JP6655553B2 - 電子デバイス用材料 - Google Patents
電子デバイス用材料 Download PDFInfo
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- JP6655553B2 JP6655553B2 JP2016562956A JP2016562956A JP6655553B2 JP 6655553 B2 JP6655553 B2 JP 6655553B2 JP 2016562956 A JP2016562956 A JP 2016562956A JP 2016562956 A JP2016562956 A JP 2016562956A JP 6655553 B2 JP6655553 B2 JP 6655553B2
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- 239000000463 material Substances 0.000 title description 30
- 150000001875 compounds Chemical class 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 239000010410 layer Substances 0.000 claims description 104
- -1 benzanthracene compound Chemical group 0.000 claims description 50
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical group C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 34
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 25
- 239000011159 matrix material Substances 0.000 claims description 23
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 22
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000412 dendrimer Substances 0.000 claims description 14
- 229920000736 dendritic polymer Polymers 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 11
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 72
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 22
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 16
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 16
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 16
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 14
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 14
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 9
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 7
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 7
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 7
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 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 5
- 230000008569 process Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000005620 boronic acid group Chemical group 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229960005544 indolocarbazole Drugs 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 238000007740 vapor 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
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 2
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-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
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-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
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
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Description
Ar1は、一つまたは複数のラジカルR2によって置換されていてもよい芳香環原子数6から40個の芳香環系、または、一つまたは複数のラジカルR2によって置換されていてもよい芳香環原子数5から40個のヘテロ芳香環系から選ばれ;
R0は、C(=O)R3、CN、Si(R3)3、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3、炭素数1から20の直鎖アルキルまたはアルコキシ基、炭素数3から20の分枝または環状アルキルまたはアルコキシ基、または、炭素数2から20のアルケニルまたはアルキニル基で、これらの基はそれぞれ一つまたは複数のラジカルR3によって置換されていてもよく、これらの基に含まれる一つまたは複数のCH2基は−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=NR3,−C(=O)O−、−C(=O)NR3−、NR3、P(=O)(R3)、−O−、−S−、SOまたはSO2で置換されていてもよく、R0はR1と結合していてもよく、さらに、環を形成していてもよく;
Lは、一つまたは複数のラジカルR2によって置換されていてもよい芳香環原子数6から40の芳香環系から選ばれるか、または、一つまたは複数のラジカルR2によって置換されていてもよい芳香環原子数5から40のヘテロ芳香環系から選ばれるn価の基であるか、あるいは、nが2のときLは化学結合であり;
上記のR1、R2は、同じでも、異なっていてもよく、それぞれ、H、D、F、C(=O)R3、CN、Si(R3)3、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3、それぞれ一つまたは複数のラジカルR3によって置換されていてもよく、かつ、含まれる一つまたは複数のCH2基が−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=NR3,−C(=O)O−、−C(=O)NR3−、NR3、P(=O)(R3)、−O−、−S−、SOまたはSO2によって置換されていてもよい炭素数1から20の直鎖アルキルまたはアルコキシ基、炭素数3から20の分枝または環状アルキルまたはアルコキシ基、あるいは、炭素数2から20のアルケニルまたはアルキニル基、一つまたは複数のラジカルR3によって置換されていてもよい芳香環原子数6から40の芳香環系、または、一つまたは複数のラジカルR3によって置換されていてもよい芳香環原子数5から40のヘテロ芳香環系であり、複数のR1またはR2は互いに結合していてもよく、さらに、環を形成していてもよく;
上記のR3は、同じでも、異なっていてもよく、それぞれ、H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4、炭素数1から20の直鎖アルキルまたはアルコキシ基、炭素数3から20の分枝または環状アルキルまたはアルコキシ基、または、炭素数2から20のアルケニルまたはアルキニル基で、これらの基はそれぞれ一つまたは複数のラジカルR4によって置換されていてもよく、これらの基に含まれる一つまたは複数のCH2基は−R4C=CR4−、−C≡C−、Si(R4)2、C=O、C=NR4,−C(=O)O−、−C(=O)NR4−、NR4、P(=O)(R4)、−O−、−S−、SO、SO2、一つまたは複数のラジカルR4によって置換されていてもよい芳香環原子数6から40の芳香環系、または、一つまたは複数のラジカルR4によって置換されていてもよい芳香環原子数5から40のヘテロ芳香環系で置換されていてもよく、複数のR3は互いに結合していてもよく、さらに、環を形成していてもよく;
上記のR4は、同じでも、異なっていてもよく、それぞれ、H、D、F、CN、または、一つまたは複数のH原子がD、FあるいはCNで置換されていてもよい炭素数1から20の脂肪族、芳香族あるいはヘテロ芳香族有機ラジカルであり、複数のR4は互いに結合していてもよく、さらに、環を形成していてもよく;
nは2、3、4、5または6であり;
式(I)または(II)の化合物は無置換として示している位置それぞれにラジカルR1を有していてもよいが;
ただし、以下の化合物は含まれない。)
Xは、それぞれ独立に、同じでも異なっていてもよく、N、CR2およびCからなる群から選ばれるが、Ar3基がXに結合している場合はXとしてはCのみが許され;
Ar2は、一つまたは複数のR2ラジカルで置換されていてもよい芳香環原子数6から30の芳香環系、および、一つまたは複数のR2ラジカルで置換されていてもよい芳香環原子数5から30のヘテロ芳香環系から選ばれ;
Ar3は、一つまたは複数のR3ラジカルで置換されていてもよい芳香環原子数6から24の芳香環系、および、一つまたは複数のR3ラジカルで置換されていてもよい芳香環原子数5から24のヘテロ芳香環系から選ばれ;
*の付いた結合はベンズアントラセン部分に基が結合する位置を示している。
R2ラジカルの位置は、それぞれで自由であり;
*の付いた結合はベンズアントラセン部分に基が結合する位置を示している。
Xは前記と同様であり、好ましくは、それぞれ独立に、同じでも異なっていてもよく、CR2およびCからなる群から選ばれるが、置換基がXに結合している場合はXとしてはCのみが許され;
R3ラジカルの位置は、それぞれで自由であり;
*の付いた結合はベンズアントラセン部分に基が結合する位置を示している。
Xは前記と同様であり、好ましくは、それぞれ独立に、同じでも異なっていてもよく、CR2およびCからなる群から選ばれるが、置換基がXに結合している場合はXとしてはCのみが許され;
R3ラジカルの位置は、それぞれで自由であり;
*の付いた結合はベンズアントラセン部分に基が結合する位置を示している。
Xは前記と同様であり、好ましくは、それぞれ独立に、同じでも異なっていてもよく、CR2およびCからなる群から選ばれるが、置換基がXに結合している場合はXとしてはCのみが許され;
R3ラジカルの位置は、それぞれで自由であり;
*の付いた結合はベンズアントラセン部分に基が結合する位置を示している。
Arは、任意の芳香環系もしくはヘテロ芳香環系であり、
Halは、ハロゲン原子もしくは他の反応性基であり、
Rは、任意の有機ラジカルである。
Arは、任意の芳香環系もしくはヘテロ芳香環系であり、
Halは、ハロゲン原子もしくは他の反応性基であり、
Rは、任意の有機ラジカルである。
Arは、任意の芳香環系もしくはヘテロ芳香環系であり、
Halは、ハロゲン原子もしくは他の反応性基であり、
Rは、任意の有機ラジカルである。
1)ベンズアントラセン誘導体と芳香環系またはヘテロ芳香環系とのカップリング反応によって、一つまたは複数の芳香環系またはヘテロ芳香環系によって置換されたベンズアントラセン化合物を得る工程、
2)得られたベンズアントラセン化合物をハロゲン化、好ましくは臭素化する工程、
3)ハロゲン化、好ましくは臭素化された位置に置換基を導入する工程
からなる合成法に関する。
I)ナフチル誘導体と無水フタル酸から置換ベンズアントラセン化合物を得る工程、
II)得られたベンズアントラセン化合物を芳香環系またはヘテロ芳香環系とカップリング反応させる工程、
からなる合成法にも関する。
(A)鈴木重合;
(B)山本重合;
(C)スティル重合;および
(D)ハートウィグ−バックワルド重合
である。
下記の合成スキームによって本発明による化合物を調製する。
WO2008/145239の実施例8に従って、4−(10−フェニルアントラセン−9−イル)ベンゾ[a]アントラセンII−iを調製する。同様にして、下記の化合物も調製する。
7−ブロモ−4−(10−フェニルアントラセン−9−イル)ベンゾ[a]アントラセン III−i
テトラヒドロフラン1Lを4−(10−フェニルアントラセン−9−イル)ベンゾ[a]アントラセンII−i(50g、104.0mmol)、n−ブロモスクシンイミド(24.02g、135mmol)および過酸化ベンゾイル(25%の水を含む)(12.7mL、20.8mmol)に加える。これを一晩、加熱還流したのち室温まで冷やしてから、800mLのクロロホルムと500mLの10%チオ硫酸ナトリウム溶液を加える。相分離したら、水相をクロロホルムで何度も抽出する。抽出液を有機相と合わせて、蒸留水で洗浄し、硫酸マグネシウムで乾燥させたら、酸化アルミニウムを通してろ過する。この有機相を蒸留し、残渣をクロロベンゼンによって沈殿させ、ヘプタンから再結晶して、化合物III−iを淡黄色の固体で得る(58.2g、理論値の87%)。
7−メチル−4−(10−フェニルアントラセン−9−イル)ベンゾ[a]アントラセン IV−i
5.47g(97%、88.6mmol)のメチルボロン酸、25g(44.3mmol)の7−ブロモ−4−(10−フェニルアントラセン−9−イル)ベンゾ[a]アントラセンIII−iおよび20.4g(88.6mmol)のK3PO4・H2Oを500mLのトルエンに懸濁させる。この懸濁液に1.09g(2.66mmol)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(S−Phos)と0.3g(1.33mmol)の酢酸パラジウムを加え、16時間加熱還流する。反応混合物を冷却した後、水で希釈し、有機相を分離して100mLの水で3回洗浄してから蒸発乾固する。粗生成物をトルエンでシリカゲルを通し、残った残渣をトルエン/ヘプタンから再結晶させる。収量は17.3g(理論値の79%)である。
B−1)気相からのデバイス製作例:OLEDの作成
本発明によるOLEDと従来技術によるOLEDを、WO04/058911による常法によって作成する。なお、ここで記載する種々の条件(層厚変化、材料など)にも、このWO04/058911を適用する。
−基板、
−ITO(50nm)、
−バッファー層(20nm)、
−正孔注入層(HTL1:95%、HIL:5%)(20nm)、
−正孔輸送層(HTL1)(20nm)、
−発光層(ホスト:95%、ドーパント:5%)(20nm)、
−電子輸送層(ETL:50%+EIL:50%)(30nm)、
−電子注入層(EIL)(3nm)、
−カソード(Al)(100nm)。
用いる材料は表1に示す通りである。
溶液からのOLEDの製造法は、例えば、WO2004/037887、WO2010/097155などの文献におおむね記載されている。下記の実施例においては、二つの製造法(気相からの成膜と溶液からの成膜)を組み合わせて、発光層を形成するまでは溶液から成膜を行い、その他の層(正孔ブロック層、電子輸送層)は真空蒸着によって形成した。なお、ここで記載する種々の条件(層厚変化、材料など)にも、上記した一般的な方法を適用し、下記のように組み合わせて用いる。
−基板、
−ITO(50nm)、
−PEDOT(20nm)、
−正孔輸送層(HTL2)(20nm)、
−発光層(ホスト:92%、ドーパント:8%)(60nm)、
−電子輸送層(ETL:50%+EIL:50%)(20nm)、
−カソード(Al)。
Claims (8)
- 下記の式(I−1−1)の化合物。
Ar1は、一つまたは複数のラジカルR2によって置換されていてもよい芳香環原子数14から18の縮合アリール基から選ばれ、ここで、Ar1は、式(I−1−1)で表されるベンズアントラセンの、下式で示される4または5位に結合し;
上記のR2は、同じでも、異なっていてもよく、それぞれ、H、D、F、C(=O)R3、CN、Si(R3)3、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3、それぞれ一つまたは複数のラジカルR3によって置換されていてもよく、かつ、含まれる一つまたは複数のCH2基が−R3C=CR3−、−C≡C−、Si(R3)2、C=O、C=NR3,−C(=O)O−、−C(=O)NR3−、NR3、P(=O)(R3)、−O−、−S−、SOまたはSO2によって置換されていてもよい炭素数1から20の直鎖アルキルまたはアルコキシ基、炭素数3から20の分枝または環状アルキルまたはアルコキシ基、あるいは、炭素数2から20のアルケニルまたはアルキニル基、一つまたは複数のラジカルR3によって置換されていてもよい芳香環原子数6から40の芳香環系、または、一つまたは複数のラジカルR3によって置換されていてもよい芳香環原子数5から40のヘテロ芳香環系であり、複数のR 2は互いに結合していてもよく;
上記のR3は、同じでも、異なっていてもよく、それぞれ、H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4、炭素数1から20の直鎖アルキルまたはアルコキシ基、炭素数3から20の分枝または環状アルキルまたはアルコキシ基、または、炭素数2から20のアルケニルまたはアルキニル基で、これらの基はそれぞれ一つまたは複数のラジカルR4によって置換されていてもよく、これらの基に含まれる一つまたは複数のCH2基は−R4C=CR4−、−C≡C−、Si(R4)2、C=O、C=NR4,−C(=O)O−、−C(=O)NR4−、NR4、P(=O)(R4)、−O−、−S−、SO、SO2、一つまたは複数のラジカルR4によって置換されていてもよい芳香環原子数6から40の芳香環系、または、一つまたは複数のラジカルR4によって置換されていてもよい芳香環原子数5から40のヘテロ芳香環系で置換されていてもよく;
上記のR4は、同じでも、異なっていてもよく、それぞれ、H、D、F、CN、または、一つまたは複数のH原子がD、FあるいはCNで置換されていてもよい炭素数1から20の脂肪族、芳香族あるいはヘテロ芳香族有機ラジカルである。) - Ar1が、それぞれ一つまたは複数のR2ラジカルで置換されていてもよい、アントラセン、ベンズアントラセン、フェナントレン、ベンズフェナントレン、ピレン、クリセン、フルオランテン、およびナフタセンからなる群より選ばれることを特徴とする、請求項1に記載の化合物。
- A)下記の工程1)から3)、すなわち、
1)ベンズアントラセン誘導体と芳香環系またはヘテロ芳香環系とのカップリング反応によって、一つもしくは複数の芳香環系またはヘテロ芳香環系によって置換されたベンズアントラセン化合物を調製する工程、
2)得られたベンズアントラセンをハロゲン化する工程、
3)ハロゲン化、好ましくは、臭素化した位置に置換基を導入する工程、
からなるか、あるいは
B)下記の工程I)からII)、すなわち、
I)ナフチル誘導体と無水フタル酸から置換ベンズアントラセン誘導体を調製する工程、II)得られた置換ベンズアントラセン誘導体を芳香環系またはヘテロ芳香環系とカップリング反応させる工程、
からなる、請求項1または2に記載の化合物の製造法。 - 請求項1または2に記載の化合物を含むオリゴマー、ポリマーまたはデンドリマーであって、前記オリゴマー、ポリマーまたはデンドリマーの結合が式(I−1−1)のR2またはR3によって置換されているどの位置にあってもよいオリゴマー、ポリマーまたはデンドリマー。
- 少なくとも一つの請求項1または2に記載の化合物あるいは少なくとも一つの請求項4に記載のオリゴマー、ポリマーまたはデンドリマー、および、少なくとも一つの溶媒からなる塗布剤。
- 有機集積回路(OIC)、有機電界効果トランジスタ(OFET)、有機薄層トランジスタ(OTFT)、有機発光トランジスタ(OLET)、有機太陽電池(OSC)、有機光学検波器、有機光受容器、有機電場消光デバイス(OFQD)、有機発光電気化学セル(OLEC)、有機レーザーダイオード(O−laser)および有機ELデバイス(OLED)からなる群より選ばれる電子デバイスであって、少なくとも一つの請求項1または2に記載の化合物、あるいは、少なくとも一つの請求項4に記載のオリゴマー、ポリマーまたはデンドリマーを含有することを特徴とする、電子デバイス。
- アノード、カソード、発光層、および、その他の任意の有機層からなる有機ELデバイスであって、少なくとも一つの化合物もしくは少なくとも一つのオリゴマー、ポリマーまたはデンドリマーがマトリックス材料として一つまたは複数の発光化合物と組み合わされて発光層内に含有されていることを特徴とする、請求項6に記載の電子デバイス。
- 請求項1または2に記載の化合物、あるいは、請求項4に記載のオリゴマー、ポリマーまたはデンドリマーの電子デバイスへの応用。
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- 2015-03-17 WO PCT/EP2015/000587 patent/WO2015158409A1/de active Application Filing
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EP3132476B1 (de) | 2023-08-23 |
EP3132476A1 (de) | 2017-02-22 |
CN106170476A (zh) | 2016-11-30 |
TW201604170A (zh) | 2016-02-01 |
CN113527032A (zh) | 2021-10-22 |
WO2015158409A1 (de) | 2015-10-22 |
US20170125686A1 (en) | 2017-05-04 |
US11063221B2 (en) | 2021-07-13 |
TWI671280B (zh) | 2019-09-11 |
JP2017514807A (ja) | 2017-06-08 |
KR102375992B1 (ko) | 2022-03-17 |
KR20160146826A (ko) | 2016-12-21 |
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