JP3932761B2 - Organometallic complex, infrared absorption filter using the same and filter for plasma display panel - Google Patents
Organometallic complex, infrared absorption filter using the same and filter for plasma display panel Download PDFInfo
- Publication number
- JP3932761B2 JP3932761B2 JP2000071475A JP2000071475A JP3932761B2 JP 3932761 B2 JP3932761 B2 JP 3932761B2 JP 2000071475 A JP2000071475 A JP 2000071475A JP 2000071475 A JP2000071475 A JP 2000071475A JP 3932761 B2 JP3932761 B2 JP 3932761B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- organometallic complex
- filter
- substituent
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000010521 absorption reaction Methods 0.000 title claims description 48
- 125000002524 organometallic group Chemical group 0.000 title claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000004313 glare Effects 0.000 claims description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000001007 phthalocyanine dye Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229940032094 squalane Drugs 0.000 description 2
- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 101150003085 Pdcl gene Proteins 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 238000007611 bar coating method Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 208000028659 discharge Diseases 0.000 description 1
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
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- FVBUAEGBCNSCDD-UHFFFAOYSA-N silicide(4-) Chemical compound [Si-4] FVBUAEGBCNSCDD-UHFFFAOYSA-N 0.000 description 1
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- 238000012916 structural analysis Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Landscapes
- Optical Filters (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は近赤外光域で吸収を示す新規な有機金属錯体、有機金属錯体色素、これを用いた赤外線吸収フィルター及びプラズマディスプレイパネル用フィルターに関する。具体的には、赤外線吸収フィルター用色素、熱線遮断用色素、遮光フィルム用色素、光記録材料用色素、データーコード用色素、レーザープリンタ用色素、一重項酸素クエンチャー、退色防止剤などに用いることができる赤外線吸収色素材料に関する。また、これらの色素を含む赤外線吸収フィルターに関し、近赤外線吸収性能、熱線吸収能、可視光線透過性能、耐光性に優れていることにより、赤外線を遮蔽するフィルター、具体的には、デジカメ用赤外線フィルター、プラズマディスプレイパネル等、画像表示装置のフィルターなどに好適に使用することができる赤外線吸収フィルターである。
【０００２】
【従来の技術】
一般に、近赤外線吸収剤を含有した樹脂からなるプラスチック性近赤外線吸フィルターは、よく知られているものである。その用途としては、サングラス、溶接用眼鏡、ビルや自動車、飛行機の窓、あるいは情報読み取りのための光学読み取り装置等が挙げられる。
【０００３】
また、最近では、大型薄型の壁掛けテレビとして注目されているプラズマディスプレイパネル（以下、「ＰＤＰ」という）が、近赤外線を発生して、コードレスホン、近赤外線リモコンを使うビデオデッキ等、周辺にある電子機器に作用し誤動作を起こすことから、ＰＤＰ用フィルターとしても近赤外線を吸収する赤外吸収フィルターの要求やデジカメ用赤外線フィルターの要求がある。
【０００４】
この要求に対し、特公平２−４８８１号公報においては、ベンゼンジチオール系金属錯体を配合した熱可塑性樹脂からなる光学フィルターが提案されている。また、特公平６−３８１２５号公報においては、アントラキノン化合物あるいは、中心に金属原子を配位するナフタロシアニン系化合物のうちの少なくとも一種を含有する近赤外線吸収フィルムあるいは板が提案されている。特開平４−１７４４０２号公報においては、アルミニウム化合物を含有する合成樹脂組成物を更に重合、硬化させた赤外線吸収フィルターが提案されている。さらに、近年、プラズマディスプレー用フィルターとして、特開平９−２３０１３４においてはジチオール系金属錯体を特開平１０−７８５０９において、フタロシアニン色素を含有するプラズマディスプレー用フィルターが提案されている。
【０００５】
また、特開昭６３−１１２５９２号公報には、アミノチオフェノレート系金属錯体色素が開示されており、その用途として赤外線吸収フィルター用色素の記載がある。 さらに、近年、アミノチオフェノレート系金属錯体として、久司らにより、Bull.Chem.Soc.Jpn.,70(7)(1997)1599-1606に、Ｎ原子とＮ原子が炭素を介してつながったタイプの配位子を有する金属錯体を報告している。
【０００６】
これらのアミノチオフェノレート系金属錯体色素は、可視領域の吸収が小さく透過率が高いことが知られているが、耐光性においては、フタロシアニン系に劣っており、実用的に十分でなかった。
【０００７】
【発明が解決しようとする課題】
本発明の目的は、近赤外光域に大きな吸収を有し、化学的に安定で、近赤外線吸収性能、熱線吸収能、可視光線透過性能および耐光性に優れ、成膜性のよい
赤外線吸収色素材料、およびこれを用いた赤外線吸収フィルターを提供することである。
【０００８】
【課題を解決するための手段】
本発明者らは、上記課題を鑑み、鋭意検討した結果、アミノチオフェノレート系金属錯体色素において、金属に配位している窒素原子どおしを炭素鎖でつなぐことにより耐光性の低下の原因となるＮ−Ｈ部位をなくしたことにより安定化し、耐光性の向上が期待され、近赤外線吸収性能、熱線吸収能、可視光線透過性能および耐光性に優れる赤外線吸収フィルター提供することができることを見出し、本発明に到達した。
すなわち、本発明の要旨は、下記一般式（１）
【０００９】
【化３】
（Ｘは、ＳまたはＳｅを表し、Ｍは、金属元素を表す。環Ａ及び環Ｂは、各々独立に、ベンゼン環以外の任意の芳香族環を表し、さらに芳香族環は任意の置換基により置換されていてもよい。Ｒ1 〜Ｒ8は、各々独立に、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよいアリール基、置換基を有していてもよいアラルキル基、置換基を有していてもよいアルコキシ基、ニトロ基、ハロゲン原子、アミノ基、置換アミノ基またはシアノ基を表す。）で表されることを特徴とする有機金属錯体、及び有機金属錯体からなる赤外線吸収色素に存する。
【００１１】
また、本発明はこの有機金属錯体を用いた赤外線吸収フィルター及びプラズマディスプレイパネル用フィルターにも関する。
【００１２】
【発明の実施の形態】
以下、本発明について詳細に説明する。
本明細書中、Ｍｅはメチル基を、Ｅｔはエチル基を、Ｂｕはブチル基を、Ｐｒはプロピル基を、Ｈｅｘはヘキシル基を、Ｐｈはフェニル基を表し、ｉ−はイソをｎ−は直鎖、ｔ−はターシャリー、ｃ−はシクロ（環状）を表す。
【００１３】
本発明の金属有機錯体は前記一般式（１）で表される化合物である。つまり、アミノチオフェノレート系等の錯体において、ベンゼン環以外の芳香族環を有しているのがその特徴である。
環Ａ及び環Ｂは、各々独立にベンゼン環以外の任意の芳香族環であり、さらに芳香族環上に任意の置換基を有していても良い。このような芳香族環としては、炭化水素芳香族の多環式化合物や、炭素以外の異項原子を有する複素環系の単環式化合物または縮合環のいずれでもよい。
【００１４】
このような芳香族炭化水素の縮合環としては、５〜７員環の２〜４個の縮合環、具体的には、ナフタレン、アントラセン、フェナントレン、ピレン、アズレン、インデン等が挙げられる。
また複素環としては、５〜６員環の単環式複素環や、５〜６員環の縮合系複素環が好ましく、異項原子として窒素、酸素、硫黄を含む５〜６員環が好ましい。具体的には、ピリジン、ピリミジン、ピリダジン、ピラジン、トリアジン、ピラン、チオピラン、ピロール、ピラゾール、イミダゾール、フラン、チオフェン、オキザソール、チアゾール、オキザジアゾール、トリアゾール、チアジアゾール、プリン、ピロロピロール等が挙げられる。縮合系複素環としては、ベンゼン環１〜３個と異項原子として窒素、酸素、硫黄を含む５〜６員環の複素環の縮合環が好ましく、具体的には、ベンゾフラン、ベンゾジオキシラン、ベンゾジオキソール、インドール、チオナフテン、ベンズイミダゾール、ベンゾチアゾール、ベンズオキザゾール、キノリン、イソキノリン、シノリン、キノキサジン、アクリジン、ジベンゾフラン、キサンテンカルバゾール、フェナントロリン、ベンゾシノリン、フェノチアジン、フェノキサジン等が挙げられる。
【００１５】
これらの中でも、有機金属錯体の安定性の点から環Ａまたは環Ｂがナフタレン環であるのが好ましく、また、複素環の中では、チオフェン、チオナフテン、ベンゾフラン、ベンゾジオキシラン等が好ましい。中でも、環Ａ、環Ｂともにナフタレン環である場合が、その錯体としての安定性の点で最も好ましい。
そして、一般式（１）が、特に下記一般式（２）または（３）である場合、最も優れた安定性を示す赤外線吸収色素が得られる。
【００１６】
【化４】
上記一般式（２）、（３）中、Ｘは、ＳまたはＳｅを表し、好ましくはＳが用いられる。Ｍは、金属元素、金属酸化物または金属ハロゲン化物を表し、好ましくはＮｉ、Ｐｄ、Ｐｔ、Ｃｏ、Ｆｅ、Ｔｉ、Ｓｎ、 またはＣｕ、さらに好ましくはＮｉ，Ｐｔ、Ｐｄ、Ｃｏが用いられ、Ｎｉである場合が、好ましい。
中でも、ＸがＳであり、ＭがＮｉである場合、性能的にも優れ、かつ経済的にも有利であることから好ましい。さらに、有機金属錯体が左右対称の化合物である場合が合成上の容易さ、安定性の面から好ましい。
【００１８】
Ｒ1 〜Ｒ8は、それぞれ独立に、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよいアリール基、置換基を有していてもよいアラルキル基、置換基を有していてもよいアルコキシ基、ニトロ基、ハロゲン原子、アミノ基、置換アミノ基またはシアノ基を表わし、好ましくは、水素原子、アルキル基、アリール基、アラルキル基、アルコキシ基、ニトロ基、ハロゲン原子、アミノ基、置換アミノ基またはシアン基を表し、さらに好ましくは、水素原子；メチル基、エチル基、ｉ−ブチル基、ｔ−ブチル基、ｎ−ブチル基、ｎ−ペンチル基などの炭素数１〜５のアルキル基；アリール基、ベンジル基、フェネチル基などのアラルキル基；メトキシ基、エトキシ基、ｔ−ブトキシ基、ｎ−ブトキシ基などの炭素数１〜５のアルコキシ基；フェノキシ基、メチルフェノキシ基などの炭素数６〜１２のアリールオキシ基；ニトロ基；塩素原子、臭素原子、フッ素原子などのハロゲン原子；アミノ基；ジメチルアミノ基、ジエチルアミノ基、ジフェニルアミノ基などの置換アミノ基；またはシアノ基が挙げられ、特に好ましくは、水素原子が用いられる。
【００１９】
Ｘ1〜Ｘ28は、それぞれ独立に、水素原子、ハロゲン原子、ヒドロキシ基、アルコキシ基、ニトロ基、シアノ基、置換されていてもよいアルキル基、置換基を有していてもよいアリール基または置換基を有していてもよいアラルキル基を表す。具体的には、水素原子及びフッ素原子、塩素原子、臭素原子、ヒドロキシ基、メトキシ基、エトキシ基、ｔ−ブトキシ基、ｎ−ブトキシ基などの炭素数１〜５のアルコキシ基、フェノキシ基、メチルフェノキシ基などの炭素数６〜１２のアリールオキシ基、ニトロ基，シアノ基，メチル基、エチル基、ｉ−ブチル基、ｔ−ブチル基、ｎ−ブチル基、ｎ−ペンチル基などの炭素数１〜５のアルキル基、トリクロロメチル基、トリフルオロメチル基等の置換アルキル基、アリール基、ベンジル基、フェネチル基などのアラキル基が挙げられ、好ましくは、水素原子及びフッ素原子、塩素原子、臭素原子、ヒドロキシ基、メトキシ基、エトキシ基、ｔ−ブトキシ基、ｎ−ブトキシ基などの炭素数１〜５のアルコキシ基、トリクロロメチル基、トリフルオロメチル基、フェノキシ基、メチルフェノキシ基、ニトロ基、シアノ基等の電子吸引性基が挙げらる。
【００２０】
本発明の有機金属錯体としては、次のような化合物が挙げられる。
【００２１】
【化５】
【化６】
【化７】
【化８】
【化９】
本発明に用いられる有機金属錯体は、環Ａ、環Ｂがナフタレン環であり、かつＸかＲである場合、一般式（２）の有機金属錯体は、例えば次のようにして製造するすることができる。
【００２７】
【化１０】
すなわち、O-アミノベンゼンチオール類に、ナフチルアルデヒドを作用させ、ベンゾチアゾリンを合成し、それに錯体ソースを反応させイミノ錯体を合成する。その後、イミノ錯体を溶媒中で加熱することにより、容易に一般式（２）で表される化合物が合成できる。（式中、Ｒ1 〜Ｒ8およびＸ1〜Ｘ14は、一般式（２）における定義と同じである。）
一般式（３）の有機金属錯体も同様にして合成できる。
この反応で用いる錯体ソースの具体例としては、ＮｉＣｌ2 、ＮｉＣｌ2 ・６Ｈ2 Ｏ、Ｎｉ（ＯＣＯＣＨ3 ）2 、Ｎｉ（ＯＣＯＣＨ3 ）2 ・４Ｈ2 Ｏ、ＮｉＳＯ4 、ＰｄＣｌ2 、ＰｄＳＯ4 、ＰｔＣｌ4 、Ｎａ2 ＰｔＣｌ6 ・６Ｈ2 Ｏ、Ｋ2 ＰｔＣｌ6 ・６Ｈ2 Ｏ、ＣｏＣｌ2 、Ｃｏ（ＯＣＯＣＨ3 ）2 、Ｃｏ（ＯＣＯＣＨ3 ）2 ・４Ｈ2 Ｏ、ＣｏＳＯ4 、ＦｅＣｌ3 、ＦｅＳＯ4 、Ｆｅ2 （ＳＯ4 ）3 、ＴｉＣｌ3 、ＴｉＣｌ4 、Ｔｉ（ＳＯ4 ）2 、Ｓｎ（ＯＣＯＣＨ3 ）2 、Ｓｎ（ＯＣＯＣＨ3 ）4 、Ｓｎ（ＯＭｅ）4 、Ｓｎ（ＯＥｔ）4 、ＳｎＣｌ2 、ＳｎＣｌ2 ・２Ｈ2 Ｏ、ＳｎＣｌ4 、ＳｎＳＯ4 、Ｔｉ（ＯＭｅ）4 、Ｔｉ（ＯＥｔ）4 、ＣｕＣｌ2 、Ｃｕ（ＯＣＯＣＨ3 ）2 、ＣｕＳＯ4 、ＣｕＳＯ4 ・４Ｈ2 Ｏ等が挙げられる。
上記の反応は、通常溶媒中で行われる。溶媒としては、例えば、テトラヒドロフラン（以下「ＴＨＦ」という）、ジエチレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、テトラエチレングリコールジメチルエーテル等のエーテル類、メタノール、エタノール、プロパノール、ブタノール、ペンタノール、ヘキサノール、シクロヘキサノール、オクタノール等のアルコール類、１，２，３−トリクロロプロパン、テトラクロルエチレン、１，１，２，２−テトラクロロエタン、１，２−ジクロロエタン等のハロゲン化脂肪族炭化水素類、シクロヘキサン、ヘキサン、オクタン等の脂肪族炭化水素類、ベンゼン、トルエン、キシレン、メシチレン、モノクロロベンゼン、ジクロロベンゼン、ニトロベンゼン、スクアラン等の芳香族炭化水素類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ，Ｎ′，Ｎ′−テトラメチル尿素等のアミド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、ジメチルスルホキシド、スルホラン等のスルホキシド類、アセトニトリル、プロパンニトリル、ベンゾニトリル等のニトリル類、酢酸エチル、プロピオン酸メチル、エナント酸メチル、リノール酸メチル、ステアリン酸メチル等のエステル類が用いられる。これらの溶媒の中で、アルコール系溶媒、エーテル系溶媒が好ましい。
【００２９】
また、反応温度は、室温もしくは、０℃〜１５０℃で円滑に実施できる。
このようにして得られる本発明に用いる有機金属錯体は、近赤外領域に強い吸収を示し、通常ブルーの色調を示す。
本発明の有機金属錯体は、種々の機能性色素、具体的には、赤外線吸収フィルター用色素、熱線遮断用色素、遮光フィルム用色素、光記録材料用色素、データーコード用色素、レーザープリンタ用色素、一重項酸素クエンチャー、退色防止剤などとして使用できる。
【００３０】
次に、本発明の赤外線吸収フィルターの製造方法について説明する。
本発明の赤外線吸収フィルターの製造方法としては、透明基板に有機金属錯体を含む塗工液をコーティングする方法、有機金属錯体を配合したフィルムなどを透明基板として用いる方法などが挙られる。
本発明の赤外線吸収フィルターを構成する透明基板としては、実質的に透明であって、吸収、散乱が大きくない基板であればよく、特に制限はない。その具体的な例としては、ガラス、ポリオレフィン系樹脂、非晶質ポリオレフィン系樹脂、ポリエステル系樹脂、ポリカーボネート系樹脂、ポリ（メタ）アクリル酸エステル系樹脂、ポリスチレン、ポリ塩化ビニル、ポリ酢酸ビニル、ポリアリレート樹脂、ポリエーテルサルホン樹脂等が挙げられる。これらの中では、特に非晶質ポリオレフィン系樹脂、ポリエステル系樹脂、ポリカーボネート系樹脂、ポリ（メタ）アクリル酸エステル系樹脂、ポリアリレート樹脂、ポリエーテルサルホン樹脂が好ましい。
【００３１】
これらの樹脂は、フェノール系、燐系などの酸化防止剤、ハロゲン系、燐酸系等の難燃剤、耐熱老化防止剤、紫外線吸収剤、滑剤、帯電防止剤等の公知の添加剤を配合していもよい。
透明基板は、これらの樹脂を射出成形、Ｔダイ成形、カレンダー成形、圧縮成形等の方法や、有機溶剤に溶解させてキャスティングする方法などの成形方法により、フィルム状に成形して用いる。フィルム状に成形された樹脂は延伸されていても未延伸でもよい。また、異なる材料からなるフィルムが積層されていても良い。
【００３２】
透明基材の厚みは、目的に応じて通常１０μｍ〜５ｍｍの範囲から選択される。
更に、透明基材は、コロナ放電処理、火炎処理、プラズマ処理、グロー放電処理、粗面化処理、薬品処理等の従来公知の方法による表面処理や、アンカーコート剤やプライマー等のコーティングを施してもよい。
【００３３】
有機金属錯体を含む塗工液は、金属錯体をバインダー樹脂とともに溶剤中に溶解させることにより、調製することができる。このとき溶剤に溶解される有機金属錯体およびバインダー樹脂などの全固形分の濃度は、通常５〜５０重量％である。また、全固形分に対する有機金属錯体の濃度は、通常１〜８０重量％、好ましくは２〜７０重量％である。
【００３４】
また、有機金属錯体を必要に応じて分散剤を用いて、粒径を通常０．１〜３μｍに微粒子化し、バインダー樹脂とともに、溶剤に分散させて調整することもできる。このとき溶剤に分散される有機金属錯体、分散剤、バインダー樹脂等の固形分の濃度は、５〜５０重量％である。また、全固形分に対する有機金属錯体の濃度は、通常１〜８０重量％、好ましくは５〜７０重量％である。用いられる分散剤としては、ポリビニルブチラール樹脂、フェノキシ樹脂、ロジン変性フェノール樹脂、石油樹脂、硬化ロジン、ロジンエステル、マレイン化ロジン、ポリウレタン樹脂等が挙げられる。その使用量は、有機金属錯体に対して、通常０〜１００重量％、好ましくは０〜７０重量％である。
【００３５】
バインダー樹脂としては、ポリメチルメタクレート樹脂、ポリエチルアクリレート樹脂、ポリカーボネート樹脂、エチレンービニルアルコール共重合体樹脂、ポリエステル樹脂等が挙げられる。その使用量は、有機金属錯体に対して、１０〜２００重量％、好ましくは３０〜１００重量％である。
溶剤としては、１，２，３−トリクロロプロパン、テトラクロルエチレン、１，１，２，２−テトラクロロエタン、１，２−ジクロロエタン等のハロゲン化脂肪族炭化水素類、メタノール、エタノール、プロパノール、ブタノール、ペンタノール、ヘキサノール、シクロヘキサノール、オクタノール等のアルコール類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、酢酸エチル、プロピオン酸メチル、エナント酸メチル、リノール酸メチル、ステアリン酸メチル等のエステル類シクロヘキサン、ヘキサン、オクタン等の脂肪族炭化水素類、ベンゼン、トルエン、キシレン、メシチレン、モノクロロベンゼン、ジクロロベンゼン、ニトロベンゼン、スクアラン等の芳香族炭化水素類、ジメチルスルホキシド、スルホラン等のスルホキシド類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ，Ｎ′，Ｎ′−テトラメチル尿素等のアミド類、テトラヒドロフラン（以下「ＴＨＦ」という）、ジエチレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、テトラエチレングリコールジメチルエーテル等のエーテル類あるいはこれらの混合物を用いることができる。
【００３６】
また、有機金属錯体を含む塗工液には、さらに他の近赤外線吸収剤を添加してもよい。他の近赤外線吸収剤としては、有機物質であるニトロソ化合物及びその金属錯塩、シアニン系化合物、スクワリリウム系化合物、チオールニッケル錯塩系化合物、フタロシアニン化合物、ナフタロシアニン化合物、トリアリルメタン系化合物、インモニウム系化合物、ジインモニウム系化合物、ナフトキノン系化合物、アントラキノン系化合物、アミノ化合物、アミニウム塩系化合物、あるいは、無機物であるカーボンブラックや、酸化インジウムスズ、酸化アンチモンスズ、周期律表４Ａ、５Ａまたは６Ａ族に属する金属の酸化物、もしくは炭化物、またはホウ化物などが挙げられる。
【００３７】
このように、本発明の有機金属錯体の他、必要であればさらに他の近赤外線吸収剤を併用しながら、波長領域８００〜１１００ｎｍの近赤外線透過率が１５％以下となるように赤外線吸収フィルターを調製するのが好ましい。特に透明性と、赤外線吸収性能の面から、本発明の金属錯体とジインモニウム系化合物とを併用して用いることが好ましく、この場合には、相互作用による性能劣化の恐れがあるため、本発明の有機金属錯体とは別の層に含有させて用いた方が望ましい。
【００３８】
有機金属錯体を含む塗工液の透明基材へのコーティングは、ディッピング法、フローコート法、スプレー法、バーコート法、グラビアコート法、ロールコート法、ブレードコート法、エアーナイフコート法等の公知の塗工方法で行われる。有機金属錯体を含む層は、乾燥後の膜厚が、通常０．１〜３０μｍ、好ましくは０．５〜１０μｍとなるように塗布される。
【００３９】
本発明の赤外線吸収フィルターは、さらに紫外線カット層を設けることにより、有機金属錯体との相乗効果によって、赤外線吸収フィルターの耐光性を著しく向上させることができる。紫外線カット層としては、４００ｎｍ以下の波長の紫外線を効率よくカットできるものであり、３５０ｎｍの波長の光を７０％以上吸収できることが好ましい。紫外線カット層の種類については、特に制限されないが、好ましくは紫外線吸収剤を含有する樹脂フィルム（紫外線カットフィルム）が好ましい。
【００４０】
紫外線カット層に用いられる紫外線吸収剤としては、３００〜４００ｎｍの間に極大吸収を有し、その領域の光を効率よくカットする化合物であれば、有機系、無機系のいずれも特に限定なく用いることができる。例えば有機系紫外線吸収剤としては、ベンゾトリアゾール系紫外線吸収剤、ベンゾフェノン系紫外線吸収剤、サリチル酸エステル系紫外線吸収剤、トリアジン系紫外線吸収剤、パラアミノ安息香酸系紫外線吸収剤、ケイ皮酸系紫外線吸収剤、アクリレート系紫外線吸収剤、ヒンダードアミン系紫外線吸収剤等が挙げられ、無機系紫外線級剤としては酸化チタン系紫外線吸収剤、酸化亜鉛系紫外線吸収剤、微粒子酸化鉄系紫外線吸収剤等が挙げられるが、無機系紫外線吸収剤の場合は紫外線カット層中で微粒子状態で存在しているため、赤外線吸収フィルターの効率を損なう恐れがあることから、有機系紫外線吸収剤が好ましい。
【００４１】
このような紫外線吸収剤としては、例えば、チバガイギー（株）のチヌビンＰ、チヌビン１２０、２１３、２３４、３２０、３２６、３２７、３２８、３２９、３８４、４００、５７１、住友化学（株）のスミソーブ２５０、３００、５７７、共同薬品（株）バイオソーブ５８２、５５０、５９１、城北化学（株）のＪＦー８６、７９、７８、８０、旭電化（株）のアデカスタブＬＡ−３２，ＬＡ−３６，ＬＡ−３４、シプロ化成（株）のシーソルブ１００、１０１、１０１Ｓ、１０２、１０３、５０１、２０１、２０２、６１２ＮＨ、大塚化学（株）のRUVA９３、３０Ｍ、３０Ｓ、ＢＡＳＦ（株）のユービナール３０３９等が挙げられる。
【００４２】
これらの紫外線吸収剤は、単独で用いても良いが、数種類組み合わせても良い。
また、紫外線を吸収して可視領域に波長変換するチバガイギー（株）のユービテックスＯＢ，ＯＢ−Ｐ等の蛍光増白剤も利用できる。
紫外線吸収剤を含有する樹脂フィルム（紫外線カットフィルム）は、ポリエチレン樹脂、ポリプロピレン樹脂、ポリ塩化ビニル樹脂、ポリスチレン樹脂、ポリメタクレート樹脂、ポリアクリレート樹脂、ポリビニルブチラール樹脂、ポリカーボネート樹脂、エチレンービニルアルコール共重合体樹脂、エチレン−酢酸ビニル共重合体樹脂、ポリエステル樹脂、メラミン樹脂、ポリウレタン樹脂等の樹脂をベースに上記の紫外線吸収剤を添加して作製できる。紫外線カットフィルムの作製方法は、溶融／押し出し、溶融／押し出し／延伸法、キャスト法、カレンダー法、コーティング法等、一般的な方法が利用できる。紫外線カットフィルムの厚みは、２μｍ〜１ｍｍ程度である。紫外線吸収剤の添加量は、樹脂の厚み、目的の吸収強度等によって異なるが、通常、フィルムの１０ｐｐｍ〜３０％である。
【００４３】
また、紫外線カットフィルムは、市販のＵＶカットフィルターを使用することもでき、例えば、富士フィルム（株）のＳＣ−３８、ＳＣ−３９、三菱レーヨン（株）のアクリプレン等が挙げられる。上記のＵＶカットフィルター、ＳＣ−３９、アクリプレンは、ともに３５０ｎｍの波長を９９％以上吸収する紫外線カットフィルムである。
【００４４】
本発明の赤外線吸収フィルターは、必要に応じて、電磁波カット層、表面への蛍光灯などの外光の写り込みを防止する反射防止層、ぎらつき防止層（ノングレア層）、紫外線カット層等を設け、ＰＤＰ用フィルターとして使用することができる。
ＰＤＰフィルターについては、特にその構成、製造等限定されるものではないが、例えば、本発明の赤外線吸収フィルターを粘着層を介して透明樹脂基板に貼り合わせ、その両面に反射防止層、あるいはノングレア層を設けた構成であり、さらに赤外線吸収フィルターのＰＤＰ側には紫外線カット層を有していたり、またＰＤＰフィルターの任意の層の間に電磁波カット層を設けていてもよい。ＰＤＰフィルターの層構成はこれに限定されるものではなく、必要に応じていずれかの層を省略したり、さらに別の層を加えたりして、ＰＤＰフィルターとしての性能が十分発揮できる範囲で適宜層構成を変えてもよい。
【００４５】
また、赤外線吸収フィルターにおいて、本発明の有機金属錯体と、他の近赤外吸収剤を併用して用いる場合、本発明の同一の層に用いてもよいが、それらの相互作用による耐光性などの性能劣化の恐れがある場合には、別々の層に分けて複数の層として積層されていてもよい。
電磁波カット層とは、ＰＤＰより放出される電磁波を遮蔽するために設けられる層であり、４００〜７００ｎｍの可視光線領域を７０％以上透過し、表面固有抵抗値が５０Ω／□以下であるのが好ましい。電磁波カット層を設けるには金属酸化物等の蒸着あるいはスパッタリング方法等が利用できる。通常は酸化インジウムスズ（ＩＴＯ）が一般的であるが、誘導体層と金属層を基材上に交互にスパッタリング等で積層させることで１０００ｎｍ以上の光をカットすることもできる。誘電体層としては酸化インジウム、酸化亜鉛、酸化アンチモンスズ、アルミニウム酸化亜鉛等の透明な金属酸化物等であり、金属層としては銀あるいは銀−パラジウム合金が一般的であり、通常、誘電体層より３層、５層、７層あるいは１１層程度積層する。基材としては、本発明の赤外線吸収フィルターをそのまま利用しても良いし、樹脂フィルムあるいはガラス上に蒸着あるいはスパッタリングして電磁波カット層を設けた後に、本発明の赤外線吸収フィルターと貼り合わせても良い。
反射防止層は、表面の反射を抑えてフィルターの透過率を向上させるために、金属酸化物、フッ化物、ケイ化物、ホウ化物、炭化物、窒化物、硫化物等の無機物を、真空蒸着法、スパッタリング法、イオンプレーティング法、イオンビームアシスト法等で単層あるいは多層に積層させる方法、アクリル樹脂、フッ素樹脂などの屈折率の異なる樹脂を単層あるいは多層に積層させる方法等がある。また、反射防止処理を施したフィルムを該フィルター上に貼り付けることもできる。
【００４６】
また、ノングレア層も設けることもできる。ノングレア層は、フィルターの視野角を広げる目的で、透過光を散乱させるために、シリカ、メラミン、アクリル等の微粉体をインキ化して、表面にコーティングする方法などを用いることができる。インキの硬化は、熱硬化あるいは光硬化を用いることができる。また、ノングレア処理したフィルムを該フィルター上に貼り付けることもできる。更に必要であれば、ハードコート層を設けることもできる。
【００４７】
更に、この赤外線吸収フィルターは単独に用いられることは勿論、さらに透明のガラスや他の透明樹脂板等と貼り合わせて積層体として用いることができる。本発明により得られる赤外線吸収フィルターは、特にＰＤＰ用フィルターとして好適に用いられる他、ディスプレイ用フィルター、熱線遮断フィルム、サングラス、保護眼鏡、リモコン受光器など幅広い用途に使用することができる。
【００４８】
【実施例】
以下に、実施例により本発明を説明するが、本発明はこれにより何ら制限されるものではない。
実施例１
メタノール約１０ｍｌに２−ナフチルアルデヒド １．５６ｇ（０．０１ｍｏｌ）を溶かし、その溶液にｏ−アミノベンゼンチオール１．１０ｍｌ（０．０１ｍｏｌ）を室温で、撹拌しながら加え、０．５時間、リフラックスさせた。その溶液にさらにエタノール２０ｍｌ、Ni(AcO)2・4H2O １．１０ｇ（０．００４４ｍｏｌ）を加えると、赤茶色の固体が析出した。さらに1時間リフラックス後、減圧ろ過、エタノール懸洗数回後、ろ過物を６０℃で真空乾燥し、下式に示す赤茶色の有機金属錯体２．３５ｇ（０．０４０ｍｏｌ：収率９１．５％）を得た。
【００４９】
【化１１】
上記有機金属錯体１．０ｇにＴＨＦ１００ｍｌを加え、反応液が、青色に変化するまで、リフラックスさせた。その後、減圧ろ過により、ろ過物を除去後、ろ液を濃縮することにより、生成物が結晶化させた。その後、結晶を減圧ろ過、６０℃で、真空乾燥させ、下記生成物０．９１ｇ（収率９１．０％）を得た。
【００５１】
【化１２】
構造解析
（１）元素分析（C26H18Cl2N2NiS2）
Found：C,68.76；H,3.75；N,4.80；S,11.14
Calc ：C,70.00；H,4.15；N,4.80；S,10.99
（２）マススペクトル：M/Z.582
（マスパターンがC34H24N2S2Niで、シュミレートしたものと一致した。）
この有機金属錯体は、テトラヒドロフラン（以下「ＴＨＦ」と略記する場合もある）中で、近赤外領域である８３０ｎｍにε＝３２０００の強い吸収を示した。
実施例２
メタノール約１０ｍｌに１−ナフチルアルデヒド １．５６ｇ（０．０１ｍｏｌ）を溶かし、その溶液にｏ−アミノベンゼンチオール１．１０ｍｌ（０．０１ｍｏｌ）を室温で、撹拌しながら加え、０．５時間、リフラックスさせた。その溶液にさらにエタノール２０ｍｌ、Ni(AcO)2・4H2O １．１０ｇ（０．００４４ｍｏｌ）を加えると、赤茶色の固体が析出した。さらに1時間リフラックス後、減圧ろ過、エタノール懸洗数回後、ろ過物を６０℃で真空乾燥し、下式に示す赤茶色の有機金属錯体２．２２ｇ（０．０３８ｍｏｌ：収率８６．５％）を得た。
【００５３】
【化１３】
上記有機金属錯体１．０ｇにＴＨＦ１００ｍｌを加え、反応液が、青色に変化するまで、リフラックスさせた。その後、減圧ろ過により、ろ過物を除去後、ろ液を濃縮することにより、生成物が結晶化させた。その後、結晶を減圧ろ過、６０℃で、真空乾燥させ、下記生成物０．７２ｇ（収率７２．０％）を得た。
【００５５】
【化１４】
実施例３
耐光性を評価するため、実施例１で得られた有機金属錯体の５重量％ＴＨＦ溶液０．０６ｇに、ポリメチルメタクリレート樹脂（商品名；ダイヤナールＢＲ−８０：三菱レイヨン株式会社製品）のＴＨＦ／トルエン（＝１／１）溶液（樹脂濃度２０重量％）を１．５ｇ添加し、超音波洗浄機にて、完全に溶解させた後、この塗工液を、バーコータ＃２４でＯＨＰフィルムに塗工し、乾燥することにより、近赤外吸収フィルムを得た。塗布膜厚は、約６μｍであった。
【００５７】
このフィルムの近赤外吸収を、日立分光光度計Ｕ−３５００で測定したところ、λｍａｘは、８３５ｎｍであった。
更にこのフィルムに、富士写真フィル製ＵＶカットフィルター(アクリプレン＋SC-39)をかぶせ、キセノンロングライフフェードメーター（ＦＡＬ−２５ＡＸ−ＨＣＢ−ＥＣ）（スガ試験機社製品）により、４００時間照射し、８３５ｎｍにおける照射前後の吸収強度を測定したところ、照射後の強度は、照射前の強度の９０．６％であり、耐光性が高いことを確認した。
実施例４
実施例１で得られた有機金属錯体の０．５重量％メチルエチルケトン溶液、０．８重量部に、ポリメチルメタクリレート樹脂（三菱レイヨン株式会社製品ダイヤナールＢＲ−８０）のＭＥＫ／トルエン（＝１／１）溶液（２０重量％溶液）１重量部、トルエン ０．２重量部を添加した塗工液を、５０μｍの厚みのポリエチレンテレフタレートフィルムに、厚み２μｍになるようコーティングした。
上記フィルムに、表面固有抵抗５Ω／□の銀・インジウム酸化錫（ＩＴＯ）の多層蒸着フィルムを貼り合わせた。
【００５８】
更に、厚み４ｍｍのポリカーボネート板と貼り合わせた後、両面にフッ素系樹脂からなる反射防止剤を１００ｎｍの厚みにコーティングして、プラズマディスプレイパネル用フィルターを得た。
得られたプラズマディスプレイパネル用フィルターは、８００〜８８０ｎｍの光線透過率が２０％以下で、更に可視光線透過率が６５％以上であった。特に４００〜５００ｎｍの透過率が７５％以上と高く、黄色味が少ないため、ディスプレイ前面に設置した場合に、画質を悪化させず、フィルターとして良好であった。
比較例１
エタノール約８０ｍｌにＫＯＨ１．７８ｇ（０．０１８ｍｏｌ）を溶かし、その溶液にｏ−アミノベンゼンチオール２．００ｇ（０．０１６ｍｏｌ）を室温で、撹拌しながら加え、リガンド溶液とした。
【００５９】
一方、エタノール２０ｍｌにニッケル（II）クロリド・６水和物１．９２ｇ（０．００８ｍｏｌ）を溶解させ、上記リガンド溶液に撹拌しながら、滴下したところ溶液は、濃紺に変化した。
その後、濾過、Ｈ2 Ｏ、エタノールによる洗浄、アセトン不溶物除去、乾燥により、式（IV）で示されるビス（２−フェニルアミノベンゼンチオール）ニッケル錯体を単離した（収量１．７２１ｇ；収率７０．５％）。この錯体は、ＴＨＦ中で、近赤外領域である８０５ｎｍにε＝３５４００の強い吸収を示した。
【００６０】
【化１５】
耐光性を評価するため、得られたビス（２−フェニルアミノベンゼンチオール）ニッケル錯体の５重量％ＴＨＦ溶液０．６ｇに、ポリメチルメタクリレート樹脂（商品名；ダイヤナールＢＲ−８０：三菱レイヨン株式会社製品）のＴＨＦ／トルエン（＝１／１）溶液（樹脂濃度２０重量％）を３．０ｇ添加し、超音波洗浄機にて、完全に溶解させた後、この塗工液を、バーコータ＃２４でＯＨＰフィルムに塗工し、近赤外吸収フィルムを得た。塗布膜厚は、６μｍであった。
【００６２】
このフィルムの近赤外吸収を、日立分光光度計Ｕ−３５００で測定したところ、λｍａｘは、８２５ｎｍであった。
更にこのフィルムに、富士写真フィル製ＵＶカットフィルター(SC-39)をかぶせ、キセノンロングライフフェードメーター（ＦＡＬ−２５ＡＸ−ＨＣＢ−ＥＣ）（スガ試験機社製品）により、４００時間照射し、８２５ｎｍにおける照射前後の吸収強度を測定したところ、照射後の強度は、照射前の強度の８１．８％であった。
【００６３】
比較例２
近赤外線吸収色素として知られているフタロシアニン色素（日本触媒社製 ＩＲ−３） の１重量％ＭＥＫ／トルエン（＝１／１）溶液 ０．８重量部に、ポリメチルメタクリレート樹脂（三菱レイヨン株式会社製品ダイヤナールＢＲ−８０）のＭＥＫ／トルエン（＝１／１）溶液（２０重量％溶液） １重量部、ＭＥＫ ０．１重量部、トルエン ０．１重量部を添加した塗工液を、５０μｍの厚みのポリエチレンテレフタレートフィルムに、厚み２μｍになるようコーティングした。
【００６４】
実施例４と同様に、上記フィルムに銀・ＩＴＯ多層蒸着フィルムを貼り合わせ、更にポリカーボネート板と貼り合わせた後、両面に反射防止剤をコーティングし、プラズマディスプレイパネル用フィルターを得た。
得られたプラズマディスプレイパネル用フィルターは、８００〜８８０ｎｍの光線透過率が２０％以下であったが、可視光線透過率は４５％以上、４００〜５００ｎｍの透過率は５８％以下であり、ディスプレイ前面に設置した場合に、画面が暗くなり、フィルターとしては好ましくなかった。
【００６５】
【発明の効果】
本発明によれば、近赤外領域に強い吸収を示す有機金属錯体を提供できる。また、この有機金属錯体は、有機溶媒に可溶なため、フィルム等に容易に加工でき、この近赤外線吸収層を設けた、近赤外線吸収性能、熱線吸収能、可視光線透過性能および長時間の耐光性に優れる近赤外線吸収フィルターを提供できる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel organometallic complex that exhibits absorption in the near-infrared light region, an organometallic complex dye, an infrared absorption filter using the same, and a filter for a plasma display panel. Specifically, it is used for dyes for infrared absorption filters, dyes for heat ray blocking, dyes for light shielding films, dyes for optical recording materials, dyes for data codes, dyes for laser printers, singlet oxygen quenchers, anti-fading agents, etc. The present invention relates to an infrared-absorbing dye material that can be used. In addition, regarding infrared absorbing filters containing these dyes, filters that shield infrared rays by being excellent in near-infrared absorbing performance, heat ray absorbing capability, visible light transmitting capability, and light resistance, specifically, infrared filters for digital cameras It is an infrared absorption filter that can be suitably used for a filter of an image display device such as a plasma display panel.
[0002]
[Prior art]
In general, a plastic near-infrared absorbing filter made of a resin containing a near-infrared absorber is well known. Applications include sunglasses, welding glasses, buildings and automobiles, airplane windows, or optical reading devices for reading information.
[0003]
Recently, a plasma display panel (hereinafter referred to as “PDP”), which has been attracting attention as a large and thin wall-mounted television, generates near infrared rays, such as a video deck using a cordless phone or a near infrared remote control. There is a demand for an infrared absorption filter that absorbs near infrared rays and a demand for an infrared filter for digital cameras as PDP filters because they act on equipment and cause malfunctions.
[0004]
In response to this requirement, Japanese Patent Publication No. 2-4881 proposes an optical filter made of a thermoplastic resin containing a benzenedithiol-based metal complex. Japanese Patent Publication No. 6-38125 proposes a near-infrared absorbing film or plate containing at least one of an anthraquinone compound or a naphthalocyanine-based compound in which a metal atom is coordinated at the center. Japanese Patent Application Laid-Open No. 4-174402 proposes an infrared absorption filter obtained by further polymerizing and curing a synthetic resin composition containing an aluminum compound. Further, in recent years, as a filter for plasma display, a filter for plasma display containing a dithiol metal complex in JP-A-9-230134 and a phthalocyanine dye in JP-A-10-78509 has been proposed.
[0005]
Japanese Patent Application Laid-Open No. 63-112292 discloses an aminothiophenolate-based metal complex dye, and describes a dye for an infrared absorption filter as its use. Further, in recent years, as an aminothiophenolate-based metal complex, Hisashi et al. Connected N. atom and N atom to Bull. Chem. Soc. Jpn., 70 (7) (1997) 1599-1606 via carbon. A metal complex with a type of ligand has been reported.
[0006]
These aminothiophenolate metal complex dyes are known to have low absorption in the visible region and high transmittance, but in terms of light resistance, they are inferior to phthalocyanines and are not practically sufficient.
[0007]
[Problems to be solved by the invention]
The object of the present invention is to have a large absorption in the near-infrared light region, chemically stable, excellent near-infrared absorption performance, heat ray absorption ability, visible light transmission performance and light resistance, and good film formability.
An infrared absorbing dye material and an infrared absorbing filter using the same are provided.
[0008]
[Means for Solving the Problems]
As a result of intensive studies in view of the above problems, the inventors of the present invention have reduced light resistance by connecting nitrogen atoms coordinated to a metal with a carbon chain in an aminothiophenolate-based metal complex dye. It is possible to provide an infrared absorption filter that is stabilized by eliminating the N—H site that is the cause, and is expected to improve light resistance, and is excellent in near infrared absorption performance, heat ray absorption performance, visible light transmission performance, and light resistance. The headline, the present invention has been reached.
That is, the gist of the present invention is the following general formula (1).
[0009]
[Chemical 3]
(X represents S or Se, M represents a metal element. Ring A and ring B each independently represent any aromatic ring other than a benzene ring, and the aromatic ring represents an optional substituent. May be substituted by R. 1 ~ R 8 Each independently has a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent. Represents an optionally substituted alkoxy group, nitro group, halogen atom, amino group, substituted amino group or cyano group. And an infrared-absorbing dye composed of the organometallic complex.
[0011]
The present invention also relates to an infrared absorption filter and a plasma display panel filter using the organometallic complex.
[0012]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
In the present specification, Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, Pr represents a propyl group, Hex represents a hexyl group, Ph represents a phenyl group, i- represents iso, n- represents Straight chain, t- represents tertiary, and c- represents cyclo (cyclic).
[0013]
The metal organic complex of the present invention is a compound represented by the general formula (1). That is, the aminothiophenolate-based complex has an aromatic ring other than the benzene ring.
Ring A and ring B are each independently an arbitrary aromatic ring other than a benzene ring, and may further have an arbitrary substituent on the aromatic ring. Such an aromatic ring may be a hydrocarbon aromatic polycyclic compound, a heterocyclic monocyclic compound having a hetero atom other than carbon, or a condensed ring.
[0014]
Examples of such aromatic hydrocarbon condensed rings include 2 to 4 condensed rings of 5 to 7 members, specifically naphthalene, anthracene, phenanthrene, pyrene, azulene, indene and the like.
The heterocyclic ring is preferably a 5- to 6-membered monocyclic heterocyclic ring or a 5- or 6-membered condensed heterocyclic ring, and a 5- or 6-membered ring containing nitrogen, oxygen, or sulfur as a hetero atom is preferable. . Specific examples include pyridine, pyrimidine, pyridazine, pyrazine, triazine, pyran, thiopyran, pyrrole, pyrazole, imidazole, furan, thiophene, oxazole, thiazole, oxadiazole, triazole, thiadiazole, purine, pyrrolopyrrole, and the like. The condensed heterocyclic ring is preferably a condensed ring of 1 to 6 benzene rings and a 5 to 6-membered heterocyclic ring containing nitrogen, oxygen and sulfur as hetero atoms, specifically, benzofuran, benzodioxirane, Examples include benzodioxole, indole, thionaphthene, benzimidazole, benzothiazole, benzoxazole, quinoline, isoquinoline, cinnoline, quinoxazine, acridine, dibenzofuran, xanthenecarbazole, phenanthroline, benzocinoline, phenothiazine, phenoxazine and the like.
[0015]
Among these, from the viewpoint of the stability of the organometallic complex, ring A or ring B is preferably a naphthalene ring, and among the heterocyclic rings, thiophene, thionaphthene, benzofuran, benzodioxirane and the like are preferable. Among them, the case where both ring A and ring B are naphthalene rings is most preferable in terms of stability as a complex thereof.
And when general formula (1) is especially the following general formula (2) or (3), the infrared rays absorption pigment | dye which shows the most outstanding stability is obtained.
[0016]
[Formula 4]
In the general formulas (2) and (3), X represents S or Se, and preferably S is used. M represents a metal element, metal oxide or metal halide, preferably Ni, Pd, Pt, Co, Fe, Ti, Sn, or Cu, more preferably Ni, Pt, Pd, Co, Ni Is preferred.
Among these, it is preferable that X is S and M is Ni because it is excellent in performance and economically advantageous. Furthermore, the case where the organometallic complex is a bilaterally symmetric compound is preferable from the viewpoint of ease of synthesis and stability.
[0018]
R 1 ~ R 8 Each independently has a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent. Represents an optionally substituted alkoxy group, nitro group, halogen atom, amino group, substituted amino group or cyano group, preferably a hydrogen atom, alkyl group, aryl group, aralkyl group, alkoxy group, nitro group, halogen atom, amino group Represents a group, a substituted amino group or a cyan group, and more preferably a hydrogen atom; C 1-5 such as methyl group, ethyl group, i-butyl group, t-butyl group, n-butyl group and n-pentyl group. Alkyl groups; aralkyl groups such as aryl groups, benzyl groups, and phenethyl groups; alkoxy having 1 to 5 carbon atoms such as methoxy groups, ethoxy groups, t-butoxy groups, and n-butoxy groups An aryloxy group having 6 to 12 carbon atoms such as a phenoxy group and a methylphenoxy group; a nitro group; a halogen atom such as a chlorine atom, a bromine atom and a fluorine atom; an amino group; a dimethylamino group, a diethylamino group and a diphenylamino group; A substituted amino group; or a cyano group, particularly preferably a hydrogen atom.
[0019]
X 1 ~ X 28 Each independently has a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, a nitro group, a cyano group, an optionally substituted alkyl group, an optionally substituted aryl group or a substituent. Represents an aralkyl group which may be present. Specifically, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a hydroxy group, a methoxy group, an ethoxy group, a t-butoxy group, an n-butoxy group, etc., an alkoxy group having 1 to 5 carbon atoms, a phenoxy group, methyl Carbon number 1 such as aryloxy group having 6 to 12 carbon atoms such as phenoxy group, nitro group, cyano group, methyl group, ethyl group, i-butyl group, t-butyl group, n-butyl group and n-pentyl group -5 alkyl groups, substituted alkyl groups such as trichloromethyl group and trifluoromethyl group, aralkyl groups such as aryl group, benzyl group and phenethyl group, preferably hydrogen atom, fluorine atom, chlorine atom, bromine atom , Hydroxy group, methoxy group, ethoxy group, t-butoxy group, n-butoxy group and the like, alkoxy groups having 1 to 5 carbon atoms, trichloromethyl group, trif Oromechiru group, a phenoxy group, methylphenoxy group, a nitro group, an electron-withdrawing group such as cyano group Ageraru.
[0020]
Examples of the organometallic complex of the present invention include the following compounds.
[0021]
[Chemical formula 5]
[Chemical 6]
[Chemical 7]
[Chemical 8]
[Chemical 9]
When the ring A and ring B are naphthalene rings and X or R, the organometallic complex used in the present invention is produced, for example, as follows. Can do.
[0027]
[Chemical Formula 10]
That is, naphthylaldehyde is allowed to act on O-aminobenzenethiols to synthesize benzothiazoline, and then a complex source is reacted to synthesize an imino complex. Then, the compound represented by General formula (2) is easily compoundable by heating an imino complex in a solvent. (Wherein R 1 ~ R 8 And X 1 ~ X 14 Is the same as defined in the general formula (2). )
The organometallic complex of the general formula (3) can be synthesized in the same manner.
Specific examples of complex sources used in this reaction include NiCl. 2 NiCl 2 ・ 6H 2 O, Ni (OCOCH Three ) 2 , Ni (OCOCH Three ) 2 ・ 4H 2 O, NiSO Four , PdCl 2 , PdSO Four , PtCl Four , Na 2 PtCl 6 ・ 6H 2 O, K 2 PtCl 6 ・ 6H 2 O, CoCl 2 , Co (OCOCH Three ) 2 , Co (OCOCH Three ) 2 ・ 4H 2 O, CoSO Four , FeCl Three , FeSO Four , Fe 2 (SO Four ) Three TiCl Three TiCl Four , Ti (SO Four ) 2 , Sn (OCOCH Three ) 2 , Sn (OCOCH Three ) Four , Sn (OMe) Four , Sn (OEt) Four , SnCl 2 , SnCl 2 ・ 2H 2 O, SnCl Four , SnSO Four , Ti (OMe) Four , Ti (OEt) Four CuCl 2 , Cu (OCOCH Three ) 2 , CuSO Four , CuSO Four ・ 4H 2 O etc. are mentioned.
The above reaction is usually performed in a solvent. Examples of the solvent include ethers such as tetrahydrofuran (hereinafter referred to as “THF”), diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, methanol, ethanol, propanol, butanol, pentanol, hexanol, cyclohexanol, octanol, and the like. Alcohols, 1,2,3-trichloropropane, tetrachloroethylene, 1,1,2,2-tetrachloroethane, 1,2-dichloroethane and other halogenated aliphatic hydrocarbons, cyclohexane, hexane, octane, etc. Aliphatic hydrocarbons, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, monochlorobenzene, dichlorobenzene, nitrobenzene, squalane, N, N-di Amides such as Tylformamide, N, N, N ′, N′-tetramethylurea, Ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, Sulfoxides such as dimethyl sulfoxide and sulfolane, Acetonitrile, Propanenitrile, Benzonitrile, etc. Nitriles such as ethyl acetate, methyl propionate, methyl enanthate, methyl linoleate, and methyl stearate are used. Among these solvents, alcohol solvents and ether solvents are preferable.
[0029]
Moreover, reaction temperature can be smoothly implemented at room temperature or 0 to 150 degreeC.
The organometallic complex used in the present invention thus obtained exhibits strong absorption in the near infrared region, and usually exhibits a blue color tone.
The organometallic complex of the present invention includes various functional dyes, specifically, infrared absorbing filter dyes, heat ray blocking dyes, light shielding film dyes, optical recording material dyes, data code dyes, and laser printer dyes. , Singlet oxygen quencher, anti-fading agent and the like.
[0030]
Next, the manufacturing method of the infrared absorption filter of this invention is demonstrated.
Examples of the method for producing the infrared absorption filter of the present invention include a method of coating a transparent substrate with a coating solution containing an organometallic complex, a method of using a film containing an organometallic complex as a transparent substrate, and the like.
The transparent substrate constituting the infrared absorption filter of the present invention is not particularly limited as long as it is substantially transparent and does not absorb and scatter much. Specific examples include glass, polyolefin resin, amorphous polyolefin resin, polyester resin, polycarbonate resin, poly (meth) acrylate resin, polystyrene, polyvinyl chloride, polyvinyl acetate, poly Examples include arylate resin and polyethersulfone resin. Among these, amorphous polyolefin resin, polyester resin, polycarbonate resin, poly (meth) acrylate resin, polyarylate resin, and polyethersulfone resin are particularly preferable.
[0031]
These resins are blended with known additives such as phenol-based and phosphorus-based antioxidants, halogen-based and phosphoric acid-based flame retardants, heat-resistant anti-aging agents, ultraviolet absorbers, lubricants, antistatic agents and the like. Also good.
The transparent substrate is used by forming these resins into a film shape by a molding method such as injection molding, T-die molding, calender molding, compression molding, or a method of dissolving and casting in an organic solvent. The resin formed into a film may be stretched or unstretched. Moreover, the film which consists of a different material may be laminated | stacked.
[0032]
The thickness of the transparent substrate is usually selected from the range of 10 μm to 5 mm depending on the purpose.
Furthermore, the transparent substrate is subjected to surface treatment by a conventionally known method such as corona discharge treatment, flame treatment, plasma treatment, glow discharge treatment, roughening treatment, chemical treatment, or coating with an anchor coating agent or a primer. Also good.
[0033]
The coating liquid containing the organometallic complex can be prepared by dissolving the metal complex in a solvent together with the binder resin. At this time, the concentration of the total solids such as the organometallic complex and the binder resin dissolved in the solvent is usually 5 to 50% by weight. Moreover, the density | concentration of the organometallic complex with respect to the total solid is 1-80 weight% normally, Preferably it is 2-70 weight%.
[0034]
Further, the organometallic complex can be adjusted by using a dispersant as necessary, and the particle size is usually made fine to 0.1 to 3 μm and dispersed in a solvent together with the binder resin. At this time, the concentration of solids such as the organometallic complex, the dispersant, and the binder resin dispersed in the solvent is 5 to 50% by weight. Moreover, the density | concentration of the organometallic complex with respect to the total solid is 1-80 weight% normally, Preferably it is 5-70 weight%. Examples of the dispersant used include polyvinyl butyral resin, phenoxy resin, rosin-modified phenol resin, petroleum resin, cured rosin, rosin ester, maleated rosin, and polyurethane resin. The amount of its use is 0-100 weight% normally with respect to an organometallic complex, Preferably it is 0-70 weight%.
[0035]
Examples of the binder resin include polymethyl methacrylate resin, polyethyl acrylate resin, polycarbonate resin, ethylene-vinyl alcohol copolymer resin, and polyester resin. The amount used is 10 to 200% by weight, preferably 30 to 100% by weight, based on the organometallic complex.
Solvents include 1,2,3-trichloropropane, tetrachloroethylene, 1,1,2,2-tetrachloroethane, halogenated aliphatic hydrocarbons such as 1,2-dichloroethane, methanol, ethanol, propanol, butanol , Alcohols such as pentanol, hexanol, cyclohexanol and octanol, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, esters cyclohexane such as ethyl acetate, methyl propionate, methyl enanthate, methyl linoleate and methyl stearate , Aliphatic hydrocarbons such as hexane, octane, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, monochlorobenzene, dichlorobenzene, nitrobenzene, squalane, dimethyl sulfoxide, sulfora Sulfoxides such as N, N-dimethylformamide, amides such as N, N, N ′, N′-tetramethylurea, tetrahydrofuran (hereinafter referred to as “THF”), diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol Ethers such as dimethyl ether or a mixture thereof can be used.
[0036]
Moreover, you may add another near-infrared absorber to the coating liquid containing an organometallic complex further. Other near infrared absorbers include organic substances such as nitroso compounds and their metal complexes, cyanine compounds, squarylium compounds, thiol nickel complex compounds, phthalocyanine compounds, naphthalocyanine compounds, triallylmethane compounds, immonium compounds Compound, diimmonium compound, naphthoquinone compound, anthraquinone compound, amino compound, aminium salt compound, inorganic carbon black, indium tin oxide, antimony tin oxide, periodic table 4A, 5A or 6A group Examples thereof include metal oxides, carbides, borides, and the like.
[0037]
Thus, in addition to the organometallic complex of the present invention, an infrared absorption filter is used so that the near-infrared transmittance in the wavelength region of 800 to 1100 nm is 15% or less while further using another near-infrared absorber if necessary. Is preferably prepared. In particular, from the viewpoint of transparency and infrared absorption performance, it is preferable to use the metal complex of the present invention in combination with a diimmonium compound. In this case, there is a risk of performance deterioration due to interaction. It is desirable to use it in a separate layer from the organometallic complex.
[0038]
Coating on a transparent substrate with a coating solution containing an organometallic complex is a known method such as dipping method, flow coating method, spray method, bar coating method, gravure coating method, roll coating method, blade coating method, air knife coating method, etc. The coating method is used. The layer containing the organometallic complex is applied so that the film thickness after drying is usually 0.1 to 30 μm, preferably 0.5 to 10 μm.
[0039]
The infrared absorption filter of the present invention can significantly improve the light resistance of the infrared absorption filter due to a synergistic effect with the organometallic complex by further providing an ultraviolet cut layer. The ultraviolet cut layer is capable of efficiently cutting ultraviolet rays having a wavelength of 400 nm or less, and preferably absorbs 70% or more of light having a wavelength of 350 nm. The type of the ultraviolet cut layer is not particularly limited, but a resin film (ultraviolet cut film) containing an ultraviolet absorber is preferable.
[0040]
As an ultraviolet absorber used for the ultraviolet cut layer, any organic or inorganic compound can be used without particular limitation as long as it has a maximum absorption between 300 to 400 nm and can efficiently cut light in the region. be able to. For example, the organic UV absorbers include benzotriazole UV absorbers, benzophenone UV absorbers, salicylic acid ester UV absorbers, triazine UV absorbers, paraaminobenzoic acid UV absorbers, and cinnamic acid UV absorbers. Acrylate ultraviolet absorbers, hindered amine ultraviolet absorbers and the like, and inorganic ultraviolet grade agents include titanium oxide ultraviolet absorbers, zinc oxide ultraviolet absorbers, and particulate iron oxide ultraviolet absorbers. In the case of inorganic ultraviolet absorbers, organic ultraviolet absorbers are preferred because they exist in the form of fine particles in the ultraviolet cut layer and may impair the efficiency of the infrared absorption filter.
[0041]
Examples of such an ultraviolet absorber include Tinuvin P, Tinuvin P, Tinuvin 120, 213, 234, 320, 326, 327, 328, 329, 384, 400, 571, Sumitomo Chemical Co., Ltd. , 300, 577, Kyodo Pharmaceutical Co., Ltd. Biosorb 582, 550, 591, Johoku Chemical Co., Ltd. JF-86, 79, 78, 80, Asahi Denka Co., Ltd. Adekastab LA-32, LA-36, LA- 34, Cipro Chemical Co., Ltd. Seasolv 100, 101, 101S, 102, 103, 501, 201, 202, 612NH, Otsuka Chemical Co., Ltd. RUVA93, 30M, 30S, BASF Corporation Ubinar 3039, etc. .
[0042]
These ultraviolet absorbers may be used alone or in combination.
In addition, fluorescent whitening agents such as Ubitex OB and OB-P manufactured by Ciba Geigy Co., Ltd. that absorb ultraviolet rays and convert the wavelength into the visible region can also be used.
Resin films containing UV absorbers (UV cut films) are made of polyethylene resin, polypropylene resin, polyvinyl chloride resin, polystyrene resin, polymethacrylate resin, polyacrylate resin, polyvinyl butyral resin, polycarbonate resin, and ethylene-vinyl alcohol. It can be produced by adding the above-described ultraviolet absorber based on a resin such as a polymer resin, an ethylene-vinyl acetate copolymer resin, a polyester resin, a melamine resin, or a polyurethane resin. As a method for producing the ultraviolet cut film, general methods such as melting / extrusion, melting / extrusion / stretching method, casting method, calendering method, coating method and the like can be used. The thickness of the ultraviolet cut film is about 2 μm to 1 mm. The addition amount of the ultraviolet absorber varies depending on the thickness of the resin, the intended absorption strength, etc., but is usually 10 ppm to 30% of the film.
[0043]
In addition, as the ultraviolet cut film, a commercially available UV cut filter can be used, and examples thereof include SC-38 and SC-39 of Fuji Film Co., Ltd. and acrylene of Mitsubishi Rayon Co., Ltd. The UV cut filter, SC-39, and acrylene are both UV cut films that absorb 99% or more of the wavelength of 350 nm.
[0044]
The infrared absorption filter of the present invention includes an electromagnetic wave cut layer, an antireflection layer for preventing external light from being reflected on the surface, a glare prevention layer (non-glare layer), an ultraviolet cut layer, etc., as necessary. It can be used as a PDP filter.
The PDP filter is not particularly limited in its configuration, production, and the like. For example, the infrared absorption filter of the present invention is bonded to a transparent resin substrate via an adhesive layer, and an antireflection layer or a non-glare layer on both sides thereof. Further, an ultraviolet cut layer may be provided on the PDP side of the infrared absorption filter, or an electromagnetic wave cut layer may be provided between arbitrary layers of the PDP filter. The layer structure of the PDP filter is not limited to this, and any layer may be omitted as necessary, or another layer may be added as appropriate, as long as the performance as a PDP filter can be sufficiently exerted. The layer configuration may be changed.
[0045]
Further, in the infrared absorption filter, when the organometallic complex of the present invention and another near infrared absorber are used in combination, they may be used in the same layer of the present invention, but light resistance due to their interaction, etc. If there is a risk of performance deterioration, the layers may be divided into separate layers and laminated as a plurality of layers.
The electromagnetic wave cut layer is a layer provided to shield the electromagnetic wave emitted from the PDP, and transmits a visible light region of 400 to 700 nm by 70% or more, and has a surface resistivity of 50Ω / □ or less. preferable. In order to provide the electromagnetic wave cut layer, vapor deposition of metal oxide or the like, sputtering method or the like can be used. Usually, indium tin oxide (ITO) is common, but light of 1000 nm or more can also be cut by alternately laminating a derivative layer and a metal layer on a substrate by sputtering or the like. The dielectric layer is a transparent metal oxide such as indium oxide, zinc oxide, antimony tin oxide, and aluminum zinc oxide. The metal layer is generally silver or a silver-palladium alloy. Three, five, seven or eleven layers are stacked. As the substrate, the infrared absorption filter of the present invention may be used as it is, or after deposition or sputtering on a resin film or glass to provide an electromagnetic wave cut layer, it may be bonded to the infrared absorption filter of the present invention. good.
In order to suppress the reflection of the surface and improve the transmittance of the filter, the antireflection layer is formed by applying an inorganic substance such as a metal oxide, fluoride, silicide, boride, carbide, nitride, sulfide, etc. There are a method of laminating a single layer or a multilayer by a sputtering method, an ion plating method, an ion beam assist method, or the like, a method of laminating a resin having a different refractive index, such as an acrylic resin or a fluorine resin, in a single layer or a multilayer. Moreover, the film which gave the antireflection process can also be affixed on this filter.
[0046]
A non-glare layer can also be provided. In order to scatter the transmitted light, the non-glare layer may be formed by coating fine powders such as silica, melamine, and acrylic and coating the surface in order to scatter transmitted light. The ink can be cured by thermal curing or photocuring. Further, a non-glare-treated film can be stuck on the filter. Further, if necessary, a hard coat layer can be provided.
[0047]
Furthermore, this infrared absorption filter can be used alone, or can be used as a laminate by further bonding with transparent glass or another transparent resin plate. The infrared absorption filter obtained by the present invention can be used for a wide range of applications such as a display filter, a heat ray blocking film, sunglasses, protective glasses, and a remote control receiver, in addition to being particularly suitably used as a PDP filter.
[0048]
【Example】
Hereinafter, the present invention will be described by way of examples, but the present invention is not limited thereto.
Example 1
Dissolve 1.56 g (0.01 mol) of 2-naphthylaldehyde in about 10 ml of methanol, and add 1.10 ml (0.01 mol) of o-aminobenzenethiol to the solution at room temperature with stirring. Fluxed. Add 20 ml of ethanol and Ni (AcO) to the solution. 2 ・ 4H 2 When 1.10 g (0.0044 mol) of O was added, a reddish brown solid precipitated. Further, after refluxing for 1 hour, after filtration under reduced pressure and ethanol washing several times, the filtrate was vacuum-dried at 60 ° C., and 2.35 g (0.040 mol: yield 91.5) of a reddish brown organometallic complex represented by the following formula: %).
[0049]
Embedded image
100 ml of THF was added to 1.0 g of the organometallic complex and refluxed until the reaction solution turned blue. Thereafter, the filtrate was concentrated by removing the filtrate by vacuum filtration, and the product was crystallized by concentrating the filtrate. Thereafter, the crystals were filtered under reduced pressure and vacuum dried at 60 ° C. to obtain 0.91 g (yield 91.0%) of the following product.
[0051]
Embedded image
Structural analysis
(1) Elemental analysis (C26H18Cl2N2NiS2)
Found: C, 68.76; H, 3.75; N, 4.80; S, 11.14
Calc: C, 70.00; H, 4.15; N, 4.80; S, 10.99
(2) Mass spectrum: M / Z.582
(The mass pattern is C 34 H twenty four N 2 S 2 Matched with Ni, simulated. )
This organometallic complex exhibited a strong absorption of ε = 32000 in tetrahydrofuran (hereinafter sometimes abbreviated as “THF”) in the near infrared region of 830 nm.
Example 2
Dissolve 1.56 g (0.01 mol) of 1-naphthylaldehyde in about 10 ml of methanol, and add 1.10 ml (0.01 mol) of o-aminobenzenethiol to the solution at room temperature with stirring. Fluxed. Add 20 ml of ethanol and Ni (AcO) to the solution. 2 ・ 4H 2 When 1.10 g (0.0044 mol) of O was added, a reddish brown solid precipitated. Further, after refluxing for 1 hour, after filtration under reduced pressure and ethanol washing several times, the filtrate was vacuum-dried at 60 ° C., and 2.22 g of reddish brown organometallic complex represented by the following formula (0.038 mol: yield 86.5). %).
[0053]
Embedded image
100 ml of THF was added to 1.0 g of the organometallic complex and refluxed until the reaction solution turned blue. Thereafter, the filtrate was concentrated by removing the filtrate by vacuum filtration, and the product was crystallized by concentrating the filtrate. Thereafter, the crystals were filtered under reduced pressure and vacuum dried at 60 ° C. to obtain 0.72 g (yield 72.0%) of the following product.
[0055]
Embedded image
Example 3
In order to evaluate light resistance, 0.06 g of a 5 wt% THF solution of the organometallic complex obtained in Example 1 was added to THF of a polymethyl methacrylate resin (trade name; Dianar BR-80: product of Mitsubishi Rayon Co., Ltd.). After adding 1.5 g of / toluene (= 1/1) solution (resin concentration 20% by weight) and completely dissolving with an ultrasonic cleaner, this coating solution is applied to an OHP film with a bar coater # 24. The near-infrared absorption film was obtained by coating and drying. The coating film thickness was about 6 μm.
[0057]
When the near infrared absorption of this film was measured with Hitachi spectrophotometer U-3500, (lambda) max was 835 nm.
Further, this film was covered with a UV cut filter (Acryprene + SC-39) manufactured by Fuji Photo Film, and irradiated for 400 hours with a xenon long life fade meter (FAL-25AX-HCB-EC) (product of Suga Test Instruments Co., Ltd.) at 835 nm. When the absorption intensity before and after irradiation was measured, the intensity after irradiation was 90.6% of the intensity before irradiation, and it was confirmed that the light resistance was high.
Example 4
To 0.5 parts by weight of a 0.5 wt% methyl ethyl ketone solution of the organometallic complex obtained in Example 1, polymethyl methacrylate resin (Mitsubishi Rayon Co., Ltd. product Dainar BR-80) MEK / toluene (= 1/1 / 1) A coating solution containing 1 part by weight of a solution (20% by weight solution) and 0.2 part by weight of toluene was coated on a 50 μm thick polyethylene terephthalate film to a thickness of 2 μm.
A multilayer deposited film of silver / indium tin oxide (ITO) having a surface resistivity of 5Ω / □ was bonded to the film.
[0058]
Further, after being bonded to a polycarbonate plate having a thickness of 4 mm, an antireflection agent made of a fluororesin was coated on both sides to a thickness of 100 nm to obtain a plasma display panel filter.
The obtained filter for plasma display panel had a light transmittance of 800 to 880 nm of 20% or less and a visible light transmittance of 65% or more. In particular, the transmittance at 400 to 500 nm is as high as 75% or more and the yellow color is small. Therefore, when installed on the front of the display, the image quality is not deteriorated and the filter is good.
Comparative Example 1
1.78 g (0.018 mol) of KOH was dissolved in about 80 ml of ethanol, and 2.00 g (0.016 mol) of o-aminobenzenethiol was added to the solution with stirring at room temperature to obtain a ligand solution.
[0059]
On the other hand, 1.92 g (0.008 mol) of nickel (II) chloride hexahydrate was dissolved in 20 ml of ethanol and added dropwise with stirring to the above ligand solution, and the solution changed to dark blue.
Then filtered, H 2 The bis (2-phenylaminobenzenethiol) nickel complex represented by the formula (IV) was isolated by washing with O, ethanol, removal of insoluble acetone, and drying (yield 1.721 g; yield 70.5%). This complex exhibited a strong absorption of ε = 35400 at 805 nm in the near infrared region in THF.
[0060]
Embedded image
In order to evaluate the light resistance, 0.6 g of a 5 wt% THF solution of the obtained bis (2-phenylaminobenzenethiol) nickel complex was added to a polymethyl methacrylate resin (trade name; Dianal BR-80: Mitsubishi Rayon Co., Ltd.). Product) in a THF / toluene (= 1/1) solution (resin concentration: 20% by weight) was added and dissolved completely in an ultrasonic cleaner, and then the coating solution was added to bar coater # 24. Was applied to an OHP film to obtain a near-infrared absorbing film. The coating film thickness was 6 μm.
[0062]
When the near infrared absorption of this film was measured with Hitachi spectrophotometer U-3500, (lambda) max was 825 nm.
Further, this film was covered with a UV cut filter (SC-39) manufactured by Fuji Photo Film, and irradiated with a xenon long life fade meter (FAL-25AX-HCB-EC) (product of Suga Test Instruments Co., Ltd.) for 400 hours at 825 nm. When the absorption intensity before and after irradiation was measured, the intensity after irradiation was 81.8% of the intensity before irradiation.
[0063]
Comparative Example 2
A polymethyl methacrylate resin (Mitsubishi Rayon Co., Ltd.) was added to 0.8 part by weight of a 1% by weight MEK / toluene (= 1/1) solution of a phthalocyanine dye (IR-3 manufactured by Nippon Shokubai Co., Ltd.) known as a near infrared absorbing dye. Product dialnal BR-80) MEK / toluene (= 1/1) solution (20% by weight solution) 1 part by weight, MEK 0.1 part by weight, toluene added 0.1 part by weight, 50 μm A polyethylene terephthalate film having a thickness of 2 μm was coated.
[0064]
In the same manner as in Example 4, a silver / ITO multilayer deposited film was bonded to the above film and further bonded to a polycarbonate plate, and then an antireflection agent was coated on both surfaces to obtain a filter for a plasma display panel.
The obtained filter for plasma display panel had a light transmittance of 800 to 880 nm of 20% or less, but a visible light transmittance of 45% or more and a transmittance of 400 to 500 nm was 58% or less. When installed on the screen, the screen becomes dark, which is not preferable as a filter.
[0065]
【The invention's effect】
According to the present invention, an organometallic complex exhibiting strong absorption in the near infrared region can be provided. In addition, since this organometallic complex is soluble in an organic solvent, it can be easily processed into a film or the like, and provided with this near infrared absorbing layer, the near infrared absorbing performance, heat ray absorbing ability, visible light transmitting ability and long-time A near-infrared absorption filter having excellent light resistance can be provided.
Claims (13)
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| JP4530790B2 (en) * | 2004-09-30 | 2010-08-25 | 株式会社エーピーアイ コーポレーション | Method for producing dithiolate-based metal complex |
| JP4530791B2 (en) * | 2004-09-30 | 2010-08-25 | 株式会社エーピーアイ コーポレーション | Method for producing dithiolate-based metal complex |
| JP5011759B2 (en) | 2006-03-07 | 2012-08-29 | トヨタ自動車株式会社 | Fuel cell with cell voltage monitor |
| CN110405224B (en) * | 2019-08-13 | 2021-10-15 | 大连理工大学 | Method for one-step rapid synthesis of copper nanoclusters by taking amino thiophenol as ligand |
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