JP6738063B2 - シクロアルキル置換多環芳香族化合物 - Google Patents
シクロアルキル置換多環芳香族化合物 Download PDFInfo
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- JP6738063B2 JP6738063B2 JP2019072134A JP2019072134A JP6738063B2 JP 6738063 B2 JP6738063 B2 JP 6738063B2 JP 2019072134 A JP2019072134 A JP 2019072134A JP 2019072134 A JP2019072134 A JP 2019072134A JP 6738063 B2 JP6738063 B2 JP 6738063B2
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- alkyl
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- -1 polycyclic aromatic compound Chemical class 0.000 title claims description 504
- 239000010410 layer Substances 0.000 claims description 337
- 125000003118 aryl group Chemical group 0.000 claims description 321
- 150000001875 compounds Chemical class 0.000 claims description 314
- 125000000217 alkyl group Chemical group 0.000 claims description 232
- 125000004432 carbon atom Chemical group C* 0.000 claims description 183
- 239000000463 material Substances 0.000 claims description 170
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 157
- 239000000203 mixture Substances 0.000 claims description 138
- 229910052739 hydrogen Inorganic materials 0.000 claims description 134
- 239000001257 hydrogen Substances 0.000 claims description 134
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 81
- 239000012044 organic layer Substances 0.000 claims description 78
- 238000002347 injection Methods 0.000 claims description 74
- 239000007924 injection Substances 0.000 claims description 74
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 69
- 125000003545 alkoxy group Chemical group 0.000 claims description 47
- 125000004986 diarylamino group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 229910052736 halogen Chemical group 0.000 claims description 32
- 150000002367 halogens Chemical group 0.000 claims description 32
- 125000004104 aryloxy group Chemical group 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 25
- 239000010409 thin film Substances 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- 239000002019 doping agent Substances 0.000 claims description 20
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 18
- 150000001454 anthracenes Chemical class 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 12
- 150000002910 rare earth metals Chemical class 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
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 230000005669 field effect Effects 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 11
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 10
- 150000001716 carbazoles Chemical class 0.000 claims description 10
- 150000003222 pyridines Chemical class 0.000 claims description 8
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 7
- 150000003918 triazines Chemical class 0.000 claims description 7
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 150000002219 fluoranthenes Chemical class 0.000 claims description 5
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 3
- 150000005041 phenanthrolines Chemical class 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 description 165
- 125000001424 substituent group Chemical group 0.000 description 147
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 123
- 239000010408 film Substances 0.000 description 117
- 229920000642 polymer Chemical class 0.000 description 107
- 238000000034 method Methods 0.000 description 101
- 238000005401 electroluminescence Methods 0.000 description 90
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 74
- 238000006243 chemical reaction Methods 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 67
- 239000000543 intermediate Substances 0.000 description 62
- 239000000758 substrate Substances 0.000 description 56
- 229910052782 aluminium Inorganic materials 0.000 description 55
- 230000015572 biosynthetic process Effects 0.000 description 51
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 48
- 238000007740 vapor deposition Methods 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000012043 crude product Substances 0.000 description 38
- 125000001624 naphthyl group Chemical group 0.000 description 38
- 239000000047 product Substances 0.000 description 38
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 36
- 229910052799 carbon Inorganic materials 0.000 description 34
- 239000013078 crystal Substances 0.000 description 34
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 34
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 34
- 230000005525 hole transport Effects 0.000 description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
- 125000005647 linker group Chemical group 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- 239000003480 eluent Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- 239000000126 substance Substances 0.000 description 25
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
- 125000003342 alkenyl group Chemical group 0.000 description 24
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 24
- 238000000576 coating method Methods 0.000 description 23
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 23
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 229910052717 sulfur Inorganic materials 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 19
- 239000000178 monomer Substances 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000002994 raw material Substances 0.000 description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 18
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- 125000003107 substituted aryl group Chemical group 0.000 description 18
- 239000008096 xylene Substances 0.000 description 18
- 238000009835 boiling Methods 0.000 description 17
- 229910052796 boron Inorganic materials 0.000 description 17
- 125000005240 diheteroarylamino group Chemical group 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- 229910052744 lithium Inorganic materials 0.000 description 16
- 229910052698 phosphorus Inorganic materials 0.000 description 16
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 15
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- 125000005561 phenanthryl group Chemical group 0.000 description 14
- 239000004065 semiconductor Substances 0.000 description 14
- 229910052763 palladium Inorganic materials 0.000 description 13
- 238000001308 synthesis method Methods 0.000 description 13
- 125000005577 anthracene group Chemical group 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 238000004132 cross linking Methods 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
- 238000001035 drying Methods 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 229910052792 caesium Inorganic materials 0.000 description 9
- 229910052750 molybdenum Inorganic materials 0.000 description 9
- 239000011733 molybdenum 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
- 238000003756 stirring Methods 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 239000003341 Bronsted base Substances 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 150000004696 coordination complex Chemical class 0.000 description 8
- 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 8
- 239000001301 oxygen Substances 0.000 description 8
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 8
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 8
- 230000000379 polymerizing effect Effects 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000001632 sodium acetate Substances 0.000 description 8
- 235000017281 sodium acetate Nutrition 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000002841 Lewis acid Substances 0.000 description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 7
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 7
- 150000001491 aromatic compounds Chemical class 0.000 description 7
- 125000005110 aryl thio group Chemical group 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 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 7
- 125000002619 bicyclic group Chemical group 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 229910052733 gallium Inorganic materials 0.000 description 7
- 125000001041 indolyl group Chemical group 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 150000002739 metals Chemical class 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
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 230000001603 reducing effect Effects 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- 238000001771 vacuum deposition Methods 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 239000011254 layer-forming composition Substances 0.000 description 6
- 239000005267 main chain polymer Substances 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000002971 oxazolyl group Chemical group 0.000 description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 125000000168 pyrrolyl group Chemical group 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 125000005580 triphenylene group Chemical group 0.000 description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 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
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229920000144 PEDOT:PSS Polymers 0.000 description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 5
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 229910052785 arsenic Inorganic materials 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
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- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
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- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
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- IECKAVQTURBPON-UHFFFAOYSA-N trimethoxymethylbenzene Chemical compound COC(OC)(OC)C1=CC=CC=C1 IECKAVQTURBPON-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Photovoltaic Devices (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Thin Film Transistor (AREA)
Priority Applications (5)
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| PCT/JP2019/015410 WO2019198699A1 (ja) | 2018-04-12 | 2019-04-09 | シクロアルキル置換多環芳香族化合物 |
| CN201980024052.3A CN111936504A (zh) | 2018-04-12 | 2019-04-09 | 环烷基取代多环芳香族化合物 |
| KR1020247022691A KR20240113603A (ko) | 2018-04-12 | 2019-04-09 | 시클로알킬 치환 다환 방향족 화합물 |
| KR1020207032450A KR102684428B1 (ko) | 2018-04-12 | 2019-04-09 | 시클로알킬 치환 다환 방향족 화합물 |
| TW108112724A TW201945374A (zh) | 2018-04-12 | 2019-04-11 | 環烷基取代多環芳香族化合物、反應性化合物、高分子、懸掛型高分子、有機器件用材料、油墨組成物、有機電致發光元件、顯示裝置以及照明裝置 |
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| JP2023200450A Pending JP2024037742A (ja) | 2018-04-12 | 2023-11-28 | シクロアルキル置換多環芳香族化合物 |
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| CN (1) | CN111936504A (ko) |
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| JP6923692B2 (ja) * | 2019-03-29 | 2021-08-25 | 住友化学株式会社 | 発光素子の製造方法 |
| JP6923691B2 (ja) * | 2019-03-29 | 2021-08-25 | 住友化学株式会社 | 発光素子 |
| CN116194301A (zh) * | 2020-09-30 | 2023-05-30 | 夏普株式会社 | 喷墨涂布用油墨组合物、显示装置的制造方法及显示装置 |
| CN114106295B (zh) * | 2020-12-29 | 2023-06-16 | 广东聚华印刷显示技术有限公司 | 可交联型聚合物及其制备方法和应用 |
| CN112961175B (zh) * | 2021-02-05 | 2022-09-09 | 吉林奥来德光电材料股份有限公司 | 多环芳族有机物、其合成工艺、发光材料和有机电致发光器件 |
| CN116964063A (zh) * | 2021-03-15 | 2023-10-27 | 学校法人关西学院 | 多环芳香族化合物 |
| WO2023282676A1 (ko) | 2021-07-07 | 2023-01-12 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
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| US20040131881A1 (en) | 2002-12-31 | 2004-07-08 | Eastman Kodak Company | Complex fluorene-containing compounds for use in OLED 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 |
| DE102010009903A1 (de) | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
| JP5591996B2 (ja) | 2011-03-03 | 2014-09-17 | 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 |
| JP5724588B2 (ja) * | 2011-04-28 | 2015-05-27 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置および照明装置 |
| TWI636056B (zh) | 2014-02-18 | 2018-09-21 | 學校法人關西學院 | 多環芳香族化合物及其製造方法、有機元件用材料及其應用 |
| 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 |
| KR102633050B1 (ko) * | 2015-03-25 | 2024-02-02 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 및 발광층 형성용 조성물 |
| JP2016181637A (ja) * | 2015-03-25 | 2016-10-13 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| JP7038371B2 (ja) * | 2016-09-07 | 2022-03-18 | 学校法人関西学院 | 多環芳香族化合物 |
| CN109863155B (zh) * | 2016-09-07 | 2022-09-13 | 学校法人关西学院 | 多环芳香族化合物、有机元件用材料、有机电场发光元件、显示装置及照明装置 |
| TWI844513B (zh) * | 2017-05-16 | 2024-06-11 | 學校法人關西學院 | 多環芳香族化合物、有機元件用材料、發光層形成用組成物、有機電場發光元件、顯示裝置及照明裝置 |
| KR101876763B1 (ko) * | 2017-05-22 | 2018-07-11 | 머티어리얼사이언스 주식회사 | 유기화합물 및 이를 포함하는 유기전계발광소자 |
| JP2019119680A (ja) * | 2017-12-28 | 2019-07-22 | 出光興産株式会社 | 新規化合物及び有機エレクトロルミネッセンス素子 |
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