JP7225094B2 - アクセプター基とドナー基を有する化合物 - Google Patents
アクセプター基とドナー基を有する化合物 Download PDFInfo
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- JP7225094B2 JP7225094B2 JP2019525862A JP2019525862A JP7225094B2 JP 7225094 B2 JP7225094 B2 JP 7225094B2 JP 2019525862 A JP2019525862 A JP 2019525862A JP 2019525862 A JP2019525862 A JP 2019525862A JP 7225094 B2 JP7225094 B2 JP 7225094B2
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- 150000001875 compounds Chemical class 0.000 title claims description 161
- 125000003118 aryl group Chemical group 0.000 claims description 209
- 239000000463 material Substances 0.000 claims description 107
- 239000011159 matrix material Substances 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 229920000642 polymer Polymers 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 239000000412 dendrimer Substances 0.000 claims description 27
- 229920000736 dendritic polymer Polymers 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 239000004020 conductor Substances 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 229910005965 SO 2 Inorganic materials 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004986 diarylamino group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
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- 125000001072 heteroaryl group Chemical group 0.000 description 40
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- 229910052751 metal Inorganic materials 0.000 description 27
- 239000002184 metal Substances 0.000 description 27
- 239000002019 doping agent Substances 0.000 description 22
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 20
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 20
- 238000002347 injection Methods 0.000 description 18
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- 125000004122 cyclic group Chemical group 0.000 description 14
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 230000007704 transition Effects 0.000 description 13
- 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 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 150000002739 metals Chemical class 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- 125000006413 ring segment Chemical group 0.000 description 11
- 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 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 239000002800 charge carrier Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 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 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 6
- 229910010272 inorganic material Inorganic materials 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 235000019557 luminance Nutrition 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 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 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 description 5
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 125000005259 triarylamine group Chemical group 0.000 description 5
- 125000005580 triphenylene group Chemical group 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
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- 239000011147 inorganic material Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
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- 238000005284 basis set Methods 0.000 description 3
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
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- 125000002883 imidazolyl group Chemical group 0.000 description 3
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- GOVDQARNNMIPTP-UHFFFAOYSA-N 1-bromo-4-[2-(4-chlorophenyl)ethynyl]benzene Chemical compound C1=CC(Cl)=CC=C1C#CC1=CC=C(Br)C=C1 GOVDQARNNMIPTP-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- BITWULPDIGXQDL-UHFFFAOYSA-N 9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene Chemical compound C=1C=C(C=2C3=CC=CC=C3C(C=3C=CC(C=C(C=4C=CC=CC=4)C=4C=CC=CC=4)=CC=3)=C3C=CC=CC3=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 BITWULPDIGXQDL-UHFFFAOYSA-N 0.000 description 2
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- 239000011261 inert gas Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000003446 ligand Substances 0.000 description 1
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- 239000004973 liquid crystal related substance Substances 0.000 description 1
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- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical group C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 230000001590 oxidative effect Effects 0.000 description 1
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
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- 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
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- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
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- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
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- 235000011056 potassium acetate Nutrition 0.000 description 1
- DBCAVMLQRAABFF-UHFFFAOYSA-M potassium;carbonic acid;hydrogen carbonate Chemical compound [K+].OC(O)=O.OC([O-])=O DBCAVMLQRAABFF-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000004882 thiopyrans Chemical class 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three 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
- C07D401/10—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
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Description
Qは、5~60個の芳香族環原子を有し、1つ以上のR1ラジカルにより置換されていてもよい芳香族またはヘテロ芳香族環系を含むアクセプター基であり;
HLは、ドナー基であり;
Ara、Arbは、同じであるかまたは異なり、5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、1つ以上のR1ラジカルにより置換されていてもよい芳香族またはヘテロ芳香族環系であり;
Ra、Rbは、同じであるかまたは異なり、H、D、F、Cl、Br、I、B(OR1)2、CHO、C(=O)R1、CR1=C(R1)2、CN、C(=O)OR1、C(=O)N(R1)2、Si(R1)3、N(R1)2、NO2、P(=O)(R1)2、OSO2R1、OR1、S(=O)R1、S(=O)2R1、1~40個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3~40個の炭素原子を有する分枝もしくは環状アルキル、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つ以上のR1ラジカルにより置換されていてもよい)(ここで、1つ以上の隣接していないCH2基は、-R1C=CR1-、-C≡C-、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、NR1、P(=O)(R1)、-C(=O)O-、-C(=O)NR1-、-O-、-S-、SOもしくはSO2により置きかえられていてもよく、1個以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2により置きかえられていてもよい)、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、各場合において1つ以上のR1ラジカルにより置換されていてもよい芳香族もしくはヘテロ芳香族環系、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、1つ以上のR1ラジカルにより置換されていてもよいアリールオキシもしくはヘテロアリールオキシ基、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、1つ以上のR1ラジカルにより置換されていてもよいアラルキルもしくはヘテロアラルキル基、または10~40個の芳香族環原子を有し、1つ以上のR1ラジカルにより置換されていてもよいジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基;またはこれらの系の組合せであり;同時に、RaおよびRbが一緒になって、またはAraもしくはArb基と共に、単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよく;
R1は、それぞれの場合において同じであるかまたは異なり、H、D、F、Cl、Br、I、B(OR2)2、CHO、C(=O)R2、CR2=C(R2)2、CN、C(=O)OR2、C(=O)N(R2)2、Si(R2)3、N(R2)2、NO2、P(=O)(R2)2、OSO2R2、OR2、S(=O)R2、S(=O)2R2、1~40個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3~40個の炭素原子を有する分枝もしくは環状アルキル、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つ以上のR2ラジカルにより置換されていてもよい)(ここで、1つ以上の隣接していないCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、NR2、P(=O)(R2)、-C(=O)O-、-C(=O)NR2-、-O-、-S-、SOもしくはSO2により置きかえられていてもよく、1個以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2により置きかえられていてもよい)、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、各場合において1つ以上のR2ラジカルにより置換されていてもよい芳香族もしくはヘテロ芳香族環系、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、1つ以上のR2ラジカルにより置換されていてもよいアリールオキシもしくはヘテロアリールオキシ基、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、1つ以上のR2ラジカルにより置換されていてもよいアラルキルもしくはヘテロアラルキル基、または10~40個の芳香族環原子を有し、1つ以上のR2ラジカルにより置換されていてもよいジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基;またはこれらの系の組合せであり;同時に、2つ以上の、好ましくは隣接するR1ラジカルが一緒になって単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよく;
R2は、それぞれの場合において同じであるかまたは異なり、H、D、F、Cl、Br、I、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、N(R3)2、NO2、P(=O)(R3)2、OSO2R3、OR3、S(=O)R3、S(=O)2R3、1~40個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3~40個の炭素原子を有する分枝もしくは環状アルキル、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つ以上のR3ラジカルにより置換されていてもよい)(ここで、1つ以上の隣接していないCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、NR3、P(=O)(R3)、-C(=O)O-、-C(=O)NR3-、-O-、-S-、SOもしくはSO2により置きかえられていてもよく、1個以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2により置きかえられていてもよい)、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、各場合において1つ以上のR3ラジカルにより置換されていてもよい芳香族もしくはヘテロ芳香族環系、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよいアリールオキシもしくはヘテロアリールオキシ基、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよいアラルキルもしくはヘテロアラルキル基、または10~40個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよいジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基、またはこれらの系の組合せであり;同時に、2つ以上の、好ましくは隣接するR2置換基が一緒になって単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよく;
R3は、それぞれの場合において同じであるかまたは異なり、H、D、F、または1~20個の炭素原子を有する脂肪族、芳香族および/またはヘテロ芳香族ヒドロカルビルラジカルであり(水素原子はFにより置きかえられていてもよい);同時に、2つ以上の、好ましくは隣接するR3置換基が一緒になって単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよい)
の少なくとも1つの構造を含む化合物を提供する。
Ar2、Ar3、Ar4は、それぞれ独立して6~40個の炭素原子を有するアリール基または3~40個の炭素原子を有するヘテロアリール基であり、これらのそれぞれは、1つ以上のR1ラジカルにより置換されていてもよく;
pは、0、1、2、3、4、5または6、好ましくは0、1、2または3、より好ましくは0、1または2であり、
Zは、CR1 2、SiR1 2、C=O、N-Ar1、BR1、PR1、POR1、SO、SO2、Se、OまたはS、好ましくはCR1 2、N-Ar1、OまたはSであり、ここで、R1ラジカルは、請求項1に記載の定義を有し、Ar1は、5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、各場合において1つ以上のR1ラジカルにより置換されていてもよい芳香族もしくはヘテロ芳香族環系、5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、各場合において1つ以上のR1ラジカルにより置換されていてもよいアリールオキシ基、または5~60個の芳香族、好ましくは5~40個の芳香族環原子を有し、各場合において1つ以上のR1ラジカルにより置換されていてもよいアラルキル基を表し、ここで、2つ以上の、好ましくは隣接するR1置換基が、1つ以上のR2ラジカルにより置換されていてもよい単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成することが任意に可能である)
から選択される基であるようにしてもよい。
から選択される基であるようにしてもよい。
の連結構造であってもよい。好ましくは、式(LAr-1)に示す基の2つの結合位置は、パラ位である。さらに好ましいのは、式(H-1)~(H-26)中の添え字pが1であり、式(LAr-1)中の添え字sが0、1、2、3、4、5または6、好ましくは0、1、2または3、より好ましくは0、1または2、とりわけ好ましくは0または1である。
で表すことができる基であるようにしてもよい。
点線で示される結合は結合位置を示し、tは、0、1、2、3、4、5または6、好ましくは0、1、2または3、より好ましくは0、1または2、とりわけ好ましくは0または1であり、ここで、R1は、とりわけ式(I)に関して上記した定義を有する)
の連結構造である。好ましくは、式(LAr-2)に示す連結構造の2つの結合位置は、パラ位である。
Q’は、各場合において同じであるかまたは異なり、CR1またはNを表し、
Q”は、NR1、OまたはSを表し;
ここで、少なくとも1つのQ’はNであり、および/または少なくとも1つのQ”は、NR1であり、
R1は、請求項1に定義する通りである)
の構造から選択されてもよい。
の構造から選択される。
の構造から選択される。ここで、式(Q-16)、(Q-17)、(Q-18)および(Q-19)の構造が好ましい。
の構造から選択されてもよい。
の構造から選択されてもよい。
の構造から選択されてもよい。
Yは、O、SまたはNR2、好ましくはOまたはSであり;
それぞれの場合のiは、独立して0、1または2であり;
それぞれの場合のjは、独立して0、1、2または3であり;
それぞれの場合のhは、独立して0、1、2、3または4であり;
それぞれの場合のgは、独立して0、1、2、3、4または5であり;
R2は、とりわけ式(I)に関して先に示した定義を有してもよく、
点線で示される結合は結合位置を示す)
から選択される基であるようにしてもよい。ここで、式R1-1~R1-54の基が好ましく、式R1-1、R1-3、R1-5、R1-6、R1-15、R1-29、R1-34、R1-35、R1-45、R1-46、R1-47および/またはR1-48の基が特に好ましい。
から選択される基を形成するようにしてもよい。
スズキカップリングまたはソノガシラ反応のための反応物質に使用される反応性反応物質化合物は、たとえば、公知のアリールまたはヘテロアリール化合物から公知のハロゲン化、好ましくは臭素化により得ることができる。
したがって、本発明は、先に詳述した式(I)の構造のうちの1つ以上または本発明の化合物を含有するオリゴマー、ポリマーまたはデンドリマーであって、ポリマー、オリゴマーまたはデンドリマーに対する本発明の化合物または式(I)の構造の1つ以上の結合が存在する、オリゴマー、ポリマーまたはデンドリマーをさらに提供する。式(I)の構造または化合物の結合により、これらは結果としてオリゴマーまたはポリマーの側鎖を形成するか、主鎖内に結合される。ポリマー、オリゴマーまたはデンドリマーは、共役、部分共役、または非共役であってもよい。オリゴマーまたはポリマーは、直鎖状、分枝または樹枝状であってもよい。オリゴマー、デンドリマーおよびポリマーにおける本発明の化合物の反復単位については、上記と同じ優先傾向が当てはまる。
Ar5、Ar6、Ar7は、それぞれの場合において同じであるかまたは異なり、5~30個の芳香族環原子を有するアリールまたはヘテロアリール基であり、これは、一置換または多置換であってもよく、
p=1、2または3であり;
ここで、Ar5、Ar6、Ar7基中のπ電子の合計は、p=1の場合少なくとも30であり、p=2の場合少なくとも36であり、p=3の場合少なくとも42である)
の化合物から選択される。
HOMO(eV)=((HEh*27.212)-0.9899)/1.1206
LUMO(eV)=((LEh*27.212)-2.0041)/1.385
本願の文脈において、これらの値を材料のHOMOおよびLUMOエネルギー準位とみなすこととする。
したがって、本発明はさらに、式(I)の構造または上記および下記の好ましい態様を有する少なくとも1種の化合物と、少なくとも1種の蛍光発光体を含む組成物に関し、「蛍光発光体」という用語は、蛍光ドーパントを意味するものとも理解される。好ましくは、本発明による化合物、オリゴマー、ポリマーまたはデンドリマーに対する蛍光発光体の重量比が、重量で0.1%~50%、重量で1%~20%、および重量で3%~15%の範囲であるようにしてもよい。
以下に続く合成は、特に断らない限り、乾燥溶媒中、保護ガス雰囲気下で行われる。金属錯体は、遮光して、または黄色光下で追加的な処理をする。溶媒および試薬は、たとえばSigma-ALDRICHまたはABCRから購入することができる。角括弧内のそれぞれの数字、または個々の化合物について引用された数字は、文献から公知の化合物のCAS番号である。
シントンの合成
例S1:
1)真空処理されたデバイス:
本発明のOLEDと先行技術によるOLEDを、WO2004/058911による一般的な方法によって製造するが、方法は、ここに記載する環境(層厚の変更、使用する材料)に適合させてある。
本発明の化合物のリン光OLEDにおける発光体材料としての使用
本発明の化合物の1つの使用は、OLEDの発光層における発光体材料(TADF)としてのものである。
低分子量の可溶性機能材料から
本発明のイリジウム錯体は、溶液から処理することもでき、真空処理されたOLEDと比較して処理技術に関して遙かに単純であるにもかかわらず、良好な特性を有するOLEDが得られる。このような部品の製造は、既に何度も文献(たとえばWO2004/037887)に記載されているポリマー発光ダイオード(PLED)の製造に基づくものである。構造は、基板/ITO/正孔注入層(60nm)/中間層(20nm)/発光層(60nm)/正孔阻止層(10nm)/電子輸送層(40nm)/カソードで構成される。この目的のため、Technoprint製の基板(ソーダ石灰ガラス)を使用し、これにITO構造(インジウムスズ酸化物、透明な導電性アノード)を適用する。基板を、クリーンルームにおいてDI水および洗浄剤(Deconex 15PF)を用いて清浄にし、次いで、UV/オゾンプラズマ処理によって活性化させる。その後、同様にクリーンルームにおいて、20nmの正孔注入層をスピンコーティングにより適用する。必要なスピン速度は、希釈度および具体的なスピンコーターの形状寸法に依存する。層から残留水を除去するために、基板を、200℃のホットプレート上で30分間加熱する。使用する中間層は、正孔注入用として機能し;この場合、Merck製のHL-Xを使用する。あるいは、中間層は、1つ以上の層により置きかえられていてもよく、これらは、その後の溶液からのEML堆積の処理工程によって再び剥離しないという条件を満たすだけでよい。発光層を製造するために、本発明の三重項発光体を、マトリックス材料と共にトルエンまたはクロロベンゼンに溶解させる。この場合のように、デバイスに特有な層厚60nmをスピンコーティングによって達成すべき場合、このような溶液の典型的な固形分は16乃至25g/lである。溶液処理された緑色タイプ1デバイスは、P:M:IrRef2(X%:Y%:Z%)で構成される発光層を含有し;赤色タイプ2デバイスは、P:M:IrRef2:IrRef3(X%:Y%:Z%:5%)で構成される発光層を含有し;換言すると、これらは、2種の異なるIr錯体を含有する。発光層を不活性ガス雰囲気、本発明の場合はアルゴン中でスピンオンし、160℃で10分間焼成する。後者の上に、正孔阻止層(10nmETM1)と電子輸送層(40nmETM1(50%)/ETM2(50%))を蒸着(Lesker製の蒸着システムまたは同様のもの、典型的な蒸着圧力は、5×10-6mbarである)する。最後に、アルミニウムのカソード(100nm)(Aldrich製高純度金属)を蒸着により適用する。空気と空気の湿気からデバイスを保護するために、最後にデバイスを封入し、次いでその特性を決定する。引用したOLEDの例は、まだ最適化されていないが、得られたデータを表3に要約する。
Claims (10)
- 式(I):
Qは、式(QL)で表されるアクセプター基であり;
Q1は、式(Q-23)および(Q-24)の構造から選択される電子求引基であり;
HLは、式(H-1)~(H-26)から選択される基を含むドナー基であり;
Ar2、Ar3、Ar4は、それぞれ独立して6~40個の炭素原子を有するアリール基であり、これらのそれぞれは、1つ以上のR1ラジカルにより置換されていてもよく;
pは、0、1または2であり;
Zは、CR1 2、N-Ar1、OまたはSであり;
Y1は、O、S、C(R1)2またはNAr1を表し、点線で示される結合は結合位置を示し、eは、0、1または2であり、jは、0、1、2または3であり、hは、0、1、2、3または4であり;
Ar1は、6~24個の芳香族環原子を有し、各場合において1つ以上のR1ラジカルにより置換されていてもよい芳香族もしくはヘテロ芳香族環系であり;
Ara、Arbは、同じであるかまたは異なり、6~18個の芳香族環原子を有し、1つ以上のR1ラジカルにより置換されていてもよい芳香族環系であり;
Ra、Rbは、独立して6~18個の芳香族環原子を有し、1つ以上のR 1 ラジカルにより置換されていてもよい芳香族環系であり;
R1は、それぞれの場合において同じであるかまたは異なり、H、D、F、Cl、Br、I、B(OR2)2、CHO、C(=O)R2、CR2=C(R2)2、CN、C(=O)OR2、C(=O)N(R2)2、Si(R2)3、N(R2)2、NO2、P(=O)(R2)2、OSO2R2、OR2、S(=O)R2、S(=O)2R2、1~40個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3~40個の炭素原子を有する分枝もしくは環状アルキル、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つ以上のR2ラジカルにより置換されていてもよい)(ここで、1つ以上の隣接していないCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、NR2、P(=O)(R2)、-C(=O)O-、-C(=O)NR2-、-O-、-S-、SOもしくはSO2により置きかえられていてもよく、1個以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2により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し、各場合において1つ以上のR2ラジカルにより置換されていてもよい芳香族もしくはヘテロ芳香族環系、または5~60個の芳香族環原子を有し、1つ以上のR2ラジカルにより置換されていてもよいアリールオキシもしくはヘテロアリールオキシ基、または5~60個の芳香族環原子を有し、1つ以上のR2ラジカルにより置換されていてもよいアラルキルもしくはヘテロアラルキル基、または10~40個の芳香族環原子を有し、1つ以上のR2ラジカルにより置換されていてもよいジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基;またはこれらの系の組合せであり;同時に、2つ以上のR1ラジカルが一緒になって単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよく;
R2は、それぞれの場合において同じであるかまたは異なり、H、D、F、Cl、Br、I、B(OR3)2、CHO、C(=O)R3、CR3=C(R3)2、CN、C(=O)OR3、C(=O)N(R3)2、Si(R3)3、N(R3)2、NO2、P(=O)(R3)2、OSO2R3、OR3、S(=O)R3、S(=O)2R3、1~40個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3~40個の炭素原子を有する分枝もしくは環状アルキル、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つ以上のR3ラジカルにより置換されていてもよい)(ここで、1つ以上の隣接していないCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、NR3、P(=O)(R3)、-C(=O)O-、-C(=O)NR3-、-O-、-S-、SOもしくはSO2により置きかえられていてもよく、1個以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2により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し、各場合において1つ以上のR3ラジカルにより置換されていてもよい芳香族もしくはヘテロ芳香族環系、または5~60個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよいアリールオキシもしくはヘテロアリールオキシ基、または5~60個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよいアラルキルもしくはヘテロアラルキル基、または10~40個の芳香族環原子を有し、1つ以上のR3ラジカルにより置換されていてもよいジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基、またはこれらの系の組合せであり;同時に、2つ以上のR2置換基が一緒になって単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよく;
R3は、それぞれの場合において同じであるかまたは異なり、H、D、F、または1~20個の炭素原子を有する脂肪族、芳香族および/またはヘテロ芳香族ヒドロカルビルラジカルであり(水素原子はFにより置きかえられていてもよい);同時に、2つ以上のR3置換基が一緒になって単環または多環式の脂肪族、ヘテロ脂肪族、芳香族またはヘテロ芳香族環系を形成していてもよい)
の少なくとも1つの構造を含む化合物。 - 式(I)中の前記Araおよび/またはArb基が、記号HLによるドナー基とは異なることを特徴とする、請求項1に記載の化合物。
- 請求項1~4の何れか1項に記載の1種以上の化合物を含有するオリゴマー、ポリマーまたはデンドリマーであって、水素原子または置換基に代わり、前記ポリマー、オリゴマーまたはデンドリマーに対する前記化合物の1つ以上の結合が存在する、オリゴマー、ポリマーまたはデンドリマー。
- 請求項1~4の何れか1項に記載の少なくとも1種の化合物、または請求項5に記載オリゴマー、ポリマーもしくはデンドリマーと、蛍光発光体、リン光発光体、ホスト材料、マトリックス材料、電子輸送材料、電子注入材料、正孔伝導材料、正孔注入材料、電子阻止材料、および正孔阻止材料からなる群から選択される少なくとも1種のさらなる化合物を含む、組成物。
- 請求項1~4の何れか1項に記載の少なくとも1種の化合物、または請求項5に記載のオリゴマー、ポリマーもしくはデンドリマー、または請求項6に記載の組成物と、少なくとも1種の溶媒を含む、調合物。
- 請求項1~4の何れか1項に記載の化合物、請求項5に記載のオリゴマー、ポリマーもしくはデンドリマー、または請求項6に記載の組成物の、電子デバイスにおけるTADF材料、ホスト材料、電子輸送材料または正孔伝導材料としての使用。
- 請求項1~4の何れか1項に記載の化合物、または請求項5に記載のオリゴマー、ポリマーもしくはデンドリマーを製造する方法であって、少なくとも1つのドナー基を含む化合物が、カップリング反応においてアクセプター基に結合されることを特徴とする、方法。
- 請求項1~4の何れか1項に記載の少なくとも1種の化合物、請求項5に記載のオリゴマー、ポリマーもしくはデンドリマー、または請求項6に記載の組成物を含む電子デバイス。
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- 2017-11-13 EP EP17803843.6A patent/EP3538623B1/de active Active
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EP4271163A2 (de) | 2023-11-01 |
KR20190085041A (ko) | 2019-07-17 |
KR102585418B1 (ko) | 2023-10-05 |
JP2020500187A (ja) | 2020-01-09 |
US20200203624A1 (en) | 2020-06-25 |
WO2018087346A1 (de) | 2018-05-17 |
TWI756292B (zh) | 2022-03-01 |
EP3538623B1 (de) | 2023-12-20 |
US20230354701A1 (en) | 2023-11-02 |
EP4271163A3 (de) | 2024-01-10 |
TW201833100A (zh) | 2018-09-16 |
EP3538623A1 (de) | 2019-09-18 |
CN109890938A (zh) | 2019-06-14 |
US11711976B2 (en) | 2023-07-25 |
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