JP2022553290A - 基材からのエレクトロルミネッセンス材料の除去 - Google Patents
基材からのエレクトロルミネッセンス材料の除去 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 48
- 239000000758 substrate Substances 0.000 title claims description 21
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 33
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 17
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical class 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- 239000012530 fluid Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 238000004140 cleaning Methods 0.000 description 12
- 238000009835 boiling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 231100000755 favorable toxicity profile Toxicity 0.000 description 3
- -1 hydrocarbon radicals Chemical class 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 2
- FAAHNQAYWKTLFD-UHFFFAOYSA-N 1-butan-2-ylpyrrolidin-2-one Chemical compound CCC(C)N1CCCC1=O FAAHNQAYWKTLFD-UHFFFAOYSA-N 0.000 description 1
- TWMIYJKVOPNZDE-UHFFFAOYSA-N 2-[difluoro-[1,1,2,3,3,3-hexafluoro-2-(trifluoromethyl)propyl]sulfanylmethyl]-1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(C(F)(F)F)(C(F)(F)F)C(F)(F)SC(C(C(F)(F)F)(C(F)(F)F)F)(F)F TWMIYJKVOPNZDE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/02—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/03—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/34—Organic compounds containing sulfur
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Abstract
Description
Rf-S-Rh (I)
[式中、Rfは、2個~9個の炭素原子を有するフッ素化又はペルフルオロ化基であり、任意に1個以上の鎖状に連結されたヘテロ原子又は塩素原子を含み、Rhは、1個~3個の炭素原子を有する非フッ素化炭化水素基である]によって表されるハイドロフルオロチオエーテルを含む。組成物は、エレクトロルミネッセンス材料を更に含む。
Rf-S-Rh (I)によって表される。
CF3CF2-S-CH3、
HCF2CF2-S-CH3、
HCFClCF2-S-CH3、
CF2ClCF2-S-CH3、
CF3CFCl-S-CH3、
CF3CF2CF2-S-CH3、
CF3OCF2CF2-S-CH3、
CF3CHFCF2-S-CH3、
(CF3)2CF-S-CH3、
(CF3)2CF-S-CH2Cl、
CF3CHFCF2-S-CH3、
CF3CF2CF2CF2-S-CH3、
(CF3)2CFCF2-S-CH3、
CF3CF(CF3)CF2-S-CH3、
CF3CF2CF(CF3)-S-CH3、
CF3OCF2CF2CF2-S-CH3、
CF3CF2CF2CF2-S-CH2CH3、
CF3CF2CF2CF2-S-CH2OCH3、
CF3CF2CF(CF3)-S-CH2CH3、
CF3CF2CF2CF2-S-CH2CH3、
(CF3)2NCF2-S-CH3、
乾燥した600mLのHastalloy Parr反応器に、昇華硫黄(36g、1.1mol)、無水噴霧乾燥フッ化カリウム(15g、260mmol)及び無水N,N-ジメチルホルムアミド(300mL)を添加した。反応器を密封し、内容物を撹拌しながら60℃に加熱した。この温度で反応器を安定化させると、ヘキサフルオロプロペン(150g、1.0mol)を6g/分の速度で添加し、温度を65℃未満に維持した。添加が完了したとき、反応物を60℃で1時間撹拌した後、周囲温度まで冷却した。得られたスラリーを、残りの試薬の添加に対応するために、2Lの丸底フラスコに移した。フッ化カリウム(116g、2.0mol)を一度に添加し、続いて硫酸ジメチル(104mL、1.1mol)を添加漏斗を介して、45℃未満の内部反応温度を維持する速度で添加した。添加が完了したら、得られた反応物を周囲温度で12時間撹拌した。次いで、不均質な溶液を濾過して固形物を除去し、次いで等量の水で3回洗浄した。下相を回収し、硫酸マグネシウム上で乾燥させ、濾過した。粗物質を淡黄色の油状物として回収した(117g、GC-fidによる93%の所望の生成物)。この物質を周囲圧力で蒸留により精製して、ペルフルオロイソプロピルメチルチオエーテル(98g、45%収率、沸点65℃)を得た。
試験混合物を、0.01g(グラム)のエレクトロルミネッセンス材料(ALQ3、又はFIrPic)のうちの1つを、3gの流体(NMP、NBP、CHO、NOVEC 73DE、又はHFTE1)のうちの1つに添加することによって調製した。各混合物を5分間撹拌し、得られた材料を、濁り及び未溶解の粒子状物質について肉眼で観察した。表2に記載されるように、定性的溶解度評価を各混合物に割り当てた。結果を表3に示す。1又は2の溶解度評価は、流体が金属メッシュなどの基材からエレクトロルミネッセンス材料を洗浄するのに有用であることを意味すると解釈された。
単一成分流体溶媒の沸点を表4に要約する。比較的低い沸点は、比較的短い乾燥時間の指標として解釈される。HFTE1の沸点は、NMP、NBP、及びCHOの沸点よりもはるかに低く、HFTE1が比較化合物よりも迅速に乾燥することを示す。
Claims (20)
- 以下の構造式(I):
Rf-S-Rh (I)
[式中、Rfは、2個~9個の炭素原子を有するフッ素化又はペルフルオロ化基であり、任意に1個以上の鎖状に連結されたヘテロ原子又は塩素原子を含み、Rhは、1個~3個の炭素原子を有する非フッ素化炭化水素基である]によって表されるハイドロフルオロチオエーテルと、
エレクトロルミネッセンス材料と、を含む、組成物。 - Rfが、2個~5個の炭素原子を有するペルフルオロ化飽和基である、請求項1に記載の組成物。
- Rhが、CH3又はCH3CH2である、請求項1又は2に記載の組成物。
- 前記エレクトロルミネッセンス材料が、銅(II)フタロシアニン、イリジウム、又は白金を含む、請求項1~3のいずれか一項に記載の組成物。
- 前記エレクトロルミネッセンス材料が、前記組成物中に溶解している、請求項1~4のいずれか一項に記載の組成物。
- 前記構造式(I)を有する化合物が、前記組成物の総重量に基づいて、少なくとも50重量%の量で前記組成物中に存在する、請求項1~5のいずれか一項に記載の組成物。
- 基材からエレクトロルミネッセンス材料を除去するためのプロセスであって、
前記基材を、以下の構造式(I):
Rf-S-Rh (I)
[式中、Rfは、2個~9個の炭素原子を有するフッ素化又はペルフルオロ化基であり、任意に1個以上の鎖状に連結されたヘテロ原子を含み、Rhは、1個~3個の炭素原子を有する非フッ素化炭化水素基である]を有するハイドロフルオロチオエーテルと接触させる工程を含む、プロセス。 - Rfが、2個~5個の炭素原子を有するペルフルオロ化飽和基である、請求項7に記載のプロセス。
- Rhが、CH3又はCH3CH2である、請求項7又は8に記載のプロセス。
- 前記エレクトロルミネッセンス材料が、銅(II)フタロシアニン、イリジウム、又は白金を含む、請求項7~9のいずれか一項に記載のプロセス。
- 前記基材が、金属を含む、請求項7~10のいずれか一項に記載のプロセス。
- 前記エレクトロルミネッセンス材料が、前記金属の外面上に配置されている、請求項11に記載のプロセス。
- 基材からエレクトロルミネッセンス材料を除去するためのプロセスであって、
前記基材を、NMP、NBP、シクロヘキサノン、及びIPAからなる群から選択される溶媒と接触させる工程と、
前記基材を、以下の構造式(I):
Rf-S-Rh (I)
[式中、Rfは、2個~9個の炭素原子を有するフッ素化又はペルフルオロ化基であり、任意に1個以上の鎖状に連結されたヘテロ原子を含み、Rhは、1個~3個の炭素原子を有する非フッ素化炭化水素基である]を有するハイドロフルオロチオエーテルと接触させる工程とを含む、プロセス。 - 前記基材をハイドロフルオロチオエーテルと接触させる工程が、前記基材を前記溶媒と接触させる工程の後に行われる、請求項13に記載のプロセス。
- Rfが、2個~5個の炭素原子を有するペルフルオロ化飽和基である、請求項13又は14に記載のプロセス。
- Rhが、CH3又はCH3CH2である、請求項13~15のいずれか一項に記載のプロセス。
- 前記エレクトロルミネッセンス材料が、銅(II)フタロシアニン、イリジウム、又は白金を含む、請求項13~16のいずれか一項に記載のプロセス。
- 前記基材が、金属を含む、請求項13~17のいずれか一項に記載のプロセス。
- 前記エレクトロルミネッセンス材料が、前記金属の外面上に配置されている、請求項18に記載のプロセス。
- 以下の構造式(II):
Xは、酸素原子又は硫黄原子であり、
(i)Rh’は、1個~4個の炭素原子及び少なくとも1個の水素原子を有する部分フッ素化アルキル基であり、任意に1個以上の鎖状に連結されたヘテロ原子又は塩素原子を含み、Rf’は、1個~4個の炭素原子を有するペルフルオロアルキル基であり、任意に1個以上の鎖状に連結されたヘテロ原子又は塩素原子を含むか、あるいは
(ii)Rh’及びRf’は一緒に結合して、少なくとも1個の水素原子を有しかつ任意に1個以上の鎖状に連結されたヘテロ原子又は塩素原子を含む5員又は6員フッ素化環を形成する]によって表されるハイドロフルオロチオエーテルと、
エレクトロルミネッセンス材料と、を含む、組成物。
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