JP7414076B2 - Light-shielding ultraviolet curable composition, light-shielding film, and method for producing article having the light-shielding film - Google Patents
Light-shielding ultraviolet curable composition, light-shielding film, and method for producing article having the light-shielding film Download PDFInfo
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- JP7414076B2 JP7414076B2 JP2021561132A JP2021561132A JP7414076B2 JP 7414076 B2 JP7414076 B2 JP 7414076B2 JP 2021561132 A JP2021561132 A JP 2021561132A JP 2021561132 A JP2021561132 A JP 2021561132A JP 7414076 B2 JP7414076 B2 JP 7414076B2
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- light
- shielding
- curable composition
- ultraviolet curable
- meth
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
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Description
本発明は、遮光用紫外線硬化性組成物、遮光膜、及び、遮光膜を有する物品を製造する方法に関する。 The present invention relates to a light-shielding ultraviolet curable composition, a light-shielding film, and a method for producing an article having the light-shielding film.
液晶表示装置等の各種表示装置に設けられる遮光膜は、カーボンブラック等の黒色顔料を含む熱硬化型又は紫外線硬化型のインクを用いて形成されることがある（例えば、特許文献１）。紫外線硬化型のインクは、遮光膜の周辺部材又は印刷装置の損傷抑制、及び、印刷精度等の点で、熱硬化型のインクと比較して有利である。 Light-shielding films provided in various display devices such as liquid crystal display devices are sometimes formed using thermosetting or ultraviolet curable ink containing a black pigment such as carbon black (for example, Patent Document 1). Ultraviolet curing ink is more advantageous than thermosetting ink in terms of suppressing damage to surrounding members of the light-shielding film or the printing device, printing accuracy, and the like.
カーボンブラックを含む遮光膜は高い遮光性を有するものの、カーボンブラックが紫外線を実質的に透過しないことから、カーボンブラックを含む紫外線硬化性組成物（又はインク）は十分な紫外線硬化性を有し難い。紫外線をある程度透過する有機黒色顔料を用いることにより、紫外線硬化性の改善が期待されるが、その場合、遮光膜の遮光性が不足する傾向がある。 Although a light-shielding film containing carbon black has high light-shielding properties, since carbon black does not substantially transmit ultraviolet rays, it is difficult for an ultraviolet curable composition (or ink) containing carbon black to have sufficient ultraviolet curability. . By using an organic black pigment that transmits ultraviolet rays to some extent, it is expected that the ultraviolet curability will be improved, but in that case, the light-shielding properties of the light-shielding film tend to be insufficient.
そこで、本発明の一側面は、十分な紫外線硬化性を有するとともに、高い遮光性を有する遮光膜を形成することができる、遮光用紫外線硬化性組成物を提供する。 Accordingly, one aspect of the present invention provides an ultraviolet curable composition for light shielding, which has sufficient ultraviolet curability and can form a light shielding film having high light shielding properties.
本発明の一側面は、光重合性モノマと、有機黒色顔料と、粒子状の光散乱材とを含む、遮光用紫外線硬化性組成物を提供する。 One aspect of the present invention provides a light-shielding ultraviolet curable composition that includes a photopolymerizable monomer, an organic black pigment, and a particulate light-scattering material.
本発明の別の一側面は、上記遮光用紫外線硬化性組成物の硬化物を含む、遮光膜を提供する。 Another aspect of the present invention provides a light-shielding film containing a cured product of the UV-curable composition for light-shielding.
本発明の更に別の一側面は、基材上に上記遮光用紫外線硬化性組成物を含む樹脂膜を形成することと、前記樹脂膜に紫外線を照射することによって、上記遮光用紫外線硬化性組成物の硬化物を含む遮光膜を形成することと、を含む、遮光膜を有する物品を製造する方法を提供する。 Yet another aspect of the present invention is to form a resin film containing the light-shielding ultraviolet curable composition on a base material, and to irradiate the resin film with ultraviolet rays to form a resin film containing the light-shielding ultraviolet curable composition. Provided is a method for manufacturing an article having a light-shielding film, the method comprising: forming a light-shielding film containing a cured product of a light-shielding film.
本発明の一側面によれば、十分な紫外線硬化性を有するとともに、高い遮光性を有する遮光膜を形成することができる、遮光用紫外線硬化性組成物が提供される。 According to one aspect of the present invention, there is provided an ultraviolet curable composition for light shielding, which has sufficient ultraviolet curability and can form a light shielding film having high light shielding properties.
以下、本発明のいくつかの実施形態について詳細に説明する。ただし本発明は、以下の実施形態に限定されるものではない。本明細書において、「（メタ）アクリロイル」はメタクリロイル又はアクリロイルを意味する。これはその他の類似の表現についても同様である。 Hereinafter, several embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments. As used herein, "(meth)acryloyl" means methacryloyl or acryloyl. This also applies to other similar expressions.
一実施形態に係る遮光用紫外線硬化性組成物は、光重合性モノマと、有機黒色顔料と、粒子状の光散乱材とを含む。この紫外線硬化性組成物は、遮光膜を形成するために用いることができる。本実施形態に係る紫外線硬化性組成物は、遮光膜を印刷法によって形成するためのインク（例えばインクジェットインク）であることができる。 A light-shielding ultraviolet curable composition according to one embodiment includes a photopolymerizable monomer, an organic black pigment, and a particulate light-scattering material. This ultraviolet curable composition can be used to form a light shielding film. The ultraviolet curable composition according to this embodiment can be an ink (for example, an inkjet ink) for forming a light-shielding film by a printing method.
光重合性モノマは、光重合性の官能基を１以上有する１種以上の化合物から構成される。光重合性の官能基は、エチレン性不飽和基であってもよい。光重合性モノマは、１以上の（メタ）アクリロイル基を有する化合物であってもよい。重合性モノマとして用いられる（メタ）アクリロイル基を有する化合物は、（メタ）アクリル酸アルキルエステル、（メタ）アクリル酸、（メタ）アクリルアミド、Ｎ－アルキル（メタ）アクリルアミド、Ｎ，Ｎ－ジアルキル（メタ）アクリルアミド、又はこれらから選ばれる２種以上の組み合わせであってもよく、（メタ）アクリル酸アルキルエステル、Ｎ－アルキル（メタ）アクリルアミド、及びＮ，Ｎ－ジアルキル（メタ）アクリルアミドが有するアルキル基は、置換基を有していてもよい。置換基の例としては、アリール基、ヒドロキシ基、カルボキシル基、グリシジル基、及びアミノ基が挙げられる。 The photopolymerizable monomer is composed of one or more compounds having one or more photopolymerizable functional groups. The photopolymerizable functional group may be an ethylenically unsaturated group. The photopolymerizable monomer may be a compound having one or more (meth)acryloyl groups. Compounds having a (meth)acryloyl group used as polymerizable monomers include (meth)acrylic acid alkyl ester, (meth)acrylic acid, (meth)acrylamide, N-alkyl(meth)acrylamide, N,N-dialkyl(meth) ) acrylamide, or a combination of two or more selected from these. , may have a substituent. Examples of substituents include aryl, hydroxy, carboxyl, glycidyl, and amino groups.
光重合性モノマは、室温（２５℃）において液状であってもよい。液状の光重合性モノマを含む紫外線硬化性組成物は、無溶剤であっても、印刷に適した流動性を有し易い。光重合性モノマは、１個の（メタ）アクリロイル基を有する単官能アクリルモノマ、２個以上の（メタ）アクリロイル基を有する多官能アクリルモノマ、又はこれらの組み合わせであってもよい。 The photopolymerizable monomer may be liquid at room temperature (25°C). An ultraviolet curable composition containing a liquid photopolymerizable monomer tends to have fluidity suitable for printing even if it is solvent-free. The photopolymerizable monomer may be a monofunctional acrylic monomer having one (meth)acryloyl group, a polyfunctional acrylic monomer having two or more (meth)acryloyl groups, or a combination thereof.
単官能アクリルモノマは、特に限定されないが、その具体例としては、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ－ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｔｅｒｔ－ブチル（メタ）アクリレート、ｎ－ペンチル（メタ）アクリレート、ｎ－ヘキシル（メタ）アクリレート、ｎ－オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、２－エチルヘキシル（メタ）アクリレート、ドデシル（メタ）アクリレート、及びステアリル（メタ）アクリレート等の炭素数１～１８のアルキル基を有する（メタ）アクリレート；２－ヒドロキシエチル（メタ）アクリレート、１－ヒドロキシエチル（メタ）アクリレート、２－ヒドロキシプロピル（メタ）アクリレート、３－ヒドロキシプロピル（メタ）アクリレート、１－ヒドロキシプロピル（メタ）アクリレート、４－ヒドロキシブチル（メタ）アクリレート、３－ヒドロキシブチル（メタ）アクリレート、２－ヒドロキシブチル（メタ）アクリレート、及び１－ヒドロキシブチル（メタ）アクリレート等の水酸基を有する（メタ）アクリレート；グリシジル（メタ）アクリレート、α－エチルグリシジル（メタ）アクリレート、α－プロピルグリシジル（メタ）アクリレート、α－ブチルグリシジル（メタ）アクリレート、２－メチルグリシジル（メタ）アクリレート、２－エチルグリシジル（メタ）アクリレート、２－プロピルグリシジル（メタ）アクリレート、３，４－エポキシブチル（メタ）アクリレート、３，４－エポキシヘプチル（メタ）アクリレート、α－エチル－６，７－エポキシヘプチル（メタ）アクリレート、及び３，４－エポキシシクロヘキシルメチル（メタ）アクリレート等のグリシジル基を有する（メタ）アクリレート；並びに、シクロペンチル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、メチルシクロヘキシル（メタ）アクリレート、トリメチルシクロヘキシル（メタ）アクリレート、ノルボルニル（メタ）アクリレート、ノルボルニルメチル（メタ）アクリレート、フェニルノルボルニル（メタ）アクリレート、シアノノルボルニル（メタ）アクリレート、イソボルニル（メタ）アクリレート、ボルニル（メタ）アクリレート、メンチル（メタ）アクリレート、フェンチル（メタ）アクリレート、アダマンチル（メタ）アクリレート、ジメチルアダマンチル（メタ）アクリレート、トリシクロ［５．２．１．０２．６］デカ－８－イル（メタ）アクリレート、トリシクロ［５．２．１．０２．６］デカ－４－メチル（メタ）アクリレート、及びシクロデシル（メタ）アクリレート等の脂環式基を有する（メタ）アクリレートが挙げられる。Monofunctional acrylic monomers are not particularly limited, but specific examples include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, and tert-butyl (meth)acrylate. , n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, and stearyl (meth)acrylate. (Meth)acrylates having an alkyl group having 1 to 18 carbon atoms such as acrylate; 2-hydroxyethyl (meth)acrylate, 1-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl ( meth)acrylate, 1-hydroxypropyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate, 3-hydroxybutyl(meth)acrylate, 2-hydroxybutyl(meth)acrylate, and 1-hydroxybutyl(meth)acrylate, etc. (Meth)acrylate having a hydroxyl group of , 2-ethylglycidyl (meth)acrylate, 2-propylglycidyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, 3,4-epoxyheptyl (meth)acrylate, α-ethyl-6,7-epoxy (meth)acrylates having a glycidyl group such as heptyl (meth)acrylate and 3,4-epoxycyclohexylmethyl (meth)acrylate; and cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, Trimethylcyclohexyl (meth)acrylate, norbornyl (meth)acrylate, norbornylmethyl (meth)acrylate, phenylnorbornyl (meth)acrylate, cyanonorbornyl (meth)acrylate, isobornyl (meth)acrylate, bornyl (meth)acrylate acrylate, menthyl (meth)acrylate, fenthyl (meth)acrylate, adamantyl (meth)acrylate, dimethyladamantyl (meth)acrylate, tricyclo[5.2.1.0 2.6 ]dec-8-yl (meth)acrylate, Examples include (meth)acrylates having an alicyclic group such as tricyclo[5.2.1.0 2.6 ]deca-4-methyl (meth)acrylate and cyclodecyl (meth)acrylate.
硬化性組成物が、液状の光重合性モノマと、ポリマ及び／又はオリゴマとを含んでいてもよい。ポリマ及びオリゴマが、光重合性基を有していてもよい。本明細書において、光重合性基を有するポリマ及びオリゴマは、光重合性モノマとみなされる。 The curable composition may contain a liquid photopolymerizable monomer and a polymer and/or oligomer. The polymer and oligomer may have a photopolymerizable group. In this specification, polymers and oligomers having photopolymerizable groups are considered photopolymerizable monomers.
光重合性モノマの含有量は、紫外線硬化性組成物の質量を基準として、１０質量％以上、２０質量％以上、３０質量％以上であってもよく、９５質量％以下であってもよい。ここでの含有量は、２種以上の化合物が光重合性モノマとして用いられる場合、それらの合計の含有量を意味する。 The content of the photopolymerizable monomer may be 10% by mass or more, 20% by mass or more, 30% by mass or more, or 95% by mass or less, based on the mass of the ultraviolet curable composition. The content here means the total content of two or more compounds when they are used as photopolymerizable monomers.
遮光用紫外線硬化性組成物は、光重合開始剤を更に含んでいてもよい。光重合開始剤は、紫外線を吸収することにより、光重合性モノマの重合反応を開始させる化合物である。光重合開始剤は、例えば光ラジカル重合開始剤、又は光カチオン重合開始剤であることができ、特に光ラジカル重合開始剤であってもよい。紫外線硬化性の観点から、光重合開始剤は、吸収スペクトルにおいて３００～４００ｎｍの範囲に極大値を示す化合物を含んでいてもよい。光重合性モノマと、有機黒色顔料と、粒子状の光散乱材とを含む組成物を、光重合開始剤と混合して遮光用紫外線硬化性組成物を製造するために用いてもよい。 The UV curable composition for light shielding may further contain a photopolymerization initiator. A photopolymerization initiator is a compound that starts a polymerization reaction of a photopolymerizable monomer by absorbing ultraviolet light. The photoinitiator can be, for example, a radical photopolymerization initiator or a cationic photopolymerization initiator, in particular a radical photopolymerization initiator. From the viewpoint of ultraviolet curability, the photopolymerization initiator may contain a compound that exhibits a maximum value in the absorption spectrum in the range of 300 to 400 nm. A composition containing a photopolymerizable monomer, an organic black pigment, and a particulate light scattering material may be mixed with a photopolymerization initiator and used to produce an ultraviolet curable composition for light shielding.
光ラジカル重合開始剤は、特に制限されないが、例えば、α－開裂型化合物、又は水素引き抜き型化合物であってもよく、２分子系ラジカル重合開始剤であってもよい。光重合開始剤の例としては、ベンゾフェノン、４－メチルベンゾフェノン、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラメチル－４，４’－ジアミノベンゾフェノン（ミヒラーケトン）、Ｎ，Ｎ－テトラエチル－４，４’－ジアミノベンゾフェノン、４－メトキシ－４’－ジメチルアミノベンゾフェノン、α－ヒドロキシイソブチルフェノン、２－エチルアントラキノン、ｔ－ブチルアントラキノン、１，４－ジメチルアントラキノン、１－クロロアントラキノン、２，３－ジクロロアントラキノン、３－クロル－２－メチルアントラキノン、１，２－ベンゾアントラキノン、２－フェニルアントラキノン、１，４－ナフトキノン、９，１０－フェナントラキノン、チオキサントン、２－クロロチオキサントン、１－ヒドロキシシクロヘキシルフェニルケトン、２，２－ジメトキシ－１，２－ジフェニルエタン－１－オン、１－［４－（２－ヒドロキシエトキシ）－フェニル］－２－ヒドロキシ－２－メチル－１－プロパン－１－オン、及び２－ヒドロキシ－２－メチル－１－フェニルプロパン－１－オン等の芳香族ケトン化合物；ベンゾイン、メチルベンゾイン、及びエチルベンゾイン等のベンゾイン化合物；ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソブチルエーテル、及びベンゾインフェニルエーテル等のベンゾインエーテル化合物；ベンジル；２，２－ジエトキシアセトフェノン；ベンジルジメチルケタール；β－（アクリジン－９－イル）（メタ）アクリル酸のエステル化合物；９－フェニルアクリジン、９－ピリジルアクリジン、及び１，７－ジアクリジノヘプタン等のアクリジン化合物；２－（ｏ－クロロフェニル）－４，５－ジフェニルイミダゾール二量体、２－（ｏ－クロロフェニル）－４，５－ジ（ｍ－メトキシフェニル）イミダゾール二量体、２－（ｏ－フルオロフェニル）－４，５－ジフェニルイミダゾール二量体、２－（ｏ－メトキシフェニル）－４，５－ジフェニルイミダゾール二量体、２－（ｐ－メトキシフェニル）－４，５－ジフェニルイミダゾール二量体、２，４－ジ（ｐ－メトキシフェニル）５－フェニルイミダゾール二量体、２－（２，４－ジメトキシフェニル）－４，５－ジフェニルイミダゾール二量体、及び２－（ｐ－メチルメルカプトフェニル）－４，５－ジフェニルイミダゾール二量体等の２，４，５－トリアリールイミダゾール二量体；２－ベンジル－２－ジメチルアミノ－１－（４－モリホリノフェニル）－１－ブタノン；２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノ－１－プロパン；ビス（２，４，６－トリメチルベンゾイル）－フェニルフォスフィンオキサイド；並びにオリゴ（２－ヒドロキシ－２－メチル－１－（４－（１－メチルビニル）フェニル）プロパノン）が挙げられる。これらの光重合開始剤は、１種を単独で用いてもよく、２種以上を組み合わせて用いてもよい。 The photoradical polymerization initiator is not particularly limited, and may be, for example, an α-cleavage type compound or a hydrogen abstraction type compound, or a bimolecular radical polymerization initiator. Examples of photoinitiators include benzophenone, 4-methylbenzophenone, N,N,N',N'-tetramethyl-4,4'-diaminobenzophenone (Michler's ketone), N,N-tetraethyl-4,4' -diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, α-hydroxyisobutylphenone, 2-ethylanthraquinone, t-butylanthraquinone, 1,4-dimethylanthraquinone, 1-chloroanthraquinone, 2,3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 1,2-benzoanthraquinone, 2-phenylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexylphenyl ketone, 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, and 2 - Aromatic ketone compounds such as hydroxy-2-methyl-1-phenylpropan-1-one; benzoin compounds such as benzoin, methylbenzoin, and ethylbenzoin; benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, and benzoin phenyl Benzoin ether compounds such as ether; benzyl; 2,2-diethoxyacetophenone; benzyl dimethyl ketal; ester compounds of β-(acridin-9-yl)(meth)acrylic acid; 9-phenylacridine, 9-pyridylacridine, and Acridine compounds such as 1,7-diacridinoheptane; 2-(o-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl) imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methoxyphenyl) )-4,5-diphenylimidazole dimer, 2,4-di(p-methoxyphenyl)5-phenylimidazole dimer, 2-(2,4-dimethoxyphenyl)-4,5-diphenylimidazole dimer and 2,4,5-triarylimidazole dimers such as 2-(p-methylmercaptophenyl)-4,5-diphenylimidazole dimer; -morpholinophenyl)-1-butanone; 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propane; bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide ; and oligo(2-hydroxy-2-methyl-1-(4-(1-methylvinyl)phenyl)propanone). These photopolymerization initiators may be used alone or in combination of two or more.
光重合開始剤の含有量は、紫外線硬化性組成物の質量を基準として、例えば０．１～１０質量％であってもよい。ここでの含有量は、２種以上の化合物が光重合開始剤として用いられる場合、それらの合計の含有量を意味する。 The content of the photopolymerization initiator may be, for example, 0.1 to 10% by mass based on the mass of the ultraviolet curable composition. The content here means the total content of two or more compounds when they are used as a photopolymerization initiator.
有機黒色顔料は、有機色素を含む黒色粒子であり、黒色顔料として通常用いられているものから選択することができる。有機黒色顔料は、例えば、ペリレン系顔料（ペリレンブラック）、ラクタム系顔料（ラクタムブラック）、アニリンブラック、シアニンブラック、リグニンブラック、及びＲＧＢブラックからなる群より選ばれる少なくとも１種であってもよい。 The organic black pigment is a black particle containing an organic dye, and can be selected from those commonly used as black pigments. The organic black pigment may be, for example, at least one selected from the group consisting of perylene pigments (perylene black), lactam pigments (lactam black), aniline black, cyanine black, lignin black, and RGB black.
紫外線硬化性組成物中に分散している有機黒色顔料の平均粒径（分散粒径）は、特に制限されないが、例えば０．０１～１．０μｍであってもよい。 The average particle size (dispersed particle size) of the organic black pigment dispersed in the ultraviolet curable composition is not particularly limited, but may be, for example, 0.01 to 1.0 μm.
有機黒色顔料の含有量は、遮光膜の適切な遮光性の観点から、紫外線硬化性組成物の質量を基準として、０．５質量％以上、又は１．０質量％以上であってもよく、５０質量％以下であってもよい。ここでの含有量は、２種以上の有機黒色顔料が用いられる場合、それらの合計の含有量を意味する。 The content of the organic black pigment may be 0.5% by mass or more, or 1.0% by mass or more, based on the mass of the ultraviolet curable composition, from the viewpoint of appropriate light-shielding properties of the light-shielding film. It may be 50% by mass or less. The content here means the total content when two or more types of organic black pigments are used.
光散乱材は、複数の粒子から構成される。通常、これら複数の粒子が紫外線硬化性組成物中に分散している。光散乱材の平均粒径は、０．０５μｍ以上であってもよく、５．０μｍ以下、４．０μｍ以下、３．０μｍ以下、２．０μｍ以下、又は１．０μｍ以下であってもよい。遮光膜の適切な遮光性の観点から、光散乱材の平均粒径が０．１～１．０μｍであってもよい。光散乱材の平均粒径は、レーザ回折・散乱法によって得られる体積基準の粒度分布から得られる値であってもよい。 The light scattering material is composed of a plurality of particles. Usually, these plurality of particles are dispersed in the ultraviolet curable composition. The average particle size of the light scattering material may be 0.05 μm or more, 5.0 μm or less, 4.0 μm or less, 3.0 μm or less, 2.0 μm or less, or 1.0 μm or less. From the viewpoint of appropriate light-shielding properties of the light-shielding film, the average particle size of the light-scattering material may be 0.1 to 1.0 μm. The average particle size of the light scattering material may be a value obtained from a volume-based particle size distribution obtained by a laser diffraction/scattering method.
光散乱材は、例えば、シリコーン粒子、シリカ粒子又はこれらの組み合わせを含んでいてもよい。光散乱材が、シリコーン粒子と、シリカ粒子、アルミナ粒子、及び酸化チタン粒子から選ばれるその他の粒子とを含んでいてもよい。光散乱材のうち一部又は全部が中空粒子であってもよい。シリコーン粒子はポリシロキサン鎖を有するシリコーンを含む粒子であり、シリコーンは、ポリシロキサン鎖が架橋された構造を有していてもよく、ポリオルガノシルセスキオキサンであってもよい。シリコーン粒子が、ポリシロキサン鎖を有するシリコーンを含む核粒子と、核粒子の表面上に形成された、ポリオルガノシルセスキオキサンを含む膜とを有する複合粒子であってもよい。 The light scattering material may include, for example, silicone particles, silica particles, or combinations thereof. The light scattering material may include silicone particles and other particles selected from silica particles, alumina particles, and titanium oxide particles. A part or all of the light scattering material may be hollow particles. The silicone particles are particles containing silicone having a polysiloxane chain, and the silicone may have a structure in which polysiloxane chains are crosslinked, or may be polyorganosilsesquioxane. The silicone particles may be composite particles having a core particle containing silicone having a polysiloxane chain and a film containing polyorganosilsesquioxane formed on the surface of the core particle.
光散乱材の含有量は、紫外線硬化性組成物の質量を基準として０．５質量％以上又は１．０質量％以上であってもよく、１０質量％以下、９．０質量％以下、８．０質量％以下、７．０質量％以下、６．０質量％以下、５．０質量％以下、又は４．０質量％以下であってもよい。ここでの含有量は、２種以上の光散乱材が用いられる場合、それらの合計の含有量を意味する。 The content of the light scattering material may be 0.5% by mass or more or 1.0% by mass or more based on the mass of the ultraviolet curable composition, and 10% by mass or less, 9.0% by mass or less, 8% by mass or less. It may be .0 mass% or less, 7.0 mass% or less, 6.0 mass% or less, 5.0 mass% or less, or 4.0 mass% or less. The content here means the total content when two or more types of light scattering materials are used.
紫外線硬化性組成物は、溶剤を実質的に含まない無溶剤の組成物であってもよい。より具体的には、溶剤の含有量が、紫外線硬化性組成物の質量を基準として１．０質量％以下であってもよく、０質量％であってもよい。溶剤を実質的に含まない組成物（インク）は、例えば、遮光膜周辺の部材への損傷防止、印刷装置の損傷防止、及び、高精度な遮光膜の形成の点で有利である。 The ultraviolet curable composition may be a solvent-free composition that does not substantially contain a solvent. More specifically, the content of the solvent may be 1.0% by mass or less, or 0% by mass, based on the mass of the ultraviolet curable composition. A composition (ink) that does not substantially contain a solvent is advantageous in terms of, for example, preventing damage to members around the light-shielding film, preventing damage to a printing device, and forming a light-shielding film with high precision.
紫外線硬化性組成物の膜が硬化することにより形成される硬化膜は、高い遮光性を有する。例えば、形成される硬化膜のＯＤ値（光学濃度）が、１．５以上、２．０以上、又は２．５以上であってもよい。ここでのＯＤ値は、厚み１３０μｍ±５μｍの硬化膜の、波長４００～７００ｎｍの光に対する平均透過率から算出される値である。 A cured film formed by curing a film of an ultraviolet curable composition has high light-shielding properties. For example, the OD value (optical density) of the cured film formed may be 1.5 or more, 2.0 or more, or 2.5 or more. The OD value here is a value calculated from the average transmittance of a cured film having a thickness of 130 μm±5 μm to light having a wavelength of 400 to 700 nm.
以上例示した実施形態に係る紫外線硬化性組成物を用いて、遮光膜を有する各種の物品を製造することができる。遮光膜を有する物品を製造する方法の一実施形態は、基材上に紫外線硬化性組成物を含む樹脂膜を形成することと、樹脂膜に紫外線を照射することにより、紫外線硬化性組成物の硬化物である遮光膜を形成することとを含む。紫外線硬化性組成物をインクとして用いた印刷（例えばインクジェット印刷）によって、樹脂膜を形成してもよい。樹脂膜を形成している紫外線硬化性組成物を硬化するための紫外線の波長は、３００～４００ｎｍであってもよい。樹脂膜（遮光膜）の厚みは、例えば２０～１０００μｍであってもよい。 Various articles having a light-shielding film can be manufactured using the ultraviolet curable composition according to the embodiments illustrated above. One embodiment of the method for producing an article having a light-shielding film includes forming a resin film containing an ultraviolet curable composition on a base material and irradiating the resin film with ultraviolet rays. This includes forming a light-shielding film that is a cured product. The resin film may be formed by printing (for example, inkjet printing) using an ultraviolet curable composition as an ink. The wavelength of ultraviolet light for curing the ultraviolet curable composition forming the resin film may be 300 to 400 nm. The thickness of the resin film (light shielding film) may be, for example, 20 to 1000 μm.
遮光膜を有する物品の例としては、画像表示装置、光学式センサー、及びレンズが挙げられる。 Examples of articles having light-shielding films include image display devices, optical sensors, and lenses.
以下、実施例を挙げて本発明をさらに具体的に説明する。ただし、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be explained in more detail with reference to Examples. However, the present invention is not limited to these examples.
１．原料
１－１．黒色顔料
有機黒色顔料
・ラクタム系顔料（分散粒径：０．１７μｍ）
・ペリレン系顔料（分散粒径：０．１７μｍ）
これらラクタム系顔料及びペリレン系顔料の透過スペクトルは、波長３００～４００ｎｍの範囲において、透過率１０％を超える部分を含む。
その他顔料
・カーボンブラック（分散粒径：０．１５μｍ）1. Raw materials 1-1. Black pigment Organic black pigment/lactam pigment (dispersed particle size: 0.17 μm)
・Perylene pigment (dispersed particle size: 0.17 μm)
The transmission spectra of these lactam pigments and perylene pigments include a portion where the transmittance exceeds 10% in the wavelength range of 300 to 400 nm.
Other pigments/carbon black (dispersed particle size: 0.15μm)
１－２．光散乱材
・シリコーン粒子（信越化学工業製、製品名：Ｘ－５２－８５４、平均粒径：０．７μｍ）
・シリコーン粒子（信越化学工業製、製品名：ＫＭＰ－７０６、平均粒径：２．０μｍ）
・シリコーン複合粒子（信越化学工業製、製品名：Ｘ－５２－７０３０、平均粒径：０．８μｍ)
・シリカ粒子（アドマテックス製、製品名：Ｓ０－Ｃ１、平均粒径：０．３μｍ)
・シリカ粒子（アドマテックス製、製品名：Ｓ０－Ｃ２、平均粒径：０．５μｍ)1-2. Light scattering material/silicone particles (manufactured by Shin-Etsu Chemical, product name: X-52-854, average particle size: 0.7 μm)
・Silicone particles (manufactured by Shin-Etsu Chemical, product name: KMP-706, average particle size: 2.0 μm)
・Silicone composite particles (manufactured by Shin-Etsu Chemical, product name: X-52-7030, average particle size: 0.8 μm)
・Silica particles (manufactured by Admatex, product name: S0-C1, average particle size: 0.3 μm)
・Silica particles (manufactured by Admatex, product name: S0-C2, average particle size: 0.5 μm)
１－３．光重合性モノマ
・４－ヒドロキシブチルアクリレート（４－ＨＢＡ）
１－４．光ラジカル重合開始剤
・１－ヒドロキシシクロヘキシルフェニルケトン（ＢＡＳＦ社製、製品名：Ｉｒｇａｃｕｒｅ－１８４）
・４－メチルベンゾフェノン（株式会社ソート製、製品名：ＳＢ－ＰＩ７１２）1-3. Photopolymerizable monomer 4-hydroxybutyl acrylate (4-HBA)
1-4. Radical photopolymerization initiator/1-hydroxycyclohexylphenyl ketone (manufactured by BASF, product name: Irgacure-184)
・4-Methylbenzophenone (manufactured by Sort Co., Ltd., product name: SB-PI712)
２．紫外線硬化性組成物（インク）
実施例１
ラクタム系顔料３．０質量部を４－ヒドロキシブチルアクリレート９１．７質量部に分散させて、ラクタム系顔料の分散粒径が０．１７μｍである分散液を得た。この分散液に、シリコーン粒子（Ｘ－５２－８５４）２．０質量部、１－ヒドロキシシクロヘキシルフェニルケトン（Ｉｒｇａｃｕｒｅ－１８４）３．０質量部、及び４－メチルベンゾフェノン（ＳＢ－ＰＩ７１２）０．３質量部を加え、混合液を自公転ミキサ（株式会社シンキー、製品名：ＡＲＥ－２５０）を用いて回転数２，０００ｒｐｍにて５分間攪拌することで、紫外線硬化性組成物を得た。2. UV curable composition (ink)
Example 1
3.0 parts by mass of the lactam pigment was dispersed in 91.7 parts by mass of 4-hydroxybutyl acrylate to obtain a dispersion liquid in which the dispersed particle size of the lactam pigment was 0.17 μm. To this dispersion were added 2.0 parts by mass of silicone particles (X-52-854), 3.0 parts by mass of 1-hydroxycyclohexylphenyl ketone (Irgacure-184), and 0.3 parts by mass of 4-methylbenzophenone (SB-PI712). Parts by mass were added, and the mixed solution was stirred for 5 minutes at a rotational speed of 2,000 rpm using a rotation-revolution mixer (Thinky Co., Ltd., product name: ARE-250) to obtain an ultraviolet curable composition.
実施例２～８及び比較例１～３
各材料及び配合量を表１に示すとおりに変更したこと以外は実施例１と同様にして、紫外線硬化性組成物を調製した。Examples 2 to 8 and Comparative Examples 1 to 3
An ultraviolet curable composition was prepared in the same manner as in Example 1 except that each material and the blending amount were changed as shown in Table 1.
３．積層フィルムの作製
実施例及び比較例の各紫外線硬化性組成物を、離型処理された表面を有する厚み７５μｍの支持フィルム（ポリエチレンテレフタラートフィルム、藤森工業製、製品名：７５Ｅ－００１０ＨＴＡ）上に、アプリケーターを用いて塗工した。形成された樹脂膜に、離型処理された厚み５０μｍの保護フィルム（ポリエチレンテレフタラートフィルム、藤森工業製、製品名：５０Ｅ－００１０ＢＤ）を被せた。保護フィルム側から、紫外線照射装置（アイグラフィックス株式会社製、メタルハライドランプ）を用いて紫外線を照射（３，０００ｍＪ／ｃｍ２）することによって樹脂膜を硬化させ、紫外線硬化性樹脂組成物の硬化物である遮光膜（厚み約１３０μｍ）を有する積層フィルムを得た。3. Preparation of laminated film Each of the ultraviolet curable compositions of Examples and Comparative Examples was placed on a 75 μm thick support film (polyethylene terephthalate film, manufactured by Fujimori Industries, product name: 75E-0010HTA) having a release-treated surface. It was applied using an applicator. The formed resin film was covered with a release-treated protective film (polyethylene terephthalate film, manufactured by Fujimori Industries, product name: 50E-0010BD) having a thickness of 50 μm. The resin film is cured by irradiating ultraviolet rays (3,000 mJ/cm 2 ) from the protective film side using an ultraviolet irradiation device (manufactured by Eye Graphics Co., Ltd., metal halide lamp), and the ultraviolet curable resin composition is cured. A laminated film having a light-shielding film (thickness approximately 130 μm) was obtained.
４．評価
４－１．反応率（紫外線硬化性）
実施例及び比較例の各紫外線硬化性組成物を、ガラス板上に１ｇ程度滴下して、ＵＶ照射前の測定サンプルとしての樹脂膜を形成した。形成された樹脂膜の赤外線吸収スペクトルを、フーリエ変換赤外線分光光度計（島津製作所製、製品名：ＩＲ Ｓｐｉｒｉｔ(ＱＡＴＲ－Ｓユニット)）を用いて、常温(２５℃)の環境下、分解能：２ｃｍ－１、積算：６４回の条件のＡＴＲ法によって測定した。4. Evaluation 4-1. Reaction rate (UV curable)
About 1 g of each of the ultraviolet curable compositions of Examples and Comparative Examples was dropped onto a glass plate to form a resin film as a measurement sample before UV irradiation. The infrared absorption spectrum of the formed resin film was measured using a Fourier transform infrared spectrophotometer (manufactured by Shimadzu Corporation, product name: IR Spirit (QATR-S unit)) at room temperature (25°C) with a resolution of 2 cm. -1 , integration: Measured by ATR method under the condition of 64 times.
遮光膜を有する積層フィルムから、１０ｍｍ×１０ｍｍのサイズを有する測定サンプルを切り出し、そこから保護フィルムを剥離した。露出した遮光膜をガラス板に貼合し、次いで、遮光膜から支持フィルムを剥離した。露出した遮光膜（ＵＶ照射後の測定サンプル）の赤外線吸収スペクトルを、上記と同様の方法で測定した。 A measurement sample having a size of 10 mm x 10 mm was cut out from a laminated film having a light-shielding film, and the protective film was peeled from it. The exposed light-shielding film was bonded to a glass plate, and then the support film was peeled off from the light-shielding film. The infrared absorption spectrum of the exposed light-shielding film (measurement sample after UV irradiation) was measured in the same manner as above.
得られた各赤外線吸収スペクトルにおいて、８１０ｃｍ－１近傍に極大を示すアクリロイル基に帰属する吸収ピークの強度（Ａ）と、１７２０ｃｍ－１近傍に極大を示すカルボニル基に帰属する吸収ピークの強度（Ｂ）とを求め、下記式により、アクリロイル基吸収ピーク比を算出した。
アクリロイル基吸収ピーク比＝（Ａ）／（Ｂ）In each of the obtained infrared absorption spectra, the intensity of the absorption peak attributed to the acryloyl group having a maximum near 810 cm -1 (A) and the intensity of the absorption peak belonging to the carbonyl group showing a maximum near 1720 cm -1 (B ) was determined, and the acryloyl group absorption peak ratio was calculated using the following formula.
Acryloyl group absorption peak ratio = (A)/(B)
ＵＶ照射前の測定サンプルの赤外線吸収スペクトルから得られたアクリロイル基吸収ピーク比α、及び、ＵＶ照射後の測定サンプルの赤外線吸収スペクトルから得られたアクリロイル基吸収ピーク比βから、下記式により、アクリロイル基の反応率を算出した。この反応率の値が大きいことは、紫外線照射によって効率的に硬化が進行したことを意味する。
反応率（％）＝（β／α）×１００From the acryloyl group absorption peak ratio α obtained from the infrared absorption spectrum of the measurement sample before UV irradiation and the acryloyl group absorption peak ratio β obtained from the infrared absorption spectrum of the measurement sample after UV irradiation, acryloyl The reaction rate of the group was calculated. A large reaction rate value means that curing progressed efficiently by ultraviolet irradiation.
Reaction rate (%) = (β/α) x 100
４－２．ＯＤ値（遮光性）
４０ｍｍ×５０ｍｍのサイズを有する遮光膜の透過率を、光源としてＤ６５が装着されたヘイズメーター（日本電色工業製、製品名：ＳＨ７０００）を用いて、４００ｎｍから７００ｎｍまで、５ｎｍごとの各波長において測定した。各波長における透過率の平均値Ｃから、下記式によってＯＤ値を算出した。ＯＤ値が大きいことは、遮光膜の可視光に対する遮蔽性（遮光性）が高いことを意味する。
ＯＤ値＝－Ｌｏｇ１０（Ｃ／１００）4-2. OD value (light blocking property)
The transmittance of a light shielding film having a size of 40 mm x 50 mm was measured at each wavelength of 5 nm from 400 nm to 700 nm using a haze meter (manufactured by Nippon Denshoku Kogyo, product name: SH7000) equipped with D65 as a light source. It was measured. The OD value was calculated from the average value C of transmittance at each wavelength using the following formula. A large OD value means that the light shielding film has a high shielding property (light shielding property) against visible light.
OD value = -Log 10 (C/100)
各実施例の紫外線硬化性組成物は、紫外線照射によって良好な硬化性で硬化するとともに、十分に高い遮光性を有する遮光膜を形成した。有機黒色顔料を含み、光散乱材を含まない比較例１の紫外線硬化性組成物から形成された遮光膜は、遮光性が低かった。カーボンブラックを含む比較例２の紫外線硬化性組成物は、高い遮光性を有する遮光膜を形成したものの、硬化性の点で十分でなかった。 The ultraviolet curable compositions of each example were cured with good curability by ultraviolet irradiation, and formed a light-shielding film having sufficiently high light-shielding properties. The light-shielding film formed from the ultraviolet curable composition of Comparative Example 1, which contained an organic black pigment and did not contain a light-scattering material, had low light-shielding properties. Although the ultraviolet curable composition of Comparative Example 2 containing carbon black formed a light-shielding film with high light-shielding properties, the curability was insufficient.
Claims (6)
ラクタム系顔料を含む有機黒色顔料と、
粒子状の光散乱材と、
を含み、
前記光散乱材の平均粒径が０．１～１．０μｍであり、前記光散乱材がシリコーン粒子を含む、
遮光用紫外線硬化性組成物。 a photopolymerizable monomer;
an organic black pigment containing a lactam pigment;
Particulate light scattering material,
including;
The average particle size of the light scattering material is 0.1 to 1.0 μm, and the light scattering material contains silicone particles .
UV curable composition for light shielding.
前記ＯＤ値が、厚み１３０μｍ±５μｍの前記硬化膜の、波長４００～７００ｎｍの光に対する平均透過率から算出される値である、
請求項１又は２に記載の遮光用紫外線硬化性組成物。 The OD value of the cured film formed by curing the film of the light-shielding ultraviolet curable composition is 1.5 or more,
The OD value is a value calculated from the average transmittance of the cured film with a thickness of 130 μm ± 5 μm to light with a wavelength of 400 to 700 nm.
The ultraviolet curable composition for light shielding according to claim 1 or 2 .
前記樹脂膜に紫外線を照射することによって、前記遮光用紫外線硬化性組成物の硬化物を含む遮光膜を形成することと、
を含む、遮光膜を有する物品を製造する方法。 Forming a resin film containing the light-shielding ultraviolet curable composition according to any one of claims 1 to 4 on a substrate;
forming a light shielding film containing a cured product of the light shielding ultraviolet curable composition by irradiating the resin film with ultraviolet rays;
A method of manufacturing an article having a light-shielding film, comprising:
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| WO2017110939A1 (en) | 2015-12-25 | 2017-06-29 | 旭硝子株式会社 | Optical filter and optical device |
| JP2018141968A (en) | 2017-02-24 | 2018-09-13 | 新日鉄住金化学株式会社 | Photosensitive resin composition for light-shielding film, light-shielding film, liquid crystal display, method for manufacturing light-shielding film having spacer function, and method for manufacturing liquid crystal display |
| JP2018155878A (en) | 2017-03-16 | 2018-10-04 | 三菱ケミカル株式会社 | Coloring photosensitive resin composition, cured product, organic electroluminescenct element, image display device, and illumination |
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| JP2010150338A (en) * | 2008-12-24 | 2010-07-08 | Nippon Shokubai Co Ltd | Methods for producing resin film and shading film |
| KR20130021128A (en) * | 2011-08-22 | 2013-03-05 | 성균관대학교산학협력단 | Black photosensitive resin composition and display device having the same |
| JP6607682B2 (en) * | 2015-03-05 | 2019-11-20 | 日鉄ケミカル＆マテリアル株式会社 | Black resin composition for light-shielding film, substrate with light-shielding film having light-shielding film obtained by curing said composition, and color filter and touch panel having said substrate with light-shielding film |
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| WO2017110939A1 (en) | 2015-12-25 | 2017-06-29 | 旭硝子株式会社 | Optical filter and optical device |
| JP2018141968A (en) | 2017-02-24 | 2018-09-13 | 新日鉄住金化学株式会社 | Photosensitive resin composition for light-shielding film, light-shielding film, liquid crystal display, method for manufacturing light-shielding film having spacer function, and method for manufacturing liquid crystal display |
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