JP7104336B2 - 光硬化性組成物 - Google Patents
光硬化性組成物 Download PDFInfo
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- JP7104336B2 JP7104336B2 JP2019539683A JP2019539683A JP7104336B2 JP 7104336 B2 JP7104336 B2 JP 7104336B2 JP 2019539683 A JP2019539683 A JP 2019539683A JP 2019539683 A JP2019539683 A JP 2019539683A JP 7104336 B2 JP7104336 B2 JP 7104336B2
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- meth
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- acrylate
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- 239000000203 mixture Substances 0.000 title claims description 73
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 72
- -1 acrylate compound Chemical class 0.000 claims description 30
- 238000002834 transmittance Methods 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
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- 239000003513 alkali Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
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- 229920000515 polycarbonate Polymers 0.000 claims description 7
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- 229920000570 polyether Polymers 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000962 organic group Chemical group 0.000 claims description 5
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
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- 239000011248 coating agent Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 2
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
-
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Description
本発明の第二の実施態様は、200μm以下の厚さの前記光硬化性組成物の硬化物を0.7mm厚の無アルカリガラス板で挟んだ状態で、385nmの光透過率が30%以下であると共に黄色度が3.0以下である、第一の実施態様に記載の光硬化性組成物である。
[実施例1~3および比較例1~9]
組成物を調製するために下記成分を準備した。
・2-(2’-ヒドロキシ-5’-tert-オクチルフェニル)ベンゾトリアゾール(一般式1におけるRの炭素数の合計が8)(JF-83 城北化学工業株式会社製)
・2-(2’-ヒドロキシ-3’-tert-ブチル-5’-メチルフェニル)-5-クロロベンゾトリアゾール(一般式1におけるRの炭素数の合計が5)(JF-79 城北化学工業株式会社製)
・2-(3,5-ジ-tert-アミル-2-ヒドロキシフェニル)ベンゾトリアゾール(一般式1におけるRの炭素数の合計が10)(SEESORB704 シプロ化成株式会社製)
(A’)成分:(A)成分以外の化合物
・2-(5-クロロ-2-ベンゾトリアゾリル)-6-tert-ブチル-p-クレゾール(一般式1におけるRの炭素数の合計が5)(LA-36 株式会社ADEKA社製)
・2,2’,4,4’-テトラヒドロベンゾフェノン(一般式1の構造ではない)(Uvinul3050 BASF社製)
・6-(2-ベンゾトリアゾリル)-4-tert-オクチル-6’-tert-ブチル-4’-メチル-2,2’-メチレンビスフェノール(一般式1におけるRの炭素数の合計が20)(JAST-500 城北化学工業株式会社製)
・2-(2’-ヒドロキシ-5’-メタクリロキシエチルフェニル)-2H-ベンゾトリアゾ-ル(一般式1におけるRが炭化水素基ではない)(RUVA-93 大塚化学株式会社製)
・2-シアノ-3,3-ジフェニルアクリル酸エチル(一般式1の構造ではない)(SEESORB501 シプロ化成株式会社製)
・2-シアノ-3,3-ジフェニルアクリル酸2-エチルヘキシル(一般式1の構造ではない)(SEESORB502 シプロ化成株式会社製)
・2,2’-メチレンビス[6-(2H-ベンゾトリアゾール-2-イル)-4-tert-オクチルフェノール](2量体)(JF-832 城北化学工業株式会社製)
(B)成分:(メタ)アクリレート化合物
・ポリカーボネートを主骨格に有するウレタン変性アクリレートオリゴマー(イソボルニルメタクリレート50%希釈品)(UN-004RU 根上工業株式会社製)
・ポリエチレングリコール#1000ジメタクリレート(NKエステル23G 新中村化学工業株式会社製)
・ポリエチレングリコール#600ジメタクリレート(NKエステル14G 新中村化学工業株式会社製)
(C)成分:成膜樹脂
・重量平均分子量:60000でビスフェノールA型エポキシ樹脂/ビスフェノールF型混合タイプ(固形分100%)(jER4250 三菱ケミカル株式会社製)
(D)成分:光開始剤
・2,4,6-トリメチルベンゾイル-ジフェニル-フォスフィンオキサイド(IRGACURE TPO BASF社製)
その他成分
・3-メタクリロキシプロピルトリメトキシシラン(KBM-503 信越化学工業株式会社製)
溶剤
・メチルエチルケトン(試薬)
(A)~(D)成分、その他成分および溶剤を撹拌釜に秤量して25℃雰囲気下で1時間撹拌した。撹拌前の総重量からメチルエチルケトンが揮発していれば、揮発した分のメチルエチルケトンを補った。詳細な調製量は表1に従い、数値は全て質量部で表記した。また、溶剤を除いた組成物全体における(A)成分(または(A’)成分)の割合も質量%で表記した。
ベルトコンベア型紫外線照射器により積算光量30kJ/m2の条件で、長さ30mm×幅30mmのシートに光照射を行い硬化させた。硬化物を直径3mmの筒状に丸め、80℃雰囲気の熱風の乾燥炉に5分間投入した。室温まで温度が下がった後、以下の評価基準に従い目視で確認して「光硬化性」とする。加熱により形状が維持出来ない様な軟化または溶解する場合は、光硬化が十分ではない。
評価基準
○:筒状を維持している
×:筒状を維持していない
[外観確認(硬化後)]
一方の離型フィルムを剥がしたシートに対して、厚さ0.7mm×幅25mm×長さ100mmの無アルカリガラス板に付着させて、80℃にロール温度を設定した熱ロールラミネーターにより転写を行った。その後、もう一方の離型フィルムを剥がして、前記無アルカリガラス板を貼り付け、真空ラミネーターを用いて80℃雰囲気下で貼り合わせを行った。ベルトコンベア型紫外線照射器により積算光量30kJ/m2の紫外線を照射してシートを無アルカリガラスで貼り合わせたテストピースを作製した。下記の評価基準に従って目視により外観を確認し、その結果を「外観(硬化後)」とする。透明性を確保する上で、好ましくは「○」である。
評価基準
○:成分の溶け残りが無い
×:成分の溶け残りが有る
[光透過率測定(硬化後)]
外観確認(硬化後)で作成したテストピースと同様のテストピースを用いて、可視・紫外分光法により透過率測定を行った。800nmから300nmの範囲の波長における透過率測定を行い、385nmの透過率(%)を読み取った。試験数はn=3として平均値を算出して、下記の評価基準に従ってその結果を「光透過率(硬化後)(単位:%)」とする。外観(硬化後)が「×」の場合、本測定は行わず「-」と表記する。被着体にダメージを与える紫外線をカットするためには385nmの波長における透過率が「◎」または「○」であり、数値としては50%以下であり、好ましくは40%以下、最も好ましくは30%以下である。
評価基準
◎:385nmの波長における透過率が5%以下
○:385nmの波長における透過率が5%より大きく、50%以下
×:385nmの波長における透過率が50%より大きい
[黄色度測定(硬化後)]
外観確認(硬化後)で作成したテストピースと同様のテストピースを用いて、可視・紫外分光法により黄色度測定を行った。800nmから300nmの範囲の波長の透過率測定を行い、JIS K7373に従い黄色度を算出した。試験数はn=3とし、平均値を算出して、下記の評価基準に従ってその結果を「黄色度(硬化後)」とする。外観(硬化後)が「×」の場合、本測定は行わず「-」と表記する。無色透明を実現するために、黄色度は「◎」または「○」であり、数値としては3.0以下である。
評価基準
◎:黄色度が1.0以下
○:黄色度が1.0より大きく、3.0以下
×:黄色度が3.0より大きい
Claims (16)
- (A)成分として下記一般式1の化合物または2-(2’-ヒドロキシ-3’-tert-ブチル-5’-メチルフェニル)-5-クロロベンゾトリアゾールを含み、
さらに、(B)成分として(メタ)アクリレート化合物、(C)成分として成膜樹脂および(D)成分として光開始剤を含み、
前記(B)成分が(メタ)アクリレートオリゴマーおよび(メタ)アクリレートモノマーを含み、
前記(メタ)アクリレートオリゴマーが主骨格がポリカーボネートであるウレタン変性(メタ)アクリレートオリゴマーである 光硬化性組成物であって、
200μm以下の厚さの前記光硬化性組成物の硬化物を0.7mm厚の無アルカリガラス板で挟んだ状態で、385nmの光透過率が50%以下であると共に黄色度が3.0以下である、光硬化性組成物。
(nは1~4の整数であり、Rは炭素数の合計が6以上の炭化水素基であり、化合物の主骨格における水素が他の有機基に置換されていてもよく、ただし、多量体は除く。) - (A)成分として下記一般式1の化合物または2-(2’-ヒドロキシ-3’-tert-ブチル-5’-メチルフェニル)-5-クロロベンゾトリアゾールを含み、
さらに、(B)成分として(メタ)アクリレート化合物、(C)成分としてフェノキシ樹脂および(D)成分として光開始剤を含む光硬化性組成物であって、
200μm以下の厚さの前記光硬化性組成物の硬化物を0.7mm厚の無アルカリガラス板で挟んだ状態で、385nmの光透過率が50%以下であると共に黄色度が3.0以下である、光硬化性組成物。
(nは1~4の整数であり、Rは炭素数の合計が6以上の炭化水素基であり、化合物の主骨格における水素が他の有機基に置換されていてもよく、ただし、多量体は除く。) - 前記(A)成分が2-(2’-ヒドロキシ-3’-tert-ブチル-5’-メチルフェニル)-5-クロロベンゾトリアゾールである場合、前記(A)成分の含有量は溶剤を除いた組成物全体に対して0.1~1.1質量%である、請求項1または2に記載の光硬化性組成物。
- 200μm以下の厚さの前記光硬化性組成物の硬化物を0.7mm厚の無アルカリガラス板で挟んだ状態で、385nmの光透過率が30%以下であると共に黄色度が3.0以下である、請求項1~3のいずれか1項に記載の光硬化性組成物。
- 前記(B)成分が(メタ)アクリレートオリゴマーおよび(メタ)アクリレートモノマーを含む、請求項2に記載の光硬化性組成物。
- 前記(メタ)アクリレートオリゴマーがウレタン変性(メタ)アクリレートオリゴマーである、請求項5に記載の光硬化性組成物。
- 前記ウレタン変性(メタ)アクリレートオリゴマーの主骨格がポリカーボネートである、請求項6に記載の光硬化性組成物。
- 前記(メタ)アクリレートモノマーの主骨格がポリエーテルである、請求項1または5に記載の光硬化性組成物。
- 前記(C)成分がフェノキシ樹脂である、請求項1に記載の光硬化性組成物。
- (D)成分にアシルホスフィンオキサイド系光開始剤を含む、請求項1~9のいずれか1項に記載の光硬化性組成物。
- 溶剤を除いた組成物全体に対して(A)成分を0.1~4.0質量%含む、請求項1~10のいずれか1項に記載の光硬化性組成物。
- 請求項1~12のいずれか1項に記載の光硬化性組成物を含む、光硬化性シート。
- 請求項1~12のいずれか1項に記載の光硬化性組成物を用いた、表示装置。
- 請求項13に記載の光硬化性シートを一方の被着体に付着させ、もう一方の被着体を前記光硬化性シートに貼り合わせる工程と、
エネルギー線を照射することにより光硬化性シートを硬化して二つの被着体を接着する工程と、
を含む、接着方法。 - 請求項15に記載の接着方法を含む、表示装置の製造方法。
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JP2009008755A (ja) | 2007-06-26 | 2009-01-15 | Sekisui Chem Co Ltd | カラムスペーサ用硬化性樹脂組成物、カラムスペーサ及び液晶表示素子 |
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