JP5926286B2 - ピリミジン化合物を含む電子デバイス - Google Patents
ピリミジン化合物を含む電子デバイス Download PDFInfo
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- JP5926286B2 JP5926286B2 JP2013546348A JP2013546348A JP5926286B2 JP 5926286 B2 JP5926286 B2 JP 5926286B2 JP 2013546348 A JP2013546348 A JP 2013546348A JP 2013546348 A JP2013546348 A JP 2013546348A JP 5926286 B2 JP5926286 B2 JP 5926286B2
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- compound
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- pyrimidine
- photoactive
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- 150000003230 pyrimidines Chemical class 0.000 title description 16
- 239000000463 material Substances 0.000 claims description 137
- -1 terphenyl compound Chemical class 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 239000002019 doping agent Substances 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 33
- 239000004065 semiconductor Substances 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 24
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- 125000002524 organometallic group Chemical group 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 229920001940 conductive polymer Polymers 0.000 claims description 12
- 238000005401 electroluminescence Methods 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 229940125904 compound 1 Drugs 0.000 claims description 5
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 4
- 229940126639 Compound 33 Drugs 0.000 claims description 4
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims description 2
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims description 2
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 229940127204 compound 29 Drugs 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims description 2
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 212
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- 239000003446 ligand Substances 0.000 description 33
- 229910052751 metal Inorganic materials 0.000 description 33
- 239000002184 metal Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 22
- 229910052760 oxygen Inorganic materials 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 19
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 17
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 17
- 229910052805 deuterium Inorganic materials 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 14
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 150000002739 metals Chemical class 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 230000006870 function Effects 0.000 description 12
- 229910052741 iridium Inorganic materials 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 10
- 238000010586 diagram Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group 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
- 230000008901 benefit Effects 0.000 description 8
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000002207 thermal evaporation Methods 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 5
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 229920000767 polyaniline Polymers 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 125000005578 chrysene group Chemical group 0.000 description 4
- 230000005669 field effect Effects 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- ZOGMQKYHEAKHQN-UHFFFAOYSA-N 2-chloro-4,6-bis(3-phenylphenyl)pyrimidine Chemical compound N=1C(Cl)=NC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=CC=1C(C=1)=CC=CC=1C1=CC=CC=C1 ZOGMQKYHEAKHQN-UHFFFAOYSA-N 0.000 description 3
- JYWMNSFPUFWPQE-UHFFFAOYSA-N 5-(3-bromophenyl)pyrimidine Chemical compound BrC1=CC=CC(C=2C=NC=NC=2)=C1 JYWMNSFPUFWPQE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 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
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 150000002390 heteroarenes Chemical class 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 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 3
- 238000000206 photolithography Methods 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
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- 229920002530 polyetherether ketone Polymers 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 2
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 2
- DZVYZTRVAYXJNI-UHFFFAOYSA-N 2-(3,5-diphenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 DZVYZTRVAYXJNI-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 238000004989 laser desorption mass spectroscopy Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000000813 microcontact printing Methods 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
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- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920001798 poly[2-(acrylamido)-2-methyl-1-propanesulfonic acid] polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
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- 239000012264 purified product Substances 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 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
- BLEACIPCPNKHPX-UHFFFAOYSA-N quinolin-8-ol;zirconium Chemical group [Zr].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 BLEACIPCPNKHPX-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- H01L2924/11—Device type
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Description
本出願は、米国特許法第119条(e)に基づき、その記載内容全体が参照により援用される2010年12月21日に出願された米国仮特許出願第61/425,556号明細書の優先権を主張する。
R1〜R4は、同一であるか、または異なって、H、D、アルキル、シリル、アルコキシ、シアノまたはアリールであり、R1〜R4の少なくとも2つはアリール基であり、かつアリール基の少なくとも1つはN,O,S−複素環を含むが、ただし、R1〜R4の2つがN−カルバゾリル基を含む場合、R1〜R4の2つはアリールではない)
Qは、単結合または炭化水素アリールであり、かつ
R5およびR6は、それぞれ、同一であるか、または異なって、H、D、アルキル、シリル、アルコキシ、シアノまたはアリールであり、R5の少なくとも1つおよび少なくともR6の1つはアリール基であり、かつアリール基の少なくとも1つはN,O,S−複素環を含む)を有するピリミジン化合物が提供される。
絶縁層と、
ゲート電極と、
ソース電極と、
ドレイン電極と、
式Iまたは式IIを有するピリミジン化合物を含んでなる有機半導体層と
を含んでなる薄膜トランジスタであって、ゲート電極および半導体層が両方とも絶縁層と接触し、ソース電極およびドレイン電極が両方とも半導体層と接触し、そして電極が互いに接触しない条件の任意の配列において、絶縁層、ゲート電極、半導体層、ソース電極およびドレイン電極を配置することができる、薄膜トランジスタも提供される。
以下に記載される実施形態の詳細を記載する前に、一部の用語について定義または説明を行う。
電子輸送材料は、光活性層および電子輸送層のホスト材料として使用されている。Al、GaまたはZrなどのキノリン配位子の金属錯体に基づく電子輸送材料がこれらの用途で使用されている。しかしながら、いくつかの不都合がある。この錯体は、ホストとして使用される場合、低い大気安定性を有する可能性がある。そのような金属錯体を使用して製造された部品をプラズマ洗浄することは困難である。低いトリプレットエネルギーによって、>2.0eVエネルギーの燐光発光の消滅を導く。いくつかの実施形態において、本明細書に記載されるピリミジン化合物は、より高いトリプレットエネルギーを有する。本明細書に使用される場合、用語「ピリミジン化合物」は、化合物内に少なくとも1つの置換されたピリミジン基構造を有する化合物を意味することが意図される。
いくつかの実施形態において、本明細書に記載されるピリミジン化合物は、式I
R1〜R4は、同一であるか、または異なって、H、D、アルキル、シリル、アルコキシ、シアノまたはアリールであり、R1〜R4の少なくとも2つはアリール基であり、かつアリール基の少なくとも1つはN,O,S−複素環を含むが、ただし、R1〜R4の2つがN−カルバゾリル基を含む場合、R1〜R4の2つはアリールではない)を有する。
R7は、それぞれ、同一であるか、または異なって、D、アルキル、アリール、シリル、アルコキシ、シロキサン、シアノまたはN,O,S−複素環であるが、ただし、少なくとも1つのR7はN,O,S−複素環であり、
iは、それぞれ、同一であるか、または異なって、0〜4の整数であり、
jは、0〜5の整数であり、かつ
mは、1〜5の整数である)を有する。
R8は、上記で定義されたとおりである)を有する。式cによる基も重水素化されてもよい。
化合物1
いくつかの実施形態において、本明細書に記載されるピリミジン化合物は、式II
Qは、単結合または炭化水素アリールであり、かつ
R5およびR6は、それぞれ、同一であるか、または異なって、H、D、アルキル、シリル、アルコキシ、シアノまたはアリールであり、R5の少なくとも1つおよび少なくともR6の1つはアリール基であり、かつアリール基の少なくとも1つはN,O,S−複素環を含む)を有する。
化合物35
(a)式Iまたは式IIを有するピリミジン化合物であるホストと、(b)380〜750nmで発光極大を有するエレクトロルミネセンスが可能なドーパントとを含んでなる組成物も提供される。式IおよびIIのピリミジン化合物は、光活性材料のホスト材料として有用である。この化合物は、単独で、または別のホスト材料と組み合わせて使用することができる。式IおよびIIの化合物は、いずれの色の発光を有するドーパントのためのホストとしても使用することができる。いくつかの実施形態において、化合物を、有機金属エレクトロルミネセント材料のためのホストとして使用する。
(式中、
L1は、炭素および窒素によって配位するシクロメタレート化されたモノアニオン二座配位子であり、
L2は、炭素によって配位しないモノアニオン二座配位子であり、
L3は、単座配位子であり、
aは1〜3であり、
bおよびcは、独立して0〜2であり、そして
a、bおよびcは、イリジウムが六配位であり、錯体が電気的に中性であるように選択される)を有する錯体である。
Aは、それぞれ、同一であるか、または異なって、3〜60個の炭素原子を有する芳香族基であり、
Q’は、単結合または3〜60個の炭素原子を有する芳香族基であり、
pおよびqは、独立して、1〜6の整数である)から選択される。
Yは、それぞれ、同一であるか、または異なって、3〜60個の炭素原子を有する芳香族基であり、
Q’’は、芳香族基、二価トリフェニルアミン残基または単結合である)を有する。
本明細書に記載の重水素化材料を含んでなる1層またはそれ以上の層を有することから有益となり得る有機電子デバイスとしては、限定されないが、(1)電気エネルギーを放射線に変換するデバイス(例えば、発光ダイオード、発光ダイオードディスプレイ、発光照明器具、またはダイオードレーザー)、(2)電子的プロセスを介して信号を検出するデバイス(例えば、光検出器、光導電セル、フォトレジスタ、光スイッチ、光トランジスタ、光電管、IR検出器)、(3)放射線を電気エネルギーに変換するデバイス(例えば、光起電力デバイスまたは太陽電池)、ならびに(4)1つ以上の有機半導体層を含む1つ以上の電子部品を含むデバイス(例えば、薄膜トランジスタまたはダイオード)が挙げられる。発明の化合物は、バイオアッセイの酸素感応性インジケータおよびルミネセントインジケータなどの用途でしばしば有用となることが可能性である。
トランジスタの特に有用な種類である薄膜トランジスタ(TFT)は、一般に、ゲート電極、ゲート電極上のゲート誘電体、ソース電極、ゲート誘電体に隣接したドレイン電極、ならびにゲート誘電体に隣接し、そしてソースおよびドレイン電極に隣接する半導体層を含む(例えば、S.M.Sze,Physics of Semiconductor Devices,2nd edition,John Wiley and Sons,page 492を参照のこと)。これらの成分は、様々な構造で組み立てることができる。有機薄膜トランジスタ(OTFT)は、有機半導体層を有することを特徴とする。
基板と、
絶縁層と、
ゲート電極と、
ソース電極と、
ドレイン電極と、
式Iまたは式IIを有するピリミジン化合物を含んでなる有機半導体層と
を含んでなり、ゲート電極および半導体層が両方とも絶縁層と接触し、ソース電極およびドレイン電極が両方とも半導体層と接触し、そして電極は互いに接触しない条件の任意の配列において、絶縁層、ゲート電極、半導体層、ソース電極およびドレイン電極を配置することができる。
また本発明は、2層の電気接触層の間に配置される少なくとも1層の電気活性層を含んでなり、デバイスの少なくとも1層の電気活性層が、式Iまたは式IIを有するピリミジン化合物を含む電子デバイスに関する。
いくつかの実施形態において、光活性層240は、上記電気活性組成物を含んでなる。
式IおよびIIのピリミジン化合物は、層250の電子輸送材料として有用である。化合物は単独でも、別の電子輸送材料と組み合わせても使用することができる。いくつかの実施形態において、電子輸送層は、式IまたはIIのピリミジン化合物から本質的になる。
デバイスの他の層は、そのような層で有用であることが知られている任意の材料から製造することができる。
本実施例は、化合物1、5−[3−(4,6−ビス−(3−ビフェニル)−2−ピリミジニル)フェニル]ピリミジンの合成を説明する。
本実施例は、化合物28、2−[2’−(5’’−ピリミジル)−4’−ピリジル]−4,6−ビス−(3−ビフェニル)ピリミジンの合成を説明する。
本実施例は、化合物33、4,6−ジ([1,1’:3’,1’’−テルフェニル]−5’−イル)−2−(3−(ピリミジン−5−イル)フェニル)ピリミジン)の合成を説明する。
(a)材料
HIJ−1は、導電性ポリマーおよびポリマーフッ素化スルホン酸の水性分散系から堆積された正孔注入材料である。そのような材料は、例えば、米国特許出願公開第2004/0102577号明細書、同第2004/0127637号明細書および同第2005/0205860号明細書、ならびに国際公開第2009/018009号パンフレットに記載されている。
溶液処理および熱蒸発技術の組み合わせによってOLEDデバイスを製造した。Thin Film Devices,Incからのパターン化されたインジウムスズ酸化物(ITO)コーティングガラス基板を使用した。これらのITO基板は、30オーム/スクエアのシート抵抗および80%の光透過率を有するITOでコーティングされたCorning 1737ガラスをベースとした。パターン化されたITO基板を洗浄水溶液中で超音波によって洗浄し、蒸留水ですすいだ。その後、パターン化されたITOをアセトン中で超音波によって洗浄し、イソプロパノールですすぎ、そして窒素流中で乾燥させた。
OLED試料は、それらの(1)電流−電圧(I−V)曲線、(2)電圧に対するエレクトロルミネセンス放射輝度、および(3)電圧に対するエレクトロルミネセンススペクトルを測定することによって特徴決定した。3つの測定は全て同時に実行されて、コンピュータで制御された。特定の電圧でのデバイスの電流効率は、LEDのエレクトロルミネセンス放射輝度をデバイスを作動するために必要とされる電流密度で割ることによって決定する。単位はcd/Aである。色座標は、Minolta CS−100メーターまたはPhotoresearch PR705メーターのいずれかを使用して決定した。
本実施例は、本明細書に記載のピリミジン化合物が電子輸送層として存在するデバイスの性能を説明する。
正孔注入層=HIJ−1=50nm
正孔輸送層=HT−1=20nm
光活性層=H1:E1(重量比13:1)=40nm
電子輸送層(上記)=10nm
電子注入層/カソード=CsF/Al=1nm/100nm
デバイス実施例2において、デバイス実施例1を繰り返した。
Claims (11)
- R 2 およびR 4 が、ビフェニルまたはテルフェニルである、請求項1に記載の化合物。
- (a)請求項1から3のいずれか一項に記載の化合物であるホストと、
(b)380〜750nmで発光極大を有するエレクトロルミネセンスが可能なドーパントと
を含んでなる組成物。 - 請求項1から3のいずれか一項に記載の化合物を含んでなる少なくとも1層を有する電子デバイス。
- 前記デバイスが、
基板と、
絶縁層と、
ゲート電極と、
ソース電極と、
ドレイン電極と、
請求項1から3のいずれか一項に記載の化合物を含んでなる有機半導体層と
を含んでなる有機薄膜トランジスタであり、前記ゲート電極および前記半導体層が両方とも前記絶縁層と接触し、前記ソース電極および前記ドレイン電極が両方とも前記半導体層と接触し、かつ前記電極が互いに接触しない条件の任意の配列で、前記絶縁層、前記ゲート電極、前記半導体層、前記ソース電極および前記ドレイン電極を配置することができる、請求項5に記載のデバイス。 - デバイスが、2層の電気接触層の間に配置された少なくとも1層の電気活性層を含んでなり、前記デバイスの前記少なくとも1層の電気活性層が請求項1から3のいずれか一項に記載の化合物を含む、請求項5に記載のデバイス。
- デバイスが、アノードと、正孔注入層と、光活性層と、電子輸送層と、カソードとを含んでなり、前記光活性層および前記電子輸送層の少なくとも1層が請求項1から3のいずれか一項に記載の化合物を含んでなる、請求項5または7に記載のデバイス。
- 前記光活性層が、(a)請求項1から3のいずれか一項に記載の化合物を含むホスト材料と、(b)有機金属エレクトロルミネセントドーパントとを含んでなる、請求項8に記載のデバイス。
- 前記正孔注入層が、少なくとも1種の導電性ポリマーと、少なくとも1種のフッ素化酸ポリマーとを含んでなる、請求項8または9に記載のデバイス。
- 前記電子輸送層が、請求項1から3のいずれか一項に記載の化合物を含んでなる、請求項8または10に記載のデバイス。
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-
2011
- 2011-12-20 KR KR1020137019094A patent/KR101802008B1/ko active IP Right Grant
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- 2011-12-20 JP JP2013546348A patent/JP5926286B2/ja active Active
- 2011-12-20 EP EP11808526.5A patent/EP2655339A1/en not_active Withdrawn
- 2011-12-20 WO PCT/US2011/066313 patent/WO2012088192A1/en active Application Filing
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CN103261172A (zh) | 2013-08-21 |
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