TWI685517B - 有機電洞型導體的p-摻雜交聯及製造電洞導電層的方法 - Google Patents
有機電洞型導體的p-摻雜交聯及製造電洞導電層的方法 Download PDFInfo
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- TWI685517B TWI685517B TW104117887A TW104117887A TWI685517B TW I685517 B TWI685517 B TW I685517B TW 104117887 A TW104117887 A TW 104117887A TW 104117887 A TW104117887 A TW 104117887A TW I685517 B TWI685517 B TW I685517B
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- Prior art keywords
- ester
- fluoro
- benzoate
- organic
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- 238000000034 method Methods 0.000 title claims abstract description 68
- 239000004020 conductor Substances 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 238000004132 cross linking Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 239000011159 matrix material Substances 0.000 claims abstract description 78
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 77
- -1 polyethylene Polymers 0.000 claims abstract description 47
- 229910052751 metal Inorganic materials 0.000 claims abstract description 31
- 239000002184 metal Substances 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 239000013110 organic ligand Substances 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 239000011593 sulfur Substances 0.000 claims abstract description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002148 esters Chemical group 0.000 claims abstract description 5
- 125000003827 glycol group Chemical group 0.000 claims abstract description 5
- 229920000728 polyester Chemical group 0.000 claims abstract description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 5
- 229920002635 polyurethane Polymers 0.000 claims abstract description 5
- 239000004814 polyurethane Substances 0.000 claims abstract description 5
- 229920000131 polyvinylidene Polymers 0.000 claims abstract description 5
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 5
- 239000011669 selenium Substances 0.000 claims abstract description 5
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 4
- 239000004698 Polyethylene Substances 0.000 claims abstract description 4
- 125000004427 diamine group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 229920000573 polyethylene Polymers 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 239000003446 ligand Substances 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 20
- 229910052797 bismuth Inorganic materials 0.000 claims description 17
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 claims description 14
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 12
- 229910052718 tin Inorganic materials 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000005259 triarylamine group Chemical group 0.000 claims description 5
- GONAVIHGXFBTOZ-UHFFFAOYSA-M 3,5-difluorobenzoate Chemical group [O-]C(=O)C1=CC(F)=CC(F)=C1 GONAVIHGXFBTOZ-UHFFFAOYSA-M 0.000 claims description 4
- MXNBDFWNYRNIBH-UHFFFAOYSA-N 3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1 MXNBDFWNYRNIBH-UHFFFAOYSA-N 0.000 claims description 4
- BBYDXOIZLAWGSL-UHFFFAOYSA-M 4-fluorobenzoate Chemical compound [O-]C(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-M 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- YZERDTREOUSUHF-UHFFFAOYSA-N pentafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1F YZERDTREOUSUHF-UHFFFAOYSA-N 0.000 claims description 4
- 229940049953 phenylacetate Drugs 0.000 claims description 4
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 claims description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 4
- 229920000767 polyaniline Polymers 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- ONOTYLMNTZNAQZ-UHFFFAOYSA-M 2,6-difluorobenzoate Chemical compound [O-]C(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-M 0.000 claims description 3
- HVFQJWGYVXKLTE-UHFFFAOYSA-M 3,5-bis(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HVFQJWGYVXKLTE-UHFFFAOYSA-M 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
- 125000003106 haloaryl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- VSJNDQWKACYTLA-UHFFFAOYSA-N (2,3,4-trifluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C(F)=C1F VSJNDQWKACYTLA-UHFFFAOYSA-N 0.000 claims description 2
- ZSHSTELIHJUGOH-UHFFFAOYSA-N (2,3,5-trifluorophenyl) acetate Chemical compound CC(=O)OC1=CC(F)=CC(F)=C1F ZSHSTELIHJUGOH-UHFFFAOYSA-N 0.000 claims description 2
- OGVVICRXLPTVCW-UHFFFAOYSA-N (2,3,6-trifluorophenyl) acetate Chemical compound CC(=O)OC1=C(F)C=CC(F)=C1F OGVVICRXLPTVCW-UHFFFAOYSA-N 0.000 claims description 2
- YEEDHQQUIZYWJP-UHFFFAOYSA-N (2,3-difluorophenyl) acetate Chemical compound CC(=O)OC1=CC=CC(F)=C1F YEEDHQQUIZYWJP-UHFFFAOYSA-N 0.000 claims description 2
- HXZAPGHNNXEZLG-UHFFFAOYSA-N (2,4,6-trifluorophenyl) acetate Chemical compound CC(=O)OC1=C(F)C=C(F)C=C1F HXZAPGHNNXEZLG-UHFFFAOYSA-N 0.000 claims description 2
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- CTWQBKXPINCJIX-UHFFFAOYSA-N (2-chloro-4-fluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C=C1Cl CTWQBKXPINCJIX-UHFFFAOYSA-N 0.000 claims description 2
- PUNIIEHHUHGISF-UHFFFAOYSA-N (2-fluorophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1F PUNIIEHHUHGISF-UHFFFAOYSA-N 0.000 claims description 2
- KKTHQHSMMDWTAL-UHFFFAOYSA-N (3,4,5-trifluorophenyl) acetate Chemical compound CC(=O)OC1=CC(F)=C(F)C(F)=C1 KKTHQHSMMDWTAL-UHFFFAOYSA-N 0.000 claims description 2
- SCDFAHSIYYBVTF-UHFFFAOYSA-N (3,4-difluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C(F)=C1 SCDFAHSIYYBVTF-UHFFFAOYSA-N 0.000 claims description 2
- BYZBCKQMMCRZDV-UHFFFAOYSA-N (3,5-difluorophenyl) acetate Chemical compound CC(=O)OC1=CC(F)=CC(F)=C1 BYZBCKQMMCRZDV-UHFFFAOYSA-N 0.000 claims description 2
- IPSIPXOXHRSGTM-UHFFFAOYSA-N (3-chloro-4-fluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C(Cl)=C1 IPSIPXOXHRSGTM-UHFFFAOYSA-N 0.000 claims description 2
- IAWZWMGUTKRLQB-UHFFFAOYSA-N (3-fluorophenyl) acetate Chemical compound CC(=O)OC1=CC=CC(F)=C1 IAWZWMGUTKRLQB-UHFFFAOYSA-N 0.000 claims description 2
- ZNOREXRHKZXVPC-UHFFFAOYSA-N (4-fluorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(F)C=C1 ZNOREXRHKZXVPC-UHFFFAOYSA-N 0.000 claims description 2
- ZKUJOCJJXCPCFS-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)COC(=O)C(F)(F)F ZKUJOCJJXCPCFS-UHFFFAOYSA-N 0.000 claims description 2
- PMWGIVRHUIAIII-UHFFFAOYSA-N 2,2-difluoropropanoic acid Chemical compound CC(F)(F)C(O)=O PMWGIVRHUIAIII-UHFFFAOYSA-N 0.000 claims description 2
- SFKRXQKJTIYUAG-UHFFFAOYSA-M 2,3,4,5-tetrafluorobenzoate Chemical compound [O-]C(=O)C1=CC(F)=C(F)C(F)=C1F SFKRXQKJTIYUAG-UHFFFAOYSA-M 0.000 claims description 2
- WEPXLRANFJEOFZ-UHFFFAOYSA-M 2,3,4-trifluorobenzoate Chemical compound [O-]C(=O)C1=CC=C(F)C(F)=C1F WEPXLRANFJEOFZ-UHFFFAOYSA-M 0.000 claims description 2
- VSDRQVXQXFLZEG-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F VSDRQVXQXFLZEG-UHFFFAOYSA-N 0.000 claims description 2
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- AKAMNXFLKYKFOJ-UHFFFAOYSA-M 2,4,5-trifluorobenzoate Chemical compound [O-]C(=O)C1=CC(F)=C(F)C=C1F AKAMNXFLKYKFOJ-UHFFFAOYSA-M 0.000 claims description 2
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- NJYBIFYEWYWYAN-UHFFFAOYSA-M 2,4-difluorobenzoate Chemical compound [O-]C(=O)C1=CC=C(F)C=C1F NJYBIFYEWYWYAN-UHFFFAOYSA-M 0.000 claims description 2
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- FBRJYBGLCHWYOE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoic acid Chemical group OC(=O)C1=CC=CC=C1C(F)(F)F FBRJYBGLCHWYOE-UHFFFAOYSA-N 0.000 claims description 2
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 claims description 2
- CGFMLBSNHNWJAW-UHFFFAOYSA-M 2-chloro-4,5-difluorobenzoate Chemical compound [O-]C(=O)C1=CC(F)=C(F)C=C1Cl CGFMLBSNHNWJAW-UHFFFAOYSA-M 0.000 claims description 2
- XNTIGDVFBDJLTQ-UHFFFAOYSA-N 2-chloro-6-fluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1Cl XNTIGDVFBDJLTQ-UHFFFAOYSA-N 0.000 claims description 2
- LIFKXWNFWIUMJT-UHFFFAOYSA-M 2-fluoro-5-(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=CC(C(F)(F)F)=CC=C1F LIFKXWNFWIUMJT-UHFFFAOYSA-M 0.000 claims description 2
- LNARMXLVVGHCRP-UHFFFAOYSA-M 2-fluoro-6-(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=C(F)C=CC=C1C(F)(F)F LNARMXLVVGHCRP-UHFFFAOYSA-M 0.000 claims description 2
- NSTREUWFTAOOKS-UHFFFAOYSA-M 2-fluorobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-M 0.000 claims description 2
- FPENCTDAQQQKNY-UHFFFAOYSA-M 3,4-difluorobenzoate Chemical compound [O-]C(=O)C1=CC=C(F)C(F)=C1 FPENCTDAQQQKNY-UHFFFAOYSA-M 0.000 claims description 2
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- XUQCONCMPCVUDM-UHFFFAOYSA-M 3-fluoro-4-methylbenzoate Chemical group CC1=CC=C(C([O-])=O)C=C1F XUQCONCMPCVUDM-UHFFFAOYSA-M 0.000 claims description 2
- NSGKIIGVPBTOBF-UHFFFAOYSA-M 3-fluoro-5-(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=CC(F)=CC(C(F)(F)F)=C1 NSGKIIGVPBTOBF-UHFFFAOYSA-M 0.000 claims description 2
- GIAVHGFPMPSIFI-UHFFFAOYSA-N 3-hydroxy-2,4,6-triiodobenzoic acid Chemical group OC(=O)C1=C(I)C=C(I)C(O)=C1I GIAVHGFPMPSIFI-UHFFFAOYSA-N 0.000 claims description 2
- QKYZQKJXAKNEPA-UHFFFAOYSA-N 3-hydroxy-5-methyl-1-phenylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1N(O)C(=O)C=2C(C)=CSC=2N1C1=CC=CC=C1 QKYZQKJXAKNEPA-UHFFFAOYSA-N 0.000 claims description 2
- SWKPKONEIZGROQ-UHFFFAOYSA-M 4-(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=CC=C(C(F)(F)F)C=C1 SWKPKONEIZGROQ-UHFFFAOYSA-M 0.000 claims description 2
- LGDCSNDMFFFSHY-UHFFFAOYSA-N 4-butyl-n,n-diphenylaniline Polymers C1=CC(CCCC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 LGDCSNDMFFFSHY-UHFFFAOYSA-N 0.000 claims description 2
- PEPCYJSDHYMIFN-UHFFFAOYSA-M 4-chloro-2,5-difluorobenzoate Chemical compound [O-]C(=O)C1=CC(F)=C(Cl)C=C1F PEPCYJSDHYMIFN-UHFFFAOYSA-M 0.000 claims description 2
- JUHPDXOIGLHXTC-UHFFFAOYSA-M 4-fluoro-2-(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=CC=C(F)C=C1C(F)(F)F JUHPDXOIGLHXTC-UHFFFAOYSA-M 0.000 claims description 2
- WZBPZYCJUADXRS-UHFFFAOYSA-M 4-fluoro-3-(trifluoromethyl)benzoate Chemical compound [O-]C(=O)C1=CC=C(F)C(C(F)(F)F)=C1 WZBPZYCJUADXRS-UHFFFAOYSA-M 0.000 claims description 2
- JVBLXLBINTYFPR-UHFFFAOYSA-M 5-fluoro-2-methylbenzoate Chemical compound CC1=CC=C(F)C=C1C([O-])=O JVBLXLBINTYFPR-UHFFFAOYSA-M 0.000 claims description 2
- 125000006416 CBr Chemical group BrC* 0.000 claims description 2
- 125000006414 CCl Chemical group ClC* 0.000 claims description 2
- 101000606537 Homo sapiens Receptor-type tyrosine-protein phosphatase delta Proteins 0.000 claims description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 2
- 102100039666 Receptor-type tyrosine-protein phosphatase delta Human genes 0.000 claims description 2
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 claims description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- IRSJDVYTJUCXRV-UHFFFAOYSA-N ethyl 2-bromo-2,2-difluoroacetate Chemical compound CCOC(=O)C(F)(F)Br IRSJDVYTJUCXRV-UHFFFAOYSA-N 0.000 claims description 2
- VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 claims description 2
- AWUPLMYXZJKHEG-UHFFFAOYSA-N methyl 2-chloro-2,2-difluoroacetate Chemical compound COC(=O)C(F)(F)Cl AWUPLMYXZJKHEG-UHFFFAOYSA-N 0.000 claims description 2
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- VJMYKESYFHYUEQ-UHFFFAOYSA-M 3,4,5-trifluorobenzoate Chemical compound [O-]C(=O)C1=CC(F)=C(F)C(F)=C1 VJMYKESYFHYUEQ-UHFFFAOYSA-M 0.000 claims 2
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- WUHVJSONZHSDFC-UHFFFAOYSA-N ethyl 2-chloro-2-fluoroacetate Chemical compound CCOC(=O)C(F)Cl WUHVJSONZHSDFC-UHFFFAOYSA-N 0.000 claims 1
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- 239000002019 doping agent Substances 0.000 description 8
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Abstract
本發明係關於一種電洞導電層之製造方法,其中使一官能化有機基質化合物與至少一種交聯試劑在基材上反應形成分子量更高之化合物,其中該官能化有機基質化合物符合下式1
其中L係一鍵結或自包含下列之群組中選出:取代或未取代、飽和或不飽和之C1-C50烷基鏈、芳基鏈、聚乙二醇鏈、聚乙二胺鏈、聚酯鏈、聚胺基甲酸酯鏈、聚偏二苯乙烯鏈、或其混合物;E1、E2可各自獨立地為氧、硫、硒、NH或NE3,其中E3係選自包含取代或未取代烷基或芳基之群組,其中E3可與R鍵結;R係自包含下列之群組中選出:H、D、C1-C10烷基矽基酯或芳基矽基酯、氟化或未氟化的分枝或無分枝之C1-C10烷基、芳基或雜芳基,
RHTL為有機電洞型導體之骨架,及該交聯試劑包含至少一個選自第13至15族之金屬原子與至少一個有機配位子。
Description
本發明係關於一種電洞導電層之製造方法,其中使一官能化有機基質化合物與至少一種交聯試劑在基材上反應形成分子量更高之化合物,其中該官能化有機基質化合物符合下式1
其中L係一鍵結或自包含下列之群組中選出:取代或未取代、飽和或不飽和之C1-C50烷基鏈、芳基鏈、聚乙二醇鏈、聚乙二胺鏈、聚酯鏈、聚胺基甲酸酯鏈、聚偏二苯乙烯鏈、或其混合物;E1、E2可各自獨立地為氧、硫、硒、NH或NE3,其中E3係選自包含取代或未取代烷基或芳基之群組,其中E3可與R鍵結;R係自包含下列之群組中選出:H、D、C1-C10烷基矽基酯或芳基矽基酯、氟化或未氟化的分枝或無分枝之C1-C10烷基、芳基或雜芳基,RHTL為有機電洞型導體之骨架,及該交聯試劑包含至少一個選自第13至15族之金屬原子與至少一個有機配位子。
有機電子裝置之市售最重要的組件目前實質上係藉由兩種不同的製造方法來得到。其一係使用濕式法,於其中有機層係藉由從溶液沉積,通過不同的印刷技術來建構,例如噴墨印刷、凹版印刷、膠板印刷、旋塗法、狹縫式塗布。其次,可進一步藉由昇華,即在真空中熱蒸鍍,從氣相來進行層的沉積。到目前為止最有效率之市售可得的有機組件,例如有機發光二極體(參見第1圖)、太陽能電池(參見第2圖)、電晶體(參見第3圖)與雙極電晶體,係藉由昇華來製造。此種零件的效率特別係藉由以許多獨立層來建構它來達成,其中每個層係基於在零件中的位置而具有特定的電子功能。
藉由溶劑法製造之有機組件,現今在結構上仍具有明顯較低的複雜性。這是因為基於加工相關的要求,即沉積的有機層在進一步的加工步驟不允許被接下來的有機溶劑溶解。為了滿足此限制條件,因此在接下來的加工必須以正交的(即與前面的溶劑不相容的)溶劑來作業。這是因為藉此位在下面的層不會被再次溶解。此作業方式限制了可使用的溶劑與可加工之有機物質之數量,並因此限縮了能濕式加工之層序列的可能性與品質。
在製造有機組件中的任何電子功能(即阻隔性、n導電性或p導電性)的有機層時,特別是在製造高效率且耐久之p導電性層時,滿足上述限制條件為一大挑戰。這是考慮到要滿足的加工條件與合適的化合物之
選擇,由該化合物所建構成的組件必須顯示高功能性,同時具長使用壽命。
具p摻雜型電洞型導體之高效有機電子零件的製造方式之一係示於例如在DE102012209523。此專利說明書中揭示一種有機零件,其含有一種基質,其中該基質係含有一種第13至15族之主族金屬錯合物作為p型摻雜劑。此錯合物進一步含有至少一個以下結構之配位子L:
其中R1與R2可各自獨立地為氧、硫、硒、NH或NR4,其中R4係自包含烷基或芳基之群組中選出,並能與R3鍵結;及R3係自包含下列之群組中選出:烷基、長鏈烷基、烷氧基、長鏈烷氧基、環烷基、鹵烷基、芳基、伸芳基、鹵芳基、雜芳基、雜伸芳基、雜環伸烷基、雜環烷基、鹵雜芳基、烯基、鹵烯基、炔基、鹵炔基、酮芳基、鹵酮芳基、酮雜芳基、酮烷基、鹵酮烷基、酮烯基、鹵酮烯基,其中在適當的殘基中,一個以上不相鄰的CH2基可各自獨立地被-O-、-S-、-NH-、-NRo-、-SiRoRoo-、-CO-、-COO-、-OCO-、-OCO-O-、-SO2-、-S-CO-、-CO-S-、-CY1=CY2或-C≡C-取代,即O及/或S原子不直接彼此鍵結,也可以任選地被較佳含1至30個C原子之芳基或雜芳基來取代。
然而對於有機電子中之系統仍有進一步要求,即能夠簡單、可重複且穩定地由濕相與氣相進行加工並產生層,且由該層所製成之零件於在運作中產生的熱應力下能顯示提高的使用壽命。
因此本發明之課題係提供一種電洞傳導層之改良製造方法,其特別適用於濕式製造,且其中所產生的層具有提高的穩定性。此外還希望該方法之基本原理也能用於有機組件中的n導電層與電子阻隔層之製造。
此課題係藉由請求項第1項之特徵得解。本發明之特定實施形態則示於附屬項中。
本發明係一種電洞導電層之製造方法,其特徵為:使一官能化有機基質化合物與至少一種交聯試劑在基材上反應形成分子量更高的化合物,其中該官能化有機基質化合物符合下式1:
其中L為一鍵結或自包含下列之群組中選出:取代或未取代、飽和或不飽和之C1-C50烷基鏈、芳基鏈、聚乙二醇鏈,聚乙二胺鏈、聚酯鏈、聚胺基甲酸酯鏈、聚偏二苯乙烯鏈或混合物;E1、E2各自獨立地可為氧、硫、硒、NH或NE3,其中E3係選自包含取代或未取代之烷基或芳基之群組,其中E3可與R鍵結;
R係自包含下列之群組中選出:H、D、C1-C10烷基矽基酯或芳基矽基酯、氟化或未氟化的分枝或無分枝之C1-C10烷基、芳基或雜芳基,RHTL係有機電洞型導體之骨架,及該交聯試劑包含至少一個選自第13至15族之金屬原子與至少一個有機配位子。已發現藉由一本發明之含有至少一個選自第13至15族的金屬原子之交聯試劑與一本發明之有機電洞型導體之官能化骨架的反應,可得到經摻雜之電洞傳導層,其能夠簡單且可重複地被製造,且具有明顯提升的使用壽命。
1‧‧‧玻璃層
2‧‧‧聚矽氧層或氧化銦錫(ITO)層
3‧‧‧電洞注入層
4‧‧‧電洞傳輸層
5‧‧‧發光層
6‧‧‧電洞阻隔層
7‧‧‧電子傳輸層
8‧‧‧電子注入層
9‧‧‧陰極層
10‧‧‧有機發光二極體
20‧‧‧具PIN結構之有機太陽能電池
21‧‧‧光
22‧‧‧由氧化銦錫構成之層
23‧‧‧p型摻雜層
24‧‧‧吸收層
25‧‧‧n型摻雜層
26‧‧‧金屬層
30‧‧‧有機場效電晶體
31‧‧‧基材
32‧‧‧閘極
33‧‧‧閘極介電質
34+35‧‧‧源極/漏極接觸
36‧‧‧有機半導體
第1圖示意顯示有機發光二極體(10)之結構。
第2圖示意顯示具PIN結構之有機太陽能電池(20)的結構。
第3圖示意顯示有機場效電晶體(30)可能的截面圖。
本發明中「使...反應」係藉由上示中間步驟之一達成。這表示不一定總是必須在交聯劑上偶合3個官能化有機基質化合物。僅與一個有機基質化合物反應就已經能夠產生本發明之電洞型導體。藉由與官能化有機基質化合物反應,可以純粹在型式上把一個電子從有機基質化合物給到作為路易士酸功能的交聯劑上。藉由該給予在形式上改變金屬原子之氧化數。藉由此過程能夠使有機基質化合物中產生正電荷,其接下來能透過基質化合物的骨架與層的其他分子來非定域化。以此方式,藉由提高層可用的電荷載體之數量來得到或提升電洞電導率。
不受限於理論,藉由以交聯反應產生更穩固(鍵聯)之層結構能產生提升的層壽命,該層結構較不傾向於結晶而對溶劑與熱應力具有提高的穩定性,並因此有提高的壽命,同時具有更高的層導電率。其中先藉由交聯劑與官能化有機基質的反應對有機基質產生穩固的鍵結,其能夠明顯提升基質的電洞傳導性質。這能夠藉由在化學交聯反應中分離交聯試劑的至少一個配位子,並以有機基質化合物的官能基取代此配位位置來達成。此新的配位子現在依據本發明與有機電洞型導體的骨架共價地鍵聯。這不同於一般的作業方式,在一般的作業方式後不會得到摻雜劑的配位子與有機電洞型導體之共價鍵聯。特別是此處形成的較高分子量之錯合物能抵銷在交聯劑的反應後層的結晶傾向。此外,第13至15族的金屬原子在官能化有機基質化合物上穩固的鍵結,能使在濕式法的範疇內有更大的加工範圍。藉由該穩固的鍵結,消除了在施加其它層時必須以正交的溶劑加工之限制條件。即使金屬原子原本在原理上可溶於接下來的溶劑中,金屬原子在基質分子上穩固的錨定也避免了相同的溶析。藉此在濕式法的範疇中能使用更廣範圍的溶劑。即可能能夠直接為欲溶解之物質調整溶劑,並能忽視摻雜劑從已經加工過的基質溶析出來的風險。這使得加工有明顯更高的彈性。此外藉由此加工過程,能夠有明顯更大量不同的金屬錯合物併入基質中,因為由第13至15族金屬與有機配位子所構成之交聯錯合物不是從一開始就必須是傳統的電洞型導體用p型摻雜劑。特別
可以想見,此交聯劑與通常的有機基質分子不會顯現提高的電洞電導率。本發明特別可為:交聯劑在與官能化基質化合物反應一開始/反應後有助於層的電洞電導率之提升,因為藉由配位子的分離與透過官能化偶合有機基質的骨架,會首先形成新的摻雜之錯合物。當然還可以想到,此種交聯劑也已經能達成有機基質化合物的電洞電導率之(低)內在提升。然而藉由與官能化基質反應,相較於不進行反應之交聯劑,會使所產生的化合物之電洞電導率明顯更高,藉此層的電洞電導率也更高。不受限於理論,具至少一個第13至15族之金屬原子之錯合物特別適合與本發明之官能化基質化合物反應。這極有可能是因為這些依據本發明官能化之金屬,基於其大小與電學性質,顯示特別快速且完全之反應。這特別可導致特別有效率之製造與高功能之層。
此外,藉由摻雜劑鍵結至有機基質上,還可以想到結合了濕式法的元素與真空法的元素之製造方法。例如能夠透過氣相法來沉積由交聯劑與官能化有機基質化合物所構成之第一層,並在接下來的加工步驟藉由溶劑法施加另外的第二層。藉由交聯劑與有機基質化合物之反應,避免了第一層之摻雜經由施加溶劑而再被摧毀。
其中至少一個取代基R1-R5為有機電洞型導體之骨架,其係透過共價鍵鍵結在官能基上。反應不必一定要完全反應交聯試劑的所有配位子,也就是進行3次,也可以控制成僅取代1或2個配位子。
於上述範例中使用交聯劑與3個官能化有機基質化合物,其在此範例中係以羧酸基官能化(E1=E2=O,R=H)。官能化有機基質化合物在交聯劑排除配位子後能與交聯劑反應。藉此得到具較高分子量之化合物。藉由與官能化有機基質化合物反應,還得到具有電洞傳導性質之化合物。特別應注意,此種交聯劑必須不具p導電性質。提升p導電率之能力實質上係直到與官能化有機基質化合物反應後才產生。在此情形,原始交聯劑化合物的配位子係相當於溶劑。
交聯劑與官能化有機基質化合物在基材上進行反應形成分子量更高之化合物。其中可使用在有機電子領域常見之基材。其可為例如惰性基材像玻璃層、聚矽氧層或塑膠層。自然還會進一步討論到在先前以濕式法或昇華法施加之功能層。交聯劑與官能化有機基質化合物,係以官能化有機基質化合物成為交聯劑的配位層之至少一部分的方式進行反應,此處配位層特別是交聯
劑的金屬原子之配位層。其原理上於金屬原子進行配位子交換。藉由在交聯劑的金屬原子之配位層吸收有機基質化合物,達成交聯劑錯合物之分子量提升。這在縮合反應中,如上述範例所示,其中苯基配位子被分離出去成為苯。交聯劑與官能化有機基質化合物的反應能例如透過NMR光譜法來定量分析。因此例如以一般的1H-NMR,以及在以鉍作為交聯劑可能的組分之情形,以鉍NMR提供來測定定量反應。另外反應也可藉由電學方法或IR光譜法來尋求定量。
有機基質化合物係包含或是由下列所構成:有機電洞型導體之骨架(RHTL)與至少一個官能基。
於本發明之方法一較佳特徵中,有機電洞型導體的骨架RHTL可自包含下列之群組中選出:C20-C200三芳基胺系電洞型導體、其含噻吩之衍生物或其混合物。原則上所有行家熟知的電洞型導體均可使用來官能化。但特別可使用C20-C200三芳基胺系電洞型導體或含噻吩之衍生物。於本發明一較佳實施形態中,有機電洞型導體的骨架可選自C20-C500三芳基胺系電洞型導體。三芳基胺系電洞型導體的含噻吩衍生物之化合物一範例為例如N4,N4'-雙(二苯并[b,d]噻吩-4-基)-N4,N4'-二苯基聯苯-4,4'-二胺(DBTPB,Cas.-No.1203895-80-0)或其寡聚物或聚合物。
作為有機電洞型導體的官能化基質之骨架RHTL中的單元,例如可為下列化合物或這些化合物之混合物:
NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)-聯苯胺)、β-NPB N,N'-雙(萘-2-基)-N,N'-雙(苯基)-聯苯胺)、TPD(N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-聯苯胺)、螺TPD(N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-聯苯胺)、螺-NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)螺)、DMFL-TPD N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二甲基茀)、DMFL-NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二甲基茀)、DPFL-TPD(N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二苯基茀)、DPFL-NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二苯基茀)、螺-TAD(2,2',7,7'-肆(N,N-二苯基胺基)-9,9'-螺聯茀)、9,9-雙[4-(N,N-雙-聯苯-4-基胺基)苯基]-9H-茀、9,9-雙[4-(N,N-雙-萘-2-基胺基)苯基]-9H-茀、9,9-雙[4-(N,N'-雙-萘-2-基-N,N'-雙-苯基-胺基)-苯基]-9H-茀、N,N'-雙(菲-9-基)-N,N'-雙(苯基)-聯苯胺、2,7-雙[N,N-雙(9,9-螺聯茀-2-基)-胺基]-9,9-螺聯茀、2,2'-雙[N,N-雙(聯苯-4-基)胺基]9,9-螺聯茀、2,2'-雙(N,N-二苯基-胺基)9,9-螺聯茀、二-[4-(N,N-二甲苯基-胺基)-苯基]環己烷、
2,2',7,7'-四(N,N-二甲苯基)胺基-螺聯茀、N,N,N',N'-四萘-2-基-聯苯胺。這些化合物也能以寡聚物或聚合物型態來使用。較佳為其中的寡聚物或聚合物可具有大於等於300Da且小於等於500000Da之分子量,更進一步為大於等於1000Da且小於等於250000Da。例如上述電洞型導體骨架RHTL在此分子量範圍特別合適,並已證實可用於本發明之交聯。有機電洞型導體之分子量能得自常用來測定分子量之方法。於此提出的是重量平均分子量,其可例如藉由GPC、黏度測定法或其他流變方法來測定。此外,也能以光散射來測定分子量。
此有機基質化合物的骨架可在其骨架的任何能取代之位置有官能基。原理上此骨架可具有多於一個的取代基。特別可為有利的,係有機基質化合物在每個骨架具有0.01-10個可交聯之官能基,較佳為0.05-5個,更佳為0.1-1個。特別較佳為官能化有機基質化合物帶有一個官能基。
交聯試劑包含或係由下列所構成:自第13至15族選出之金屬原子與至少一個能以本發明之官能基分離之有機配位子。與多個官能化骨架之交聯能發生自2個可分離之配位子,其中僅與一個官能化骨架簡單鍵結之交聯劑也是符合本發明的。
術語「自第13至15族選出之金屬原子」係理解為1t.IUPAC第13至15族的金屬,即鋁、鎵、銦、矽、鍺、錫、鉛、鉈、砷、銻、鉍或其混合物。較佳為第14與15族之金屬,即矽、鍺、錫、鉛、砷、銻、鉍。
交聯劑包含至少一個有機配位子。其中在本發明中配位子係低分子量有機分子,其可以不帶電或帶電,具有最多250道耳頓之分子量。其中該低分子量有機分子可為脂族及芳族,具有雜原子例如氧或硫,為環狀或直鏈。
於本發明中名詞「p型摻雜劑」係包含或意指特別為具有路易士酸度之材料,及/或在與基質材料形成錯合物時此材料能發揮路易士酸的作用(即便只是形式上)。
此外作為官能化有機基質化合物的連結基L,可為例如:a.脂族鏈,如-(CH2)n-R,其中n=1-20,較佳n=1-5;b.氟化烷基鏈,於鏈中具1-12個碳原子,特佳為6-10個碳原子;c.不飽和烷基鏈,具1-20個碳原子與共軛或非共軛雙鍵;d.不飽和烷基鏈,具1-20個碳原子與共軛或非共軛三鍵,也與芳烴組合;e.也可使用下列來替代烷基鏈:聚乙二醇鏈、聚乙二胺鏈、聚酯鏈、聚胺基甲酸酯鏈、聚偏二苯乙烯鏈;f.含有用於導電性偶合的芳烴或多烯之鏈;g.由a-g構成之混合變體。
於本發明之方法一特定實施形態中,式1的E1與E2可為氧。羧酸或羧酸鹽已被證實特別適合於本發
明之方法的範疇中與本發明可使用之交聯劑反應。特別是以羧酸或羧酸鹽作為有機基質化合物之官能基,能藉由與交聯劑反應產生特別是對溫度與對溶劑穩定之層。不限制於理論,其中產生一種金屬-羧酸鹽錯合物,其為路易士酸活性並能特別良好地與有機基質化合物的骨架交互作用。藉此能得到特別穩定的p導電層,於其中金屬原子特別穩固地(因為配位)鍵結在有機基質化合物上,使得例如在進一步的濕式法中沒有摻雜劑會自上述層析出。此外,要能夠快速且完整的與交聯劑反應,以羧酸酯與羧酸作為官能基顯然是特別適合的。
於本發明之方法另一組態,交聯試劑可包含從由鉍、錫、鉛或其混合物所構成之群組選出之金屬原子。已發現,特別是鉍、錫與鉛或其混合物能夠快速且完整地與官能化有機基質化合物反應並以此形成較高分子量之化合物。因此,這些金屬原子之後藉由其他溶劑也只能困難地從有機基質化合物移除。這使得本發明之層能有更佳的製造性,藉由例如濕式法。此外這些金屬原子藉由其在較高分子量的錯合物中的電子組態與路易士酸度,促使所產生的層有特別良好的電洞傳導性。
於本發明之方法另一實施可能中,交聯試劑可包含鉍或錫,且交聯試劑至少一個配位子可自包含下列之群組中選出:取代或未取代C1-C200芳基、烷基、烷氧基、環烷基、伸芳基、鹵芳基、雜芳基、雜伸芳基、雜環伸烷基、雜環烷基、鹵雜芳基、烯基、鹵烯基、炔基、鹵炔基、酮芳基、鹵酮芳基、酮雜芳基、酮烷基、
鹵酮烷基、酮烯基、鹵酮烯基,其中在適當的殘基中,一個以上不相鄰的CH2基可各自獨立地以-O-、-S-、-NH-、-NRo-、-SiRoRoo-、-CO-、-COO-、-OCO-、-OCO-O-、-SO2-、-S-CO-、-CO-S-、-C=C-或-C≡C-加以取代,即O及/或S原子不直接彼此鍵結。特別是錫與鉍基於其可得性、環境友善性與其電子性質已被證實特別適用於p導電層之製造。此外特別是具所列取代基的這些金屬之錯合物可產生一種交聯劑,其特別快速與完整地與本發明之官能化有機基質分子反應。藉此能得到特別穩定之p導電層。不限制於理論,藉由取代基的特定立體與電子組態,與官能化基質化合物產生快速且完整的反應。此外這些取代基也會導致交聯劑有適當的路易士酸度,該酸度還有助於交聯劑與官能化有機基質化合物快速與完整的反應。上述配位子特別可為能藉由與官能化有機基質反應從交聯試劑分離出來之配位子。
於本發明之方法另一組態中,有機電洞型導體的骨架可自包含下列之群組或由下列所構成之群組中選出:PEDOT(聚(3,4-伸乙基二氧噻吩))、PVK(聚(9-乙烯咔唑))、PTPD(聚(N,N‘-雙(4-丁基苯基)-N,N‘-雙(苯基)聯苯胺)、PANI(聚苯胺)、P3HT(聚(3-己基噻吩))或其混合物。已發現,於本發明之方法的範疇中在有機電洞型導體上的這些基特別能被良好的處理。這對於在濕式法的範疇中的這些官能化骨架之交聯更是成立。這些以濕式法製成的p導電層可具有特別高的p導電性,且由此製成之層能透過本發明之交聯顯示特別長的壽命。
於本發明之方法另一組態中,有機電洞型導體的官能化基質之骨架RHTL中的單元係自下列化合物或這些化合物之混合物中選出:NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)-聯苯胺)、β-NPB(N,N'-雙(萘-2-基)-N,N'-雙(苯基)-聯苯胺)、TPD(N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-聯苯胺)、螺TPD(N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-聯苯胺)、螺-NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)-螺)、DMFL-TPD N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二甲基茀)、DMFL-NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二甲基茀)DPFL-TPD(N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二苯基茀)、DPFL-NPB(N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二苯基茀)、螺-TAD(2,2',7,7'-肆(N,N-二苯基胺基)-9,9’-螺聯茀)、9,9-雙[4-(N,N-雙-聯苯-4-基-胺基)苯基]-9H-茀、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-茀、9,9-雙[4-(N,N'-雙-萘-2-基-N,N'-雙-苯基-胺基)-苯基]-9H-茀、N,N'-雙(菲-9-基)-N,N'-雙(苯基)-聯苯胺、2,7-雙[N,N-雙(9,9-螺聯茀-2-基)-胺基]-9,9-螺聯茀、2,2'-雙[N,N-雙(聯苯-4-基)胺基]9,9-螺聯茀、2,2'-雙(N,N-二苯基胺基)9,9-螺聯茀、二[4-(N,N-二甲苯基胺基)-苯基]環己烷、2,2',7,7'-四(N,N-二甲苯基)胺基螺聯茀、N,N,N',N'-四萘-2-基-聯苯胺。於有機電洞型導體的骨架中這些單元顯示良好的電洞傳導性質,且還能依據本發明準確的官能化。可使用單體、單體混合物、單一種單體物種之寡聚物或聚合物、或者多種單體物種之寡聚物或聚合物。
於本發明之方法的另一組態中也可製造電子阻隔層。為此,自包含以下之群組或由以下所構成之群組中選出一種以上電子傳導性化合物依據本發明官能化,並與本發明之交聯劑一起反應係合適的:2,2',2"-(1,3,5-苯三基)-參(1-苯基-1-H-苯并咪唑)、2-(4-聯苯基)-5-(4-三級丁基苯基)-1,3,4-二唑、2,9-二甲基-4,7-二苯基-1,10-啡啉、8-羥基喹啉鋰、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、1,3-雙[2-(2,2'-聯吡啶-6-基)-1,3,4-二唑-5-基]苯、4,7-二苯基-1,10-啡啉、3-(4-聯苯基)-4-苯基-5-三級丁基苯基-1,2,4-三唑、雙(2-甲基-8-羥基喹啉-N1,O8)-4-(1,1’-聯苯-4羥基)鋁、6,6'-雙[5-(聯苯-4-基)-1,3,4-二唑-2-基]-2,2'-聯吡啶、2-苯基-9,10-二(萘-2-基)-蒽、2,7-雙[2-(2,2'-聯吡啶-6-基)-1,3,4-二唑-5-基]-9,9-二甲基茀、1,3-雙[2-(4-三級丁基苯)-1,3,4-二唑-5-基]苯、2-(萘-2-基)-4,7-二苯基-1,10-啡啉、2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡啉、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑[4,5-f][1,10]啡啉。以此方式可得到穩定的電子阻隔層。本方法能使用在濕式法之範疇與氣相沉積之範疇,並特別能使用於高效率OLED之製造。
依據本發明之方法的另一態樣,交聯試劑可含至少一個如下式2之取代基
其中n=0-20。此外,式2中各氟原子可各自獨立地以取代或未取代之雜環來取代。較佳為取代基可自如下列的取代與未取代之雜環中選出:呋喃、噻吩、吡咯、唑、噻唑、咪唑、異唑、異噻唑、吡唑、吡啶、吡、嘧啶、1,3,6-三、吡喃鎓、α-哌喃酮、γ-哌喃酮、苯并呋喃、苯并噻吩、吲哚、2H-異吲哚、苯并噻唑、2-苯并噻吩、1H-苯并咪唑、1H-苯并三唑、1,3-苯并唑、2-苯并呋喃、7H-嘌呤、喹啉、異喹啉、喹唑啉、喹啉、呔、1,2,4-苯并三、吡啶并[2,3-d]嘧啶、吡啶并[3,2-d]嘧啶、喋啶、吖啶、啡、苯并[g]喋啶、9H-咔唑與聯吡啶及其衍生物。此種結構之交聯試劑的至少一個配位子已證實特別適用於本發明之方法。不受限於理論,配位子改變金屬的路易士酸度,藉此能控制反應速度與反應完整度。於本發明一實施形態中,如式2之配位子的數量係限制於在金屬原子上最多2個配位子。
除了鉍以外,交聯試劑當然也可包含其他第13至15族之金屬。此外有機基質化合物顯示沒有連結基L。除了過氧化氫,當然也可為其他行家所熟知的氧化劑。藉由添加氧化劑能在適當情形對反應速率與反應率產生有利影響。
其中m為1至7的Ym可各自獨立地自包含下列之群組中選出:C-H、C-D、C-F、C-CF3、C-NO2、C-CN、C-Cl、C-Br、C-CN3、C-OCN、C-NCO、C-CNO、C-SCN、C-NCS、C-SeCN。這些交聯試劑上的配位子已證實特別適合與官能化有機基質化合物反應。這極有可能是基於其立體組態與藉由所選擇的取代基型式來控制交聯劑的路易士酸度之特殊能力。以此方式能控制反應速率與反應的完整性。
於本發明另一組態中,交聯試劑可包含鉍或錫,且其至少一個取代基係自包含下列之群組或由下列所構成之群組中選出:2,6-二氟苯甲酸酯、4-氟苯甲酸酯、3-氟苯甲酸酯、3,5-二氟苯甲酸酯、3,4,5-三氟苯甲
酸酯、3,5-雙(三氟甲基)苯甲酸酯、全氟苯甲酸酯、4-全氟甲苯甲酸酯或其混合物。
於本發明另一態樣中,交聯試劑可包含至少一個自包含下列之群組中選出之取代基:氟化苯甲酸酯,例如:2-(三氟甲基)苯甲酸酯;3,5-二氟苯甲酸酯;3-羥基-2,4,6-三碘苯甲酸酯;3-氟-4-甲基苯甲酸酯;3-(三氟甲氧基)苯甲酸酯;4-(三氟甲氧基)苯甲酸酯;4-氯-2,5-二氟苯甲酸酯;2-氯-4,5-二氟苯甲酸酯;2,4,5-三氟苯甲酸酯;2-氟苯甲酸酯;4-氟苯甲酸酯;2,3,4-三氟苯甲酸酯;2,3,5-三氟苯甲酸酯;2,3-二氟苯甲酸酯;2,4-雙(三氟甲基)苯甲酸酯;2,4-二氟苯甲酸酯;2,5-二氟苯甲酸酯;2,6-雙(三氟甲基)苯甲酸酯;2,6-二氟苯甲酸酯;2-氯-6-氟苯甲酸酯;2-氟-4-(三氟甲基)苯甲酸酯;2-氟-5-(三氟甲基)苯甲酸酯;2-氟-6-(三氟甲基)苯甲酸酯;3,4,5-三氟苯甲酸酯;3,4-二氟苯甲酸酯;3,5-雙(三氟甲基)苯甲酸酯;3-(三氟甲基)苯甲酸酯;3-氯-4-氟苯甲酸酯;3-氟-5-(三氟甲基)苯甲酸酯;3-氟苯甲酸酯;4-氟-2-(三氟甲基)苯甲酸酯;4-氟-3-(三氟甲基)苯甲酸酯;5-氟-2-甲基苯甲酸酯;2-(三氟甲氧基)苯甲酸酯;2,3,5-三氯苯甲酸酯;4-(三氟甲基)苯甲酸酯;五氟苯甲酸酯;2,3,4,5-四氟苯甲酸酯;2,3,5,6-四氟-4-(三氟甲基)苯甲酸酯;氟化或未氟化苯乙酸酯,例如:2-氟-苯乙酸酯;3-氟-苯乙酸酯;4-氟-苯乙酸酯;2,3-二氟-苯乙酸酯;2,4-二氟-苯乙酸酯;2,6-二氟-苯乙
酸酯;3,4-二氟-苯乙酸酯;3,5-二氟-苯乙酸酯;五氟苯乙酸酯;2-氯-6-氟-苯乙酸酯;2-氯-3,6-二氟-苯乙酸酯;3-氯-2,6-二氟-苯乙酸酯;3-氯-4-氟-苯乙酸酯;5-氯-2-氟-苯乙酸酯;2,3,4-三氟-苯乙酸酯;2,3,5-三氟-苯乙酸酯;2,3,6-三氟-苯乙酸酯;2,4,5-三氟-苯乙酸酯;2,4,6-三氟-苯乙酸酯;3,4,5-三氟-苯乙酸酯;3-氯-2-氟-苯乙酸酯;α-氟-苯乙酸酯;4-氯-2-氟-苯乙酸酯;2-氯-4-氟-苯乙酸酯;α,α-二氟-苯乙酸酯;2,2-二氟-2-苯基乙酸乙酯;氟化或未氟化乙酸酯,例如:三氟乙酸甲酯;三氟乙酸烯丙酯;三氟乙酸乙酯;三氟乙酸異丙酯;三氟乙酸2,2,2-三氟乙酯;二氟乙酸酯;三氟乙酸酯;二氟氯乙酸甲酯;二氟溴乙酸乙酯;二氟氯乙酸酯;氟氯乙酸乙酯;二氟乙酸乙酯;二氟乙酸(3-氯苯酯);二氟乙酸(3,5-二氟苯酯);二氟乙酸(4-丁基苯酯);二氟乙酸(4-三級丁基苯酯);二氟乙酸(3,4-二甲基苯酯);二氟乙酸(3-氯-4-氟苯酯);二氟乙酸(4-氯苯酯);3',5'-二氟乙酸-2-聯苯酯;3',5'-二氟乙酸-3-聯苯酯;3',5'-二氟乙酸-4-聯苯酯;3',4'-二氟乙酸-2-聯苯酯;3',4'-二氟乙酸-3-聯苯酯;3',4'-二氟乙酸-4-聯苯酯與2,2-二氟丙酸酯。
在交聯試劑上的這些配位子已被證實特別適用於快速反應。其能以短加工時間得到高效率的電洞傳導層。這些化合物之較高同系物也能使用。較佳為交聯劑的各配位子也可自上述化合物中選出。此外交聯試劑的各配位子僅為上述化合物之一也是有利的。
本發明之方法一較佳實施形態中,交聯試劑可為取代或未取代之三芳基鉍錯合物。特別是具伸芳基的交聯試劑(其含鉍)的配位子對稱的選擇者,已被證實係特別適合本發明之方法。不限制於理論,藉由對稱的選擇配位子特別能夠使芳基能特別容易被官能化有機基質化合物分離。此外較佳為作為脫離基係包含苯、甲苯或二甲苯,其也經常在濕式法中使用作為溶劑。
於本發明之方法的另一特徵中,官能化有機基質化合物可進一步包含比例大於等於0重量%且小於等於50重量%之未官能化基質化合物。在本發明之方法的組態中,不是全部量的有機基質化合物都被官能化,或是混入未官能化之基質化合物是有助益的。藉由此比例的未官能化有機基質化合物,可例如影響p導電層之測定性質,例如成長行為或結晶行為。較佳可添加大於等於0重量%且小於等於20重量%之非官能化有機基質化合物,更佳為大於等於0重量%且小於等於10重量%。
於本發明之方法的另一態樣中,交聯試劑與有機基質化合物能藉由在大於等於50℃且小於等於300℃之範圍內的溫度處理於基材上進行反應。為了交聯試劑與官能化有機基質化合物之確實且完全的反應,藉由在上述溫度範圍溫度處理帶來更快且完全的反應是有利的。此外這也可對加工經濟產生有利效果。此外,此溫度處理可在濕式法的範疇中使用來去除溶劑。以此方式,以低能量消耗達成溶劑之去除以及交聯之快速反應。
此外,依據本發明之有機電子零件,係包含至少一層依據本發明之方法製造的電洞導電層。特別是在有機電子零件中可特佳地安裝本發明之電洞傳導層。上述加工過程一方面能夠實現及最有效率且成本低之製造,另一方面藉由摻雜劑在有機基質上穩固的鍵結而得到特別耐久且抗溶劑之p導電層。這能有助於讓所得到的組件有高度可靠性與良好的再加工性。
依據本發明之方法製成之層特別可使用於如有機太陽能電池、有機電晶體、有機發光零件、有機發光二極體及/或有機發光電化學電池等等零件中。所述方法與可藉此製作之功能化層能相應地使用於吸收組件,如發光二極體或太陽能電池。本發明之方法特別也適用於雙極電晶體之製造。此方法相容於此組件的標準製造步驟,並能以此得到成本低、耐用且有效率之組件。
關於上述有機半導體組件之進一步優點與特徵,特此在本文中參照本發明之用途以及本發明之方法詳細說明。本發明之方法的本發明之特徵與優點,也可用於本發明之組件與本發明之用途,並被視為揭示,反之亦然。只要沒有特別排除,由至少二個說明書及/或申請專利範圍中揭示之特徵構成的所有組合也包含在本發明中。
上述本發明之性質、特徵與優點以及達成它們的方式,在本文中以下面實施例之說明而變得更清楚、更易於理解,該等實施例在本文中以圖式進一步說明。
下面依據圖式進一步說明用於有機電子之組件的層結構。圖式中顯示:第1圖示意顯示有機發光二極體(10)之結構。該發光二極體係由下列層所構成:玻璃層(1);聚矽氧層或氧化銦錫(ITO)層(2);電洞注入層(3);電洞傳輸層(HTL)(4);發光層(EML)(5);電洞阻隔層(HBL)(6);電子傳輸層(ETL)(7);電子注入層(8)與陰極層(9)。
第2圖示意顯示具PIN結構之有機太陽能電池(20)的結構,該PIN結構將光(21)轉化為電流。該太陽能電池係由下列層所組成:由氧化銦錫構成之層(22);p型摻雜層(23);吸收層(24);n型摻雜體(25)與金屬層(26)。
第3圖示意顯示有機場效電晶體(30)可能的截面圖。在基材(31)上施加有閘極(32)、閘極介電質(33)、源極/漏極接觸(34+35)與有機半導體(36)。陰影位置顯示接觸摻雜有助益之位置。
層的沉積與交聯能依序進行或在同一個作業步驟中進行。也可組合真空加工與濕式加工。下面提出幾個實施形態,其原理上可組合或可延伸:
a.在真空中與含Bi的交聯劑一起蒸鍍出羧酸官能化電洞型導體(寡聚物或低分子)。接下來使層在80~300℃回火。得到完全交聯。
b.在真空中單獨蒸鍍出羧酸官能化電洞型導體(寡聚物或低分子)。接下來使層暴露於交聯劑的蒸氣或溶液中,以接著藉由熱或光來開始交聯。
c.與交聯試劑一起自溶液沉積出羧酸官能化電洞型導體(寡聚物或低分子)。接下來使層在80~300℃回火。
d.單獨自溶液沉積出羧酸官能化電洞型導體(寡聚物或低分子)。接下來使層暴露於交聯劑的蒸氣或溶液中,以接著藉由熱或光來開始交聯。
雖然本發明以較佳實施例進一步詳細說明,但本發明不受限於揭示的實施例,在不脫離本發明之保護範圍內,行家能推衍出其他變化。
1‧‧‧玻璃層
2‧‧‧聚矽氧層或氧化銦錫(ITO)層
3‧‧‧電洞注入層
4‧‧‧電洞傳輸層
5‧‧‧發光層
6‧‧‧電洞阻隔層
7‧‧‧電子傳輸層
8‧‧‧電子注入層
9‧‧‧陰極層
10‧‧‧有機發光二極體
Claims (15)
- 一種電洞導電層之製造方法,其特徵為:使一官能化有機基質化合物與至少一種交聯試劑在基材上反應形成分子量更高的化合物,其中該官能化有機基質化合物符合下式1:
- 如請求項1之方法,其中式1中的E1與E2係氧。
- 如請求項1或2之方法,其中該交聯試劑係包含從由鉍、錫、鉛或其混合物所構成之群組中所選出的金屬原子。
- 如請求項1或2之方法,其中該交聯試劑係包含鉍或錫,且該交聯試劑的至少一個配位子係自包含下列之群組中選出:取代或未取代之C1-C200芳基、烷基、烷氧基、環烷基、伸芳基、鹵芳基、雜芳基、雜伸芳基、雜環伸烷基、雜環烷基、鹵雜芳基、烯基、鹵烯基、炔基、鹵炔基、酮芳基、鹵酮芳基、酮雜芳基、酮烷基、鹵酮烷基、酮烯基、鹵酮烯基,其中在適當的殘基中,一個以上不相鄰的CH2基可各自獨立地以-O-、-S-、-NH-、-CO-、-COO-、-OCO-、-OCO-O-、-SO2-、-S-CO-、-CO-S-、-C=C-或-C≡C-加以取代,即O及/或S原子不直接彼此鍵結。
- 如請求項1或2之方法,其中該有機電洞型導體的骨架係自包含下列之群組中選出:PEDOT(聚(3,4-伸乙基二氧噻吩))、PVK(聚(9-乙烯咔唑))、PTPD(聚(N,N‘-雙(4-丁基苯基)-N,N‘-雙(苯基)聯苯胺)、PANI(聚苯胺)、P3HT(聚(3-己基噻吩))或其混合物。
- 如請求項1或2之方法,其中該交聯試劑包含至少一個取代基,其係自包含下列之群組中選出:2-(三氟甲基)苯甲酸酯;3,5-二氟苯甲酸酯;3-羥基-2,4,6-三碘苯甲酸酯;3-氟-4-甲基苯甲酸酯;3-(三氟甲氧基)苯甲酸酯;4-(三氟甲氧基)苯甲酸酯;4-氯-2,5-二氟苯甲酸酯;2-氯-4,5-二氟苯甲酸酯;2,4,5-三氟苯甲酸酯;2-氟苯甲酸酯;4-氟苯甲酸酯;2,3,4-三氟苯甲酸酯;2,3,5-三氟苯甲酸酯;2,3-二氟苯甲酸酯;2,4-雙(三氟甲基)苯甲酸酯;2,4-二氟苯甲酸酯;2,5-二氟苯甲酸酯;2,6-雙(三氟甲基)苯甲酸酯;2,6-二氟苯甲酸酯;2-氯-6-氟苯甲酸酯;2-氟-4-(三氟甲基)苯甲酸酯;2-氟-5-(三氟甲基)苯甲酸酯;2-氟-6-(三氟甲基)苯甲酸酯;3,4,5-三氟苯甲酸酯;3,4-二氟苯甲酸酯;3,5-雙(三氟甲基)苯甲酸酯;3-(三氟甲基)苯甲酸酯;3-氯-4-氟苯甲酸酯;3-氟-5-(三氟甲基)苯甲酸酯;3-氟苯甲酸酯;4- 氟-2-(三氟甲基)苯甲酸酯;4-氟-3-(三氟甲基)苯甲酸酯;5-氟-2-甲基苯甲酸酯;2-(三氟甲氧基)苯甲酸酯;2,3,5-三氯苯甲酸酯;4-(三氟甲基)苯甲酸酯;五氟苯甲酸酯;2,3,4,5-四氟苯甲酸酯;2,3,5,6-四氟-4-(三氟甲基)苯甲酸酯;2-氟-苯乙酸酯;3-氟-苯乙酸酯;4-氟-苯乙酸酯;2,3-二氟-苯乙酸酯;2,4-二氟-苯乙酸酯;2,6-二氟-苯乙酸酯;3,4-二氟-苯乙酸酯;3,5-二氟-苯乙酸酯;五氟苯乙酸酯;2-氯-6-氟-苯乙酸酯;2-氯-3,6-二氟-苯乙酸酯;3-氯-2,6-二氟-苯乙酸酯;3-氯-4-氟-苯乙酸酯;5-氯-2-氟-苯乙酸酯;2,3,4-三氟-苯乙酸酯;2,3,5-三氟-苯乙酸酯;2,3,6-三氟-苯乙酸酯;2,4,5-三氟-苯乙酸酯;2,4,6-三氟-苯乙酸酯;3,4,5-三氟-苯乙酸酯;3-氯-2-氟-苯乙酸酯;α-氟-苯乙酸酯;4-氯-2-氟-苯乙酸酯;2-氯-4-氟-苯乙酸酯;α,α-二氟-苯乙酸酯;2,2-二氟-2-苯基乙酸乙酯;三氟乙酸甲酯;三氟乙酸烯丙酯;三氟乙酸乙酯;三氟乙酸異丙酯;三氟乙酸2,2,2-三氟乙酯;二氟乙酸酯;三氟乙酸酯;二氟氯乙酸甲酯;二氟溴乙酸乙酯;二氟氯乙酸酯;氟氯乙酸乙酯;二氟乙酸乙酯;二氟乙酸(3-氯苯酯);二氟乙酸(3,5-二氟苯酯);二氟乙酸(4-丁基苯酯);二氟乙酸(4-三級丁基苯酯);二氟乙酸(3,4-二甲基苯酯);二氟乙酸(3-氯-4-氟苯酯);二氟乙酸(4-氯苯酯);3',5'-二氟乙酸-2-聯苯酯;3',5'-二氟乙酸-3-聯苯酯;3',5'-二氟乙酸-4-聯苯酯;3',4'-二氟乙酸-2-聯苯酯; 3',4'-二氟乙酸-3-聯苯酯;3',4'-二氟乙酸-4-聯苯酯與2,2-二氟丙酸酯。
- 如請求項1或2之方法,其中該交聯試劑係包含鉍或錫,且其至少一個取代基係自包含下列之群組中選出:2,6-二氟苯甲酸酯、4-氟苯甲酸酯、3-氟苯甲酸酯、3,5-二氟苯甲酸酯、3,4,5-三氟苯甲酸酯、3,5-雙(三氟甲基)苯甲酸酯、全氟苯甲酸酯、4-全氟甲苯甲酸酯或其混合物。
- 如請求項1或2之方法,其中該有機電洞型導體的骨架RHTL係自包含下列之群組中選出:C20-C200三芳基胺系電洞型導體、其含噻吩之衍生物或其混合物。
- 如請求項1或2之方法,其中該交聯試劑係取代或未取代之三芳基鉍錯合物。
- 如請求項1或2之方法,其中該交聯試劑與該有機基質化合物係藉由在大於等於50℃且小於等於300℃之範圍的溫度處理而於基材上進行反應。
- 如請求項1或2之方法,其中該官能化有機基質化合物係進一步包含比例大於等於0重量%且小於等於50重量%之未官能化基質化合物。
- 一種包含至少一層電洞導電層之有機電子零件,其中該電洞導電層係以如請求項1至13中任一項之方法製成。
- 一種如請求項14之零件之用途,其係作為有機太陽能電池、有機電晶體、發光有機零件、有機發光二極體及/或有機發光電化學電池。
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