JP5162592B2 - ジイモニウム塩及びそれを含む近赤外線吸収フィルム - Google Patents
ジイモニウム塩及びそれを含む近赤外線吸収フィルム Download PDFInfo
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- JP5162592B2 JP5162592B2 JP2009527297A JP2009527297A JP5162592B2 JP 5162592 B2 JP5162592 B2 JP 5162592B2 JP 2009527297 A JP2009527297 A JP 2009527297A JP 2009527297 A JP2009527297 A JP 2009527297A JP 5162592 B2 JP5162592 B2 JP 5162592B2
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- phenylenediamine
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- 239000000126 substance Substances 0.000 claims description 36
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000010521 absorption reaction Methods 0.000 claims description 13
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
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- 239000010452 phosphate Substances 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
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- 125000003118 aryl group Chemical group 0.000 claims description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
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- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical compound FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/30—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups quaternised
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Optical Filters (AREA)
- Fireproofing Substances (AREA)
Description
前記化学式1において、nは、1又は2の整数であり、R1乃至R8は、それぞれ独立に置換又は非置換の炭素数1乃至10の直鎖又は分枝状のアルキル基である。前記アルキル基の置換基は、シアノ基、ニトロ基、カルボキシル基、スルホン基、ハロゲン基、ヒドロキシ基、炭素数1乃至8のアルコキシ基、アルコキシアルコキシ基、アシルオキシ基、アルキルアミノ基、又は炭素数6乃至18のアリール基若しくはアリールオキシ基であり、X−は、下記化学式2で表される置換されたフルオロアルキルリン酸陰イオンである。
前記化学式1において、nは、1又は2の整数であり、R1乃至R8は、それぞれ独立に置換又は非置換の炭素数1乃至10の直鎖又は分枝状のアルキル基である。前記アルキル基の置換基は、シアノ基、ニトロ基、カルボキシル基、スルホン基、ハロゲン基、ヒドロキシ基、炭素数1乃至8のアルコキシ基、アルコキシアルコキシ基、アシルオキシ基、アルキルアミノ基、又は炭素数6乃至18のアリール基若しくはアリールオキシ基である。好ましくは、前記アルキル基は、メチル基、エチル基、プロピル基、ブチル基、t−ブチル基、ペンチル基を含む。前記ハロゲン基は、F、Cl、Brを含む。前記アルコキシ基は、メトキシ基、エトキシ基及びイソブトキシ基を含む。前記アルコキシアルコキシ基は、メトキシエトキシ基を含む。前記アシルオキシ基は、アセチルオキシ基、ブチリルオキシ基、ヘキシリルオキシ基及びベンゾイルオキシ基を含む。前記アルキルアミノ基は、メチルアミノ基及びジメチルアミノ基を含む。前記アリール基は、フェニル基及びナフチル基を含む。前記アリールオキシ基は、フェノキシ基を含む。
前記化学式1において、nは、1又は2の整数であり、R1乃至R8は、それぞれ独立に置換又は非置換の炭素数1乃至10の直鎖又は分枝状のアルキル基であり、前記アルキル基の置換基は、シアノ基、ニトロ基、カルボキシル基、スルホン基、ハロゲン基、ヒドロキシ基、炭素数1乃至8のアルコキシ基、アルコキシアルコキシ基、アシルオキシ基、アルキルアミノ基、又は炭素数6乃至18のアリール基若しくはアリールオキシ基である。X−は、下記化学式2で示される置換されたフルオロアルキルリン酸陰イオンである。
[ジイモニウム塩の合成]
工程1.[テトラキスジブチルアミノフェニル−p−フェニレンジアミンの合成]
ジメチルホルムアミド(DMF)800gにN,N,N’,N’−テトラキス(アミノフェニル)−p−フェニレンジアミン95.2g(0.2モル)、1−ブロモブタン548g(4.0モル)及び無水炭酸カリウム330gを加え、130℃で24時間反応させ、反応液を冷却させた後に濾過した。得られた濾過液にイソプロピルアルコール500mlを投入した後、1時間撹拌して、生成した物質を濾過し、再びメタノールで洗浄した後に乾燥させて、目標生成物である茶色の物質96gを得た。
トリス(トリフルオロメチル)二フッ化リン((CF3)3PF2)30g(0.1モル)及びフッ化セシウム(CsF)30.4g(0.2モル)をアセトニトリル200mlに加え、常温(25℃)で15時間反応させた。反応が完了した後、反応液の溶媒を減圧蒸溜させた。残存する茶色の物質に水を添加して抽出物を得た後、抽出された溶液を凍結乾燥させて、目標生成物である白色の物質34gを得た(分析結果; C:8.41%、F:53.3%)。
前記工程1で得られたテトラキスジブチルアミノフェニル−p−フェニレンジアミン18g(0.02モル)及び硝酸銀6.8g(0.04モル)をジメチルホルムアミド50gに溶解させ、60℃で30分間反応させた。反応が完了した後、沈澱した銀を濾別し、工程2で得られたセシウムトリス(トリフルオロメチル)トリフルオロリン酸17.1g(0.04モル)をその濾過液に添加して30分F間撹拌した。次いで、これに水100mlをゆっくり加えて沈殿物を生成させた。沈澱した茶色の物質を濾過した後、水で洗浄してジイモニウム塩28gを得た(分析結果; H:7.6%、C:66.2%、N:4.7%、F:18.8%、λmax:1097nm、モル吸光係数:108,000、分解温度:262℃)。
[ジイモニウム塩の合成]
1−ブロモブタンの代わりに2−ブロモブタンを使用した以外は前記実施例1と同様の方法でジイモニウム塩26gを製造した(分析結果; H:7.7%、C:66.3%、N:4.7%、F:18.8%、λmax:1102nm、モル吸光係数:103,000、分解温度:266℃)。
[近赤外線吸収フィルムの製造]
ポリメチルメタクリレートバインダー樹脂をメチルエチルケトンに溶解させて、20重量%のバインダー樹脂溶液を製造した後、これに前記実施例1で製造されたジイモニウム塩を添加して、ジイモニウム塩の濃度を0.02%とした。その後、前記溶液を均一に混合して近赤外線吸収フィルム用のコーティング組成物を製造した。次いで、バーコーティング機を利用して、製造された近赤外線吸収フィルム用のコーティング組成物を透明フィルム(10cm×10cm)上に3μmの厚さでコーティングして近赤外線吸収フィルムを製造した。
[近赤外線吸収フィルムの製造]
前記実施例1で得られたジイモニウム塩の代わりに、前記実施例2で得られたジイモニウム塩を使用した以外は、前記実施例3と同様の方法で近赤外線吸収フィルムを製造した。
[近赤外線吸収フィルムの製造]
前記実施例1で得られたジイモニウム塩の代わりに、N,N,N’,N’−テトラキス−[p−ジ(n−ブチル)アミノフェニル−p−ペニルレンジイモニウムトリフルオロメチルスルホニルイミドを使用した以外は、前記実施例3と同様の方法で近赤外線吸収フィルムを製造した。
[透過率の評価]
前記実施例3、実施例4及び比較例1で製造した近赤外線吸収フィルムの透過率を、近赤外線(850nm)及び可視光線(430nm)領域で紫外−可視分光光度計を使用して測定した。近赤外線吸収フィルムを、耐候性試験機(スガ試験機社製)を使用して湿度80%、100℃で150キロルクスの光源に100時間露光し、近赤外線吸収フィルムの透過率を再び紫外−可視分光光度計にて測定した。その結果を下記表1に示す。図1は、前記実施例2で製造された近赤外線吸収フィルムの透過率を示すUVスペクトルである。
Claims (4)
- 下記化学式1で示される近赤外線吸収フィルム用ジイモニウム塩。
- 前記化学式1のジイモニウム塩のジイモニウム陽イオンが、N,N,N’,N’−テトラキス{p−ジメチルアミノフェニル}−p−フェニレンジアミン、N,N,N’,N’−テトラキス{p−ジエチルアミノフェニル}−p−フェニレンジアミン、N,N,N’,N’−テトラキス{p−ジ(n−ブチル)アミノフェニル}−p−フェニレンジアミン、N,N,N’,N’−テトラキス{p−ジ(イソ−ブチル)アミノフェニル}−p−フェニレンジアミン、N,N’,N’−テトラキス{p−ジ(シアノプロピル)アミノフェニル}−p−フェニレンジアミン、N,N,N’,N’−テトラキス{p−ジ(2−ヒドロキシエチル)アミノフェニル}−p−フェニレンジアミン、N,N,N’,N’−テトラキス{p−ジベンジルアミノフェニル}−p−フェニレンジアミン、及びN,N,N’,N’−テトラキス{p−ジ(1−ナフチルメチル)アミノフェニル}−p−フェニレンジアミンからなる群より選択されることを特徴とする請求項1に記載の近赤外線吸収フィルム用ジイモニウム塩。
- 前記フルオロアルキルリン酸陰イオンが、[CF3PF5]−、[(CF3)2PF4]−、[(CF3)3PF3]−、[C2F5PF5]−、[(C2F5)2PF4]−、[(C2F5)3PF3]−からなる群より選択されることを特徴とする請求項1に記載の近赤外線吸収フィルム用ジイモニウム塩。
- 下記化学式1で示されるジイモニウム塩を含む近赤外線吸収フィルム。
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KR1020060085529A KR100791931B1 (ko) | 2006-09-06 | 2006-09-06 | 디이모늄염 및 이를 포함하는 근적외선 흡수필름 |
KR10-2006-0085529 | 2006-09-06 | ||
PCT/KR2007/004289 WO2008030039A1 (en) | 2006-09-06 | 2007-09-05 | Diimmonium salt and near infrared ray absorption film containing the same |
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JP (1) | JP5162592B2 (ja) |
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JP5534731B2 (ja) * | 2009-07-22 | 2014-07-02 | カーリットホールディングス株式会社 | 近赤外線吸収色素及び近赤外線遮断フィルター |
KR101251898B1 (ko) * | 2010-12-28 | 2013-04-08 | 에스케이케미칼주식회사 | 디이모늄계 화합물 및 이를 이용한 근적외선 흡수 필터 |
JP5965639B2 (ja) * | 2011-12-27 | 2016-08-10 | 富士フイルム株式会社 | 赤外線カットフィルタの製造方法、該製造方法に用いられる赤外線吸収性液状組成物、及びカメラモジュールの製造方法 |
WO2014030628A1 (ja) * | 2012-08-23 | 2014-02-27 | 旭硝子株式会社 | 近赤外線カットフィルタおよび固体撮像装置 |
KR101665379B1 (ko) | 2014-11-18 | 2016-10-12 | 주식회사 앰트 | 나노와이어를 이용한 투명 열차단 코팅액 조성물, 그 제조방법, 상기 조성물을 이용하여 제조된 투명 열차단 필름 및 투명 열차단 유리 |
US11300719B2 (en) | 2016-11-14 | 2022-04-12 | Nippon Sheet Glass Company, Limited | Light-absorbing composition and optical filter |
KR101977347B1 (ko) | 2018-10-01 | 2019-05-10 | 주식회사 앰트 | 근적외선 차단용 코팅 조성물에 포함되는 코어-쉘 구조의 황화구리 나노입자 및 이의 제조 방법 |
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US20040137367A1 (en) * | 2001-07-04 | 2004-07-15 | Yasuyuki Kitayama | Diimonium salt compound, near-infrared ray absorbing filter and optical information recording medium |
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