JP5966955B2 - 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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- JP5966955B2 JP5966955B2 JP2013019391A JP2013019391A JP5966955B2 JP 5966955 B2 JP5966955 B2 JP 5966955B2 JP 2013019391 A JP2013019391 A JP 2013019391A JP 2013019391 A JP2013019391 A JP 2013019391A JP 5966955 B2 JP5966955 B2 JP 5966955B2
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- 239000011342 resin composition Substances 0.000 title claims description 24
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- -1 olefin compound Chemical class 0.000 claims description 283
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
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- 125000004122 cyclic group Chemical group 0.000 claims description 35
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 31
- 229920005989 resin Polymers 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 31
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 28
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 23
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- 125000001424 substituent group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 229910052697 platinum Inorganic materials 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
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- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
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- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001875 compounds Chemical class 0.000 description 35
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- 239000000203 mixture Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
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- SBXUOBILXDPGKB-UHFFFAOYSA-N dimethylsilyloxy-[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-dimethylsilane Chemical compound C[SiH](C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C SBXUOBILXDPGKB-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000002347 octyl 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])[H] 0.000 description 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- 125000002948 undecyl 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])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
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- 125000005375 organosiloxane group Chemical group 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
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- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 5
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
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- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000003493 decenyl group Chemical group [H]C([*])=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])[H] 0.000 description 4
- 125000006038 hexenyl group Chemical group 0.000 description 4
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
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- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 3
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
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- 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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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、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]又は[II]記載の蛍光性化合物。
[IV][I]〜[III]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。
[V]
樹脂が、シリコーン樹脂である[IV]記載の蛍光性樹脂組成物。
[VI]
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 (6)
- 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、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又は2記載の蛍光性化合物。
- 請求項1〜3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4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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TWI561613B (en) | 2016-12-11 |
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