芳香族化合物 Download PDFInfo
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- CN114026147A CN114026147A CN202080043697.4A CN202080043697A CN114026147A CN 114026147 A CN114026147 A CN 114026147A CN 202080043697 A CN202080043697 A CN 202080043697A CN 114026147 A CN114026147 A CN 114026147A
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- -1 Polycyclic aromatic compound Chemical class 0.000 title claims abstract description 585
- 125000003118 aryl group Chemical group 0.000 claims abstract description 669
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 431
- 150000001875 compounds Chemical class 0.000 claims abstract description 317
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 272
- 239000001257 hydrogen Substances 0.000 claims abstract description 272
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 130
- 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 108
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 43
- 229910052736 halogen Chemical group 0.000 claims abstract description 43
- 150000002367 halogens Chemical group 0.000 claims abstract description 43
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 713
- 125000000217 alkyl group Chemical group 0.000 claims description 470
- 239000000243 solution Substances 0.000 claims description 439
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 336
- 125000001424 substituent group Chemical group 0.000 claims description 169
- 239000010410 layer Substances 0.000 claims description 166
- 150000002431 hydrogen Chemical group 0.000 claims description 133
- 239000000463 material Substances 0.000 claims description 132
- 239000000126 substance Substances 0.000 claims description 109
- 229920000642 polymer Polymers 0.000 claims description 103
- 125000005647 linker group Chemical group 0.000 claims description 81
- 125000004986 diarylamino group Chemical group 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
- 150000003254 radicals Chemical class 0.000 claims description 59
- 125000004104 aryloxy group Chemical group 0.000 claims description 56
- 238000002347 injection Methods 0.000 claims description 52
- 239000007924 injection Substances 0.000 claims description 52
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 46
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 42
- 125000003107 substituted aryl group Chemical group 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 229910052698 phosphorus Inorganic materials 0.000 claims description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
- 229920006037 cross link polymer Polymers 0.000 claims description 30
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 30
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 24
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 230000005525 hole transport Effects 0.000 claims description 21
- 125000002950 monocyclic group Chemical group 0.000 claims description 21
- 125000002619 bicyclic group Chemical group 0.000 claims description 20
- 229910052796 boron Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000002019 doping agent Substances 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 15
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 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
- 239000002841 Lewis acid Substances 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 150000004820 halides Chemical class 0.000 claims description 12
- 150000007517 lewis acids Chemical class 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 12
- 229910052785 arsenic Inorganic materials 0.000 claims description 11
- 238000004132 cross linking Methods 0.000 claims description 11
- 239000000539 dimer Substances 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052733 gallium Inorganic materials 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 229910052701 rubidium Inorganic materials 0.000 claims description 11
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 150000001454 anthracenes Chemical class 0.000 claims description 9
- 238000006263 metalation reaction Methods 0.000 claims description 9
- 150000003222 pyridines Chemical class 0.000 claims description 9
- 239000003341 Bronsted base Substances 0.000 claims description 8
- 229910004790 P—O Inorganic materials 0.000 claims description 8
- 229910004839 P—S Inorganic materials 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 8
- 150000002910 rare earth metals Chemical class 0.000 claims description 8
- 230000005669 field effect Effects 0.000 claims description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 239000013638 trimer Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000007336 electrophilic substitution reaction Methods 0.000 claims description 6
- 150000002219 fluoranthenes Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 6
- 150000007514 bases Chemical class 0.000 claims description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 4
- 239000005267 main chain polymer Substances 0.000 claims description 4
- 150000003918 triazines Chemical class 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- 150000003967 siloles Chemical class 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 claims description 2
- 150000007979 thiazole derivatives Chemical class 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims 1
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 90
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 36
- 125000001624 naphthyl group Chemical group 0.000 description 36
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 32
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 description 28
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 27
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 26
- 238000005401 electroluminescence Methods 0.000 description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 24
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 22
- 125000003342 alkenyl group Chemical group 0.000 description 22
- 239000000758 substrate Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 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 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 235000010338 boric acid Nutrition 0.000 description 17
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
- 238000006467 substitution reaction Methods 0.000 description 17
- 235000010290 biphenyl Nutrition 0.000 description 16
- 239000004305 biphenyl Substances 0.000 description 16
- 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 16
- 239000004327 boric acid Substances 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 125000005561 phenanthryl group Chemical group 0.000 description 15
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 14
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- 125000000732 arylene group Chemical group 0.000 description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 125000005549 heteroarylene group Chemical group 0.000 description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 125000005577 anthracene group Chemical group 0.000 description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 125000005580 triphenylene group Chemical group 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 230000006870 function Effects 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
- 125000001725 pyrenyl group Chemical group 0.000 description 9
- 125000006267 biphenyl group Chemical group 0.000 description 8
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 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 8
- 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 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 8
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 7
- 125000005110 aryl thio group Chemical group 0.000 description 7
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([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
- 125000001041 indolyl group Chemical group 0.000 description 7
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 7
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 6
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011593 sulfur Chemical group 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 5
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 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
- 125000004429 atom Chemical group 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
- 239000003795 chemical substances by application Substances 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 5
- 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 4
- 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 4
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- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 4
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Images
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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KR20220148952A (ko) | 2021-04-26 | 2022-11-07 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 |
KR20220156748A (ko) * | 2021-05-19 | 2022-11-28 | 김진우 | 신규한 유기화합물 및 이를 포함하는 유기전계발광소자 |
KR102760954B1 (ko) * | 2021-06-02 | 2025-01-24 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
CN115703803A (zh) | 2021-08-11 | 2023-02-17 | 学校法人关西学院 | 多环芳香族化合物、有机器件用材料、有机电致发光元件、显示装置及照明装置 |
KR20230034895A (ko) | 2021-09-03 | 2023-03-10 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 |
WO2023043299A1 (en) * | 2021-09-20 | 2023-03-23 | Samsung Display Co., Ltd. | Organic molecules for optoelectronic devices |
KR20230043732A (ko) | 2021-09-24 | 2023-03-31 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 |
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KR20230140484A (ko) | 2022-03-22 | 2023-10-06 | 가꼬우 호징 관세이 가쿠잉 | 다환방향족 화합물 |
WO2024166913A1 (ja) * | 2023-02-07 | 2024-08-15 | 国立大学法人京都大学 | 多環芳香族化合物 |
KR20240171012A (ko) | 2023-05-29 | 2024-12-06 | 고쿠리츠 다이가쿠 호진 교토 다이가쿠 | 다환 방향족 화합물 |
CN119241574A (zh) | 2023-07-03 | 2025-01-03 | 国立大学法人京都大学 | 多环芳香族化合物、有机电致发光元件、显示装置及照明装置 |
KR20250023292A (ko) | 2023-08-09 | 2025-02-18 | 고쿠리츠 다이가쿠 호진 교토 다이가쿠 | 다환 방향족 화합물 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103460428A (zh) * | 2011-03-28 | 2013-12-18 | 住友化学株式会社 | 电子设备、高分子化合物、有机化合物及高分子化合物的制备方法 |
CN104254930A (zh) * | 2012-04-09 | 2014-12-31 | 三菱化学株式会社 | 有机场致发光元件用组合物和有机场致发光元件 |
CN105431439A (zh) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | 多环芳香族化合物 |
WO2016152544A1 (ja) * | 2015-03-24 | 2016-09-29 | 学校法人関西学院 | 有機電界発光素子 |
US20180069182A1 (en) * | 2016-09-07 | 2018-03-08 | Kwansei Gakuin Educational Foundation | Polycyclic aromatic compound |
KR20180120619A (ko) * | 2017-04-27 | 2018-11-06 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
WO2018203666A1 (ko) * | 2017-05-02 | 2018-11-08 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
WO2018216990A1 (ko) * | 2017-05-22 | 2018-11-29 | 머티어리얼사이언스 주식회사 | 유기화합물 및 이를 포함하는 유기전계발광소자 |
CN109155368A (zh) * | 2016-04-26 | 2019-01-04 | 学校法人关西学院 | 有机电场发光元件 |
WO2019088799A1 (ko) * | 2017-11-06 | 2019-05-09 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040131881A1 (en) | 2002-12-31 | 2004-07-08 | Eastman Kodak Company | Complex fluorene-containing compounds for use in OLED devices |
DE102010009903A1 (de) | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
WO2012118164A1 (ja) | 2011-03-03 | 2012-09-07 | 国立大学法人九州大学 | 新規化合物、電荷輸送材料および有機デバイス |
WO2016152418A1 (ja) * | 2015-03-25 | 2016-09-29 | 学校法人関西学院 | 多環芳香族化合物および発光層形成用組成物 |
KR102094830B1 (ko) * | 2018-11-30 | 2020-03-30 | 에스에프씨 주식회사 | 다환 방향족 유도체 화합물 및 이를 이용한 유기발광소자 |
WO2020111830A1 (ko) * | 2018-11-30 | 2020-06-04 | 에스에프씨 주식회사 | 다환 방향족 유도체 화합물을 이용한 유기발광소자 |
-
2020
- 2020-06-12 CN CN202080043697.4A patent/CN114026147A/zh active Pending
- 2020-06-12 TW TW109119854A patent/TWI869412B/zh active
- 2020-06-12 JP JP2021526175A patent/JP7599175B2/ja active Active
- 2020-06-12 WO PCT/JP2020/023312 patent/WO2020251049A1/ja not_active Application Discontinuation
- 2020-06-12 KR KR1020227000819A patent/KR102845886B1/ko active Active
- 2020-06-12 KR KR1020257024794A patent/KR20250119652A/ko active Pending
-
2024
- 2024-11-25 JP JP2024204352A patent/JP2025032148A/ja active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103460428A (zh) * | 2011-03-28 | 2013-12-18 | 住友化学株式会社 | 电子设备、高分子化合物、有机化合物及高分子化合物的制备方法 |
CN104254930A (zh) * | 2012-04-09 | 2014-12-31 | 三菱化学株式会社 | 有机场致发光元件用组合物和有机场致发光元件 |
CN105431439A (zh) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | 多环芳香族化合物 |
WO2016152544A1 (ja) * | 2015-03-24 | 2016-09-29 | 学校法人関西学院 | 有機電界発光素子 |
CN109155368A (zh) * | 2016-04-26 | 2019-01-04 | 学校法人关西学院 | 有机电场发光元件 |
US20180069182A1 (en) * | 2016-09-07 | 2018-03-08 | Kwansei Gakuin Educational Foundation | Polycyclic aromatic compound |
KR20180120619A (ko) * | 2017-04-27 | 2018-11-06 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
WO2018203666A1 (ko) * | 2017-05-02 | 2018-11-08 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
WO2018216990A1 (ko) * | 2017-05-22 | 2018-11-29 | 머티어리얼사이언스 주식회사 | 유기화합물 및 이를 포함하는 유기전계발광소자 |
WO2019088799A1 (ko) * | 2017-11-06 | 2019-05-09 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113348171A (zh) * | 2019-11-29 | 2021-09-03 | 株式会社Lg化学 | 化合物和包含其的有机发光元件 |
US11685751B2 (en) | 2019-11-29 | 2023-06-27 | Lg Chem, Ltd. | Compound and organic light-emitting element comprising same |
US11780856B2 (en) | 2019-11-29 | 2023-10-10 | Lg Chem, Ltd. | Compound and organic light-emitting device comprising same |
CN114867729A (zh) * | 2019-12-19 | 2022-08-05 | 默克专利有限公司 | 用于有机电致发光器件的多环化合物 |
CN113201003A (zh) * | 2021-05-08 | 2021-08-03 | 吉林奥来德光电材料股份有限公司 | 一种有机电致发光化合物及其应用 |
CN117384194A (zh) * | 2022-06-29 | 2024-01-12 | 江苏三月科技股份有限公司 | 一种含硼有机化合物及其制备的有机电致发光器件 |
CN117384194B (zh) * | 2022-06-29 | 2025-08-01 | 江苏三月科技股份有限公司 | 一种含硼有机化合物及其制备的有机电致发光器件 |
CN115724869A (zh) * | 2022-11-15 | 2023-03-03 | 深圳市华星光电半导体显示技术有限公司 | 有机化合物、发光元件及显示面板 |
CN116120353A (zh) * | 2023-01-16 | 2023-05-16 | 北京八亿时空液晶科技股份有限公司 | 一种含硼原子的咔唑衍生物及其应用 |
CN118955547A (zh) * | 2024-10-15 | 2024-11-15 | 浙江华显光电科技有限公司 | 一种硼氮化合物、具有该化合物的oled和有机发光装置 |
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TW202104239A (zh) | 2021-02-01 |
KR102845886B1 (ko) | 2025-08-12 |
JP2025032148A (ja) | 2025-03-11 |
JPWO2020251049A1 (enrdf_load_stackoverflow) | 2020-12-17 |
WO2020251049A1 (ja) | 2020-12-17 |
JP7599175B2 (ja) | 2024-12-13 |
TWI869412B (zh) | 2025-01-11 |
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