JP2013177377A - 蛍光性化合物及びその製造方法並びに蛍光性樹脂組成物 - Google Patents
蛍光性化合物及びその製造方法並びに蛍光性樹脂組成物 Download PDFInfo
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- JP2013177377A JP2013177377A JP2013019391A JP2013019391A JP2013177377A JP 2013177377 A JP2013177377 A JP 2013177377A JP 2013019391 A JP2013019391 A JP 2013019391A JP 2013019391 A JP2013019391 A JP 2013019391A JP 2013177377 A JP2013177377 A JP 2013177377A
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- C07C13/38—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing six carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- C07D471/04—Ortho-condensed systems
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Abstract
[R1〜R10は一価炭化水素基、アルコキシ基、アリーロキシ基、ハロゲン原子、水素原子、アミノ基、シアノ基及び下記式(2)で表されるシロキサン含有基から選択される置換基を表す。但し、R1〜R10のうち少なくとも一つは、下記式(2)で表されるシロキサン含有基である。
(Sxはオルガノシロキサニル基を、Aは単結合、−O−、−S−、−NR−又はそれらの組み合わせを含んでもよい二価炭化水素基を表す。Rは一価炭化水素基である。)]
【効果】有機溶媒や樹脂との相溶性に優れており、種々の媒体に均一に分散させることができるため、透明性や明度、彩度の高い蛍光性樹脂組成物が容易に得られる。また、単一化合物であるため、高純度まで精製することができ、蛍光効率が高い。
【選択図】なし
Description
また、特許文献2の化合物は有機溶剤に対する溶解性が乏しく、脂肪族炭化水素やシリコーン樹脂のような極性の低い溶剤や樹脂にはほとんど溶解しない。
[I]
下記一般式(1)で表される蛍光性化合物。
[II]
一般式(1)において、式(2)で表されるシロキサン含有基のケイ素原子数の総和が5以上である[I]記載の蛍光性化合物。
[III]
一般式(1)において、R1及びR2のいずれか一方又は両方が、式(2)で表されるシロキサン含有基である[I]又は[II]記載の蛍光性化合物。
[IV]
一般式(1)において、R4及びR9のいずれか一方又は両方がビフェニル基である[I]〜[III]のいずれかに記載の蛍光性化合物。
[V]
[I]〜[IV]のいずれかに記載の蛍光性化合物及び樹脂を含有する蛍光性樹脂組成物。
[VI]
樹脂が、シリコーン樹脂である[V]記載の蛍光性樹脂組成物。
[VII]
下記一般式(3)で表されるオレフィン化合物と、下記一般式(4)で表されるSi−H基を有するシロキサン化合物を、白金触媒存在下で反応させることを特徴とする下記一般式(1’)で表される蛍光性化合物の製造方法。
アルコキシ基の例としては、メトキシ基、エトキシ基、ブトキシ基、tert−ブトキシ基、ヘキシルオキシ基等が挙げられる。
アリーロキシ基の例としては、フェノキシ基、p−メチルフェノキシ基、ナフトキシ基等が挙げられる。
ハロゲン原子の例としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
アミノ基の例としては、ジメチルアミノ基、ジエチルアミノ基等が挙げられる。
2,7−ジブロモ−9,9’−ジ−[3−(1−トリメチルシロキシ−1,3,3,3−テトラメチルジシロキサン−1−イル)プロピル]−フルオレン、
2,7−ビス(ビフェニル)−9,9’−ジ−[3−(1−トリメチルシロキシ−1,3,3,3−テトラメチルジシロキサン−1−イル)プロピル]−フルオレン、
2,7−ジブロモ−9,9’−ジ−[3−(ウンデカメチルペンタシロキサン−1−イル)プロピル]−フルオレン、
2,7−ビス(ビフェニル)−9,9’−ジ−[3−(ウンデカメチルペンタシロキサン−1−イル)プロピル]−フルオレン
等を挙げることができる。
アルコキシ基の例としては、メトキシ基、エトキシ基、ブトキシ基、tert−ブトキシ基、ヘキシルオキシ基等が挙げられる。
アリーロキシ基の例としては、フェノキシ基、p−メチルフェノキシ基、ナフトキシ基等が挙げられる。
ハロゲン原子の例としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
アミノ基の例としてはジメチルアミノ基、ジエチルアミノ基等が挙げられる。
A’の具体例としては、Aの具体例として挙げたもの(炭素数1のものを除く)と同じものを挙げることができる。また、式(2’)の具体例としては式(2)の具体例として挙げたもの(Aが炭素数1の場合を除く)と同じものを例示できる。
アルコキシ基の例としては、メトキシ基、エトキシ基、ブトキシ基、tert−ブトキシ基、ヘキシルオキシ基等が挙げられる。
アリーロキシ基の例としては、フェノキシ基、p−メチルフェノキシ基、ナフトキシ基等が挙げられる。
ハロゲン原子の例としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
アミノ基の例としてはジメチルアミノ基、ジエチルアミノ基等が挙げられる。
100mLの3つ口フラスコに還流冷却器、攪拌機を取り付け、内部を窒素置換した。このフラスコに、2,7−ジブロモ−9,9’−ジアリルフルオレン845.0mg(2.11ミリモル)、白金(0)1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン錯体の2質量%キシレン溶液15.2mgと脱水トルエン5mLを仕込み、1,1,1,3,5,5,5−ヘプタメチルトリシロキサン1.01g(4.54ミリモル)を10分かけて滴下した。滴下終了後、反応液を室温で6時間攪拌した。得られた溶液を減圧濃縮し、水とトルエンを加えた後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮し、薄黄色液体1.70gを得た。
この溶液のMALDI−TOFMSスペクトルを測定した結果、2,7−ジブロモ−9,9’−ジ−[3−(1−トリメチルシロキシ−1,3,3,3−テトラメチルジシロキサン−1−イル)プロピル]−フルオレンであることが確認された。
MALDI−TOFMS m/z:846.2(M+)
100mLの3つ口フラスコに還流冷却器、攪拌機を取り付け、内部を窒素置換した。このフラスコに、2,7−ジブロモ−9,9’−ジ−[3−(1−トリメチルシロキシ−1,3,3,3−テトラメチルジシロキサン−1−イル)プロピル]−フルオレン1.70g(2.00ミリモル)、ビフェニルボロン酸1.02g(5.15ミリモル)、テトラキストリフェニルホスフィン131.4mg(0.11ミリモル)、ジメトキシエタン20mLを仕込み、炭酸カリウム1.10g(7.96ミリモル)を水4mLに溶解させた溶液を加えた。滴下終了後、反応液を67℃で4.5時間攪拌した。得られた溶液に、水とトルエンを加えた後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮した後、HPLCにより精製して白色固体1.48gを得た。
この固体のNMRスペクトル及びMALDI−TOFMSスペクトルを測定した結果、2,7−ビス(ビフェニル)−9,9’−ジ−[3−(1−トリメチルシロキシ−1,3,3,3−テトラメチルジシロキサン−1−イル)プロピル]−フルオレンであることが確認された。
1H−NMR(600MHz,d in CDCl3):−0.18(s,6H),−0.10(s,36H),0.25−0.30(m,4H),0.77−0.89(m,4H),7.26(t,2H),7.49(t,4H),7.61−7.63(m,4H),7.67−7.76(m,12H),7.78−7.81(m,2H)
MALDI−TOFMS m/z:994.6(M+)
100mLの3つ口フラスコに還流冷却器、攪拌機を取り付け、内部を窒素置換した。このフラスコに、2,7−ジブロモ−9,9’−ジアリルフルオレン1.33g(3.29ミリモル)、白金(0)1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン錯体の2質量%キシレン溶液15.0mgと脱水トルエン6mLを仕込み、1,1,3,3,5,5,7,7,9,9,9−ウンデカメチルトリシロキサン3.00g(8.09ミリモル)を10分かけて滴下した。滴下終了後、反応液を室温で7時間攪拌した。得られた溶液に水とトルエンを加えた後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮した後、シリカゲルクロマトグラフィーによる精製を行い薄黄色液体2.63gを得た。
この溶液のMALDI−TOFMSスペクトルを測定した結果、2,7−ジブロモ−9,9’−ジ−[3−(ウンデカメチルペンタシロキサン−1−イル)プロピル]−フルオレンであることが確認された。
MALDI−TOFMS m/z:1142.2(M+)
100mLの3つ口フラスコに還流冷却器、攪拌機を取り付け、内部を窒素置換した。このフラスコに、2,7−ジブロモ−9,9’−ジ−[3−(ウンデカメチルペンタシロキサン−1−イル)プロピル]−フルオレン2.02g(1.76ミリモル)、ビフェニルボロン酸807.3mg(4.08ミリモル)、テトラキストリフェニルホスフィン98.0mg(0.085ミリモル)、ジメトキシエタン13mLを仕込み、炭酸カリウム848.0mg(6.14ミリモル)を水5mLに溶解させた溶液を加えて84℃で7時間攪拌した。得られた溶液に、水とトルエンを加えた後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮した後、HPLCにより精製して無色液体1.15gを得た。
この溶液のNMRスペクトル及びMALDI−TOFMSスペクトルを測定した結果、2,7−ビス(ビフェニル)−9,9’−ジ−[3−(ウンデカメチルペンタシロキサン−1−イル)プロピル]−フルオレンであることが確認された。
1H−NMR(600MHz,d in CDCl3):−0.12(s,12H),−0.10(s,12H),−0.012(s,12H),−0.010(s,12H),0.070(s,18H),0.35−0.40(m,4H),0.80−0.86(m,4H),2.08−2.14(m,4H),7.36−7.40(m,2H),7.46−7.51(m,4H),7.60−7.65(m,4H),7.66−7.69(m,4H),7.69−7.78(m,8H),7.78−7.81(m,2H)
MALDI−TOFMS m/z:1290.5(M+)
ガラスバイアル中に実施例2で製造した化合物2を114.2mg秤量し、透明シリコーン樹脂SIM−360主剤(信越化学工業(株)製)を室温下で攪拌しながら少量ずつ添加した。溶液が透明となったときに溶解したと判断し、溶解度を計算すると1.3ミリモル/Lであった。この混合物に主剤に対して10質量%の硬化剤を添加して混合し、脱泡後に150℃で30分加熱して硬化させ、蛍光性のシリコーン樹脂組成物を得た。なお、化合物2の濃度は上記の濃度以下で任意に変更することが可能であった。
実施例5と同様にして化合物4のSIM−360主剤への溶解度を測定したところ、6.0ミリモル/Lであった。この混合物に主剤に対して10質量%の硬化剤を添加して混合し、脱泡後に150℃で30分加熱して硬化させ、蛍光性のシリコーン樹脂組成物を得た。なお、化合物4の濃度は上記の濃度以下で任意に変更することが可能であった。
Claims (7)
- 下記一般式(1)で表される蛍光性化合物。
- 一般式(1)において、式(2)で表されるシロキサン含有基のケイ素原子数の総和が5以上である請求項1記載の蛍光性化合物。
- 一般式(1)において、R1及びR2のいずれか一方又は両方が、式(2)で表されるシロキサン含有基である請求項1又は2記載の蛍光性化合物。
- 一般式(1)において、R4及びR9のいずれか一方又は両方がビフェニル基である請求項1〜3のいずれか1項記載の蛍光性化合物。
- 請求項1〜4のいずれか1項記載の蛍光性化合物及び樹脂を含有する蛍光性樹脂組成物。
- 樹脂が、シリコーン樹脂である請求項5記載の蛍光性樹脂組成物。
- 下記一般式(3)で表されるオレフィン化合物と、下記一般式(4)で表されるSi−H基を有するシロキサン化合物を、白金触媒存在下で反応させることを特徴とする下記一般式(1’)で表される蛍光性化合物の製造方法。
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JP5966955B2 (ja) | 2016-08-10 |
KR101681357B1 (ko) | 2016-11-30 |
CN103254222B (zh) | 2017-06-20 |
TW201402774A (zh) | 2014-01-16 |
KR20130092496A (ko) | 2013-08-20 |
US9062246B2 (en) | 2015-06-23 |
EP2626400B1 (en) | 2014-10-08 |
EP2626400A1 (en) | 2013-08-14 |
TWI561613B (en) | 2016-12-11 |
CN103254222A (zh) | 2013-08-21 |
US20130207041A1 (en) | 2013-08-15 |
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