JP2016106094A - 有機エレクトロルミネセンスデバイス用材料 - Google Patents
有機エレクトロルミネセンスデバイス用材料 Download PDFInfo
- Publication number
- JP2016106094A JP2016106094A JP2015247681A JP2015247681A JP2016106094A JP 2016106094 A JP2016106094 A JP 2016106094A JP 2015247681 A JP2015247681 A JP 2015247681A JP 2015247681 A JP2015247681 A JP 2015247681A JP 2016106094 A JP2016106094 A JP 2016106094A
- Authority
- JP
- Japan
- Prior art keywords
- organic
- group
- radicals
- atoms
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 50
- 238000005401 electroluminescence Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 63
- -1 NR 13 Inorganic materials 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001454 anthracenes Chemical group 0.000 claims description 4
- 125000005620 boronic acid group Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 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
- 239000010703 silicon Substances 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000005518 electrochemistry Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 abstract description 8
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 150000003254 radicals Chemical class 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 0 *N1NOCCCCCC1 Chemical compound *N1NOCCCCCC1 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 11
- 230000006872 improvement Effects 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 150000002736 metal compounds Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000010533 azeotropic distillation Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 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 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KTNZKRQCQCEYRN-UHFFFAOYSA-N 2-(10-bromoanthracen-9-yl)-5-phenylpyrimidine Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C(N=C1)=NC=C1C1=CC=CC=C1 KTNZKRQCQCEYRN-UHFFFAOYSA-N 0.000 description 3
- VGNJKZMRXOUJHK-UHFFFAOYSA-N 2-anthracen-9-yl-5-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=CN=C(C=2C3=CC=CC=C3C=C3C=CC=CC3=2)N=C1 VGNJKZMRXOUJHK-UHFFFAOYSA-N 0.000 description 3
- DZRZHUDQXZFUEB-UHFFFAOYSA-N 5-anthracen-9-yl-2-pyridin-2-ylpyrimidine Chemical compound N1=CC=CC=C1C1=NC=C(C=2C3=CC=CC=C3C=C3C=CC=CC3=2)C=N1 DZRZHUDQXZFUEB-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 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 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- HWSFMWIXWXGLNN-UHFFFAOYSA-N 2-(10-benzo[a]anthracen-4-ylanthracen-9-yl)-5-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=CN=C(C=2C3=CC=CC=C3C(C=3C4=C(C5=CC6=CC=CC=C6C=C5C=C4)C=CC=3)=C3C=CC=CC3=2)N=C1 HWSFMWIXWXGLNN-UHFFFAOYSA-N 0.000 description 2
- JAXPLQOGKYSCMO-UHFFFAOYSA-N 4-anthracen-9-ylbenzo[a]anthracene Chemical compound C1=CC=C2C(C3=C4C=CC=5C(C4=CC=C3)=CC3=CC=CC=C3C=5)=C(C=CC=C3)C3=CC2=C1 JAXPLQOGKYSCMO-UHFFFAOYSA-N 0.000 description 2
- AMZJAMGOBVDLDC-UHFFFAOYSA-N 5-(10-benzo[a]anthracen-4-ylanthracen-9-yl)pyrimidine Chemical compound C=1C2=CC=CC=C2C=C(C2=CC=C3)C=1C=CC2=C3C(C1=CC=CC=C11)=C2C=CC=CC2=C1C1=CN=CN=C1 AMZJAMGOBVDLDC-UHFFFAOYSA-N 0.000 description 2
- JQZLTENYFIIBRN-UHFFFAOYSA-N 5-(10-bromoanthracen-9-yl)-2-pyridin-2-ylpyrimidine Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C(C=N1)=CN=C1C1=CC=CC=N1 JQZLTENYFIIBRN-UHFFFAOYSA-N 0.000 description 2
- FLIUZAGAOLWTAJ-UHFFFAOYSA-N 5-(10-phenanthren-3-ylanthracen-9-yl)-2-pyridin-2-ylpyrimidine Chemical compound N1=CC=CC=C1C1=NC=C(C=2C3=CC=CC=C3C(C=3C=C4C5=CC=CC=C5C=CC4=CC=3)=C3C=CC=CC3=2)C=N1 FLIUZAGAOLWTAJ-UHFFFAOYSA-N 0.000 description 2
- UZDQWRMXMWSAQP-UHFFFAOYSA-N 5-bromo-2-pyridin-2-ylpyrimidine Chemical compound N1=CC(Br)=CN=C1C1=CC=CC=N1 UZDQWRMXMWSAQP-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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- VHHDLIWHHXBLBK-UHFFFAOYSA-N anthracen-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=C(C=CC=C3)C3=CC2=C1 VHHDLIWHHXBLBK-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- DGGWKWSROZRHIX-UHFFFAOYSA-N benzo[a]anthracen-2-ylboronic acid Chemical compound C1=CC=C2C=C(C=3C(=CC=C(C=3)B(O)O)C=C3)C3=CC2=C1 DGGWKWSROZRHIX-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical class [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- UPYVSYVLGOADDG-UHFFFAOYSA-N phenanthren-3-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C=CC2=C1 UPYVSYVLGOADDG-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HZFPPBMKGYINDF-UHFFFAOYSA-N pyrimidin-5-ylboronic acid Chemical compound OB(O)C1=CN=CN=C1 HZFPPBMKGYINDF-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- OXKGTVPXFGKAQG-UHFFFAOYSA-N 10-(1-bromoanthracen-9-yl)benzo[a]anthracene Chemical compound C1=CC=C2C3=CC4=CC(C=5C6=CC=CC=C6C=C6C=CC=C(C=56)Br)=CC=C4C=C3C=CC2=C1 OXKGTVPXFGKAQG-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- IGHOZKDBCCFNNC-UHFFFAOYSA-N 1h-imidazole;quinoxaline Chemical compound C1=CNC=N1.N1=CC=NC2=CC=CC=C21 IGHOZKDBCCFNNC-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- PFRPMHBYYJIARU-UHFFFAOYSA-N 2,3-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CC=C2N=NC3=CC=CC4=CC=C1C2=C43 PFRPMHBYYJIARU-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- INJBTFKWNNQGGN-UHFFFAOYSA-N 2-bromo-5-phenylpyrimidine Chemical compound C1=NC(Br)=NC=C1C1=CC=CC=C1 INJBTFKWNNQGGN-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- PGFIHORVILKHIA-UHFFFAOYSA-N 2-bromopyrimidine Chemical compound BrC1=NC=CC=N1 PGFIHORVILKHIA-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- BNGNNFQSUWVWCW-UHFFFAOYSA-N 3-bromophenanthrene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3C=CC2=C1 BNGNNFQSUWVWCW-UHFFFAOYSA-N 0.000 description 1
- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 description 1
- BFDFTUBEVVONBF-UHFFFAOYSA-N 4-(10-bromoanthracen-9-yl)benzo[a]anthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=CC2=C1C=CC1=CC3=CC=CC=C3C=C21 BFDFTUBEVVONBF-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- IUKNPBPXZUWMNO-UHFFFAOYSA-N 5,12-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4,6,8(16),9,11,13-octaene Chemical compound N1=CC=C2C=CC3=NC=CC4=CC=C1C2=C43 IUKNPBPXZUWMNO-UHFFFAOYSA-N 0.000 description 1
- NHWJSCHQRMCCAD-UHFFFAOYSA-N 5,14-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CN=C2C=CC3=NC=CC4=CC=C1C2=C43 NHWJSCHQRMCCAD-UHFFFAOYSA-N 0.000 description 1
- PODJSIAAYWCBDV-UHFFFAOYSA-N 5,6-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaene Chemical compound C1=NN=C2C=CC3=CC=CC4=CC=C1C2=C43 PODJSIAAYWCBDV-UHFFFAOYSA-N 0.000 description 1
- ZEZKXPQIDURFKA-UHFFFAOYSA-N 5-bromo-2-iodopyrimidine Chemical compound BrC1=CN=C(I)N=C1 ZEZKXPQIDURFKA-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 1
- LSHHYTYLJPONMG-UHFFFAOYSA-N 9H-carbazole 2H-isoindole Chemical compound C1=CC=CC=2C3=CC=CC=C3NC12.C=1NC=C2C=CC=CC12 LSHHYTYLJPONMG-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- 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 1
- KHNYNFUTFKJLDD-UHFFFAOYSA-N Benzo[j]fluoranthene Chemical compound C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- ZPIPUFJBRZFYKJ-UHFFFAOYSA-N C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 Chemical compound C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 ZPIPUFJBRZFYKJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101150037194 EIL2 gene Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910013184 LiBO Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100232347 Mus musculus Il11ra1 gene Proteins 0.000 description 1
- UKRQQTUHXSUNPV-UHFFFAOYSA-N N1NNN=CC1 Chemical compound N1NNN=CC1 UKRQQTUHXSUNPV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- VGRJHHLDEYYRNF-UHFFFAOYSA-N ac1lasce Chemical compound C1C2=CC=CC=C2C(C=2C3=CC=CC=C3CC=22)=C1C1=C2CC2=CC=CC=C21 VGRJHHLDEYYRNF-UHFFFAOYSA-N 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 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 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 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 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- 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 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000011532 electronic conductor Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 201000001366 familial temporal lobe epilepsy 2 Diseases 0.000 description 1
- 201000001379 familial temporal lobe epilepsy 3 Diseases 0.000 description 1
- 201000001380 familial temporal lobe epilepsy 4 Diseases 0.000 description 1
- 201000001382 familial temporal lobe epilepsy 5 Diseases 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 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 1
- VDVPPMSJJGBHHI-UHFFFAOYSA-N phenazine;10h-phenoxazine Chemical compound C1=CC=CC2=NC3=CC=CC=C3N=C21.C1=CC=C2NC3=CC=CC=C3OC2=C1 VDVPPMSJJGBHHI-UHFFFAOYSA-N 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- FXJZOUPFQNMFOR-UHFFFAOYSA-N pyrimidin-2-ylboronic acid Chemical class OB(O)C1=NC=CC=N1 FXJZOUPFQNMFOR-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000000927 vapour-phase epitaxy Methods 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Arは、10〜30個の芳香族環原子を有する縮合したアリールまたはヘテロアリール基(これは、1以上のラジカルR12により置換されていてもよい)であり;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、CHO、N(R13)2、N(Ar1)2、B(Ar1)2、Si(R13)2、Si(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR13=CR13Ar1、CN、NO2、Si(R13)3、B(OR13)2、B(R13)2、B(N(R13)2)2、OSO2R13、1〜40個のC原子を有する直鎖のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基、または3〜40個のC原子を有する分枝状もしくは環状のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR13により置換されていてもよい)(ここで、1以上の隣接していないCH2基は、R13C=CR13、C≡C、Si(R13)2、Ge(R13)2、Sn(R13)2、C=O、C=S、C=Se、C=NR13、P(=O)(R13)、SO、SO2、NR13、O、SまたはCONR13によって置きかえられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2によって置きかえられていてもよい)、または5〜60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(これは、それぞれの場合に、1以上のラジカルR13により置換されていてもよい)、または5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これは、1以上のラジカルR13により置換されていてもよい)、またはこれらの系の組合せであり;ここで、2個以上の隣接する置換基R1〜R12は、互いに、単環または多環式の脂肪族または芳香族環系を形成していてもよく;
Ar1は、出現するごとに同一であるかまたは異なり、5〜30個の芳香族環原子を有する芳香族またはヘテロ芳香族環系(これは、1以上のラジカルR13により置換されていてもよい)であり;ここで、同一の窒素、リン、ケイ素またはホウ素原子に結合している2個のラジカルAr1は、単結合により、またはB(R13)、C(R13)2、Si(R13)2、C=O、C=NR13、C=C(R13)2、O、S、S=O、SO2、N(R13)、P(R13)およびP(=O)R13から選択される架橋により、互いに連結されていてもよく;
R13は、出現するごとに同一であるかまたは異なり、H、Dまたは1〜20個のC原子を有する脂肪族、芳香族および/もしくはヘテロ芳香族炭化水素ラジカル(ここで更に、H原子は、DまたはFによって置きかえられていてもよい)であり;ここで、2個以上の隣接する置換基13は、互いに、単環または多環式の脂肪族または芳香族環系を形成していてもよい。
この層は、電子注入層としての役割を果たす。この目的に適するものは、例えば、アルカリ金属またはアルカリ土類金属フッ化物であるが、対応する酸化物、炭酸塩または他の塩、およびまた他の金属(例えば、LiF、Li2O、LiBO2、K2SiO3、CsF、Cs2CO3、BaF2、MgO、NaF、Al2O3等)、およびまた例えば、リチウムキノリネートなどの有機アルカリ金属化合物でもある。この層の層厚は、好ましくは0.5〜5nmである。
1.本発明による有機エレクトロルミネセンスデバイスは、非常に高い効率を有する。
効率の改善は、電子輸送層から発光層への電子注入の改善に起因する可能性がある。
収量:20.4g、理論の55%、HPLCによる純度約98%。
500mg(0.414mmol)のPd(PPh3)4をこの懸濁液に加え、混合物を還流下で12時間加熱する。冷却後、沈殿固体を吸引によりろ過し、水およびエタノールで洗浄し、乾燥する。残留物を熱トルエンで抽出し、トルエンから再結晶し、最後に高真空中で昇華させる。純度は99.9%である。収量:10g、理論の50%。
冷却後、ジクロロメタンを反応混合物に加え、水相を分離し、トルエンを用いる共沸蒸留により有機相を濃縮し、その後、蒸発乾固する。残留物をトルエンから再結晶し、最後に高真空中で昇華させる。純度は99.9%である。収量:16g、理論の60%。
OLEDの製造
本発明によるOLEDおよび従来技術によるOLEDを、ここで述べる状況(層厚変動、使用する材料)に適合させた国際公開第2004/058911号に従って一般的な方法により製造する。
カソードは、100nmの厚さを有するアルミニウム層により形成されている。OLEDの正確な構造を表1に示す。OLEDの製造に使用する材料を表3に示す。
本発明による例6〜20によるOLEDは、本発明による式(1)の化合物の使用という利点を示す。
Claims (15)
- 式(1)の化合物
Pymは、以下の式(2)または(3)の基
Arは、10〜30個の芳香族環原子を有する縮合したアリールまたはヘテロアリール基(これは、1以上のラジカルR12により置換されていてもよい)であり;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12は、出現するごとに同一であるかまたは異なり、H、D、F、Cl、Br、I、CHO、N(R13)2、N(Ar1)2、B(Ar1)2、Si(R13)2、Si(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR13=CR13Ar1、CN、NO2、Si(R13)3、B(OR13)2、B(R13)2、B(N(R13)2)2、OSO2R13、1〜40個のC原子を有する直鎖のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基、または3〜40個のC原子を有する分枝状もしくは環状のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR13により置換されていてもよい)(ここで、1以上の隣接していないCH2基は、R13C=CR13、C≡C、Si(R13)2、Ge(R13)2、Sn(R13)2、C=O、C=S、C=Se、C=NR13、P(=O)(R13)、SO、SO2、NR13、O、SまたはCONR13によって置きかえられていてもよく、1以上のH原子は、D、F、Cl、Br、I、CNまたはNO2によって置きかえられていてもよい)、または5〜60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(これは、それぞれの場合に、1以上のラジカルR13により置換されていてもよい)、または5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これは、1以上のラジカルR13により置換されていてもよい)、またはこれらの系の組合せであり;ここで、2個以上の隣接する置換基R1〜R12は、互いに、単環または多環式の脂肪族または芳香族環系を形成していてもよく;
Ar1は、出現するごとに同一であるかまたは異なり、5〜30個の芳香族環原子を有する芳香族またはヘテロ芳香族環系(これは、1以上のラジカルR13により置換されていてもよい)であり;ここで、同一の窒素、リン、ケイ素またはホウ素原子に結合する2個のラジカルAr1は、単結合により、またはB(R13)、C(R13)2、Si(R13)2、C=O、C=NR13、C=C(R13)2、O、S、S=O、SO2、N(R13)、P(R13)およびP(=O)R13から選択される架橋により、互いに連結されていてもよく;
R13は、出現するごとに同一であるかまたは異なり、H、Dまたは1〜20個のC原子を有する脂肪族、芳香族および/もしくはヘテロ芳香族炭化水素ラジカル(ここで更に、H原子は、DまたはFによって置きかえられていてもよい)であり;ここで、2個以上の隣接する置換基13は、互いに、単環または多環式の脂肪族または芳香族環系を形成していてもよい。 - 基Arが、10〜16個のC原子を有する縮合したアリール基(これは、1以上のラジカルR12により置換されていてもよい)、好ましくはナフタレン、アントラセン、フェナントレン、ベンズアントラセン、クリセン、ベンゾフェナントレンまたはピレン(これらのそれぞれは、1以上のラジカルR12により置換されていてもよい)を表すことを特徴とする請求項1〜3の何れか一項に記載の化合物。
- ラジカルR1〜R12は、出現するごとに同一であるかまたは異なり、H、D、F、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CN、Si(R13)3、1〜10個のC原子を有する直鎖のアルキル基、または3〜10個のC原子を有する分枝状もしくは環状のアルキル基(これらのそれぞれは、1以上のラジカルR13により置換されていてもよい)(ここで、1以上の隣接していないCH2基は、R13C=CR13によって置きかえられていてもよく、1以上のH原子は、DまたはFによって置きかえられていてもよい)、または5〜30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(これは、それぞれの場合に、1以上のラジカルR13により置換されていてもよい)からなる群より選択され;ここで、2個以上の隣接する置換基R1〜R12は、互いに、単環または多環式の脂肪族または芳香族環系を形成していてもよいことを特徴とする請求項1〜6の何れか一項に記載の化合物。
- ラジカルR9、R10およびR11は、出現するごとに同一であるかまたは異なり、Hまたは5〜24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(これは、それぞれの場合に、1以上のラジカルR13により置換されていてもよい)を表すことを特徴とする請求項1〜7の何れか一項に記載の化合物。
- 反応性離脱基によって置換されているアントラセン誘導体を、ボロン酸基もしくはボロン酸エステル基によって置換されているピリミジン誘導体と反応させること、またはボロン酸基もしくはボロン酸エステル基によって置換されているアントラセン誘導体を、反応性離脱基によって置換されているピリミジン誘導体と反応させることを含む請求項1〜8の何れか一項に記載の化合物の合成方法。
- 電子デバイス、とりわけ有機エレクトロルミネセンスデバイスにおける、請求項1〜8の何れか一項に記載の化合物の使用。
- 有機エレクトロルミネセンスデバイス、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、有機色素増感太陽電池、有機光学検出器、有機感光体、有機電場消光デバイス、発光電気化学セル、有機レーザーダイオードおよび有機プラズモン発光デバイスからなる群より好ましくは選択される、請求項1〜8の何れか一項に記載の少なくとも1種の化合物を含む電子デバイス。
- 請求項1〜8の何れか一項に記載の化合物が、電子輸送層において、および/または電子注入層において、および/または正孔遮断層において、および/または発光層における蛍光エミッターのためのマトリクス材料として、使用されることを特徴とする請求項11に記載の有機エレクトロルミネセンスデバイス。
- 請求項1〜8の何れか一項に記載の化合物が、電子輸送層または電子注入層において、更なる電子輸送材料または電子注入材料と組み合わせて、とりわけ有機アルカリ金属化合物と組み合わせて、使用されることを特徴とする請求項12に記載の有機エレクトロルミネセンスデバイス。
- 請求項1〜8の何れか一項に記載の少なくとも1種の化合物と、少なくとも1種の有機アルカリ金属化合物とを含む混合物。
- 請求項1〜8の何れか一項に記載の少なくとも1種の化合物と、少なくとも1種の溶媒とを含む配合物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102010013806.1A DE102010013806B4 (de) | 2010-04-03 | 2010-04-03 | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010013806.1 | 2010-04-03 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013503022A Division JP6230908B2 (ja) | 2010-04-03 | 2011-03-09 | 有機エレクトロルミネセンスデバイス用材料 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016106094A true JP2016106094A (ja) | 2016-06-16 |
JP6141397B2 JP6141397B2 (ja) | 2017-06-07 |
Family
ID=43927620
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013503022A Active JP6230908B2 (ja) | 2010-04-03 | 2011-03-09 | 有機エレクトロルミネセンスデバイス用材料 |
JP2015247681A Active JP6141397B2 (ja) | 2010-04-03 | 2015-12-18 | 有機エレクトロルミネセンスデバイス用材料 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013503022A Active JP6230908B2 (ja) | 2010-04-03 | 2011-03-09 | 有機エレクトロルミネセンスデバイス用材料 |
Country Status (4)
Country | Link |
---|---|
US (1) | US9796684B2 (ja) |
JP (2) | JP6230908B2 (ja) |
DE (1) | DE102010013806B4 (ja) |
WO (1) | WO2011120626A1 (ja) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8171567B1 (en) | 2002-09-04 | 2012-05-01 | Tracer Detection Technology Corp. | Authentication method and system |
US7995196B1 (en) | 2008-04-23 | 2011-08-09 | Tracer Detection Technology Corp. | Authentication method and system |
DE102010013806B4 (de) | 2010-04-03 | 2021-06-10 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102011117364A1 (de) * | 2011-10-29 | 2013-05-02 | Merck Patent Gmbh | Hautaufheller in der Phototherapie |
CN103130724A (zh) * | 2011-11-23 | 2013-06-05 | 海洋王照明科技股份有限公司 | 含萘基蒽的有机半导体材料、其制备方法和应用 |
CN103288730A (zh) * | 2012-02-27 | 2013-09-11 | 海洋王照明科技股份有限公司 | 含喹啉有机半导体材料、其制备方法及有机电致发光器件 |
GB201403096D0 (en) * | 2014-02-21 | 2014-04-09 | Oxford Nanopore Tech Ltd | Sample preparation method |
US10693078B2 (en) * | 2014-07-25 | 2020-06-23 | Hodogaya Chemical Co., Ltd. | Organic electroluminescent device |
CN107078226B (zh) * | 2014-11-18 | 2020-02-28 | 保土谷化学工业株式会社 | 有机电致发光器件 |
JP6731355B2 (ja) * | 2015-01-20 | 2020-07-29 | 保土谷化学工業株式会社 | ピリミジン誘導体および有機エレクトロルミネッセンス素子 |
KR102471110B1 (ko) * | 2015-08-11 | 2022-11-28 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
EP3341448B1 (en) * | 2015-08-28 | 2020-02-12 | Merck Patent GmbH | Compounds for electronic devices |
KR102209936B1 (ko) * | 2018-03-22 | 2021-02-01 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN113631550A (zh) * | 2019-03-22 | 2021-11-09 | 株式会社半导体能源研究所 | 有机化合物、发光器件、发光装置、电子设备及照明装置 |
KR20210008979A (ko) * | 2019-07-15 | 2021-01-26 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함하는 유기 발광 소자 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004002297A (ja) * | 2002-04-11 | 2004-01-08 | Idemitsu Kosan Co Ltd | 新規含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2006176448A (ja) * | 2004-12-22 | 2006-07-06 | Idemitsu Kosan Co Ltd | アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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 |
WO2010114256A2 (en) * | 2009-03-31 | 2010-10-07 | Dow Advanced Display Materials,Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
WO2010114266A2 (en) * | 2009-03-31 | 2010-10-07 | Dow Advanced Display Materials,Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
JP2013523788A (ja) * | 2010-04-03 | 2013-06-17 | 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センスデバイス用材料 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
EP0676461B1 (de) | 1994-04-07 | 2002-08-14 | Covion Organic Semiconductors GmbH | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE19652261A1 (de) | 1996-12-16 | 1998-06-18 | Hoechst Ag | Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen |
GB9826406D0 (en) | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Quinolates |
CN100489056C (zh) | 2002-12-23 | 2009-05-20 | 默克专利有限公司 | 有机电致发光元件 |
EP1582516B1 (en) | 2003-01-10 | 2013-07-17 | Idemitsu Kosan Co., Ltd. | Nitrogenous heterocyclic derivative and organic electroluminescent element employing the same |
DE10333232A1 (de) | 2003-07-21 | 2007-10-11 | Merck Patent Gmbh | Organisches Elektrolumineszenzelement |
JP4496949B2 (ja) * | 2004-12-13 | 2010-07-07 | 株式会社豊田自動織機 | 有機el素子 |
US7767317B2 (en) | 2005-10-26 | 2010-08-03 | Global Oled Technology Llc | Organic element for low voltage electroluminescent devices |
US20070092759A1 (en) | 2005-10-26 | 2007-04-26 | Begley William J | Organic element for low voltage electroluminescent devices |
JP5532705B2 (ja) * | 2008-07-01 | 2014-06-25 | 東レ株式会社 | 発光素子 |
EP2335288A4 (en) | 2008-09-15 | 2013-07-17 | Osi Optoelectronics Inc | THIN ACTIVE LAYER FISHING BODY PHOTODIODE HAVING NOW LOW PROFILE LAYER AND PROCESS FOR PRODUCING THE SAME |
KR101177172B1 (ko) | 2009-09-22 | 2012-08-24 | 주식회사 두산 | 신규한 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자 |
-
2010
- 2010-04-03 DE DE102010013806.1A patent/DE102010013806B4/de active Active
-
2011
- 2011-03-09 WO PCT/EP2011/001143 patent/WO2011120626A1/de active Application Filing
- 2011-03-09 JP JP2013503022A patent/JP6230908B2/ja active Active
- 2011-03-09 US US13/638,975 patent/US9796684B2/en active Active
-
2015
- 2015-12-18 JP JP2015247681A patent/JP6141397B2/ja active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004002297A (ja) * | 2002-04-11 | 2004-01-08 | Idemitsu Kosan Co Ltd | 新規含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2006176448A (ja) * | 2004-12-22 | 2006-07-06 | Idemitsu Kosan Co Ltd | アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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 |
WO2010114256A2 (en) * | 2009-03-31 | 2010-10-07 | Dow Advanced Display Materials,Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
WO2010114266A2 (en) * | 2009-03-31 | 2010-10-07 | Dow Advanced Display Materials,Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
JP2013523788A (ja) * | 2010-04-03 | 2013-06-17 | 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センスデバイス用材料 |
Also Published As
Publication number | Publication date |
---|---|
JP6230908B2 (ja) | 2017-11-15 |
WO2011120626A1 (de) | 2011-10-06 |
DE102010013806A1 (de) | 2011-10-06 |
JP6141397B2 (ja) | 2017-06-07 |
DE102010013806B4 (de) | 2021-06-10 |
JP2013523788A (ja) | 2013-06-17 |
US9796684B2 (en) | 2017-10-24 |
US20130032764A1 (en) | 2013-02-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7167200B2 (ja) | 有機エレクトロルミネッセント素子のための材料 | |
JP6141397B2 (ja) | 有機エレクトロルミネセンスデバイス用材料 | |
JP6695936B2 (ja) | 化合物および有機エレクトロルミッセンス素子 | |
KR102602818B1 (ko) | 6,9,15,18-테트라히드로-s-인다세노[1,2-b:5,6-b']디플루오렌 유도체 및 전자 소자에서의 이의 용도 | |
JP6250754B2 (ja) | 有機エレクトロルミネッセンス素子のためのトリフェニレン系材料 | |
KR101756611B1 (ko) | 전자 소자용 재료 | |
KR102540425B1 (ko) | 유기 전계발광 소자 (oled) 용 재료로서 비스벤조푸란-융합된 2,8-디아미노인데노[1,2-b]플루오렌 유도체 및 관련 화합물 | |
KR102268222B1 (ko) | 플루오렌 및 이를 함유하는 전자 소자 | |
JP5726734B2 (ja) | 電子デバイス用化合物 | |
KR102143742B1 (ko) | 전자 소자용 접속부 | |
JP5944319B2 (ja) | 有機エレクトロルミネセンス素子のための材料 | |
JP5694194B2 (ja) | 有機エレクトロルミネセンスデバイスのための材料 | |
KR20100129101A (ko) | 유기 전계발광 장치용 물질 | |
KR20160074630A (ko) | 전자 소자용 물질 | |
JP2018035168A (ja) | 有機エレクトロルミネッセンス素子のための化合物 | |
KR20200090817A (ko) | 전자 디바이스용 재료 | |
KR102585423B1 (ko) | 전자 디바이스용 화합물 | |
JP2023123425A (ja) | 電子デバイス用材料 | |
KR20230020434A (ko) | 전자 디바이스용 재료 | |
KR20180077216A (ko) | 유기 전계발광 소자용 재료 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160825 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160913 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20161208 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170310 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170404 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170502 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6141397 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |