JP2023036659A - 光学素子、光学機器及び化合物 - Google Patents
光学素子、光学機器及び化合物 Download PDFInfo
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- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
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- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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Abstract
Description
アッベ数[νd]=(nd-1)/(nF-nC)
2次分散特性[θg,F]=(ng-nF)/(nF-nC)
(上記式において、ndは波長587.6nmでの屈折率、nFは波長486.1nmでの屈折率、nCは波長656.3nmでの屈折率、ngは波長435.8nmでの屈折率をそれぞれ表す。)
本発明の他の観点は、該トリアリールアミン化合物の重合物(硬化物)を含む光学材料である。
本発明のさらに他の観点は、該光学材料を成形してなる光学素子である。
本発明のさらに別の観点は、該光学素子を有する光学機器である。
本発明の一つの観点は、下記一般式(1)で表されることを特徴とするトリアリールアミン化合物である。
上記一般式(1)において、重合性官能基の数は、硬化性の観点から二つ以上が好ましく、合成容易性の観点から二つがより好ましい。
前記トリアリールアミン化合物の製造方法としては、特定の製造ルートに限定されず、どの様な製造方法でも採用することが可能である。本発明における一般式(1)で表される構造を有する誘導体は、例えば特開2000-066425号公報、特開2008-165248号公報に記載の公知の合成方法を用いて合成することが可能である。
本発明に係る光学材料は、上記のトリアリールアミン化合物と重合開始剤、前記重合禁止剤、さらに必要に応じて光増感剤、耐熱安定剤、耐光安定剤、酸化防止剤や樹脂を含有する組成物からなる。
本発明の光学素子は、上記の成形体を有することを特徴とする。図2は、本発明の光学素子の例を示す概略図である。図2(a)の光学素子は、光学材料(または光学用組成物)を成形加工してなる薄膜(光学部材10)がレンズ基板20の片方の面上に設けられている。図2(a)の光学素子を作製する方法としては、例えば、光透過性材料からなる基板上に膜厚の薄い層構造を形成する方法が採用される。具体的には、金属材料からなる型をガラス基板から一定の距離を置いて設け、この型とガラス基板との間にある空隙に流動性の光学材料又は光学用組成物を充填してから、軽く抑えることで、型成形を行う。そして必要に応じてその状態に保ったまま光学材料又は光学用組成物の重合を行う。
(化合物例N1の製造)
(1)N1中間体の合成
1H-NMR(CDCl3):δ 1.52(s、6H)、6.96(d、1H)、7.31-7.37(m、3H)、7.44(d、1H)、7.50-7.55(m、2H)、7.67(d、1H)、7.70-7.75(m、4H)、7.93(s、1H)、11.96(s、2H)
窒素雰囲気下、100mL三口フラスコに、N1中間体2.0g、クロロホルム30mL、ヒドロキノンモノメチルエーテル(MEHQ)0.14g、ピリジン10mLを投入した。反応容器を0℃まで冷却し、メタクリロイルクロリド1.0mLを滴下した。反応液をトルエン30mLで希釈後に2N塩酸水溶液で反応を停止させ、得られた有機層を酸性及び塩基性水溶液で洗浄した後、飽和食塩水及び無水硫酸マグネシウムで有機層を乾燥させた。溶剤を除去して得られた粗生成物をシリカゲルクロマトグラフィーで精製することでN1を1.25g(収率50%)得た。生成物は1HNMRによりその構造を確認した。また、生成物の光学特性を表6に示す。
1H-NMR(CDCl3):δ 1.49(s、6H)、1.54(s、6H)、5.88(t、2H)、6.46(t、2H)、7.10(d、1H)、7.28-7.43(m、5H)、7.63-7.71(m、4H)、7.78(d、1H)、8.10(d、1H)、8.17(d、1H)
(化合物例N22の製造)
(1)N22中間体1の合成
窒素雰囲気下、200mL三口フラスコに、N22中間体1の4.0g、4-ブロモベンジルアルコール3.37g、ナトリウム tert-ブトキシド4.95g、ビス(ジベンジリデンアセトン)パラジウム0.37g、2-ジシクロヘキシルホスフィノ-2’,4’,6’-トリイソプロピルビフェニル0.61g、オルトキシレン140mLを入れ、130℃まで加熱した後、その温度(130℃)で10時間撹拌を行った。加熱後、室温まで放冷した後、有機相をクロロホルムで抽出した。得られた有機相を飽和食塩水、水の順で洗浄し、無水硫酸マグネシウムで乾燥した。得られた粗生成物をカラムクロマトグラフィーで精製することでN22中間体2を3.4g(収率63%)得た。
1H-NMR(CDCl3):δ δ 1.49(s、6H)、1.53(s、6H)、5.05-5.11(m、2H)、5.50(t、1H)、6.02(t、1H)、6.85(dd、1H)、7.05(dd、1H)、7.19(d、4H)、7.30-7.36(m、2H)、7.40(d、1H)、7.48(d、4H)、7.63(d、2H)
(化合物例N31の製造)
(1)N31中間体1の合成
窒素雰囲気下、1L三口フラスコに、N31中間体1の15.0g、2-ブロモフルオレン12.05g、ナトリウム tert-ブトキシド18.89g、ビス(ジベンジリデンアセトン)パラジウム0.28g、及び2-ジシクロヘキシルホスフィノ-2’,4’,6’-トリイソプロピルビフェニル0.47g、オルトキシレン500mLを入れ、120℃まで加熱した後、その温度(120℃)において10時間撹拌を行った。加熱後、室温まで放冷した後、有機相を酢酸エチルで抽出した。得られた有機相を飽和食塩水、水の順で洗浄し、無水硫酸マグネシウムで乾燥した。得られた粗生成物をカラムクロマトグラフィーで精製することでN31中間体2を10.5g(収率46%)得た。
窒素雰囲気下、500mL三口フラスコにN31中間体2の9.44g、N,N-ジメチルアセトアミド160mLを入れて撹拌した後に、ナトリウム tert-ブトキシド6.77gを入れ、5℃まで冷却し、酢酸4-ブロモブチル10.21gをN,N-ジメチルアセトアミド40mLに溶解させた溶液を30分かけて滴下した。滴下後、20℃まで昇温した後、その温度(20℃)において20時間撹拌を行った。撹拌後、5℃まで冷却し、次いでナトリウムメトキシド5.44gを入れ、20℃まで徐々に昇温した。昇温後、その温度(20℃)において10時間撹拌を行った。撹拌後、氷水に反応液を投入し、トルエンで有機層を抽出した。得られた有機相を飽和食塩水、水の順で洗浄し、無水硫酸マグネシウムで乾燥した。得られた粗生成物をカラムクロマトグラフィーで精製することでN31中間体3を5.5g(収率45%)得た。生成物は1HNMRによりその構造を確認した。
1H-NMR(CDCl3):δ 0.71(t、2H)、1.38(d、4H)、1.60(d、4H)、1.94-2.00(m、4H)、3.22-3.29(m、4H)、7.08(dd、1H)、7.17(d、1H)、7.26-7.43(m、11H)、7.67(t、2H)
1H-NMR(CDCl3):δ 1.42(d、4H)、1.71(d、4H)、1.78(s、6H)、2.13-2.18(m、4H)、3.22-3.27(m、4H)、5.43(t、2H)、5.80(t、2H)、6.90(dd、1H)、7.10(dd、1H)、7.22(d、4H)、7.30-7.36(m、2H)、7.42(d、1H)、7.50(d、4H)、7.65(d、2H)
(化合物例N32の製造)
(1)N32中間体1の合成
1H-NMR(CDCl3):δ 0.71(t、2H)、2.21-2.27(m、2H)、2.31-2.37(m、2H)、3.02-3.12(m、4H)、7.08(dd、1H)、7.18(d、1H)、7.27-7.44(m、11H)、7.67(t、2H)
1H-NMR(CDCl3):δ 1.78(s、6H)、2.29-2.34(m、2H)、2.42-2.47(m、2H)、3.45-3.50(m、2H)、3.61-3.66(m、2H)、5.43(t、2H)、5.81(t、2H)、6.90(dd、1H)、7.10(dd、1H)、7.21(d、4H)、7.30-7.36(m、2H)、7.42(d、1H)、7.51(d、4H)、7.65(d、2H)
(化合物例N33の製造)
(1)N33中間体1の合成
1H-NMR(CDCl3):δ 0.69(t、2H)、1.36(d、4H)、1.62(d、4H)、1.96(dd、4H)、3.08(dd、4H)、7.10(dd、1H)、7.17(dd、4H)、7.22(d、1H)、7.32-7.40(m、2H)、7.43(d、1H)、7.51(d、4H)、7.68(t、2H)
1H-NMR(CDCl3):δ 1.79(t、6H)、1.41(d、4H)、1.73(d、4H)、2.12-2.19(m、4H)、3.22-3.29(m、4H)、5.43(t、2H)、5.80(t、2H)、6.91(dd、1H)、7.13(dd、1H)、7.22(d、4H)、7.30-7.38(m、2H)、7.43(d、1H)、7.54(d、4H)、7.67(d、2H)
(化合物例N34の製造)
(1)N34中間体1の合成
1H-NMR(CDCl3):δ 0.69(t、2H)、2.25-2.37(m、4H)、3.09(dd、4H)、7.11(dd、1H)、7.16(dd、4H)、7.22(d、1H)、7.32-7.40(m、2H)、7.43(d、1H)、7.51(d、4H)、7.68(t、2H)
1H-NMR(CDCl3):δ 1.79(t、6H)、2.30-2.37(m、2H)、2.40-2.49(m、2H)、3.46-3.51(m、2H)、3.62-3.67(m、2H)、5.43(t、2H)、5.82(t、2H)、6.91(dd、1H)、7.11(dd、1H)、7.22(d、4H)、7.31-7.37(m、2H)、7.43(d、1H)、7.52(d、4H)、7.66(d、2H)
(化合物例N35の製造)
1H-NMR(CDCl3):δ 1.52(d、4H)、1.78(s、6H)、1.90(d、4H)、3.47-3.52(m、2H)、3.60-3.65(m、2H)、5.43(t、2H)、5.81(t、2H)、6.90(dd、1H)、7.10(dd、1H)、7.21(d、4H)、7.30-7.36(m、2H)、7.42(d、1H)、7.51(d、4H)、7.65(d、2H)
(化合物例N40の製造)
実施例3で用いた3-アミノベンゾトリフルオリドを4-アミノベンゾニトリルに、3-ブロモベンゾトリフルオリドを2-ブロモ-m-キシレンに、酢酸4-ブロモブチルを酢酸2-ブロモエチルにそれぞれ代えた以外は、実施例3と同様の反応、精製を行った。また、生成物の光学特性は表6に示す。
(化合物例N23の製造)
実施例2で用いた2-アミノ-9,9-ジメチルフルオレンを3,5-ビス(トリフルオロメチル)アニリンに、4-ブロモベンゾニトリルを2-ブロモ-9,9-ジ-n-オクチルフルオレンに、4-ブロモベンジルアルコールを2-(4-ブロモフェニル)エチルアルコールにそれぞれ代えた以外は、実施例2と同様の反応、精製を行った。また、生成物の光学特性は表6に示す。
(化合物例N46の製造)
実施例3で用いた3-ブロモベンゾトリフルオリドを4-ブロモベンジルアルコールに、2-ブロモフルオレンを3-[2-ブロモ-9-(3-ヒドロキシ-プロピル)-9H-フルオレン-9-イル]-プロパン-1-オルにそれぞれ代えた以外は、実施例3と同様の反応、精製を行った。また、生成物の光学特性は表6に示す。
(化合物例N2の製造)
1H-NMR(CDCl3):δ 1.54(s、6H)、4.55-4.62(m、4H)、5.43(d、2H)、5.88(t、2H)、6.46(t、2H)、7.10(d、1H)、7.27-7.42(m、5H)、7.62-7.69(m、4H)、7.78(d、1H)、8.10(d、1H)、8.17(d、1H)
屈折率はアッベ屈折計(カルニュー光学工業(株)製)を用いて測定した。
透過率は、光路長の異なる2種類の膜を成形し、(株)日立ハイテクノロジーズ製分光光度計U-4000(製品名)でそれぞれ測定し、450nmでの内部透過率(500μm)に換算した結果を表6に示す。
20 レンズ基板
30 レンズ基板
40 レンズ基板
本発明の他の観点は、該化合物の重合物(硬化物)を含む光学素子である。
本発明のさらに他の観点は、該光学素子を有する光学機器である。
Claims (9)
- 光学材料が成形された光学素子であって、
前記光学材料は、下記一般式(1)で表される化合物が単独重合又は共重合されていることを特徴とする光学素子。
- 前記重合性官能基がアクリロイルオキシ基、メタクリロイルオキシ基、ビニル基、又はエポキシ基である請求項1に記載の光学素子。
- R5、R6、R9、R10のうち少なくとも一つが電子吸引性基であり、該電子吸引性基がシアノ基又はトリフルオロメチル基である請求項1又は2に記載の光学素子。
- 請求項1~3のいずれか一項に記載された、前記一般式(1)で表される化合物が単独重合又は共重合された光学材料。
- 請求項1~3のいずれか一項に記載の光学素子を有する光学機器。
- 前記光学素子がレンズであり、前記光学機器がカメラである請求項5に記載の光学機器。
- 前記重合性官能基が、アクリロイルオキシ基、メタクリロイルオキシ基、ビニル基、又はエポキシ基である請求項7に記載のトリアリールアミン化合物。
- R5、R6、R9、R10のうち少なくとも一つが電子吸引性基であり、該電子吸引性基がシアノ基又はトリフルオロメチル基である請求項7又は8に記載のトリアリールアミン化合物。
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