JP5575754B2 - 電子デバイスのための化合物 - Google Patents
電子デバイスのための化合物 Download PDFInfo
- Publication number
- JP5575754B2 JP5575754B2 JP2011509866A JP2011509866A JP5575754B2 JP 5575754 B2 JP5575754 B2 JP 5575754B2 JP 2011509866 A JP2011509866 A JP 2011509866A JP 2011509866 A JP2011509866 A JP 2011509866A JP 5575754 B2 JP5575754 B2 JP 5575754B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- aromatic
- groups
- carbon atoms
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims description 102
- -1 aromatic radicals Chemical class 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 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
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 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 claims description 3
- 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 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 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 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000012039 electrophile Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005259 triarylamine group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 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 claims description 2
- 125000005266 diarylamine group Chemical group 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000006263 metalation reaction Methods 0.000 claims description 2
- FGGAOQTXQHKQOW-UHFFFAOYSA-N n,n-diphenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 FGGAOQTXQHKQOW-UHFFFAOYSA-N 0.000 claims description 2
- VWYDYNGPYMOCMD-UHFFFAOYSA-N n,n-diphenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 VWYDYNGPYMOCMD-UHFFFAOYSA-N 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 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 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 61
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 230000005525 hole transport Effects 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 238000000151 deposition Methods 0.000 description 14
- 230000008021 deposition Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 101150107979 MS4A3 gene Proteins 0.000 description 4
- 102100032517 Membrane-spanning 4-domains subfamily A member 3 Human genes 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 238000009835 boiling Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000004007 reversed phase HPLC Methods 0.000 description 4
- 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 4
- SAVIMLRIKAZZCZ-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-2-methylbenzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1C SAVIMLRIKAZZCZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 229910005965 SO 2 Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000001976 improved effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- MBDOURHGFJKGKI-UHFFFAOYSA-N (4-borono-2,3-dimethylphenyl)boronic acid Chemical compound CC1=C(C)C(B(O)O)=CC=C1B(O)O MBDOURHGFJKGKI-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- OVDRBOQAUCTJMN-UHFFFAOYSA-N 1,2-dimethylindeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=C(C)C(C)=CC=C5C4=CC=C3C2=C1 OVDRBOQAUCTJMN-UHFFFAOYSA-N 0.000 description 2
- IVJJDBCZDJFMNZ-UHFFFAOYSA-N 1,4-dibromo-2,3-dimethylbenzene Chemical compound CC1=C(C)C(Br)=CC=C1Br IVJJDBCZDJFMNZ-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- ARZIVALJTPLLHF-VAWYXSNFSA-N 1-methyl-2-[(e)-2-(2-methylphenyl)ethenyl]benzene Chemical compound CC1=CC=CC=C1\C=C\C1=CC=CC=C1C ARZIVALJTPLLHF-VAWYXSNFSA-N 0.000 description 2
- SKDSEEONZGTDMQ-UHFFFAOYSA-N 4,6,6,10,12,12-hexamethyl-2-n,2-n,8-n,8-n-tetraphenylindeno[1,2-b]fluorene-2,8-diamine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC(C(C2=C3)(C)C)=C1C2=CC(C1(C)C)=C3C(C(=C2)C)=C1C=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 SKDSEEONZGTDMQ-UHFFFAOYSA-N 0.000 description 2
- PPLOZHSBWFBGJZ-UHFFFAOYSA-N 4,7-dimethylindeno[2,1-a]fluorene Chemical compound C1=CC=C(C)C2=C1C=C1C3=CC(C=CC=C4C)=C4C3=CC=C12 PPLOZHSBWFBGJZ-UHFFFAOYSA-N 0.000 description 2
- AJZGKLGLYFGFGS-UHFFFAOYSA-N 5,6,11,11,12,12-hexamethyl-2-n,2-n,9-n,9-n-tetraphenylindeno[2,1-a]fluorene-2,9-diamine Chemical compound CC=1C(C)=C2C3=CC=C(N(C=4C=CC=CC=4)C=4C=CC=CC=4)C=C3C(C)(C)C2=C(C(C2=C3)(C)C)C=1C2=CC=C3N(C=1C=CC=CC=1)C1=CC=CC=C1 AJZGKLGLYFGFGS-UHFFFAOYSA-N 0.000 description 2
- DGVJLRROUAICJR-UHFFFAOYSA-N 5,6,11,11,12,12-hexamethylindeno[2,1-a]fluorene Chemical compound C1=CC=C2C(C)(C)C3=C4C(C)(C)C5=CC=CC=C5C4=C(C)C(C)=C3C2=C1 DGVJLRROUAICJR-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SNOSCMXECSATAH-UHFFFAOYSA-N [2-(hydroxymethyl)-3,6-bis(2-methylphenyl)phenyl]methanol Chemical compound CC1=CC=CC=C1C1=CC=C(C=2C(=CC=CC=2)C)C(CO)=C1CO SNOSCMXECSATAH-UHFFFAOYSA-N 0.000 description 2
- VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- BODYVHJTUHHINQ-UHFFFAOYSA-N (4-boronophenyl)boronic acid Chemical class OB(O)C1=CC=C(B(O)O)C=C1 BODYVHJTUHHINQ-UHFFFAOYSA-N 0.000 description 1
- 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
- QFSHYSQSCJXOSU-UHFFFAOYSA-N 1,2-dibromoindeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=C(Br)C(Br)=CC=C5C4=CC=C3C2=C1 QFSHYSQSCJXOSU-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
- 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
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- JBYLHICABMOUQN-UHFFFAOYSA-N 1-fluoroanthracene Chemical compound C1=CC=C2C=C3C(F)=CC=CC3=CC2=C1 JBYLHICABMOUQN-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
- 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 1
- IHMXLLPBNYRXHE-UHFFFAOYSA-N 2,8-dibromo-4,6,6,10,12,12-hexamethylindeno[1,2-b]fluorene Chemical compound CC1=CC(Br)=CC(C(C2=C3)(C)C)=C1C2=CC(C1(C)C)=C3C2=C1C=C(Br)C=C2C IHMXLLPBNYRXHE-UHFFFAOYSA-N 0.000 description 1
- YGLHOZKQYSQAEP-UHFFFAOYSA-N 2,9-dibromo-5,6,11,11,12,12-hexamethylindeno[2,1-a]fluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=C4C(C)(C)C5=CC(Br)=CC=C5C4=C(C)C(C)=C3C2=C1 YGLHOZKQYSQAEP-UHFFFAOYSA-N 0.000 description 1
- IWYLRXWJGKHSDI-UHFFFAOYSA-N 2-[2-(carboxymethyl)-3,6-bis(2-methylphenyl)phenyl]acetic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C=2C(=CC=CC=2)C)C(CC(O)=O)=C1CC(O)=O IWYLRXWJGKHSDI-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 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
- XRXMNWGCKISMOH-UHFFFAOYSA-M 2-bromobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-M 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- LGLDSEPDYUTBNZ-UHFFFAOYSA-N 3-phenylbuta-1,3-dien-2-ylbenzene Chemical class C=1C=CC=CC=1C(=C)C(=C)C1=CC=CC=C1 LGLDSEPDYUTBNZ-UHFFFAOYSA-N 0.000 description 1
- WRJNKKJDFWEOHY-UHFFFAOYSA-N 4,6,6,10,12,12-hexamethylindeno[1,2-b]fluorene Chemical compound CC1=CC=CC(C(C2=C3)(C)C)=C1C2=CC(C1(C)C)=C3C2=C1C=CC=C2C WRJNKKJDFWEOHY-UHFFFAOYSA-N 0.000 description 1
- CYGLNILEPKWXIB-UHFFFAOYSA-N 4,7,11,11,12,12-hexamethyl-2-n,2-n,9-n,9-n-tetraphenylindeno[2,1-a]fluorene-2,9-diamine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC(C(C2=C3C4(C)C)(C)C)=C1C2=CC=C3C(C(=C1)C)=C4C=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 CYGLNILEPKWXIB-UHFFFAOYSA-N 0.000 description 1
- XMDDWXXFIKMQHK-UHFFFAOYSA-N 4,7,11,11,12,12-hexamethylindeno[2,1-a]fluorene Chemical compound CC1=CC=CC(C(C2=C3C4(C)C)(C)C)=C1C2=CC=C3C1=C4C=CC=C1C XMDDWXXFIKMQHK-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
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
- 239000005964 Acibenzolar-S-methyl Substances 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YKZBDEWUCZPXIA-UHFFFAOYSA-N C=1C=NON=1.C1=NN=CO1 Chemical compound C=1C=NON=1.C1=NN=CO1 YKZBDEWUCZPXIA-UHFFFAOYSA-N 0.000 description 1
- 101100394073 Caenorhabditis elegans hil-1 gene Proteins 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- SZJVIIHVFXWGMW-UHFFFAOYSA-N Cc1ccccc1C(C=CC1c2c(C)cccc2)C(C(OC)=O)=C1C(OC)=O Chemical compound Cc1ccccc1C(C=CC1c2c(C)cccc2)C(C(OC)=O)=C1C(OC)=O SZJVIIHVFXWGMW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 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
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 239000012298 atmosphere Substances 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
- 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
- 244000309464 bull Species 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical class OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- ADLSYZKOWMZIRC-UHFFFAOYSA-N diethyl 2,3-dibromobenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C(Br)=C1Br ADLSYZKOWMZIRC-UHFFFAOYSA-N 0.000 description 1
- DLFOQUNXTOTZHR-UHFFFAOYSA-N diethyl 2,5-bis(2-methylphenyl)benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC(C=2C(=CC=CC=2)C)=C(C(=O)OCC)C=C1C1=CC=CC=C1C DLFOQUNXTOTZHR-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
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 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
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 238000006138 lithiation reaction Methods 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- SWGQITQOBPXVRC-UHFFFAOYSA-N methyl 2-bromobenzoate Chemical compound COC(=O)C1=CC=CC=C1Br SWGQITQOBPXVRC-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 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
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 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
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 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
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring 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
- 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
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed 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
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thin Film Transistor (AREA)
- Photovoltaic Devices (AREA)
Description
1.特に蛍光OLEDにおいては、効率が未だに低く、改善されるべきである。
Yは、それぞれ同じまたは異なり、B、N、P、P=O、PF2、C=O、O、S、S=OまたはSO2である;
Arは、それぞれ同じまたは異なり、5〜40の芳香環原子を有する芳香環または芳香族複素環構造であり、1以上の基R1で置換されてよい;
Xは、それぞれ同じまたは異なり、B(R1)、C(R1)2、-CR1=CR1-、-CR1=N-、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、SO2、N(R1)、またはP(=O)R1から選択される基であるか、これらの基の2つ、3つまたは4つの組み合わせである;
Zは、Xが基Zに結合する場合にCであり、基Xが基Zに結合しない場合には、それぞれ同じまたは異なり、CRまたはNである;
Wは、それぞれ同じまたは異なり、CHまたはNである;
Rは、それぞれ同じまたは異なり、H、D、F、CN、B(OR2)2、Si(R2)3、N(Ar)2、C(=O)Ar、P(=O)Ar2、S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、1〜40の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または2〜40の炭素原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40の炭素原子を有する分枝鎖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である(これらはそれぞれ1以上の基R2で置換されてよく、1以上の隣接しないCH2基は、-R2C=CR2-、Si(R2)2、C=O、C=S、C=NR2、-O-、-S-、-COO-または-CONR2-で置換されてよく、1以上のH原子は、F、Cl、Br、I、CNもしくはNO2で置換されてよい)か、または1以上の非芳香族基R1で置換されてよい、5〜40の芳香環原子を有する芳香環または芳香族複素環であるか、または1以上の非芳香族基R1で置換されてよい、5〜40の芳香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であるか、またはこれらの組み合わせであり;ここでの2以上の隣接する置換基Rは、互いに単環式または多環式の構造を形成してもよい;
Eは、それぞれ同じまたは異なり、単結合、N(R1)、O、S、C(R1)2、C(R1)2-C(R1)2、Si(R1)2またはB(R1)である;
R1は、それぞれ同じまたは異なり、H、D、F、Cl、Br、I、CN、NO2、B(OR2)2、Si(R2)3、1〜40の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または2〜40の炭素原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40の炭素原子を有する分枝鎖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である(これらはそれぞれ1以上の基R2で置換されてよく、1以上の隣接しないCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、-O-、-S-、-COO-もしくは-CONR2-で置換されてよく、1以上のH原子は、F、Cl、Br、I、CNもしくはNO2で置換されてよい)か、または1以上の非芳香族基R1で置換されてよい、5〜40の芳香環原子を有する芳香環もしくは芳香族複素環であるか、または1以上の非芳香族基R1で置換されてよい、5〜40の芳香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であるか、またはこれらの組み合わせであり;ここでの2以上の置換基R1は、互いに単環式または多環式の構造を形成してもよい;
R2は、それぞれ同じまたは異なり、Hまたは1〜20の炭素原子を有する脂肪族もしくは芳香族炭化水素基である;
m、nは、0または1であり、ただしm+n=1である;
qは、それぞれ、基Yの対応する中心原子が主基(main group)3または5に由来する要素である場合に1であり、基Yの対応する中心原子が主基4または6に由来する要素である場合には0である;
sは、1、2または3である;
tは、それぞれ同じまたは異なり、0または1であり、t=0の場合には、基R1が基Eの代わりに結合することを意味し;さらに、q=0の場合にt=0である;
vは0または1であり、v=0の場合、水素または基Rが基Yの代わりに結合してよい;
少なくとも1の基Rは、HまたはD以外の置換基を意味することを特徴とする。
本発明の好ましい実施形態において、式(1)の化合物における2つ以下の記号ZはNを意味し、他の記号ZはCまたはCRを意味する。本発明の特に好ましい実施形態において、全ての記号ZがCもしくはCRを意味するか、またはちょうど2つの記号ZはNを意味し、他の記号ZはCもしくはCRを意味する。
a)所定の位置において基Yの代わりに水素を有するインデノフルオレン骨格または対応する複素環誘導体を合成することと;
b)ハロゲン化により、所定の位置において基Yの代わりにハロゲンで置換されたインデノフルオレンまたは対応する複素環誘導体を得ることと;
c)ハロゲン化インデノフルオレンをジアリールアミンと反応させるか、またはメタレーションし、求電子試薬と反応させること。
1.正孔輸送層および/または正孔注入層における正孔輸送材料として本発明の化合物を使用する場合、本発明の化合物におけるいずれかの位置にいずれかの置換基Rを含まないか、またはインデノフルオレン骨格に窒素を含まない先行技術の化合物と比較して、必要とされる電圧が低い。
本発明は、限定することなく、以下の実施例によりさらに詳細に説明する。
a)ジエチル 2,2''-ジメチル[1,1';4',1'']テルフェニル-2',5'-ジカルボキシレート
a)1,4-ジブロモ-2,3-ジメチルベンゼン
本発明によるOLEDは、ここに記載した条件(層の厚みの変化、使用する材料)に適応したWO 04/058911に記載されている一般的な方法により作製される。
加工性の検討のために、先行技術におけるHTM1と本発明による化合物としてのHTM3とを、同一の蒸着条件下において、0.1 nm/sの速度で蒸着する。この工程の間に、1時間および2時間の蒸気コーティングの後で蒸着源を調べる。1時間蒸着しただけで、HTM1の透明な結晶が蒸着源の縁に現れ、2時間蒸着した後には蒸着源は完全に塞がれる。対照的に、HTM3を用いた場合、2時間蒸着した後であっても蒸着源の縁には全く結晶が現れず、蒸着源を詰まらせる傾向は全くない。本発明による化合物HTM4およびHTM5を使用した場合にも、同様の結果が得られる。本発明による化合物は、それ故、先行技術による化合物HTM1と比較して、大量生産における使用に対して有意に適している。
Claims (15)
- 以下の式(1)で表される化合物:
Arは、それぞれ同じまたは異なり、5〜40の芳香環原子を有する芳香環または芳香族複
素環構造であり、1以上の基R1で置換されてよく;
Xは、C(R 1 ) 2 であり;
Zは、Xが基Zに結合する場合にCであり、基Xが基Zに結合しない場合には、それぞれ同じまたは異なり、CRであり;
Wは、CHであり;
Rは、それぞれ同じまたは異なり、H、D、F、CN、B(OR2)2、Si(R2)3、N(Ar)2、C(=O)Ar
、P(=O)Ar2、S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、1〜40の炭素原子を有する直鎖アルキル、
アルコキシもしくはチオアルコキシ基、または2〜40の炭素原子を有する直鎖アルケニル
もしくはアルキニル基、または3〜40の炭素原子を有する分枝鎖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である(これらはそれ
ぞれ1以上の基R2で置換されてよく、1以上の隣接しないCH2基は、-R2C=CR2-、Si(R2)2、C=O、C=S、C=NR2、-O-、-S-、-COO-または-CONR2-で置換されてよく、1以上のH原子は、F、Cl、Br、I、CNもしくはNO2で置換されてよい)か、または1以上の非芳香族基R1で置換されてよい5〜40の芳香環原子を有する芳香環または芳香族複素環であるか、または1以上の非芳香族基R1で置換されてよい5〜40の芳香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であるか、またはこれらの組み合わせであり;ここでの2以上の隣接する置換基Rは、互いに単環式または多環式の構造を形成してもよく;
Eは、それぞれ同じまたは異なり、単結合、N(R1)、O、S、C(R1)2、C(R1)2-C(R1)2、Si(
R1)2またはB(R1)であり;
R1は、それぞれ同じまたは異なり、H、D、F、Cl、Br、I、CN、NO2、B(OR2)2、Si(R2)3
、1〜40の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、また
は2〜40の炭素原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40の炭素原子を有する分枝鎖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である(これらはそれぞれ1以上の基R2で置換されてよく、1以上の隣接しないCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、-O-、-S-、-COO-もしくは-CONR2-で置換されてよく、1以上のH原子は、F、Cl、Br、I、CNもしくはNO2で置換されてよい)か、または1以上の非芳香族基R1で置換されてよい5〜40の芳香環原子を有する芳香環もしくは芳香族複素環であるか、または1以上の非芳香族基R1で置換されてよい5〜40の芳香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であるか、またはこれらの組み合わせであり;ここでの2以上の置換基R1は、互いに単環式または多環式の構造を形成してもよく;
R2は、それぞれ同じまたは異なり、Hまたは1〜20の炭素原子を有する脂肪族もしくは芳香族炭化水素基であり;
m、nは、0または1であり、ただしm+n=1であり;
qは、それぞれ、基Yの対応する中心原子が主基(main group)3または5に由来する要素である場合に1であり、基Yの対応する中心原子が主基4または6に由来する要素である場合には0であり;
sは、1であり;
tは、それぞれ同じまたは異なり、0または1であり、t=0の場合には、基R1が基Eの代わりに結合することを意味し;さらに、q=0の場合にt=0であり;
vは0または1であり、v=0の場合、水素または基Rが基Yの代わりに結合してよく;
少なくとも1の基Rは、HまたはD以外の置換基を意味する。 - 請求項1または2に記載の化合物であって、記号Arは、それぞれ同じまたは異なり、5〜16の芳香環原子を有する芳香環もしくは芳香族複素環構造、トリアリールアミンまたはスピロビフルオレンを意味し、それぞれ1以上の基R1で置換されてよいことを特徴とする化合物。
- 請求項3に記載の化合物であって、芳香環または芳香族複素環構造は、ベンゼン、オルト-、メタ-もしくはパラ-ビフェニル、フルオレン、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、ピリジン、ピレン、チオフェン、トリフェニルアミン、ジフェニル-1-ナフチルアミン、ジフェニル-2-ナフチルアミン、フェニルジ(1-ナフチル)アミンおよびフェニルジ(2-ナフチル)アミンから選択され、それぞれR1で置換されてよいことを特徴とする化合物。
- 請求項1〜4のいずれか1項に記載の化合物であって、前記添え字t=0または添え字t=1であり、対応する記号Eは、単結合、C(R1)2、SまたはN(R1)であることを特徴とする化合物。
- 請求項1〜6のいずれか1項に記載の化合物であって、水素または重水素以外の基Rは
、それぞれ同じまたは異なり、1〜20の炭素原子を有する直鎖状のアルキル基または3〜20の炭素原子を有する分枝鎖状もしくは環状のアルキル基であり、これらのそれぞれは、1以上の基R2で置換されてよく、1以上のH原子は、F、または1以上の非芳香族性基R1で置換されてよい5〜20の芳香環原子を有する芳香環もしくは芳香族複素環構造、あるいはこれらの構造の組み合わせにより置換されてよく;ここでの2以上の隣接する置換基Rは、互いに単環または多環構造を形成してもよいことを特徴とする化合物。 - 請求項7に記載の化合物であって、水素以外の基Rは、それぞれ同じまたは異なり、1〜10の炭素原子を有する直鎖状のアルキル基または3〜10の炭素原子を有する分枝鎖状もしくは環状のアルキル基であり、これらのそれぞれは、1以上の基R2で置換されてよいことを特徴とする化合物。
- 請求項7に記載の化合物であって、水素以外の基Rは、それぞれ同じまたは異なり、メチル、エチル、n-プロピル、i-プロピル、n-ブチル、i-ブチル、s-ブチル、t-ブチル、2-メチルブチル、n-ペンチル、s-ペンチル、tert-ペンチル、2-ペンチル、シクロペンチル、n-ヘキシル、s-ヘキシル、tert-ヘキシル、2-ヘキシル、3-ヘキシル、シクロヘキシル、2-メチルペンチル、n-ヘプチル、2-ヘプチル、3-ヘプチル、4-ヘプチル、シクロヘプチル、1-メチルシクロヘキシル、n-オクチル、2-エチルヘキシル、シクロオクチル、1-ビシクロ[2.2.2]オクチル、2-ビシクロ[2.2.2]オクチル、2-(2,6-ジメチル)オクチルまたは3-(3,7-ジメチル)オクチルであることを特徴とする化合物。
- 請求項1〜10のいずれか1項に記載の化合物の製造方法であって、以下の工程を含む
方法:
a)所定の位置において基Yの代わりに水素を有するインデノフルオレン骨格または対
応する複素環誘導体を合成することと;
b)ハロゲン化により、所定の位置において基Yの代わりにハロゲンで置換されたイン
デノフルオレンまたは対応する複素環誘導体を得ることと;
c)ハロゲン化インデノフルオレンをジアリールアミンと反応させるか、またはメタレ
ーションし、求電子試薬と反応させること。 - 電子デバイスにおける請求項1〜10のいずれか1項に記載の化合物の使用。
- 電子デバイスが、有機エレクトロルミネッセンス素子である請求項12に記載の使用。
- 請求項1〜10のいずれか1項に記載の化合物を少なくとも1つ含む有機電子デバイスであって、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機発光トランジスタ(O-LET)、有機集積回路(O-IC)、有機太陽電池(O-SC)、有機電場消光素子(O-FQD)、発光電気化学電池(LEC)、有機感光体および有機レーザーダイオード(O-laser)からなる群より選択される有機電子デバイス。
- 請求項14に記載の有機電子デバイスであって、請求項1〜10のいずれか1項に記載の化合物は、正孔輸送材料および/または正孔注入材料として使用されることを特徴とする有機電子デバイス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008024182.2 | 2008-05-19 | ||
DE102008024182A DE102008024182A1 (de) | 2008-05-19 | 2008-05-19 | Verbindungen für organische elektronische Vorrichtung |
PCT/EP2009/001554 WO2009141026A1 (de) | 2008-05-19 | 2009-03-05 | Verbindungen für elektronische vorrichtungen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011523943A JP2011523943A (ja) | 2011-08-25 |
JP5575754B2 true JP5575754B2 (ja) | 2014-08-20 |
Family
ID=41151772
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011509866A Active JP5575754B2 (ja) | 2008-05-19 | 2009-03-05 | 電子デバイスのための化合物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8766001B2 (ja) |
EP (1) | EP2276723B1 (ja) |
JP (1) | JP5575754B2 (ja) |
KR (2) | KR100938796B1 (ja) |
CN (1) | CN102026958B (ja) |
DE (1) | DE102008024182A1 (ja) |
TW (1) | TWI534123B (ja) |
WO (1) | WO2009141026A1 (ja) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009009277B4 (de) | 2009-02-17 | 2023-12-07 | Merck Patent Gmbh | Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen |
CN102725290B (zh) | 2009-07-27 | 2016-03-09 | 吉利德科学股份有限公司 | 作为离子通道调节剂的稠合杂环化合物 |
DE102009052428A1 (de) | 2009-11-10 | 2011-05-12 | Merck Patent Gmbh | Verbindung für elektronische Vorrichtungen |
JP5605604B2 (ja) * | 2010-01-26 | 2014-10-15 | 独立行政法人科学技術振興機構 | 光電変換素子およびその製造方法 |
DE102010010631A1 (de) * | 2010-03-09 | 2011-09-15 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
CA2802288C (en) | 2010-07-02 | 2018-08-21 | Gilead Sciences, Inc. | Triazolopyridinone compounds as ion channel modulators |
CN102372663B (zh) * | 2010-08-20 | 2013-10-30 | 清华大学 | 一种吡啶基茚并芴类化合物及应用 |
JP5699581B2 (ja) * | 2010-12-15 | 2015-04-15 | Jnc株式会社 | 縮合ピロール多環化合物、発光層用材料およびこれを用いた有機電界発光素子 |
US9627626B2 (en) | 2011-01-13 | 2017-04-18 | Merck Patent Gmbh | Compounds for organic electroluminescent devices |
EP3275870B1 (en) | 2011-05-10 | 2020-02-05 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
TWI549944B (zh) | 2011-07-01 | 2016-09-21 | 吉李德科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
NO3175985T3 (ja) | 2011-07-01 | 2018-04-28 | ||
JP2014150083A (ja) * | 2011-09-30 | 2014-08-21 | Fujifilm Corp | 有機電界発光素子 |
JP2015534258A (ja) | 2012-08-21 | 2015-11-26 | チェイル インダストリーズ インコーポレイテッド | 有機光電子素子用化合物、これを含む有機発光素子および前記有機発光素子を含む表示装置 |
EP2892876B1 (de) * | 2012-09-04 | 2018-11-07 | Merck Patent GmbH | Verbindungen für elektronische vorrichtungen |
CN105849112A (zh) | 2014-01-14 | 2016-08-10 | 三星Sdi株式会社 | 缩合环化合物以及含有其的有机发光元件 |
KR102375992B1 (ko) * | 2014-04-16 | 2022-03-17 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
KR102242791B1 (ko) | 2014-08-29 | 2021-04-21 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2016150544A1 (en) | 2015-03-25 | 2016-09-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN107573306B (zh) * | 2016-07-05 | 2020-04-28 | 上海和辉光电有限公司 | 一种有机电致发光化合物 |
CN111194313A (zh) * | 2017-07-12 | 2020-05-22 | 弗莱克因艾伯勒有限公司 | 闭环反应 |
KR20200051721A (ko) * | 2017-09-08 | 2020-05-13 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
EP3679024B1 (de) | 2017-09-08 | 2022-11-02 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
KR20240025066A (ko) * | 2017-12-15 | 2024-02-26 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 치환된 방향족 아민 |
JP2022514875A (ja) * | 2018-12-20 | 2022-02-16 | メルク パテント ゲーエムベーハー | 電子デバイス用の材料 |
Family Cites Families (17)
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 |
DE10207859A1 (de) | 2002-02-20 | 2003-09-04 | Univ Dresden Tech | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
GB0226010D0 (en) | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
KR101030158B1 (ko) | 2002-12-23 | 2011-04-18 | 메르크 파텐트 게엠베하 | 유기 전자발광 부품 |
US7271406B2 (en) | 2003-04-15 | 2007-09-18 | 3M Innovative Properties Company | Electron transport agents for organic electronic devices |
DE10333232A1 (de) | 2003-07-21 | 2007-10-11 | Merck Patent Gmbh | Organisches Elektrolumineszenzelement |
DE10357044A1 (de) | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
KR101030010B1 (ko) | 2004-09-18 | 2011-04-20 | 삼성모바일디스플레이주식회사 | 청색 발광 고분자 및 이를 채용한 유기 전계 발광 소자 |
KR100613810B1 (ko) * | 2004-12-17 | 2006-08-17 | 주식회사 두산 | 전계 발광 소자용 화합물 및 이를 포함하는 유기 전계발광소자 |
KR20090040398A (ko) | 2005-03-18 | 2009-04-23 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그것을 사용한 유기 전기발광 소자 |
US8334058B2 (en) | 2005-04-14 | 2012-12-18 | Merck Patent Gmbh | Compounds for organic electronic devices |
DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
CN100548984C (zh) * | 2007-11-26 | 2009-10-14 | 山东大学 | 一种吲哚[3,2-b]咔唑衍生物类有机电致发光材料 |
WO2009099060A1 (ja) * | 2008-02-04 | 2009-08-13 | Idemitsu Kosan Co., Ltd. | 芳香族アミ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 |
-
2008
- 2008-05-19 DE DE102008024182A patent/DE102008024182A1/de not_active Withdrawn
- 2008-09-12 KR KR1020080090538A patent/KR100938796B1/ko active IP Right Grant
-
2009
- 2009-03-05 US US12/993,352 patent/US8766001B2/en active Active
- 2009-03-05 JP JP2011509866A patent/JP5575754B2/ja active Active
- 2009-03-05 EP EP09749516.2A patent/EP2276723B1/de active Active
- 2009-03-05 CN CN200980116960.1A patent/CN102026958B/zh active Active
- 2009-03-05 WO PCT/EP2009/001554 patent/WO2009141026A1/de active Application Filing
- 2009-03-24 TW TW098109551A patent/TWI534123B/zh active
- 2009-11-16 KR KR1020090110304A patent/KR20100009523A/ko not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
TWI534123B (zh) | 2016-05-21 |
JP2011523943A (ja) | 2011-08-25 |
KR100938796B1 (ko) | 2010-01-27 |
US8766001B2 (en) | 2014-07-01 |
CN102026958B (zh) | 2014-08-20 |
KR20090120381A (ko) | 2009-11-24 |
KR20100009523A (ko) | 2010-01-27 |
WO2009141026A1 (de) | 2009-11-26 |
DE102008024182A1 (de) | 2009-11-26 |
EP2276723A1 (de) | 2011-01-26 |
TW200951101A (en) | 2009-12-16 |
US20110092701A1 (en) | 2011-04-21 |
CN102026958A (zh) | 2011-04-20 |
EP2276723B1 (de) | 2016-01-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5575754B2 (ja) | 電子デバイスのための化合物 | |
JP5951544B2 (ja) | 有機エレクトロルミネセンス素子のための新規材料 | |
JP5730784B2 (ja) | 電子デバイスのための化合物 | |
JP5726734B2 (ja) | 電子デバイス用化合物 | |
JP5405297B2 (ja) | 有機エレクトロルミネセンス素子のための材料 | |
JP5694159B2 (ja) | 有機エレクトロルミネセントデバイス | |
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 | |
JP5864263B2 (ja) | エレクトロルミネセンスデバイスのための材料 | |
JP5638960B2 (ja) | 有機エレクトロルミネセントデバイスのための新規材料 | |
KR100923037B1 (ko) | 유기 전계발광 소자용 신규 물질 | |
JP5944319B2 (ja) | 有機エレクトロルミネセンス素子のための材料 | |
RU2419648C2 (ru) | Соединения для органических электронных устройств | |
KR20100129101A (ko) | 유기 전계발광 장치용 물질 | |
KR20110095130A (ko) | 유기 전계발광 소자용 재료 | |
JP2012531383A (ja) | 有機エレクトロルミネセンス素子のための材料 | |
JP2015212261A (ja) | 有機エレクトロルミネセンス素子のための新規な材料 | |
KR20110085876A (ko) | 유기 전계발광 소자용 재료 | |
JP2016106094A (ja) | 有機エレクトロルミネセンスデバイス用材料 | |
KR102088150B1 (ko) | 유기 전계발광 소자용 화합물 | |
KR20140025456A (ko) | 전자 소자용 재료 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120229 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131022 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131024 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140115 |
|
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: 20140603 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140702 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5575754 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 |
|
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 |