KR20200140744A - 아미노 치환 다환 방향족 화합물 - Google Patents
아미노 치환 다환 방향족 화합물 Download PDFInfo
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- KR20200140744A KR20200140744A KR1020200068437A KR20200068437A KR20200140744A KR 20200140744 A KR20200140744 A KR 20200140744A KR 1020200068437 A KR1020200068437 A KR 1020200068437A KR 20200068437 A KR20200068437 A KR 20200068437A KR 20200140744 A KR20200140744 A KR 20200140744A
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- KR
- South Korea
- Prior art keywords
- ring
- aryl
- carbon atoms
- alkyl
- substituted
- Prior art date
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- -1 Amino-substituted polycyclic aromatic compounds Chemical class 0.000 title claims abstract description 783
- 125000003118 aryl group Chemical group 0.000 claims abstract description 672
- 125000001424 substituent group Chemical group 0.000 claims abstract description 229
- 239000000463 material Substances 0.000 claims abstract description 136
- 125000003277 amino group Chemical group 0.000 claims abstract description 47
- 229910052796 boron Inorganic materials 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 500
- 125000000217 alkyl group Chemical group 0.000 claims description 427
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 425
- 125000001072 heteroaryl group Chemical group 0.000 claims description 406
- 150000001875 compounds Chemical class 0.000 claims description 340
- 229910052739 hydrogen Inorganic materials 0.000 claims description 290
- 239000001257 hydrogen Substances 0.000 claims description 290
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 179
- 239000010410 layer Substances 0.000 claims description 179
- 150000001924 cycloalkanes Chemical class 0.000 claims description 132
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 123
- 229920000642 polymer Polymers 0.000 claims description 87
- 125000005647 linker group Chemical group 0.000 claims description 85
- 125000003545 alkoxy group Chemical group 0.000 claims description 73
- 125000004986 diarylamino group Chemical group 0.000 claims description 72
- 229910052736 halogen Chemical group 0.000 claims description 61
- 150000002367 halogens Chemical group 0.000 claims description 61
- 238000002347 injection Methods 0.000 claims description 60
- 239000007924 injection Substances 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 51
- 125000004104 aryloxy group Chemical group 0.000 claims description 50
- 229910052805 deuterium Inorganic materials 0.000 claims description 47
- 229910052698 phosphorus Inorganic materials 0.000 claims description 42
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 39
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 35
- 125000003107 substituted aryl group Chemical group 0.000 claims description 35
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 34
- 239000002184 metal Substances 0.000 claims description 34
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 29
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 29
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 27
- 230000005525 hole transport Effects 0.000 claims description 26
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 23
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 22
- 229910052782 aluminium Inorganic materials 0.000 claims description 22
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 21
- 229910052733 gallium Inorganic materials 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 229910052785 arsenic Inorganic materials 0.000 claims description 16
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 16
- 239000002019 doping agent Substances 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 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 16
- 125000002619 bicyclic group Chemical group 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 11
- 238000004132 cross linking Methods 0.000 claims description 11
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical group [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 10
- 150000001454 anthracenes Chemical class 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 239000005267 main chain polymer Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical group 0.000 claims description 9
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000006686 (C1-C24) alkyl group Chemical group 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
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 8
- 150000002910 rare earth metals Chemical class 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 7
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 7
- 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
- 150000003222 pyridines Chemical class 0.000 claims description 7
- 150000003918 triazines Chemical class 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 5
- 150000002219 fluoranthenes Chemical class 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 150000005041 phenanthrolines Chemical class 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 3
- 150000007981 azolines Chemical class 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 150000007979 thiazole derivatives Chemical class 0.000 claims description 2
- 239000013638 trimer Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 26
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 147
- 125000001624 naphthyl group Chemical group 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
- 238000005401 electroluminescence Methods 0.000 description 31
- 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 27
- 125000003342 alkenyl group Chemical group 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 23
- 239000002994 raw material Substances 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 22
- 125000005842 heteroatom Chemical group 0.000 description 19
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 238000009833 condensation Methods 0.000 description 16
- 230000005494 condensation Effects 0.000 description 16
- 229910052744 lithium Inorganic materials 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 238000001308 synthesis method Methods 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 125000005561 phenanthryl group Chemical group 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000001301 oxygen 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
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 11
- 125000005577 anthracene group Chemical group 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 11
- 150000001716 carbazoles Chemical class 0.000 description 11
- 125000001041 indolyl group Chemical group 0.000 description 11
- 125000004957 naphthylene group Chemical group 0.000 description 11
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 11
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 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 10
- 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 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 10
- 125000003003 spiro group Chemical group 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000003341 Bronsted base Substances 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 9
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 239000002841 Lewis acid Substances 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- 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 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- 150000007517 lewis acids Chemical class 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
- 125000000168 pyrrolyl group Chemical group 0.000 description 8
- 125000005110 aryl thio group Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000470 constituent Substances 0.000 description 7
- 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 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 125000002883 imidazolyl group Chemical group 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 7
- 125000003373 pyrazinyl group Chemical group 0.000 description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- 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 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000003838 furazanyl group Chemical group 0.000 description 6
- 125000002541 furyl group Chemical group 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
- 125000000842 isoxazolyl group Chemical group 0.000 description 6
- 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 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
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 125000003226 pyrazolyl group Chemical group 0.000 description 6
- 125000001725 pyrenyl group Chemical group 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- 125000004434 sulfur atom Chemical group 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
- 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 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 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- 125000005955 1H-indazolyl group Chemical group 0.000 description 5
- 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 description 5
- 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 5
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 5
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 230000004888 barrier function Effects 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
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 5
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- 125000004122 cyclic group Chemical group 0.000 description 5
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3247—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing combinations of different heteroatoms other than nitrogen and oxygen or nitrogen and sulfur
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
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- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
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| JP2019107010 | 2019-06-07 | ||
| JPJP-P-2019-107010 | 2019-06-07 | ||
| JPJP-P-2019-143720 | 2019-08-05 | ||
| JP2019143720 | 2019-08-05 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022145773A1 (ko) * | 2021-01-04 | 2022-07-07 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
| WO2022145774A1 (ko) * | 2021-01-04 | 2022-07-07 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
| WO2023043299A1 (en) * | 2021-09-20 | 2023-03-23 | Samsung Display Co., Ltd. | Organic molecules for optoelectronic devices |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111333671B (zh) * | 2020-03-16 | 2022-12-23 | 清华大学 | 一种发光材料及其应用以及包含其的有机电致发光器件 |
| JPWO2023022233A1 (ja) * | 2021-08-20 | 2023-02-23 | ||
| EP4151697A1 (en) | 2021-09-17 | 2023-03-22 | Idemitsu Kosan Co., Ltd. | Compound and an organic electroluminescence device comprising the compound |
| JP2023050133A (ja) * | 2021-09-29 | 2023-04-10 | 住友化学株式会社 | 発光素子 |
| JP2023050130A (ja) * | 2021-09-29 | 2023-04-10 | 住友化学株式会社 | 発光素子 |
| EP4215535A1 (en) | 2022-01-24 | 2023-07-26 | Idemitsu Kosan Co.,Ltd. | Compound and an organic electroluminescence device comprising the compound |
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| WO2004061047A2 (en) | 2002-12-31 | 2004-07-22 | Eastman Kodak Company | Complex fluorene-containing compounds for use in organic light emitting devices |
| JP2005170911A (ja) | 2003-12-15 | 2005-06-30 | Idemitsu Kosan Co Ltd | 芳香族化合物およびそれを用いた有機エレクトロルミネッセンス素子 |
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| WO2015102118A1 (ja) | 2014-02-18 | 2015-07-09 | 学校法人関西学院 | 多環芳香族化合物 |
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| TWI688137B (zh) * | 2015-03-24 | 2020-03-11 | 學校法人關西學院 | 有機電場發光元件、顯示裝置以及照明裝置 |
| US11502261B2 (en) * | 2017-05-02 | 2022-11-15 | Lg Chem Ltd. | Compound and organic light emitting device using the same |
| KR101876763B1 (ko) * | 2017-05-22 | 2018-07-11 | 머티어리얼사이언스 주식회사 | 유기화합물 및 이를 포함하는 유기전계발광소자 |
| CN110799571B (zh) * | 2017-06-30 | 2022-09-20 | 住友化学株式会社 | 高分子化合物及使用其的发光元件 |
| CN109411633B (zh) * | 2018-08-31 | 2020-12-15 | 昆山国显光电有限公司 | 一种有机电致发光器件及其制备方法和显示装置 |
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- 2020-06-05 KR KR1020200068437A patent/KR20200140744A/ko active Search and Examination
- 2020-06-05 CN CN202010510681.1A patent/CN112047967A/zh active Pending
- 2020-06-05 JP JP2020098433A patent/JP2021014446A/ja active Pending
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| JP2001172232A (ja) | 1999-12-21 | 2001-06-26 | Univ Osaka | エレクトロルミネッセンス素子 |
| WO2004061047A2 (en) | 2002-12-31 | 2004-07-22 | Eastman Kodak Company | Complex fluorene-containing compounds for use in organic light emitting devices |
| JP2005170911A (ja) | 2003-12-15 | 2005-06-30 | Idemitsu Kosan Co Ltd | 芳香族化合物およびそれを用いた有機エレクトロルミネッセンス素子 |
| WO2011107186A2 (de) | 2010-03-02 | 2011-09-09 | 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 |
| WO2015102118A1 (ja) | 2014-02-18 | 2015-07-09 | 学校法人関西学院 | 多環芳香族化合物 |
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| WO2022145773A1 (ko) * | 2021-01-04 | 2022-07-07 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
| WO2022145774A1 (ko) * | 2021-01-04 | 2022-07-07 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
| WO2023043299A1 (en) * | 2021-09-20 | 2023-03-23 | Samsung Display Co., Ltd. | Organic molecules for optoelectronic devices |
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