JP2018095587A - Tin chelate complex, method for producing the same, and transparent conductive film formed of tin chelate complex - Google Patents
Tin chelate complex, method for producing the same, and transparent conductive film formed of tin chelate complex Download PDFInfo
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- JP2018095587A JP2018095587A JP2016240984A JP2016240984A JP2018095587A JP 2018095587 A JP2018095587 A JP 2018095587A JP 2016240984 A JP2016240984 A JP 2016240984A JP 2016240984 A JP2016240984 A JP 2016240984A JP 2018095587 A JP2018095587 A JP 2018095587A
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- tin
- chelate complex
- tin chelate
- producing
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- -1 Tin chelate complex Chemical class 0.000 title claims abstract description 185
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 239000003446 ligand Substances 0.000 claims abstract description 21
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 claims abstract description 20
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 7
- 125000000962 organic group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 239000013522 chelant Substances 0.000 claims description 6
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 abstract description 28
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 abstract description 22
- 229910001887 tin oxide Inorganic materials 0.000 abstract description 22
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002123 temporal effect Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 6
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000004697 chelate complex Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- KHMOASUYFVRATF-UHFFFAOYSA-J tin(4+);tetrachloride;pentahydrate Chemical compound O.O.O.O.O.Cl[Sn](Cl)(Cl)Cl KHMOASUYFVRATF-UHFFFAOYSA-J 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000004549 pulsed laser deposition Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- MXGLXCNJJYLFKV-UHFFFAOYSA-N 2-chloroethenoxybenzene Chemical class ClC=COC1=CC=CC=C1 MXGLXCNJJYLFKV-UHFFFAOYSA-N 0.000 description 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 1
- LREQLEBVOXIEOM-UHFFFAOYSA-N 6-amino-2-methyl-2-heptanol Chemical compound CC(N)CCCC(C)(C)O LREQLEBVOXIEOM-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
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- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
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- 239000005354 aluminosilicate glass Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
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- 230000009920 chelation Effects 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
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- 125000003824 heptacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC7=CC=CC=C7C=C6C=C5C=C4C=C3C=C12)* 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明は、スズキレート錯体、その製造方法、およびスズキレート錯体から形成されてなる透明導電膜に関するものであり、更に詳しくは、種々の溶媒への溶解性、溶液の透明性、更に経時安定性に優れ、酸化スズ膜等の透明導電膜の形成材料として有用なスズキレート錯体、その製造方法、およびスズキレート錯体から形成されてなる透明導電膜に関するものである。 The present invention relates to a tin chelate complex, a method for producing the same, and a transparent conductive film formed from the tin chelate complex. More specifically, the present invention relates to solubility in various solvents, solution transparency, and stability over time. The present invention relates to a tin chelate complex useful as a material for forming a transparent conductive film such as a tin oxide film, a production method thereof, and a transparent conductive film formed from a tin chelate complex.
近年、透明導電膜の利用が高まっており、例えば、ディスプレイの大型化、太陽電池の高性能化、タッチパネル搭載電子機器の増加に伴って、透明導電膜が益々利用されている。金属酸化物系の透明導電膜としては、ITO、FTO、GZO、IGZO、AZO、ATO、BZO、ZnO、SnO2等が用いられるが、中でも耐熱性や耐酸・塩基性の点から酸化スズ系が有利であり、例えば、薄膜シリコン太陽電池、色素増感太陽電池、ペロブスカイト型太陽電池などで検討が進んでいる。 In recent years, the use of transparent conductive films has increased. For example, transparent conductive films have been increasingly used with the increase in the size of displays, the performance of solar cells, and the increase in electronic devices with touch panels. ITO, FTO, GZO, IGZO, AZO, ATO, BZO, ZnO, SnO 2 and the like are used as the metal oxide-based transparent conductive film. Among them, tin oxide-based is preferable from the viewpoint of heat resistance, acid resistance and basicity. For example, studies are progressing on thin film silicon solar cells, dye-sensitized solar cells, perovskite solar cells, and the like.
通常、酸化スズ膜はスパッタリングやパルスレーザー堆積法(PLD法)などの真空条件を必要とする方法(乾式法)で製膜されているため、サイズ制限やロールtoロールでの製膜が困難とされている。そこで、ロールtoロールでの製膜のために、金属源含有溶液を使う製膜法(湿式法)での酸化スズ膜の製膜が求められている。 Usually, tin oxide film is formed by a method (dry method) that requires vacuum conditions such as sputtering and pulsed laser deposition (PLD method). Has been. Thus, for film formation by roll-to-roll, there is a demand for film formation of a tin oxide film by a film formation method (wet method) using a metal source-containing solution.
現在、湿式法での酸化スズ膜作製には、酸化スズナノ微粒子溶液を用いた製膜が主に行われているが、酸化スズナノ微粒子を利用すると膜の機能発現のための他の元素の添加が難しくなるため、高機能な酸化スズ膜を製膜するにあたり、スズ溶液を出発原料とする酸化スズ膜作製が必要であり、これに適応するスズ化合物が必要となる。
湿式法の酸化スズ膜の製造においては、アルコールや水等の溶媒に溶解できるなどの理由のため、通常は塩化スズが出発原料として用いられ、塩化スズ以外のスズ化合物ではアルコールや水等への溶解が難しく、酸化スズ膜を形成するのに良好な原料とはならないのである(例えば、特許文献1を参照)。
Currently, the tin oxide film is prepared by wet method mainly using a tin oxide nanoparticle solution. However, when tin oxide nanoparticles are used, other elements can be added to develop the function of the film. Since it becomes difficult, when forming a highly functional tin oxide film, it is necessary to produce a tin oxide film using a tin solution as a starting material, and a tin compound adapted to this is required.
In the production of wet-type tin oxide films, tin chloride is usually used as a starting material because it can be dissolved in a solvent such as alcohol or water, and tin compounds other than tin chloride can be used for alcohol or water. It is difficult to dissolve and is not a good raw material for forming a tin oxide film (see, for example, Patent Document 1).
上述のとおり、スズ溶液を用いた酸化スズ膜の製造においては、アルコールや水等の溶媒に溶解できることから通常、塩化スズ(IV)を出発原料として用いられるが、使用する溶媒の種類によっては溶液の安定性が劣る場合があり、経時的に溶液が白濁することがある。従って、使用する溶媒の種類が制限されると、薄膜作製の工程において加工温度や目的物により溶媒を使い分けることなどが困難となり、薄膜作製の工程が制限されるおそれがある。
また、製膜後の酸化スズ膜中に塩素が残留してしまい、素子作製時に金属電極の腐食や性能悪化が危惧される。
As described above, in the production of a tin oxide film using a tin solution, tin (IV) chloride is usually used as a starting material because it can be dissolved in a solvent such as alcohol or water, but depending on the type of solvent used, May be inferior in stability, and the solution may become cloudy over time. Therefore, when the type of solvent to be used is limited, it becomes difficult to properly use the solvent depending on the processing temperature and the target in the thin film manufacturing process, which may limit the thin film manufacturing process.
In addition, chlorine remains in the tin oxide film after film formation, and there is a concern that the metal electrode is corroded and performance is deteriorated during device fabrication.
そこで、本発明はこのような背景下において、種々の溶媒への溶解性、溶液の透明性、更に経時安定性に優れ、酸化スズ膜等の透明導電膜の形成材料として有用なスズキレート錯体の提供を目的とするものである。 In view of the above, the present invention is based on such a background, and the tin chelate complex useful as a material for forming a transparent conductive film such as a tin oxide film is excellent in solubility in various solvents, solution transparency, and stability over time. It is for the purpose of provision.
しかるに、本発明者らが上記課題を解決すべく鋭意検討を行った結果、スズ溶液を作製するにあたり、水酸化スズに二座以上の配位子を反応させて、キレート構造を有するスズキレート錯体を形成することにより、種々の極性プロトン性溶媒(アルコール、水、酢酸等)に溶解可能であり、溶液の透明性に優れ、更に溶液が経時的に安定であり、透明導電膜の形成に有用な材料が得られることを見出し、本発明を完成した。 However, as a result of intensive studies by the present inventors to solve the above-mentioned problems, a tin chelate complex having a chelate structure by reacting tin hydroxide with a bidentate or more ligand in producing a tin solution. Can be dissolved in various polar protic solvents (alcohol, water, acetic acid, etc.), excellent in the transparency of the solution, and more stable over time, useful for the formation of transparent conductive films As a result, the present invention was completed.
すなわち、本発明の要旨は、下記一般式(1)で示されることを特徴とするスズキレート錯体である。
また、本発明は、水酸化スズ(A)を用いることを特徴とする、上記一般式(1)で示されるスズキレート錯体の製造方法にも関するものである。更に、本発明は、上記スズキレート錯体から形成されてなることを特徴とする透明導電膜にも関するものである。 Moreover, this invention relates to the manufacturing method of the tin chelate complex shown by the said General formula (1) characterized by using a tin hydroxide (A). Furthermore, this invention relates to the transparent conductive film characterized by being formed from the said tin chelate complex.
本発明のスズキレート錯体は、種々の溶媒への溶解性、溶液の透明性、更に経時安定性に優れ、酸化スズ膜等の透明導電膜の形成材料として有用である。また本発明のスズキレート錯体から形成されてなる透明導電膜は膜の均質性に優れる。更に、本発明のスズキレート錯体の製造方法によれば、本発明のスズキレート錯体を効率的に製造することができる。 The tin chelate complex of the present invention has excellent solubility in various solvents, solution transparency, and stability over time, and is useful as a material for forming a transparent conductive film such as a tin oxide film. The transparent conductive film formed from the tin chelate complex of the present invention is excellent in film uniformity. Furthermore, according to the method for producing a tin chelate complex of the present invention, the tin chelate complex of the present invention can be efficiently produced.
以下、本発明の構成につき詳細に説明するが、これらは望ましい実施態様の一例を示すものであり、本発明はこれらの内容に特定されるものではない。 Hereinafter, although it demonstrates in detail about the structure of this invention, these show an example of a desirable embodiment, and this invention is not specified by these content.
<スズキレート錯体>
本発明のスズキレート錯体は下記一般式(1)で示されるスズキレート錯体である。
The tin chelate complex of the present invention is a tin chelate complex represented by the following general formula (1).
式中、R1はヘテロ環中のNとOを結合する結合鎖である。結合鎖の主鎖の原子数は1〜20であり、好ましくは1〜15、特に好ましくは1〜10である。かかる原子数が多すぎると、キレート構造を形成し難くなる傾向がある。
かかる結合鎖を構成する原子としては、例えば、炭素、水素、酸素、窒素の各原子が挙げられる。原子数が1〜20の結合鎖としては、例えば、炭素原子が1、水素原子が2で、原子数が3のメチレン基、炭素原子が2、水素原子が4で、原子数が6のエチレン基などが挙げられる。
R1の結合鎖は側鎖を有していても良い。かかる側鎖としては、例えば、下記R2の説明で記載されている有機基と同様の有機基等が挙げられ、当該有機基等のうち特に原子数が10以下のものが好適に挙げられる。
In the formula, R 1 is a bond chain that bonds N and O in the heterocycle. The number of atoms in the main chain of the bonding chain is 1 to 20, preferably 1 to 15, particularly preferably 1 to 10. When there are too many such atoms, it tends to be difficult to form a chelate structure.
Examples of the atoms constituting such a bond chain include carbon, hydrogen, oxygen, and nitrogen atoms. Examples of the bond chain having 1 to 20 atoms include ethylene having 1 carbon atom, 2 hydrogen atoms, 3 methylene groups, 2 carbon atoms, 4 hydrogen atoms, and 6 atoms. Group and the like.
The bonding chain of R 1 may have a side chain. Examples of such a side chain include organic groups similar to the organic groups described in the description of R 2 below. Among these organic groups, those having 10 or less atoms are particularly preferable.
式中、R2は水素原子または有機基であり、かかる有機基としては、特に限定しないが、例えば、アルキル基、アリール基、複素環基、アルコキシル基、アルキルチオ基、アリールチオ基、ニトロ基、シアノ基、チオシアン酸基、イソチオシアン酸基、アミノ基、モノアルキルアミノ基、ジアルキルアミノ基、アリールオキシ基、モノアリールアミノ基、ジアリールアミノ基、アルキルカルボニル基(アシル基)、アリールカルボニル基、スルホン酸アミド基、スルホン酸エステル基、フタルイミドメチル基等が挙げられる。 In the formula, R 2 is a hydrogen atom or an organic group, and such an organic group is not particularly limited, and examples thereof include an alkyl group, an aryl group, a heterocyclic group, an alkoxyl group, an alkylthio group, an arylthio group, a nitro group, and a cyano group. Group, thiocyanic acid group, isothiocyanic acid group, amino group, monoalkylamino group, dialkylamino group, aryloxy group, monoarylamino group, diarylamino group, alkylcarbonyl group (acyl group), arylcarbonyl group, sulfonic acid amide Group, sulfonic acid ester group, phthalimidomethyl group and the like.
アルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ネオペンチル基、tert−ペンチル基、ヘキシル基、イソヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等が挙げられ、好ましくはメチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基等の炭素数1〜4のアルキル基である。 Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, and isohexyl. Group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group And a cyclohexyl group, preferably an alkyl group having 1 to 4 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group and tert-butyl group.
アリール基としては、例えば、フェニル基、ビフェニリル基、ターフェニリル基、クオーターフェニリル基、o−、m−、およびp−トリル基、キシリル基、o−、m−、およびp−クメニル基、メシチル基、ペンタレニル基、インデニル基、ナフチル基、ビナフタレニル基、ターナフタレニル基、クオーターナフタレニル基、アズレニル基、ヘプタレニル基、ビフェニレニル基、インダセニル基、フルオランテニル基、アセナフチレニル基、アセアントリレニル基、フェナレニル基、フルオレニル基、アントリル基、ビアントラセニル基、ターアントラセニル基、クオーターアントラセニル基、アントラキノリル基、フェナントリル基、トリフェニレニル基、ピレニル基、クリセニル基、ナフタセニル基、プレイアデニル基、ピセニル基、ペリレニル基、ペンタフェニル基、ペンタセニル基、テトラフェニレニル基、ヘキサフェニル基、ヘキサセニル基、ルビセニル基、コロネニル基、トリナフチレニル基、ヘプタフェニル基、ヘプタセニル基、ピラントレニル基、オバレニル基等が挙げられる。 Examples of the aryl group include a phenyl group, a biphenylyl group, a terphenylyl group, a quarterphenylyl group, an o-, m-, and p-tolyl group, a xylyl group, an o-, m-, and a p-cumenyl group, and a mesityl group. , Pentarenyl group, indenyl group, naphthyl group, binaphthalenyl group, turnaphthalenyl group, quarternaphthalenyl group, azulenyl group, heptaenyl group, biphenylenyl group, indacenyl group, fluoranthenyl group, acenaphthylenyl group, aceanthrylenyl group, phenalenyl group, Fluorenyl group, anthryl group, bianthracenyl group, teranthracenyl group, quarteranthracenyl group, anthraquinolyl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, preadenyl group, picenyl group, Rireniru group, pentaphenyl group, pentacenyl group, tetraphenylenyl les group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl groups, trinaphthylenyl groups, heptacenyl groups, pyranthrenyl groups, ovalenyl group and the like.
複素環基としては、例えば、チエニル基、ベンゾ[b]チエニル基、ナフト[2, 3−b]チエニル基、チアントレニル基、フリル基、ピラニル基、イソベンゾフラニル基、クロメニル基、キサンテニル基、フェノキサチイニル基、2H−ピロリル基、ピロリル基、イミダゾリル基、ピラゾリル基、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、インドリジニル基、イソインドリル基、3H−インドリル基、インドリル基、1H−インダゾリル基、プリニル基、4H−キノリジニル基、イソキノリル基、キノリル基、フタラジニル基、ナフチリジニル基、キノキサニリル基、キナゾリニル基、シンノリニル基、プテリジニル基、4aH−カルバゾリル基、カルバゾリル基、β−カルボリニル基、フェナントリジニル基、アクリジニル基、ペリミジニル基、フェナントロリニル基、フェナジニル基、フェナルサジニル基、イソチアゾリル基、フェノチアジニル基、イソキサゾリル基、フラザニル基、フェノキサジニル基、イソクロマニル基、クロマニル基、ピロリジニル基、ピロリニル基、イミダゾリジニル基、イミダゾリニル基、ピラゾリジニル基、ピラゾリニル基、ピペリジル基、ピペラジニル基、インドリニル基、イソインドリニル基、キヌクリジニル基、モルホリニル基等が挙げられる。 Examples of the heterocyclic group include thienyl group, benzo [b] thienyl group, naphtho [2,3-b] thienyl group, thiantenyl group, furyl group, pyranyl group, isobenzofuranyl group, chromenyl group, xanthenyl group, Phenoxathiinyl group, 2H-pyrrolyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolizinyl group, isoindolyl group, 3H-indolyl group, indolyl group, 1H-indazolyl group , Purinyl group, 4H-quinolidinyl group, isoquinolyl group, quinolyl group, phthalazinyl group, naphthyridinyl group, quinoxanilyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, 4aH-carbazolyl group, carbazolyl group, β-carbolinyl group, phenanthridinyl group Group, Acry Zinyl, perimidinyl, phenanthrolinyl, phenazinyl, phenalsadinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, phenoxazinyl, isochromanyl, chromanyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl Group, pyrazolidinyl group, pyrazolinyl group, piperidyl group, piperazinyl group, indolinyl group, isoindolinyl group, quinuclidinyl group, morpholinyl group and the like.
アルコキシル基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基、イソプロポキシ基、イソブトキシ基、sec−ブトキシ基、tert−ブトキシ基、ペンチルオキシ基、ヘキシルオキシ基、イソペンチルオキシ基等が挙げられる。 Examples of the alkoxyl group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, an isopropoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, and an isopentyloxy group. Can be mentioned.
アルキルチオ基としては、例えば、メチルチオ基、エチルチオ基、プロピルチオ基、ブチルチオ基、イソプロピルチオ基、イソブチルチオ基、sec-ブチルチオ基、tert−ブチルチオ基、ペンチルチオ基、ヘキシルチオ基、イソペンチルチオ基等が挙げられる。 Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, an isopropylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, and an isopentylthio group. It is done.
アリールチオ基としては、例えば、フェニルチオ基、1−ナフチルチオ基、2−ナフチルチオ基、9−アンスリルチオ基、9−フェナントリルチオ基が挙げられる。 Examples of the arylthio group include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a 9-anthrylthio group, and a 9-phenanthrylthio group.
モノアルキルアミノ基としては、例えば、メチルアミノ基、エチルアミノ基、プロピルアミノ基、ブチルアミノ基、ペンチルアミノ基、ヘキシルアミノ基、ヘプチルアミノ基、オクチルアミノ基、ノニルアミノ基、デシルアミノ基、ドデシルアミノ基、オクタデシルアミノ基、イソプロピルアミノ基、イソブチルアミノ基、イソペンチルアミノ基、sec−ブチルアミノ基、tert−ブチルアミノ基、sec−ペンチルアミノ基、tert−ペンチルアミノ基、tert−オクチルアミノ基、ネオペンチルアミノ基、シクロプロピルアミノ基、シクロブチルアミノ基、シクロペンチルアミノ基、シクロヘキシルアミノ基、シクロヘプチルアミノ基、シクロオクチルアミノ基、シクロドデシルアミノ基、1−アダマンタミノ基、2−アダマンタミノ基等が挙げられる。 Examples of the monoalkylamino group include a methylamino group, an ethylamino group, a propylamino group, a butylamino group, a pentylamino group, a hexylamino group, a heptylamino group, an octylamino group, a nonylamino group, a decylamino group, and a dodecylamino group. , Octadecylamino group, isopropylamino group, isobutylamino group, isopentylamino group, sec-butylamino group, tert-butylamino group, sec-pentylamino group, tert-pentylamino group, tert-octylamino group, neopentyl Amino group, cyclopropylamino group, cyclobutylamino group, cyclopentylamino group, cyclohexylamino group, cycloheptylamino group, cyclooctylamino group, cyclododecylamino group, 1-adamantamino group, 2-adamantamino group and the like can be mentioned.
ジアルキルアミノ基としては、例えば、ジメチルアミノ基、ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミノ基、ジペンチルアミノ基、ジヘキシルアミノ基、ジヘプチルアミノ基、ジオクチルアミノ基、ジノニルアミノ基、ジデシルアミノ基、ジドデシルアミノ基、ジオクタデシルアミノ基、ジイソプロピルアミノ基、ジイソブチルアミノ基、ジイソペンチルアミノ基、メチルエチルアミノ基、メチルプロピルアミノ基、メチルブチルアミノ基、メチルイソブチルアミノ基、シクロプロピルアミノ基、ピロリジノ基、ピペリジノ基、ピペラジノ基等が挙げられる。 Examples of the dialkylamino group include dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group, dipentylamino group, dihexylamino group, diheptylamino group, dioctylamino group, dinonylamino group, didecylamino group, didodecylamino group. Group, dioctadecylamino group, diisopropylamino group, diisobutylamino group, diisopentylamino group, methylethylamino group, methylpropylamino group, methylbutylamino group, methylisobutylamino group, cyclopropylamino group, pyrrolidino group, piperidino group Group, piperazino group and the like.
アリールオキシ基としては、例えば、フェニルオキシ基、ビフェニリルオキシ基、ターフェニリルオキシ基、クオーターフェニリルオキシ基、o−、m−、およびp−トリルオキシ基、キシリルオキシ基、o−、m−、およびp−クメニルオキシ基、メシチルオキシ基、ペンタレニルオキシ基、インデニルオキシ基、ナフチルオキシ基、ビナフタレニルオキシ基、ターナフタレニルオキシ基、クオーターナフタレニルオキシ基、アズレニルオキシ基、ヘプタレニルオキシ基、ビフェニレニルオキシ基、インダセニルオキシ基、フルオランテニルオキシ基、アセナフチレニルオキシ基、アセアントリレニルオキシ基、フェナレニルオキシ基、フルオレニルオキシ基、アントリルオキシ基、ビアントラセニルオキシ基、ターアントラセニルオキシ基、クオーターアントラセニルオキシ基、アントラキノリルオキシ基、フェナントリルオキシ基、トリフェニレニルオキシ基、ピレニルオキシ基、クリセニルオキシ基、ナフタセニルオキシ基、プレイアデニルオキシ基、ピセニルオキシ基、ペリレニルオキシ基、ペンタフェニルオキシ基、ペンタセニルオキシ基、テトラフェニレニルオキシ基、ヘキサフェニルオキシ基、ヘキサセニルオキシ基、ルビセニルオキシ基、コロネニルオキシ基、トリナフチレニルオキシ基、ヘプタフェニルオキシ基、ヘプタセニルオキシ基、ピラントレニルオキシ基、オバレニルオキシ基等が挙げられる。 Examples of the aryloxy group include phenyloxy group, biphenylyloxy group, terphenylyloxy group, quarterphenylyloxy group, o-, m-, and p-tolyloxy group, xylyloxy group, o-, m-, And p-cumenyloxy group, mesityloxy group, pentarenyloxy group, indenyloxy group, naphthyloxy group, binaphthalenyloxy group, tarnaphthalenyloxy group, quarternaphthalenyloxy group, azulenyloxy group, heptare Nyloxy group, biphenylenyloxy group, indacenyloxy group, fluoranthenyloxy group, acenaphthylenyloxy group, aceanthrylenyloxy group, phenalenyloxy group, fluorenyloxy group, anthryloxy Group, bianthracenyloxy group, teranthracenyloxy group , Quarter anthracenyloxy group, anthraquinolyloxy group, phenanthryloxy group, triphenylenyloxy group, pyrenyloxy group, chrysenyloxy group, naphthacenyloxy group, preadenyloxy group, picenyloxy group, perylenyloxy group, penta Phenyloxy group, pentacenyloxy group, tetraphenylenyloxy group, hexaphenyloxy group, hexacenyloxy group, rubicenyloxy group, coronenyloxy group, trinaphthylenyloxy group, heptaphenyloxy group, heptacene Examples include a nyloxy group, a pyrantrenyloxy group, and an oberenyloxy group.
モノアリールアミノ基としては、例えば、N−アリールアミノ基、アニリノ基、1−ナフチルアミノ基、2−ナフチルアミノ基、o−トルイジノ基、m−トルイジノ基、p−トルイジノ基、2−ビフェニルアミノ基、3−ビフェニルアミノ基、4−ビフェニルアミノ基、1−フルオレンアミノ基、2−フルオレンアミノ基、2−チアゾールアミノ基、p−ターフェニルアミノ基等が挙げられる。 Examples of the monoarylamino group include an N-arylamino group, anilino group, 1-naphthylamino group, 2-naphthylamino group, o-toluidino group, m-toluidino group, p-toluidino group, and 2-biphenylamino group. , 3-biphenylamino group, 4-biphenylamino group, 1-fluoreneamino group, 2-fluoreneamino group, 2-thiazoleamino group, p-terphenylamino group and the like.
ジアリールアミノ基としては、例えば、ジアリールアミノ基、ジフェニルアミノ基、ジトリルアミノ基、N−フェニル−1−ナフチルアミノ基、N−フェニル−2−ナフチルアミノ基等が挙げられる。 Examples of the diarylamino group include a diarylamino group, a diphenylamino group, a ditolylamino group, an N-phenyl-1-naphthylamino group, and an N-phenyl-2-naphthylamino group.
アルキルカルボニル基としては、例えば、ホルミル基、アセチル基、プロピオニル基、ブチリル基、イソブチリル基、バレリル基、イソバレリル基、ピバロイル基、ラウロイル基、ミリストイル基、パルミトイル基、ステアロイル基、シクロペンチルカルボニル基、シクロヘキシルカルボニル基、アクリロイル基、メタクリロイル基、クロトノイル基、イソクロトノイル基、オレオイル基等が挙げられる。 Examples of the alkylcarbonyl group include formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group, lauroyl group, myristoyl group, palmitoyl group, stearoyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl Group, acryloyl group, methacryloyl group, crotonoyl group, isocrotonoyl group, oleoyl group and the like.
アリールカルボニル基としては、例えば、ベンゾイル基、2−メチルベンゾイル基、4−メトキシベンゾイル基、1−ナフトイル基、2−ナフトイル基、シンナモイル基、3−フロイル基、2−テノイル基、ニコチノイル基、イソニコチノイル基、9−アンスロイル基、5−ナフタセノイル基等が挙げられる。 As the arylcarbonyl group, for example, benzoyl group, 2-methylbenzoyl group, 4-methoxybenzoyl group, 1-naphthoyl group, 2-naphthoyl group, cinnamoyl group, 3-furoyl group, 2-thenoyl group, nicotinoyl group, isonicotinoyl Group, 9-anthroyl group, 5-naphthacenoyl group and the like.
上記の有機基の各々は、2以上の有機基が複合したものであってもよく、また二重結合を有する基を有していてもよい。二重結合を有する基としては、例えば、ビニル基、アリル基、2−メチルアリル基、クロチル基、イソクロチル基、クロトノイル基、イソクロトノイル基、(メタ)アクリロイル基、(メタ)アクリロキシ基等が挙げられる。 Each of the above organic groups may be a composite of two or more organic groups, or may have a group having a double bond. Examples of the group having a double bond include vinyl group, allyl group, 2-methylallyl group, crotyl group, isocrotyl group, crotonoyl group, isocrotonoyl group, (meth) acryloyl group, (meth) acryloxy group and the like.
上記一般式(1)で示されるスズキレート錯体としては、例えば、アミノ基および/またはイミノ基ならびに水酸基を有する二座以上の配位子(B)がスズに配位されたスズキレート錯体が挙げられる。 Examples of the tin chelate complex represented by the general formula (1) include a tin chelate complex in which a bidentate or higher ligand (B) having an amino group and / or imino group and a hydroxyl group is coordinated to tin. It is done.
かかる二座以上の配位子(B)としては、好ましくは、例えば、エチレングリコール、プロピレングリコール、1,4−ブタンジオール、1,6−ヘキサンジオール、ジエチレングリコール、カテコール、レゾルシノール、ヒドロキノン、グリセリン、ヒドロキシキノール、フロログルシノール、ピロガロールなどの多価アルコール;エタノールアミン、ヘプタミノール、イソエタリン、1−アミノ−2−プロパノール、プスフィンゴシン、メタノールアミン、ジメチルエタノールアミン、N−メチルエタノールアミン、2,2´−イミノジエタノールなどのアミノ基および/またはイミノ基ならびに水酸基を含有する化合物などが挙げられ、キレート化の収率の点で、アミノ基および/またはイミノ基ならびに水酸基を含有する化合物が特に好ましく、入手の容易さの点で、更に1−アミノ−2−プロパノール、2,2´−イミノジエタノールが好ましい。 The bidentate or higher ligand (B) is preferably, for example, ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, catechol, resorcinol, hydroquinone, glycerin, hydroxy Polyhydric alcohols such as quinol, phloroglucinol, pyrogallol; ethanolamine, heptaminol, isoethalin, 1-amino-2-propanol, psphingosine, methanolamine, dimethylethanolamine, N-methylethanolamine, 2,2'-imino Examples include compounds containing amino groups and / or imino groups and hydroxyl groups such as diethanol, and in terms of chelation yield, compounds containing amino groups and / or imino groups and hydroxyl groups are particularly preferred. Preferred, from the viewpoint of easy availability, further 1-amino-2-propanol, 2,2'-iminodiethanol is preferred.
上記二座以上の配位子(B)の分子量は、キレート錯体の形成のしやすさの点で、500以下が好ましく、特に450以下が好ましく、更に400以下が好ましい。二座以上の配位子(B)の分子量が高すぎると、サイズが大きすぎて1分子で金属に二座以上配位したキレート錯体になり難くなる傾向がある。なお、分子量の下限は通常40であり、好ましくは50である。 The molecular weight of the bidentate or higher ligand (B) is preferably 500 or less, particularly preferably 450 or less, and more preferably 400 or less, from the viewpoint of easy formation of a chelate complex. If the molecular weight of the bidentate or higher ligand (B) is too high, the size is too large, and it tends to be difficult to form a chelate complex in which one molecule is coordinated to the bidentate or more. In addition, the minimum of molecular weight is 40 normally, Preferably it is 50.
また、上記二座以上の配位子(B)の沸点は、製膜条件の低温化の点で、300℃以下が好ましく、特に250℃以下が好ましく、更に200℃以下が好ましい。沸点の低い配位子(B)を用いることにより低温加熱で製膜することができるため、省エネルギーで製膜可能である。なお、沸点の下限は通常25℃であり、好ましくは50℃である。 The boiling point of the bidentate or higher ligand (B) is preferably 300 ° C. or lower, particularly preferably 250 ° C. or lower, and more preferably 200 ° C. or lower, from the viewpoint of lowering the film forming conditions. By using a ligand (B) having a low boiling point, the film can be formed by low-temperature heating, so that the film can be formed with energy saving. In addition, the minimum of a boiling point is 25 degreeC normally, Preferably it is 50 degreeC.
<スズキレート錯体の製造方法>
一般式(1)で示されるスズキレート錯体は、例えば、水酸化スズ(A)を用いることによって製造することができる。
水酸化スズ(A)は、塩化スズ(IV)より得ることができ、例えば、塩化スズ(IV)と塩基性化合物を反応させて得ることができる。
また、水酸化スズ(A)は、塩化スズ(IV)以外からも得ることができ、例えば、スズ(IV)の硫酸溶液に大量の水を加えることで生成させることができる。
<Method for producing tin chelate complex>
The tin chelate complex represented by the general formula (1) can be produced, for example, by using tin hydroxide (A).
Tin hydroxide (A) can be obtained from tin (IV) chloride, and can be obtained, for example, by reacting tin (IV) chloride with a basic compound.
Further, tin hydroxide (A) can be obtained from other than tin (IV) chloride, and can be produced, for example, by adding a large amount of water to a sulfuric acid solution of tin (IV).
水酸化スズ(A)を用いて一般式(1)で示されるスズキレート錯体を製造する方法としては、例えば、水酸化スズ(A)とアミノ基及び水酸基を有する二座以上の配位子(B)とを反応させてキレート構造を形成する方法が挙げられる。
水酸化スズ(A)と二座以上の配位子(B)とを反応させるに際しては、水酸化スズ(A)1モルに対して、二座以上の配位子(B)を通常2〜200モル、好ましくは5〜100モル、特に好ましくは10〜20モルを反応させる。
反応時の温度は、好ましくは20〜300℃、更に好ましくは50〜280℃、特に好ましくは70〜250℃、殊に好ましくは100〜200℃である。反応時間は、好ましくは1〜1440分間、特に好ましくは10〜1000分間、更に好ましくは20〜500分間である。
反応温度が低すぎる場合は反応が進行しない傾向があり,高すぎる場合は配位子(B)が揮発する傾向がある。また、反応時間が短すぎる場合は反応が進行しない傾向があり,長すぎる場合は着色する傾向がある。
As a method for producing a tin chelate complex represented by the general formula (1) using tin hydroxide (A), for example, tin hydroxide (A) and a bidentate or higher ligand having an amino group and a hydroxyl group ( And a method of forming a chelate structure by reacting with B).
When reacting tin hydroxide (A) with a bidentate or higher ligand (B), the bidentate or higher ligand (B) is usually added in an amount of 2 to 1 mol per mole of tin hydroxide (A). 200 mol, preferably 5 to 100 mol, particularly preferably 10 to 20 mol, are reacted.
The temperature during the reaction is preferably 20 to 300 ° C, more preferably 50 to 280 ° C, particularly preferably 70 to 250 ° C, and particularly preferably 100 to 200 ° C. The reaction time is preferably 1 to 1440 minutes, particularly preferably 10 to 1000 minutes, and further preferably 20 to 500 minutes.
When the reaction temperature is too low, the reaction tends not to proceed, and when it is too high, the ligand (B) tends to volatilize. Moreover, when reaction time is too short, there exists a tendency for reaction not to advance, and when too long, there exists a tendency to color.
以上の製造方法によって、常温下、目視で無色透明な液体である本発明のスズキレート錯体が得られる。本発明のスズキレート錯体は、種々の溶媒に容易に溶解することができ、例えばメタノール、プロパノールなどのアルコール系溶媒、蒸留水などの水、酢酸などのカルボン酸系溶媒などの溶媒に混和させた場合に、経時的に白濁することもなく安定に存在することかできる。 By the above manufacturing method, the tin chelate complex of the present invention, which is a visually transparent liquid at room temperature, is obtained. The tin chelate complex of the present invention can be easily dissolved in various solvents, such as alcohol solvents such as methanol and propanol, water such as distilled water, and solvents such as carboxylic acid solvents such as acetic acid. In some cases, it can exist stably without becoming cloudy over time.
本発明のスズキレート錯体の分解温度は、300℃以下が好ましく、特に250℃以下が好ましく、更に200℃以下が好ましい。分解温度の低いスズキレート錯体を用いることによって、基材上に透明導電膜を製膜する際の加熱温度を低くすることができ、省エネルギーで製膜可能である。なお、分解温度の下限は通常180℃であり、好ましくは100℃である。 The decomposition temperature of the tin chelate complex of the present invention is preferably 300 ° C. or lower, particularly preferably 250 ° C. or lower, and more preferably 200 ° C. or lower. By using a tin chelate complex having a low decomposition temperature, the heating temperature when forming the transparent conductive film on the substrate can be lowered, and the film can be formed with energy saving. In addition, the minimum of decomposition temperature is 180 degreeC normally, Preferably it is 100 degreeC.
本発明のスズキレート錯体は、種々の溶媒への溶解性、溶液の透明性、更に経時安定性に優れているため、湿式法による酸化スズ膜の製造に好適に使用することができる。
以下に、本発明のスズキレート錯体から本発明の透明導電膜を形成する方法について説明する。
Since the tin chelate complex of the present invention is excellent in solubility in various solvents, solution transparency, and stability over time, it can be suitably used for producing a tin oxide film by a wet method.
Below, the method to form the transparent conductive film of this invention from the tin chelate complex of this invention is demonstrated.
<透明導電膜>
本発明の透明導電膜は、本発明のスズキレート錯体から形成され、例えば、本発明のスズキレート錯体を含有する酸化スズ膜製膜用液を基材上に塗布し、加熱することにより形成される。
<Transparent conductive film>
The transparent conductive film of the present invention is formed from the tin chelate complex of the present invention. For example, the transparent conductive film of the present invention is formed by applying a tin oxide film-forming solution containing the tin chelate complex of the present invention on a substrate and heating. The
本発明で用いられる酸化スズ膜製膜用液は、本発明のスズキレート錯体を含有するペーストまたは溶液である。
かかるペーストまたは溶液に用いられる溶媒としては、例えば、蒸留水、イオン交換水などの水;エタノール、イソプロピルアルコール、ベンジルアルコールなどのアルコール系溶媒;酢酸などのカルボン酸系溶媒:アセトニトリル、プロピオニトリルなどのニトリル系溶媒;クロロホルム、ジクロロメタン、クロロベンゼン等のハロゲン系溶媒;ジエチルエーテル、テトラヒドロフラン等のエーテル系溶媒;酢酸エチル、サクサンブチル等のエステル系溶媒;アセトン、メチルエチルケトン、シクロヘキサノン等のケトン系溶媒;炭酸ジエチル、炭酸プロピレン等の炭酸エステル系溶媒;ヘキサン、オクタン、トルエン、キシレン等の炭水化物系溶媒;ジメチルホルムアミド、ジメチルアセトアミド、ジメチルスルホキシド、1, 3−ジメチルイミダゾリノン、Nメチルピロリドンなどが挙げられ、これら溶媒のうち二種類以上の溶媒を混合して用いることができる。好ましくは、メタノール、プロパノールなどのアルコール系溶媒溶剤、蒸留水などの水、酢酸などのカルボン酸系溶媒である。
The tin oxide film-forming solution used in the present invention is a paste or solution containing the tin chelate complex of the present invention.
Examples of the solvent used in the paste or solution include water such as distilled water and ion exchange water; alcohol solvents such as ethanol, isopropyl alcohol, and benzyl alcohol; carboxylic acid solvents such as acetic acid: acetonitrile, propionitrile, and the like. A nitrile solvent such as chloroform, dichloromethane, chlorobenzene, etc .; an ether solvent such as diethyl ether, tetrahydrofuran, etc .; an ester solvent such as ethyl acetate, saxan butyl; a ketone solvent such as acetone, methyl ethyl ketone, cyclohexanone; Carbonate solvents such as propylene carbonate; carbohydrate solvents such as hexane, octane, toluene, xylene; dimethylformamide, dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl Le imidazolinones, such as N-methylpyrrolidone and the like, may be used by mixing two or more solvents of these solvents. Preferred are alcohol solvent solvents such as methanol and propanol, water such as distilled water, and carboxylic acid solvents such as acetic acid.
本発明のスズキレート錯体を含有するペーストを用いる場合、ペースト中のスズキレート錯体の含有量は、固形分にて、好ましくは0.1〜90重量%であり、特に好ましくは20〜80重量%、更に好ましくは50〜70重量%である。スズキレート錯体の含有量が少なすぎると製膜が困難になる傾向があり、含有量が多すぎるとペーストとして分散させるのが困難になる傾向がある。
かかるペーストを基材上に塗布する方法としては、例えば、スピンコーターによる塗布方法、スクリーン印刷法、スキージーを用いた塗布方法、ディップ法、吹き付け法、ローラー法などが挙げられる。
When the paste containing the tin chelate complex of the present invention is used, the content of the tin chelate complex in the paste is preferably 0.1 to 90% by weight, particularly preferably 20 to 80% by weight in solid content. More preferably, it is 50 to 70% by weight. When the content of the tin chelate complex is too small, film formation tends to be difficult, and when the content is too large, it tends to be difficult to disperse as a paste.
Examples of the method for applying the paste on the substrate include a spin coater application method, a screen printing method, a squeegee application method, a dipping method, a spraying method, and a roller method.
本発明のスズキレート錯体を含有する溶液を用いる場合、溶液中のスズキレート錯体の含有量は、固形分にて、好ましくは0.001〜30重量%であり、特に好ましくは0.01〜10重量%、更に好ましくは0.02〜2重量%である。スズキレート錯体の含有量が少なすぎると製膜が困難になる傾向があり、含有量が多すぎると、透明度の低い薄膜になる傾向がある。
かかる溶液を基材上に塗布する方法としては、例えば、浸漬法、スプレー法、スピンコーティング法、インクジェット印刷、グラビア印刷などが挙げられる。
When using the solution containing the tin chelate complex of the present invention, the content of the tin chelate complex in the solution is preferably 0.001 to 30% by weight, particularly preferably 0.01 to 10% by solid content. % By weight, more preferably 0.02 to 2% by weight. When the content of the tin chelate complex is too small, film formation tends to be difficult, and when the content is too large, a thin film with low transparency tends to be obtained.
Examples of a method for applying such a solution on a substrate include an immersion method, a spray method, a spin coating method, ink jet printing, and gravure printing.
本発明のスズキレート錯体を含有するペーストまたは溶液は、必要に応じて、増粘成分としてのバインダー樹脂を含有していてもよい。
バインダー樹脂としては、例えば、セルロース系、ポリエチレングリコール系、アクリル系、ウレタン系、ポリオール系、ポリエチレン系、ポリアミド系などが挙げられる。
本発明のスズキレート錯体を含有するペーストまたは溶液中のバインダー樹脂の含有量は、固形分にて、好ましくは1〜50重量%である。
また、本発明のスズキレート錯体を含有するペーストまたは溶液は、ペーストや溶液の保存安定性、乾燥性、基材密着性、成膜適正等の性質を向上させる目的で、種々の添加剤を含有していてもよい。
The paste or solution containing the tin chelate complex of the present invention may contain a binder resin as a thickening component, if necessary.
Examples of the binder resin include cellulose, polyethylene glycol, acrylic, urethane, polyol, polyethylene, and polyamide.
The content of the binder resin in the paste or solution containing the tin chelate complex of the present invention is preferably 1 to 50% by weight in solid content.
In addition, the paste or solution containing the tin chelate complex of the present invention contains various additives for the purpose of improving properties such as storage stability, drying property, substrate adhesion, and film formation property of the paste or solution. You may do it.
本発明のスズキレート錯体を含有する酸化スズ膜製膜用液を塗布する基材としては、例えば、石英、ソーダ石灰ガラス、硼珪酸ガラス、アルミノ珪酸ガラス等のガラス基材;ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリイミド、ポリエステル、ポリエチレン、ポリカーボネート、ポリビニルブチラート、ポリプロピレン、テトラアセチルセルロース、シンジオクタチックポリスチレン、ポリフェニレンスルフィド、ポリアリレート、ポリスルフォン、ポリエステルスルフォン、ポリエーテルイミド、環状ポリオレフィン、ブロム化フェノキシ、塩化ビニル等の樹脂基材が挙げられる。 Examples of the substrate on which the tin oxide film-forming solution containing the tin chelate complex of the present invention is applied include, for example, glass substrates such as quartz, soda-lime glass, borosilicate glass, and aluminosilicate glass; polyethylene terephthalate, polyethylene naphthalate Phthalate, polyimide, polyester, polyethylene, polycarbonate, polyvinyl butyrate, polypropylene, tetraacetylcellulose, syndioctaic polystyrene, polyphenylene sulfide, polyarylate, polysulfone, polyester sulfone, polyetherimide, cyclic polyolefin, brominated phenoxy, vinyl chloride Examples of the resin base material include:
基材上に透明導電膜を製膜するに際しては、加熱後の膜厚が通常10〜2000nm、好ましくは50〜400nmになるように、スズキレート錯体を含有する酸化スズ膜製膜用液を基材上に塗布した後、加熱を行なう。加熱温度は、スズキレート錯体が分解する温度以上で、かつ基材の変形温度以下であり、例えば、通常50〜500℃、好ましくは100〜400℃である。加熱時間は、例えば、1分間〜数時間である。 When forming a transparent conductive film on a substrate, a tin oxide film-forming solution containing a tin chelate complex is used so that the film thickness after heating is usually 10 to 2000 nm, preferably 50 to 400 nm. After coating on the material, heating is performed. The heating temperature is not less than the temperature at which the tin chelate complex decomposes and not more than the deformation temperature of the substrate, and is usually 50 to 500 ° C, preferably 100 to 400 ° C, for example. The heating time is, for example, 1 minute to several hours.
以下、実施例を挙げて本発明を更に具体的に説明するが、本発明はその要旨を超えない限り、以下の実施例に限定されるものではない。
なお、例中の「%」とあるのは重量基準を意味する。
EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further more concretely, this invention is not limited to a following example, unless the summary is exceeded.
In the examples, “%” means a weight basis.
<実施例1>
(配位子(B):2,2´−イミノジエタノール(ジエタノールアミン))
塩化スズ(IV)五水和物(3mmol)を蒸留水5mlに溶解させ、この水溶液に28%アンモニア水(5.4ml)を加え、白色沈殿(水酸化スズ)を生じさせた。この白色沈殿に対し、トミー精工製、遠心分離装置「MX−307」を用い、遠心分離(15000rpm,10分間)を行い、上澄みを廃棄し、沈殿に蒸留水10mlを加え超音波を印加した。この水洗作業を2回行ったところ、Sn:Cl=1:0.09(mol)となり、塩素の残留量が低減されたことが分かる。
水洗後の沈殿(水酸化スズ)にジエタノールアミン(30mmol)を加え、130℃で60分間、加熱攪拌して、スズキレート錯体を得た。
得られたスズキレート錯体は、一般式(1)において、R1がエチレン基であり、R2がヒドロキシエキル基である。
なお、ジエタノールアミンの分子量は75.1g/mol、沸点は160℃である。
<Example 1>
(Ligand (B): 2,2'-iminodiethanol (diethanolamine))
Tin (IV) chloride pentahydrate (3 mmol) was dissolved in 5 ml of distilled water, and 28% aqueous ammonia (5.4 ml) was added to the aqueous solution to form a white precipitate (tin hydroxide). The white precipitate was centrifuged (15000 rpm, 10 minutes) using a centrifuge “MX-307” manufactured by Tommy Seiko, the supernatant was discarded, 10 ml of distilled water was added to the precipitate, and ultrasonic waves were applied. When this washing operation was performed twice, it was found that Sn: Cl = 1: 0.09 (mol), and the residual amount of chlorine was reduced.
Diethanolamine (30 mmol) was added to the precipitate after washing with water (tin hydroxide), and the mixture was heated and stirred at 130 ° C. for 60 minutes to obtain a tin chelate complex.
In the obtained tin chelate complex, in general formula (1), R 1 is an ethylene group, and R 2 is a hydroxyethyl group.
Diethanolamine has a molecular weight of 75.1 g / mol and a boiling point of 160 ° C.
<実施例2>
(配位子(B):1−アミノ−2−プロパノール)
塩化スズ(IV)五水和物(3mmol)を蒸留水5mlに溶解させ、この水溶液に28%アンモニア水(5.4ml)を加え、白色沈殿(水酸化スズ)を生じさせた。この白色沈殿に対し、実施例1と同様に、遠心分離(15000rpm,10分間)を行い、上澄みを廃棄し、沈殿に蒸留水10mlを加え超音波を印加した。この水洗作業を2回行った。
水洗後の沈殿(水酸化スズ)に1−アミノ−2−プロパノール(30mmol)を加え、110℃で90分間、加熱攪拌して、スズキレート錯体を得た。
得られたスズキレート錯体は、一般式(1)において、R1がプロピレン基であり、R2が水素原子である。
なお、1−アミノ−2−プロパノールの分子量は105.1g/mol、沸点は280℃である。
<Example 2>
(Ligand (B): 1-amino-2-propanol)
Tin (IV) chloride pentahydrate (3 mmol) was dissolved in 5 ml of distilled water, and 28% aqueous ammonia (5.4 ml) was added to the aqueous solution to form a white precipitate (tin hydroxide). The white precipitate was centrifuged (15000 rpm, 10 minutes) in the same manner as in Example 1, the supernatant was discarded, 10 ml of distilled water was added to the precipitate, and ultrasonic waves were applied. This washing operation was performed twice.
1-Amino-2-propanol (30 mmol) was added to the precipitate after washing with water (tin hydroxide), and the mixture was heated and stirred at 110 ° C. for 90 minutes to obtain a tin chelate complex.
In the obtained tin chelate complex, in general formula (1), R 1 is a propylene group, and R 2 is a hydrogen atom.
The molecular weight of 1-amino-2-propanol is 105.1 g / mol, and the boiling point is 280 ° C.
<比較例1>
(配位子:酢酸)
塩化スズ(IV)五水和物(3mmol)を蒸留水5mlに溶解させ、この水溶液に28%アンモニア水(5.4ml)を加え、白色沈殿(水酸化スズ)を生じさせた。この白色沈殿に対し、実施例1と同様に、遠心分離(15000rpm,10分間)を行い、上澄みを廃棄し、沈殿に蒸留水10mlを加え超音波を印加した。この水洗作業を2回行った。
水洗後の沈殿(水酸化スズ)に酢酸(30mmol)を加え、110℃で90分間、加熱攪拌して、スズキレート錯体を得た。
<Comparative Example 1>
(Ligand: Acetic acid)
Tin (IV) chloride pentahydrate (3 mmol) was dissolved in 5 ml of distilled water, and 28% aqueous ammonia (5.4 ml) was added to the aqueous solution to form a white precipitate (tin hydroxide). The white precipitate was centrifuged (15000 rpm, 10 minutes) in the same manner as in Example 1, the supernatant was discarded, 10 ml of distilled water was added to the precipitate, and ultrasonic waves were applied. This washing operation was performed twice.
Acetic acid (30 mmol) was added to the precipitate after washing with water (tin hydroxide), and the mixture was heated and stirred at 110 ° C. for 90 minutes to obtain a tin chelate complex.
<実験例>
実施例および比較例のスズキレート錯体を用いて、下記の評価を行なった。
(透明性:表1)
容量10mLのサンプル瓶に、スズキレート錯体溶液(500μl)と各種溶媒(5ml)を重量比で1:10(体積比)で混和させたものを入れ、その直後に目視で濁り具合を評価した。
○:透明である。
×:白濁しており、瓶の向こう側が見えない。
(経時安定性:表2)
上記サンプル瓶を1日放置し、同様の評価を行った。
○:透明である。
×:白濁しており、瓶の向こう側が見えない。
<Experimental example>
The following evaluation was performed using the tin chelate complexes of Examples and Comparative Examples.
(Transparency: Table 1)
A sample bottle having a capacity of 10 mL was mixed with a tin chelate complex solution (500 μl) and various solvents (5 ml) mixed at a weight ratio of 1:10 (volume ratio), and immediately after that, the turbidity was evaluated visually.
○: Transparent.
X: It is cloudy and the other side of the bottle cannot be seen.
(Stability over time: Table 2)
The sample bottle was allowed to stand for 1 day, and the same evaluation was performed.
○: Transparent.
X: It is cloudy and the other side of the bottle cannot be seen.
表1および表2に示す結果から、本発明に係る実施例1および2のスズキレート錯体は蒸留水、酢酸、メタノール、エタノール、プロパノールの各溶媒に対して、溶解性、溶液の透明性、および経時安定性に優れることが分かる。 From the results shown in Tables 1 and 2, the tin chelate complexes of Examples 1 and 2 according to the present invention are soluble in each solvent of distilled water, acetic acid, methanol, ethanol, and propanol, the transparency of the solution, and It can be seen that the stability over time is excellent.
本発明のスズキレート錯体は、種々の溶媒への溶解性、溶液の透明性、更に経時安定性に優れていることから、湿式法による酸化スズ膜の製膜に好適に利用することができ、例えば、ディスプレイ、太陽電池、タッチパネルなどに用いられる透明導電膜の製造に利用することができる。
Since the tin chelate complex of the present invention is excellent in solubility in various solvents, solution transparency, and stability over time, it can be suitably used for forming a tin oxide film by a wet method, For example, it can utilize for manufacture of the transparent conductive film used for a display, a solar cell, a touch panel, etc.
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