JP2018528936A - フルオレン構造を有する化合物 - Google Patents
フルオレン構造を有する化合物 Download PDFInfo
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- JP2018528936A JP2018528936A JP2018504277A JP2018504277A JP2018528936A JP 2018528936 A JP2018528936 A JP 2018528936A JP 2018504277 A JP2018504277 A JP 2018504277A JP 2018504277 A JP2018504277 A JP 2018504277A JP 2018528936 A JP2018528936 A JP 2018528936A
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- aromatic
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 187
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title abstract description 23
- 239000011159 matrix material Substances 0.000 claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims description 128
- 150000003254 radicals Chemical class 0.000 claims description 80
- 239000000463 material Substances 0.000 claims description 69
- -1 fluorene radical Chemical group 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 48
- 229920000642 polymer Polymers 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 239000000412 dendrimer Substances 0.000 claims description 25
- 229920000736 dendritic polymer Polymers 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000005259 triarylamine group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000004020 conductor Substances 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 125000001072 heteroaryl group Chemical group 0.000 description 25
- 238000000034 method Methods 0.000 description 25
- 239000002019 doping agent Substances 0.000 description 21
- 125000004122 cyclic group Chemical group 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical group C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 9
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 230000006872 improvement Effects 0.000 description 9
- 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 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000021615 conjugation Effects 0.000 description 5
- 230000004907 flux Effects 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000001194 electroluminescence spectrum Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 3
- 229960005544 indolocarbazole Drugs 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical class C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- ULJWETNCQFMZLI-UHFFFAOYSA-N 4-[3-(7'-bromo-9,9'-spirobi[fluorene]-4'-yl)phenyl]-1-phenylbenzimidazole Chemical compound BrC1=CC=C2C=3C(=CC=CC=3C3(C4=CC=CC=C4C=4C=CC=CC3=4)C2=C1)C=1C=C(C=CC=1)C1=CC=CC=2N(C=NC=21)C1=CC=CC=C1 ULJWETNCQFMZLI-UHFFFAOYSA-N 0.000 description 2
- NGJHKXORTXSGHR-UHFFFAOYSA-N 4-[9-(9H-fluoren-9-yl)-9H-fluoren-1-yl]-2-phenylquinazoline Chemical compound C1(=CC=CC=2C3=CC=CC=C3C(C1=2)C1C2=CC=CC=C2C=2C=CC=CC1=2)C1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1 NGJHKXORTXSGHR-UHFFFAOYSA-N 0.000 description 2
- OBHKONRNYCDRKM-UHFFFAOYSA-N 4-chloro-2-phenylquinazoline Chemical compound N=1C2=CC=CC=C2C(Cl)=NC=1C1=CC=CC=C1 OBHKONRNYCDRKM-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- HHVLTCJSRNNRPJ-UHFFFAOYSA-N CC1(C2=CC=CC(=C2C=2C=CC(=CC1=2)B(O)O)C1=NC2=CC=CC=C2C(=N1)C1=CC=CC=C1)C Chemical compound CC1(C2=CC=CC(=C2C=2C=CC(=CC1=2)B(O)O)C1=NC2=CC=CC=C2C(=N1)C1=CC=CC=C1)C HHVLTCJSRNNRPJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 101100398600 Cryphonectria parasitica LAC-1 gene Proteins 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
式(I)、(II)、(Ia)、(IIa)、(Ib)、(IIb)で表されるフルオレン構造中の9位で炭素原子に結合している2つラジカルR1が、それぞれ、5〜30個の芳香族環原子を有し、かつ、1つ以上のラジカルR1で置換されていてもよい、芳香族もしくはヘテロ芳香族環系であり、ここで、式(I)、(II)、(Ia)、(IIa)、(Ib)、(IIb)で表されるフルオレン構造中の9位で炭素原子に結合している2つ環系が互いに連結されていないことを特徴とする化合物;または、
式(I)、(II)、(Ia)、(IIa)、(Ib)、(IIb)で表されるフルオレン構造中の9位で炭素原子に結合している2つラジカルR1が、それぞれ独立して、H、D、1〜40個の炭素原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個の炭素原子を有する、分枝状もしくは環状の、アルキル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1つ以上のラジカルR2で置換されていてもよく、ここで1つ以上の非隣接の基CH2は、−R2C=CR2−、−C≡C−、Si(R2)2、C=O、C=S、C=NR2、−(C=O)O−、−C(=O)NR2−、NR2、(P=O)(R2)、−O−、−S−、SOもしくはSO2で置換されていてもよく、かつ、ここで、1個以上の水素原子はD、F、Cl、Br、I、CNもしくはNO2で置き換えられていてもよいことを特徴とする化合物;または、
式(I)、(II)、(Ia)、(IIa)、(Ib)、(IIb)で表されるフルオレン構造中の9位で炭素原子に結合している2つ基R1の1つが、それぞれ、5〜30個の芳香族環原子を有し、かつ、1つ以上のラジカルR1で置換されていてもよい、芳香族もしくはヘテロ芳香族環系であり、そして式(I)、(II)、(Ia)、(IIa)、(Ib)、(IIb)で表されるフルオレン構造中の9位で炭素原子に結合している2つラジカルR1の1つが、H、D、1〜40個の炭素原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個の炭素原子を有する、分枝状もしくは環状の、アルキル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1つ以上のラジカルR2で置換されていてもよく、ここで1つ以上の非隣接のCH2基は、−R2C=CR2−、−C≡C−、Si(R2)2、C=O、C=S、C=NR2、−(C=O)O−、−C(=O)NR2−、NR2、(P=O)(R2)、−O−、−S−、SOもしくはSO2で置換されていてもよく、かつ、ここで、1個以上の水素原子はD、F、Cl、Br、I、CNもしくはNO2で置き換えられていてもよいことを特徴とする化合物。
Yは、O、SもしくはNR2、好ましくはOもしくはSであり;
iは、出現毎に独立して、0、1もしくは2であり;
jは、出現毎に独立して、0、1、2もしくは3であり;
hは、出現毎に独立して、0、1、2、3もしくは4であり;
gは、出現毎に独立して、0、1、2、3、4もしくは5であり;
R2は、上記された定義、特に式(I)および/または式(II)に対する定義を有することができ、そして、破線の結合は、接続位置を示す。
LUMO(eV)=((LEh*27.212)−2.0041)/1.385
以下の合成は、特に明記しない限り、保護ガス雰囲気下、乾燥溶媒中で行われる。溶媒および試薬は、例えば、シグマ−アルドリッチ社(Sigma−Aldrich)またはエービーシーアール社(ABCR)から購入できる。文献から知られている化合物に対しては、それぞれの場合において、対応するCAS番号が示されている。
a)4−ブロモ−9−メチル−9−フェニル−9H−フルオレン
ジエチルエーテル1500ml中、106g(270ミリモル)の1−ブロモ−9−スピロビフルオレンの、−78℃に冷却した溶液に、110ml(276ミリモル)のn−ブチルリチウム(へキサン中、2.5M)を滴下する。反応混合物を−78℃で30分間攪拌する。混合物を室温になるまで放置し、再び−78℃に冷却した後、ジエチルエーテル50ml中に40ml(351ミリモル)のホウ酸トリメチルの混合物を迅速に添加する。−10℃に温めた後、135mlの2N−塩酸で加水分解させる。有機相を分離し、水で洗浄し、硫酸ナトリウムで乾燥し、濃縮乾固させる。残留物を300mlのn−ヘプタンに取り、無色の固体を吸引濾過し、n−ヘプタンで洗浄し、減圧下で乾燥させる。収量:94.5g(255ミリモル)、理論値の99%。純度:HPLCにより、99%。
56.8g(110ミリモル)のスピロ−9,9’−ビフルオレン−1−ボロン酸、26g(110.0ミリモル)の4−クロロ−2−フェニルキナゾリンおよび44.6g(210.0ミリモル)のリン酸三カリウムを、500mlのトルエン、500mlのジオキサンおよび500mlの水に懸濁させる。この懸濁液に、913mg(3.0ミリモル)のトリ−o−トリルホスフィンを、次いで112mg(0.5ミリモル)の酢酸パラジウム(II)を添加し、その後、反応混合物を還流下で16時間加熱する。冷却後、有機相を分離し、シリカゲルを通して濾過し、200mlの水で3回洗浄し、次いで濃縮乾固する。残渣を、トルエンから、そしてジクロロメタン/イソプロパノールから再結晶させ、最終的に、高真空下(p=5×10−5ミリバール、T=350℃)で昇華させる。収率は、理論値の80%に相当する64g(43.5ミリモル)である。
同様な方法により、下記の化合物が得られる:
バリアントAに類似の手順;テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに、0.01当量の酢酸パラジウム(II)および0.01当量のジシクロヘキシル(2’,6’−ジメトキシビフェニル−2−イル)ホスフィン(SPhos)を使用する。
1lの三つ口フラスコに、200mlのトルエン、200mlの1,4−ジオキサンおよび100ml脱イオン水の中の、21.0g(29.5ミリモル、1.00当量)の1−フェニル−2−[3−[7’−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−9,9’−スピロビ[フルオレン]−2’−イル]フェニル]ベンゾイミダゾールおよび7.2g(29.5ミリモル、1.00当量)の4−クロロ−2−フェニルキナゾリンを装入し、さらに混合物を20分間脱気する。1.02g(0.885ミリモル、0.0300当量)のテトラキス(トリフェニルホスフィン)パラジウム(0)を添加し、混合物を還流下で2日間加熱し、さらに反応の終了後、冷却する。沈殿した固体を吸引濾過し、水と少量のトルエンで洗浄し、そしてその後、トルエン/ヘプタンから、>99.9%のHPLC純度が達成されるまで繰り返し再結晶させる。昇華後、11.5g(14.0ミリモル、46%)の無色固体を得る。
バリアントAに類似の手順;テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに、0.01当量の酢酸パラジウム(II)および0.04当量のトリ(o−トリル)ホスフィン(SPhos)を使用する。
バリアントAに類似の手順;テトラキス(トリフェニルホスフィン)パラジウム(0)の代わりに、0.01当量の酢酸パラジウム(II)および0.01当量のジシクロヘキシル(2’,6’−ジメトキシビフェニル−2−イル)ホスフィン(SPhos)を使用する。
以下の例C1〜I14(表1および2を参照)に、種々のOLEDのデータを示す。
本発明に係る材料は、燐光発光性のOLED中で正孔ブロック層(HBL)として使用されると、効率に関して従来技術に優る著しい改善をもたらす。本発明の化合物24e、52eおよび58eの使用は、従来技術PA1、PA2およびPA3と比較して約10%の外部量子効率の向上を観察することができる。本発明に係る材料の電子輸送層(ETL)における使用においても、従来技術に優る外部量子効率の改善を達成することができる(例C4と例I4との比較)。
Claims (18)
- 式(I)および/または式(II)で表される構造を含んでなる化合物。
Xは、出現毎に同一であるかまたは異なり、NまたはCR1、好ましくは、CR1であり、但し、1つの環中の2つ以下の基XがNであり;
Qは、電子輸送性基であり;
L1は、結合、C(=O)、または5〜24個の芳香族環原子を有し、かつ1つ以上のラジカルR1によって置換されてもよい、芳香族環系であり;
R1は、出現毎に同一であるかまたは異なり、H、D、1〜40個の炭素原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個の炭素原子を有する、分枝状もしくは環状の、アルキル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1つ以上のラジカルR2で置換されていてもよく、ここで1つ以上の非隣接のCH2基は、−R2C=CR2−、−C≡C−、Si(R2)2、C=O、C=S、C=NR2、−(C=O)O−、−C(=O)NR2−、NR2、(P=O)(R2)、−O−、−S−、SOもしくはSO2で置換されていてもよく、かつ、ここで、1つ以上の水素原子はD、F、Cl、Br、I、CNもしくはNO2で置き換えられていてもよく、または5〜40個の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系であり、これらの各々は1つ以上のラジカルR2で置換されていてもよく、または5〜40個の芳香族環原子を有し、かつ1つ以上のラジカルR2で置換されていてもよい、アリールオキシもしくはヘテロアリールオキシ基、またはこれらの系の組み合わせであり;同時に、2つ以上の隣接する置換基R1はまた、互いに、単環式もしくは多環式の、脂肪族もしくは芳香族環系を形成していてもよく;
R2は、出現毎に同一であるかまたは異なり、H、D、1〜40個の炭素原子を有する、直鎖の、アルキル、アルコキシもしくはチオアルコキシ基、または3〜40個の炭素原子を有する、分枝状もしくは環状の、アルキル、アルコキシもしくはチオアルコキシ基であり、これらの各々は1つ以上のラジカルR3で置換されていてもよく、ここで1つ以上の非隣接のCH2基は、−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=S、C=NR3、−(C=O)O−、−C(=O)NR3−、NR3、(P=O)(R3)、−O−、−S−、SOもしくはSO2で置換されていてもよく、かつ、ここで、1つ以上の水素原子はD、F、Cl、Br、I、CNもしくはNO2で置き換えられていてもよく、または5〜40個の芳香族環原子を有する、芳香族もしくはヘテロ芳香族環系であり、これらの各々は1つ以上のラジカルR3で置換されていてもよく、または5〜40個の芳香族環原子を有し、かつ1つ以上のラジカルR3で置換されていてもよい、アリールオキシもしくはヘテロアリールオキシ基、またはこれらの系の組み合わせであり;同時に、2つ以上の隣接する置換基R2はまた、互いに、単環式もしくは多環式の、脂肪族もしくは芳香族環系を形成していてもよく;
R3は、出現毎に同一であるかまたは異なり、H、D、F、または1〜20個の炭素原子を有し、1つ以上の水素原子がDもしくはFにより置き換えられていてもよい脂肪族炭化水素基、または5〜30個の炭素原子を有し、1つ以上の水素原子がDもしくはFにより置き換えられていてもよい、芳香族および/またはヘテロ芳香族環系あり;同時に、2つ以上の隣接する置換基R3はまた、互いに、単環式もしくは多環式の、脂肪族もしくは芳香族環系を形成していてもよい。 - 式(I)、(Ia)、(II)、(IIa)、(III)、(IIIa)、(IV)および(IVa)において、2つ以下の基XがNであり、好ましくは1つ以下の基XがNであり、そして好ましくは、全てのXがCR1であり、ここでXが表わすCR1基の、好ましくは最大で4つ、より好ましくは最大で3つ、特に好ましくは最大で2つが基CHではないことを特徴とする、請求項1〜3のいずれか一項に記載の化合物。
- 基Qが、1つ以上のラジカルR1によって置換されていてもよい、少なくとも2つの縮合環を有するヘテロ芳香族環系であり、ここで、少なくとも2つの縮合環の環原子は、少なくとも1つの窒素原子を含んでなることを特徴とする、請求項1〜5のいずれか一項に記載の化合物。
- 基Qが、9〜14個の、好ましくは10個の環原子を有し、かつ、1つ以上のラジカルR1によって置換されていてもよいヘテロ芳香族環系であることを特徴とする、請求項1〜6のいずれか一項に記載の化合物。
- 基Qが、式(Q−1)、(Q−2)および/または(Q−3)で表される構造から選択されることを特徴とする、請求項1〜7のいずれか一項に記載の化合物。
- 前記化合物が、カルバゾールおよび/またはトリアリールアミン基を含まないことを特徴とする、請求項1〜10のいずれか一項に記載の化合物。
- 前記化合物が、正孔輸送性基を含まないことを特徴とする、請求項1〜11のいずれか一項に記載の化合物。
- 請求項1〜12のいずれか一項に記載の化合物を1つ以上含む、ポリマー、オリゴマーまたはデンドリマーであって、化合物中に、オリゴマー、ポリマーまたはデンドリマーへの1つ以上の結合が存在することを特徴とする、ポリマー、オリゴマーまたはデンドリマー。
- 請求項1〜12のいずれか一項に記載の化合物および/または請求項13項に記載の、オリゴマー、ポリマーもしくはデンドリマー、並びに蛍光エミッター、燐光エミッター、ホスト材料、マトリックス材料、電子輸送材料、電子注入材料、正孔伝導材料、正孔注入材料、電子ブロック材料および正孔ブロック材料からなる群から選択される少なくとも1つの更なる化合物を含んでなる組成物。
- 少なくとも1つの、請求項1〜12のいずれか一項に記載の化合物、請求項13項に記載の、オリゴマー、ポリマーもしくはデンドリマー、および/または少なくとも1つの、請求項14に記載の組成物、および少なくとも1つの溶剤を含んでなる配合物。
- カップリング反応で、少なくとも1つの電子輸送性基を含む化合物を、少なくとも1つのフルオレンラジカルを含む化合物と反応させることを特徴とする、請求項1〜12のいずれか一項に記載の化合物、または請求項13項に記載の、オリゴマー、ポリマーもしくはデンドリマーの製造方法。
- 請求項1〜12のいずれか一項に記載の化合物の、請求項13項に記載の、オリゴマー、ポリマーもしくはデンドリマーの、または請求項14に記載の組成物の、電子素子における、正孔ブロック材料、電子注入材料および/または電子輸送材料としての使用。
- 少なくとも1つの、請求項1〜12のいずれか一項に記載の化合物、請求項13項に記載の、オリゴマー、ポリマーもしくはデンドリマー、または請求項14に記載の組成物を含んでなり、好ましくは、有機エレクトロルミネッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機太陽電池、有機光検出器、有機感光体、有機電場消光素子、発光電気化学セル、および有機レーザーダイオードからなる群から選択される電子素子。
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TWI603960B (zh) * | 2016-09-01 | 2017-11-01 | 有機電激發光化合物及有機電激發光元件 | |
KR20180057109A (ko) * | 2016-11-21 | 2018-05-30 | 주식회사 두산 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
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US11608333B2 (en) * | 2018-03-20 | 2023-03-21 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
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Citations (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009249378A (ja) * | 2008-04-02 | 2009-10-29 | Gracel Display Inc | 新規な有機電界発光化合物及びこれを用いる有機電界発光素子 |
KR20120116272A (ko) * | 2011-04-12 | 2012-10-22 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
JP2014501699A (ja) * | 2010-10-13 | 2014-01-23 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料のための新規化合物、およびこれを使用する有機電界発光素子 |
KR20140020208A (ko) * | 2012-08-07 | 2014-02-18 | 주식회사 동진쎄미켐 | 아크리딘 유도체를 포함하는 유기발광 화합물 및 이를 포함하는 유기발광소자 |
KR20140030786A (ko) * | 2012-09-03 | 2014-03-12 | 희성소재 (주) | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
JP2014513083A (ja) * | 2011-04-12 | 2014-05-29 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料のための新規化合物およびこれらを使用した有機エレクトロルミネセント素子 |
WO2014097711A1 (ja) * | 2012-12-21 | 2014-06-26 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および電子機器 |
JP2014518900A (ja) * | 2011-06-09 | 2014-08-07 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料用の新規な化合物および同化合物を使用した有機電界発光素子 |
JP2014522400A (ja) * | 2011-05-30 | 2014-09-04 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機エレクトロニクス材料用の新規化合物およびそれを使用した有機エレクトロルミネッセンス素子 |
US20140284580A1 (en) * | 2013-03-22 | 2014-09-25 | E-Ray Optoelectronics Techonology Co., Ltd. | Electron transporting compounds and organic electroluminescent devices using the same |
JP2014531747A (ja) * | 2011-09-01 | 2014-11-27 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 新規有機エレクトロルミネッセンス化合物およびこれを使用した有機エレクトロルミネッセンス素子 |
KR20150044668A (ko) * | 2013-10-17 | 2015-04-27 | (주)더블유에스 | 안트라센 유도체 및 이를 포함한 유기 전계발광 소자 |
JP2015513530A (ja) * | 2012-02-14 | 2015-05-14 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のためのスピロビフルオレン化合物 |
WO2015090504A2 (de) * | 2013-12-19 | 2015-06-25 | Merck Patent Gmbh | Heterocyclische spiroverbindungen |
KR20160004513A (ko) * | 2014-07-03 | 2016-01-13 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20160027940A (ko) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | 유기 발광 소자 |
WO2016068633A2 (ko) * | 2014-10-29 | 2016-05-06 | 희성소재(주) | 함질소 다환 화합물 및 이를 이용한 유기발광소자 |
WO2017111420A1 (ko) * | 2015-12-23 | 2017-06-29 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005009087A1 (ja) * | 2003-07-02 | 2005-01-27 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子及びそれを用いた表示装置 |
DE102008041487A1 (de) * | 2008-08-22 | 2010-02-25 | BSH Bosch und Siemens Hausgeräte GmbH | Haushaltsgerät für den Einbau in einen Möbelrahmen |
KR20150044658A (ko) | 2013-10-17 | 2015-04-27 | 혜성음료 주식회사 | 빨대와 물품을 보관하는 덮개가 구비된 젤리용기 |
EP3082542B1 (en) | 2013-12-19 | 2018-11-28 | Aktiebolaget Electrolux | Sensing climb of obstacle of a robotic cleaning device |
-
2016
- 2016-07-26 TW TW105123602A patent/TWI734694B/zh not_active IP Right Cessation
- 2016-07-28 CN CN201680044334.6A patent/CN107849016B/zh active Active
- 2016-07-28 EP EP16745623.5A patent/EP3328850B1/de active Active
- 2016-07-28 KR KR1020187005628A patent/KR20180030914A/ko not_active Application Discontinuation
- 2016-07-28 US US15/747,398 patent/US11201296B2/en active Active
- 2016-07-28 JP JP2018504277A patent/JP6884751B2/ja active Active
- 2016-07-28 WO PCT/EP2016/001308 patent/WO2017016667A1/de active Application Filing
Patent Citations (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009249378A (ja) * | 2008-04-02 | 2009-10-29 | Gracel Display Inc | 新規な有機電界発光化合物及びこれを用いる有機電界発光素子 |
JP2014501699A (ja) * | 2010-10-13 | 2014-01-23 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料のための新規化合物、およびこれを使用する有機電界発光素子 |
KR20120116272A (ko) * | 2011-04-12 | 2012-10-22 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
JP2014513083A (ja) * | 2011-04-12 | 2014-05-29 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料のための新規化合物およびこれらを使用した有機エレクトロルミネセント素子 |
JP2014522400A (ja) * | 2011-05-30 | 2014-09-04 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機エレクトロニクス材料用の新規化合物およびそれを使用した有機エレクトロルミネッセンス素子 |
JP2014518900A (ja) * | 2011-06-09 | 2014-08-07 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電子材料用の新規な化合物および同化合物を使用した有機電界発光素子 |
JP2014531747A (ja) * | 2011-09-01 | 2014-11-27 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 新規有機エレクトロルミネッセンス化合物およびこれを使用した有機エレクトロルミネッセンス素子 |
JP2015513530A (ja) * | 2012-02-14 | 2015-05-14 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のためのスピロビフルオレン化合物 |
KR20140020208A (ko) * | 2012-08-07 | 2014-02-18 | 주식회사 동진쎄미켐 | 아크리딘 유도체를 포함하는 유기발광 화합물 및 이를 포함하는 유기발광소자 |
KR20140030786A (ko) * | 2012-09-03 | 2014-03-12 | 희성소재 (주) | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
WO2014097711A1 (ja) * | 2012-12-21 | 2014-06-26 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および電子機器 |
US20140284580A1 (en) * | 2013-03-22 | 2014-09-25 | E-Ray Optoelectronics Techonology Co., Ltd. | Electron transporting compounds and organic electroluminescent devices using the same |
KR20150044668A (ko) * | 2013-10-17 | 2015-04-27 | (주)더블유에스 | 안트라센 유도체 및 이를 포함한 유기 전계발광 소자 |
WO2015090504A2 (de) * | 2013-12-19 | 2015-06-25 | Merck Patent Gmbh | Heterocyclische spiroverbindungen |
KR20160004513A (ko) * | 2014-07-03 | 2016-01-13 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20160027940A (ko) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | 유기 발광 소자 |
WO2016068633A2 (ko) * | 2014-10-29 | 2016-05-06 | 희성소재(주) | 함질소 다환 화합물 및 이를 이용한 유기발광소자 |
WO2017111420A1 (ko) * | 2015-12-23 | 2017-06-29 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
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TWI734694B (zh) | 2021-08-01 |
EP3328850A1 (de) | 2018-06-06 |
KR20180030914A (ko) | 2018-03-26 |
TW201718519A (zh) | 2017-06-01 |
WO2017016667A1 (de) | 2017-02-02 |
US11201296B2 (en) | 2021-12-14 |
CN107849016A (zh) | 2018-03-27 |
CN107849016B (zh) | 2021-10-22 |
EP3328850B1 (de) | 2020-11-11 |
JP6884751B2 (ja) | 2021-06-09 |
US20180226587A1 (en) | 2018-08-09 |
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