WO2019198699A1 - Composé aromatique polycyclique substitué par cycloalkyle - Google Patents
Composé aromatique polycyclique substitué par cycloalkyle Download PDFInfo
- Publication number
- WO2019198699A1 WO2019198699A1 PCT/JP2019/015410 JP2019015410W WO2019198699A1 WO 2019198699 A1 WO2019198699 A1 WO 2019198699A1 JP 2019015410 W JP2019015410 W JP 2019015410W WO 2019198699 A1 WO2019198699 A1 WO 2019198699A1
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- WO
- WIPO (PCT)
- Prior art keywords
- ring
- aryl
- substituted
- carbon atoms
- compound
- Prior art date
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- -1 polycyclic aromatic compound Chemical class 0.000 title claims abstract description 501
- 125000003118 aryl group Chemical group 0.000 claims abstract description 328
- 239000000463 material Substances 0.000 claims abstract description 179
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 161
- 229910052796 boron Inorganic materials 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims description 341
- 239000010410 layer Substances 0.000 claims description 327
- 125000004432 carbon atom Chemical group C* 0.000 claims description 266
- 125000000217 alkyl group Chemical group 0.000 claims description 230
- 125000001072 heteroaryl group Chemical group 0.000 claims description 176
- 229910052739 hydrogen Inorganic materials 0.000 claims description 140
- 239000001257 hydrogen Substances 0.000 claims description 140
- 125000001424 substituent group Chemical group 0.000 claims description 137
- 229920000642 polymer Polymers 0.000 claims description 128
- 239000000203 mixture Substances 0.000 claims description 100
- 238000005401 electroluminescence Methods 0.000 claims description 99
- 238000002347 injection Methods 0.000 claims description 87
- 239000007924 injection Substances 0.000 claims description 87
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 80
- 239000012044 organic layer Substances 0.000 claims description 79
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 229910052782 aluminium Inorganic materials 0.000 claims description 49
- 230000005525 hole transport Effects 0.000 claims description 40
- 125000004986 diarylamino group Chemical group 0.000 claims description 39
- 125000005647 linker group Chemical group 0.000 claims description 35
- 229910052736 halogen Chemical group 0.000 claims description 33
- 150000002367 halogens Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 239000003960 organic solvent Substances 0.000 claims description 29
- 125000004104 aryloxy group Chemical group 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- 239000010409 thin film Substances 0.000 claims description 25
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 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
- 239000000178 monomer Substances 0.000 claims description 22
- 229910052698 phosphorus Inorganic materials 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
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 21
- 239000002019 doping agent Substances 0.000 claims description 20
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229920006037 cross link polymer Polymers 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 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
- 150000001454 anthracenes Chemical class 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 230000005669 field effect Effects 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 229910052733 gallium Inorganic materials 0.000 claims description 9
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 9
- 150000002910 rare earth metals Chemical class 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 229910052785 arsenic Inorganic materials 0.000 claims description 8
- 239000005267 main chain polymer Substances 0.000 claims description 8
- 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 description 7
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 7
- 150000004820 halides Chemical class 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
- 150000003222 pyridines Chemical class 0.000 claims description 7
- 125000005346 substituted cycloalkyl group Chemical group 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
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000011243 crosslinked material Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 123
- 239000010408 film Substances 0.000 description 101
- 238000000034 method Methods 0.000 description 99
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 74
- 238000006243 chemical reaction Methods 0.000 description 74
- 230000032258 transport Effects 0.000 description 70
- 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 62
- 239000000543 intermediate Substances 0.000 description 60
- 239000000243 solution Substances 0.000 description 58
- 239000000758 substrate Substances 0.000 description 56
- 230000015572 biosynthetic process Effects 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 39
- 239000012043 crude product Substances 0.000 description 39
- 125000001624 naphthyl group Chemical group 0.000 description 37
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 36
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 36
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 34
- 229910052751 metal Inorganic materials 0.000 description 34
- 239000002184 metal Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 32
- 239000013078 crystal Substances 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 28
- 238000007740 vapor deposition Methods 0.000 description 28
- 239000003480 eluent Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000002994 raw material Substances 0.000 description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
- 125000003342 alkenyl group Chemical group 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 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
- 238000000576 coating method Methods 0.000 description 22
- 238000001816 cooling Methods 0.000 description 22
- 238000000151 deposition Methods 0.000 description 22
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 239000000126 substance Substances 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
- 230000008021 deposition Effects 0.000 description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 238000001308 synthesis method Methods 0.000 description 18
- 239000008096 xylene Substances 0.000 description 18
- 238000009835 boiling Methods 0.000 description 17
- 239000011248 coating agent Substances 0.000 description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 16
- 239000011254 layer-forming composition Substances 0.000 description 16
- 229910052744 lithium Inorganic materials 0.000 description 16
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 16
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 125000005561 phenanthryl group Chemical group 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 239000004065 semiconductor Substances 0.000 description 14
- 125000005577 anthracene group Chemical group 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 229910052763 palladium Inorganic materials 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
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 150000001716 carbazoles Chemical class 0.000 description 10
- 239000003054 catalyst Substances 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
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000001931 aliphatic group Chemical group 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000011159 matrix material Substances 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
- 239000001301 oxygen Substances 0.000 description 9
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 125000001544 thienyl group Chemical group 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 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
- 125000000732 arylene group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 8
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 8
- 238000002360 preparation method Methods 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
- 239000001632 sodium acetate Substances 0.000 description 8
- 235000017281 sodium acetate Nutrition 0.000 description 8
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 8
- 239000003341 Bronsted base Substances 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
- 125000005110 aryl thio group Chemical group 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000000460 chlorine Substances 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
- 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 7
- 125000001041 indolyl group Chemical group 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 238000007122 ortho-metalation reaction Methods 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
- 239000002244 precipitate Substances 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-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
- 239000007983 Tris buffer Substances 0.000 description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 239000002585 base 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
- 150000002739 metals Chemical class 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 6
- 125000000168 pyrrolyl 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
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Images
Classifications
-
- 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 System
- C07F5/02—Boron compounds
-
- 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
Abstract
La présente invention peut augmenter le nombre de choix de matériaux pour des dispositifs organiques tels que des matériaux pour des éléments EL organiques, par introduction d'un groupe cycloalkyle dans un nouveau composé aromatique polycyclique qui comprend une pluralité de cycles aromatiques reliés par, par exemple, un atome de bore et un atome d'oxygène. Le nouveau composé aromatique polycyclique substitué par cycloalkyle peut être utilisé en tant que matériau pour des éléments EL organiques pour fournir, par exemple, un élément électroluminescent organique ayant d'excellentes performances de luminescence et de durée de vie.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020207032450A KR20200143438A (ko) | 2018-04-12 | 2019-04-09 | 시클로알킬 치환 다환 방향족 화합물 |
| CN201980024052.3A CN111936504A (zh) | 2018-04-12 | 2019-04-09 | 环烷基取代多环芳香族化合物 |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018-076859 | 2018-04-12 | ||
| JP2018076859 | 2018-04-12 | ||
| JP2018235404 | 2018-12-17 | ||
| JP2018-235404 | 2018-12-17 | ||
| JP2019-072134 | 2019-04-04 | ||
| JP2019072134A JP6738063B2 (ja) | 2018-04-12 | 2019-04-04 | シクロアルキル置換多環芳香族化合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2019198699A1 true WO2019198699A1 (fr) | 2019-10-17 |
Family
ID=68164256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2019/015410 WO2019198699A1 (fr) | 2018-04-12 | 2019-04-09 | Composé aromatique polycyclique substitué par cycloalkyle |
Country Status (2)
| Country | Link |
|---|---|
| TW (1) | TW201945374A (fr) |
| WO (1) | WO2019198699A1 (fr) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020075760A1 (fr) * | 2018-10-09 | 2020-04-16 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique faisant appel à celui-ci |
| WO2020075758A1 (fr) * | 2018-10-09 | 2020-04-16 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique faisant appel à celui-ci |
| WO2020101001A1 (fr) * | 2018-11-15 | 2020-05-22 | 学校法人関西学院 | Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage |
| US20200176679A1 (en) * | 2017-05-22 | 2020-06-04 | Material Science Co., Ltd. | Organic compound and organic electroluminescent device comprising the same |
| CN112500298A (zh) * | 2019-12-27 | 2021-03-16 | 陕西莱特光电材料股份有限公司 | 芳胺化合物和有机电致发光器件 |
| WO2021107741A1 (fr) * | 2019-11-29 | 2021-06-03 | 주식회사 엘지화학 | Élément électroluminescent organique |
| WO2021230133A1 (fr) * | 2020-05-13 | 2021-11-18 | 学校法人関西学院 | Composé aromatique polycyclique |
| KR20220007702A (ko) * | 2019-12-31 | 2022-01-18 | 산시 라이트 옵토일렉스로닉스 머터리얼 코포레이션 리미티드 | 유기 화합물과 그 용도 및 유기 전계 발광 소자 |
| CN114181094A (zh) * | 2020-09-15 | 2022-03-15 | 材料科学有限公司 | 有机化合物及包含有机化合物的有机电致发光元件 |
| WO2022230643A1 (fr) * | 2021-04-28 | 2022-11-03 | 東レ株式会社 | Composé aromatique polycyclique, composition de conversion de couleur, feuille de conversion de couleur, unité de source lumineuse, afficheur, et dispositif d'éclairage |
| WO2023273416A1 (fr) * | 2021-07-01 | 2023-01-05 | 陕西莱特光电材料股份有限公司 | Composé organique, dispositif électroluminescent organique et appareil électronique |
| KR20230093426A (ko) | 2020-10-26 | 2023-06-27 | 미쯔비시 케미컬 주식회사 | 유기 전계 발광 소자, 유기 el 표시 장치 및 유기 el 조명 |
| KR20230123948A (ko) | 2020-12-23 | 2023-08-24 | 미쯔비시 케미컬 주식회사 | 유기 전계 발광 소자, 유기 el 표시 장치, 유기 el 조명 및 유기 전계 발광 소자의 제조 방법 |
| KR20230124575A (ko) | 2020-12-24 | 2023-08-25 | 미쯔비시 케미컬 주식회사 | 조성물, 유기 전계 발광 소자 및 그 제조 방법, 유기 전계 발광 표시 장치 및 그 제조 방법, 유기 전계 발광 조명 및 그 제조 방법 |
| US11744149B2 (en) | 2019-05-31 | 2023-08-29 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| KR20230156725A (ko) | 2021-03-15 | 2023-11-14 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 |
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| WO2015102118A1 (fr) * | 2014-02-18 | 2015-07-09 | 学校法人関西学院 | Composé aromatique polycyclique |
| WO2016152418A1 (fr) * | 2015-03-25 | 2016-09-29 | 学校法人関西学院 | Composé aromatique polycyclique et composition de formation de couche d'émission de lumière |
| WO2016152544A1 (fr) * | 2015-03-24 | 2016-09-29 | 学校法人関西学院 | Élément électroluminescent organique |
| JP2018043984A (ja) * | 2016-09-07 | 2018-03-22 | 学校法人関西学院 | 多環芳香族化合物 |
| WO2018216990A1 (fr) * | 2017-05-22 | 2018-11-29 | 머티어리얼사이언스 주식회사 | Composé organique et élément électroluminescent organique le comprenant |
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- 2019-04-09 WO PCT/JP2019/015410 patent/WO2019198699A1/fr active Application Filing
- 2019-04-11 TW TW108112724A patent/TW201945374A/zh unknown
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| WO2015102118A1 (fr) * | 2014-02-18 | 2015-07-09 | 学校法人関西学院 | Composé aromatique polycyclique |
| WO2016152544A1 (fr) * | 2015-03-24 | 2016-09-29 | 学校法人関西学院 | Élément électroluminescent organique |
| WO2016152418A1 (fr) * | 2015-03-25 | 2016-09-29 | 学校法人関西学院 | Composé aromatique polycyclique et composition de formation de couche d'émission de lumière |
| JP2018043984A (ja) * | 2016-09-07 | 2018-03-22 | 学校法人関西学院 | 多環芳香族化合物 |
| WO2018216990A1 (fr) * | 2017-05-22 | 2018-11-29 | 머티어리얼사이언스 주식회사 | Composé organique et élément électroluminescent organique le comprenant |
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| US20200176679A1 (en) * | 2017-05-22 | 2020-06-04 | Material Science Co., Ltd. | Organic compound and organic electroluminescent device comprising the same |
| WO2020075760A1 (fr) * | 2018-10-09 | 2020-04-16 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique faisant appel à celui-ci |
| WO2020075758A1 (fr) * | 2018-10-09 | 2020-04-16 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique faisant appel à celui-ci |
| WO2020101001A1 (fr) * | 2018-11-15 | 2020-05-22 | 学校法人関西学院 | Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage |
| US11744149B2 (en) | 2019-05-31 | 2023-08-29 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| WO2021107741A1 (fr) * | 2019-11-29 | 2021-06-03 | 주식회사 엘지화학 | Élément électroluminescent organique |
| CN112500298B (zh) * | 2019-12-27 | 2022-03-04 | 陕西莱特光电材料股份有限公司 | 芳胺化合物和有机电致发光器件 |
| CN112500298A (zh) * | 2019-12-27 | 2021-03-16 | 陕西莱特光电材料股份有限公司 | 芳胺化合物和有机电致发光器件 |
| KR20220007702A (ko) * | 2019-12-31 | 2022-01-18 | 산시 라이트 옵토일렉스로닉스 머터리얼 코포레이션 리미티드 | 유기 화합물과 그 용도 및 유기 전계 발광 소자 |
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| WO2021230133A1 (fr) * | 2020-05-13 | 2021-11-18 | 学校法人関西学院 | Composé aromatique polycyclique |
| CN114181094A (zh) * | 2020-09-15 | 2022-03-15 | 材料科学有限公司 | 有机化合物及包含有机化合物的有机电致发光元件 |
| KR20230093426A (ko) | 2020-10-26 | 2023-06-27 | 미쯔비시 케미컬 주식회사 | 유기 전계 발광 소자, 유기 el 표시 장치 및 유기 el 조명 |
| KR20230123948A (ko) | 2020-12-23 | 2023-08-24 | 미쯔비시 케미컬 주식회사 | 유기 전계 발광 소자, 유기 el 표시 장치, 유기 el 조명 및 유기 전계 발광 소자의 제조 방법 |
| KR20230124575A (ko) | 2020-12-24 | 2023-08-25 | 미쯔비시 케미컬 주식회사 | 조성물, 유기 전계 발광 소자 및 그 제조 방법, 유기 전계 발광 표시 장치 및 그 제조 방법, 유기 전계 발광 조명 및 그 제조 방법 |
| KR20230156725A (ko) | 2021-03-15 | 2023-11-14 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 |
| WO2022230643A1 (fr) * | 2021-04-28 | 2022-11-03 | 東レ株式会社 | Composé aromatique polycyclique, composition de conversion de couleur, feuille de conversion de couleur, unité de source lumineuse, afficheur, et dispositif d'éclairage |
| WO2023273416A1 (fr) * | 2021-07-01 | 2023-01-05 | 陕西莱特光电材料股份有限公司 | Composé organique, dispositif électroluminescent organique et appareil électronique |
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