JP2016169181A - Benzotriazole derivative compound and polymer therefrom - Google Patents
Benzotriazole derivative compound and polymer therefrom Download PDFInfo
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- JP2016169181A JP2016169181A JP2015049998A JP2015049998A JP2016169181A JP 2016169181 A JP2016169181 A JP 2016169181A JP 2015049998 A JP2015049998 A JP 2015049998A JP 2015049998 A JP2015049998 A JP 2015049998A JP 2016169181 A JP2016169181 A JP 2016169181A
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- carbon atoms
- alkyl group
- wavelength conversion
- benzotriazole derivative
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- -1 Benzotriazole derivative compound Chemical class 0.000 title claims abstract description 121
- 229920000642 polymer Polymers 0.000 title description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 62
- 239000000463 material Substances 0.000 claims abstract description 43
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 229920001577 copolymer Polymers 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
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- 230000001747 exhibiting effect Effects 0.000 abstract 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 21
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- 239000003505 polymerization initiator Substances 0.000 description 9
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- ZIJVCFXOXVVYEB-UHFFFAOYSA-N 2-(5-aminobenzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=C(N)C=CC3=N2)=C1 ZIJVCFXOXVVYEB-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- RPJUVNYXHUCRMG-UHFFFAOYSA-N 2-amino-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N)=C1 RPJUVNYXHUCRMG-UHFFFAOYSA-N 0.000 description 3
- GMORVOQOIHISPT-UHFFFAOYSA-N 2-ethylhexanamide Chemical compound CCCCC(CC)C(N)=O GMORVOQOIHISPT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
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- 238000000862 absorption spectrum Methods 0.000 description 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 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
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- HTNMNMJBZYKXPQ-UHFFFAOYSA-N 6-amino-2-[2-[2-hydroxy-5-(2-hydroxyethyl)phenyl]benzotriazol-5-yl]benzo[de]isoquinoline-1,3-dione Chemical compound NC=1C=CC=2C(N(C(C3=CC=CC1C23)=O)C2=CC=3C(=NN(N3)C3=C(C=CC(=C3)CCO)O)C=C2)=O HTNMNMJBZYKXPQ-UHFFFAOYSA-N 0.000 description 2
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- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/52—PV systems with concentrators
Landscapes
- Optical Filters (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Photovoltaic Devices (AREA)
Abstract
Description
本発明は、ナフタルイミドを含有する新規なベンゾトリアゾール誘導体化合物、及びそれらの重合体に関し、さらに、これらを含有する波長変換材料、及びそれを用いた波長変換フィルム及び太陽電池に関する。さらに詳しくは、360nm付近の紫外線を強く吸収して460nm付近で強い青色発光を示す優れた波長変換性を示し、同時に優れた耐光性を示す波長変換材料、及びそれを用いた波長変換フィルム及び太陽電池に関する。 The present invention relates to novel benzotriazole derivative compounds containing naphthalimide and polymers thereof, and further relates to a wavelength conversion material containing these, a wavelength conversion film and a solar cell using the same. More specifically, a wavelength conversion material that strongly absorbs ultraviolet rays near 360 nm and exhibits strong blue light emission near 460 nm and at the same time exhibits excellent light resistance, and a wavelength conversion film and the sun using the same It relates to batteries.
波長変換材料は照射された特定の波長の光を吸収して別の波長の光を放出する材料であり、単体、有機溶媒中、フィルム中などで用いられ、幅広い分野で使用されている。 A wavelength converting material is a material that absorbs light having a specific wavelength and emits light having a different wavelength, and is used in a single substance, in an organic solvent, in a film, and the like, and is used in a wide range of fields.
太陽電池は一般的に紫外域の感度が低く、太陽光に含まれる紫外線を十分活用できていないため、紫外線を可視光に変換する波長変換フィルムを太陽電池表面に取り付けることで、感度が高い可視光域の光をより多く取り入れて、太陽電池の効率を向上させることが実施されている。また、ビニールハウスのフィルムに波長変換材料を添加することで、特定の波長の光をより多く植物に当て、植物の生育を促進させることが実施されている。 Since solar cells generally have low sensitivity in the ultraviolet region and cannot fully utilize the ultraviolet rays contained in sunlight, high sensitivity is achieved by attaching a wavelength conversion film that converts ultraviolet rays to visible light on the surface of the solar cell. Increasing the efficiency of solar cells by incorporating more light in the light region is being implemented. Further, by adding a wavelength conversion material to a greenhouse film, more light of a specific wavelength is applied to the plant to promote the growth of the plant.
上記の各用途で使用される波長変換材料には、紫外線または可視光を十分吸収して強い光を発する、優れた波長変換性があることが求められており、さらに太陽光が直接照射されることから、太陽光に含まれる紫外線により変質しない高い安定性が要求される。すなわち、物質が光を吸収する程度を示す指標であるモル吸光係数が高く、吸収された光子数に対する放出された光子数の比で表される蛍光量子効率が高く、紫外線に対する耐性の指標である耐光性が高い波長変換材料が求められており、モル吸光係数、蛍光量子効率及び耐光性が高いほど優れた波長変換材料となる。 The wavelength conversion material used in each of the above applications is required to have excellent wavelength conversion properties that sufficiently absorb ultraviolet light or visible light to emit strong light, and is directly irradiated with sunlight. For this reason, high stability that does not deteriorate due to ultraviolet rays contained in sunlight is required. That is, the molar extinction coefficient, which is an index indicating the degree of light absorption by a substance, is high, the fluorescence quantum efficiency expressed by the ratio of the number of emitted photons to the number of absorbed photons is high, and is an index of resistance to ultraviolet rays. There is a demand for wavelength conversion materials with high light resistance, and the higher the molar extinction coefficient, fluorescence quantum efficiency, and light resistance, the better the wavelength conversion material.
波長変換材料はフィルム等の樹脂中で使用されることが多く、固体状態で波長変換性が優れていることが求められており、さらに、波長変換材料自体のブリードが起こらないような、樹脂との相溶性が高い波長変換材料が求められている。また、波長変換材料はフィルム等の表面に成膜して使用されることが多く、成膜時に有機溶媒に溶解させる必要があり、有機溶媒に溶解しやすい波長変換材料が求められている。 The wavelength conversion material is often used in a resin such as a film, and is required to have excellent wavelength conversion properties in a solid state. Further, the wavelength conversion material itself does not cause bleeding. There is a demand for wavelength conversion materials having high compatibility. Further, the wavelength conversion material is often used after being formed on the surface of a film or the like, and needs to be dissolved in an organic solvent at the time of film formation, and a wavelength conversion material that is easily dissolved in an organic solvent is desired.
これまで波長変換性に優れた波長変換材料が各種提案されており、それを用いた波長変換フィルムを取り付けることで、太陽電池の効率向上や植物の生育促進が示されている。しかしながら、耐光性に優れた波長変換材料は少なく、特に紫外線を青色光に効率よく変換する波長変換性と耐光性を両立する波長変換材料はほとんどない。 Various wavelength conversion materials excellent in wavelength conversion properties have been proposed so far, and the improvement of the efficiency of solar cells and the promotion of plant growth have been shown by attaching a wavelength conversion film using the same. However, there are few wavelength conversion materials excellent in light resistance, and particularly there are few wavelength conversion materials that achieve both wavelength conversion properties and light resistance for efficiently converting ultraviolet light into blue light.
波長変換材料としては一般的に有機蛍光色素が用いられており、例えば非特許文献1に記載されているように、オキサジアゾール誘導体、トリアゾール誘導体等が提案されている。しかし、これらの化合物のモル吸光係数及び蛍光量子効率はすべてが十分大きいと言えず、特に青色蛍光色素の固体蛍光量子効率が不十分であり、波長変換性が高いとは言えない。また、青色蛍光色素の耐光性の記載がされていない。 As the wavelength conversion material, an organic fluorescent dye is generally used. For example, as described in Non-Patent Document 1, oxadiazole derivatives, triazole derivatives, and the like have been proposed. However, it cannot be said that the molar extinction coefficient and the fluorescence quantum efficiency of these compounds are all sufficiently high. In particular, the solid fluorescent quantum efficiency of the blue fluorescent dye is insufficient, and it cannot be said that the wavelength conversion property is high. Moreover, the light resistance of the blue fluorescent dye is not described.
太陽電池用及び農業用波長変換フィルムでは、例えば特許文献1〜3に記載されているように、ベンゾ複素環誘導体、キノリノール誘導体の金属錯体、フェナジン誘導体、オキサゾール誘導体等を波長変換材料として使用することが提案されており、波長変換フィルムを用いることで太陽電池の効率向上及び植物の生育促進が示されている。しかしながら、これら波長変換材料の耐光性は十分ではないか、または耐光性への言及がない。 In solar cell and agricultural wavelength conversion films, for example, as described in Patent Documents 1 to 3, a benzoheterocyclic derivative, a metal complex of a quinolinol derivative, a phenazine derivative, an oxazole derivative, or the like is used as a wavelength conversion material. Has been proposed, and the use of a wavelength conversion film has been shown to improve the efficiency of solar cells and promote the growth of plants. However, the light resistance of these wavelength conversion materials is not sufficient or there is no mention of light resistance.
このような状況下、本発明における課題は、溶液及びフィルム状態において紫外線を青色光に効率よく変換する優れた波長変換性を示し、紫外線が照射しても劣化しない優れた耐光性を示す波長変換材料に有用な新規化合物を提供することにある。 Under such circumstances, the problem in the present invention is that wavelength conversion that exhibits excellent wavelength conversion property that efficiently converts ultraviolet light into blue light in a solution and film state and that does not deteriorate even when irradiated with ultraviolet light. It is to provide a novel compound useful for a material.
本発明では、新規化合物を下記一般式(1)で示されるベンゾトリアゾール誘導体化合物を上記課題の最も主要な解決手段とする。
[式中R1はホルミル基、炭素数2〜18のアルキルカルボニル基、置換されていてもよいベンゾイル基、アクリロイル基またはメタクリロイル基を表し、R2及びR3はそれぞれ独立して、水素原子、ハロゲン原子、炭素数1〜18のアルキル基、炭素数1〜18のアルコキシ基、ヒドロキシル基、アミノ基、炭素数1〜4の直鎖または分鎖のモノ置換アミノ基、炭素数1〜4の直鎖または分鎖のジ置換アミノ基、ニトロ基、カルボキシル基、アルキル基の炭素数が1〜8のアルキルオキシカルボニル基、炭素数1〜8のヒドロキシアルキル基、アルキル基の炭素数の合計が2〜9のアルキルカルボニルオキシアルキル基、アルキル基の炭素数が1〜3のカルボキシアルキル基、アルキル基の炭素数の合計が2〜10のアルキルオキシカルボニルアルキル基、アリール基、アシル基、スルホ基、シアノ基、アルキル基の炭素数が1〜2のアクリロイルオキシアルキル基またはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基を表す。]
In the present invention, a novel compound is a benzotriazole derivative compound represented by the following general formula (1) as the main means for solving the above problems.
[Wherein R 1 represents a formyl group, an alkylcarbonyl group having 2 to 18 carbon atoms, an optionally substituted benzoyl group, an acryloyl group or a methacryloyl group, and R 2 and R 3 each independently represent a hydrogen atom, A halogen atom, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyl group, an amino group, a linear or branched mono-substituted amino group having 1 to 4 carbon atoms, and an alkyl group having 1 to 4 carbon atoms The total of carbon number of linear or branched di-substituted amino group, nitro group, carboxyl group, alkyloxycarbonyl group having 1 to 8 carbon atoms, hydroxyalkyl group having 1 to 8 carbon atoms, alkyl group. An alkylcarbonyloxyalkyl group having 2 to 9 carbon atoms, a carboxyalkyl group having 1 to 3 carbon atoms in the alkyl group, and an alkyloxyalkyl having 2 to 10 carbon atoms in total. Boniruarukiru group, an aryl group, an acyl group, a sulfo group, a cyano group, methacryloyloxy alkyl group having a carbon number of 1-2 acryloyloxy alkyl group or an alkyl group having carbon atoms in the alkyl group 1-2. ]
上記一般式(1)で示されるベンゾトリアゾール誘導体化合物は、好ましくは、R1がホルミル基、炭素数2〜8のアルキルカルボニル基、ベンゾイル基、アクリロイル基またはメタクリロイル基であり、R2が炭素数1〜4のアルキル基、アルキル基の炭素数の合計が2〜9のアルキルカルボニルオキシアルキル基、アルキル基の炭素数が1〜2のアクリロイルオキシアルキル基またはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基であり、R3が水素原子である化合物である。 In the benzotriazole derivative compound represented by the general formula (1), preferably, R 1 is a formyl group, an alkylcarbonyl group having 2 to 8 carbon atoms, a benzoyl group, an acryloyl group, or a methacryloyl group, and R 2 is a carbon number. 1 to 4 alkyl groups, an alkylcarbonyloxyalkyl group having 2 to 9 carbon atoms in total, an acryloyloxyalkyl group having 1 to 2 carbon atoms, or an alkyl group having 1 to 2 carbon atoms It is a compound which is a methacryloyloxyalkyl group and R 3 is a hydrogen atom.
本発明の一般式(1)で示されるベンゾトリアゾール誘導体化合物、及びそれらを有する重合体は、360nm付近の紫外線を強く吸収して460nm付近で強い青色発光を示し、モル吸光係数が約30000であり、蛍光量子効率が溶液で約40%、フィルムで約20%であることから、紫外線を青色光に変換する波長変換性が高く、さらに耐光性が従来の波長変換材料より高いため、従来技術の課題を解決し得る波長変換材料、波長変換フィルム及び太陽電池として有用である。 The benzotriazole derivative compound represented by the general formula (1) of the present invention and the polymer having them exhibit strong blue light emission at around 460 nm and strong blue light emission at around 460 nm, and a molar extinction coefficient of about 30000. Since the fluorescence quantum efficiency is about 40% for the solution and about 20% for the film, the wavelength conversion property for converting ultraviolet light into blue light is high, and the light resistance is higher than that of conventional wavelength conversion materials. It is useful as a wavelength conversion material, a wavelength conversion film and a solar cell that can solve the problem.
以下に本発明につき詳細に説明する。本発明は波長変換材料、波長変換フィルム及び太陽電池として、下記一般式(1)で示されるベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を用いたものである。以下に下記一般式(1)において表される化合物について説明する。 The present invention will be described in detail below. The present invention uses a benzotriazole derivative compound represented by the following general formula (1) and a polymer having them as a wavelength conversion material, a wavelength conversion film and a solar cell. The compounds represented by the following general formula (1) will be described below.
一般式(1)中、R1はホルミル基;アセチル基、プロピオニル基、ブチリル基、イソブチリル基、ヘキサノイル基、オクタノイル基、2−エチルヘキサノイル基、ラウロイル基、ステアロイル基等の置換されても良い炭素数2〜18の直鎖または分岐のアルキルカルボニル基;置換されていてもよいベンゾイル基;アクリロイル基またはメタクリロイル基を表し、R2及びR3はそれぞれ独立して、水素原子;フッ素、塩素、ヨウ素などのハロゲン原子;メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ヘキシル基、オクチル基、2−エチルヘキシル基、ラウリル基、ステアリル基等の置換されても良い炭素数1〜18の直鎖または分岐のアルキル基;メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、イソブトキシ基、sec−ブトキシ基、tert−ブトキシ基、ヘキシルオキシ基、オクチルオキシ基、2−エチルヘキシルオキシ基、ラウリルオキシ基、ステアリルオキシ基等の置換されても良い炭素数1〜18の直鎖または分岐のアルコキシ基;ヒドロキシル基;アミノ基;モノメチルアミノ基、ジメチルアミノ基、モノエチルアミノ基、ジエチルアミノ基、モノプロピルアミノ基、ジプロピルアミノ基、モノイソプロピルアミノ基、ジイソプロピルアミノ基等の置換されても良い炭素数1〜4の直鎖または分岐のアミノ基;ニトロ基;カルボキシル基;メトキシカルボニル基、エトキシカルボニル基、イソプロポキシカルボニル基、ブトキシカルボニル基、イソブトキシカルボニル基、sec−ブトキシカルボニル基、tert−ブトキシカルボニル基、ヘキシルオキシカルボニル基、オクチルオキシカルボニル基、2−エチルヘキシルオキシカルボニル基等の置換されても良いアルキル基の炭素数1〜8の直鎖または分岐のアルキルオキシカルボニル基;ヒドロキシエチル基、ヒドロキシブチル基、ヒドロキシオクチル基等の炭素数1〜8のヒドロキシアルキル基;下記(化2〜化5)の−R4OCOR5で表されるアルキル基の炭素数の合計が2〜9のアルキルカルボニルオキシアルキル基;カルボキシエチル基、カルボキシプロピル基等のアルキル基の炭素数が1〜3のカルボキシアルキル基;下記(化6〜化8)の−R6COOR7で表されるアルキル基の炭素数の合計が2〜10のアルキルオキシカルボニルアルキル基;フェニル基、ベンジル基、トリル基、キシリル基等のアリール基;ホルミル基、アセチル基、プロピオニル基、ブチリル基、ベンゾイル基等のアシル基;スルホ基;シアノ基;アクリロイルオキシメチル基、アクリロイルオキシエチル基等のアルキル基の炭素数が1〜2のアクリロイルオキシアルキル基;メタクリロイルオキシメチル基、メタクリロイルオキシエチル基等のアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基が挙げられる。 In general formula (1), R 1 may be substituted with a formyl group; an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a hexanoyl group, an octanoyl group, a 2-ethylhexanoyl group, a lauroyl group, a stearoyl group, and the like. A linear or branched alkylcarbonyl group having 2 to 18 carbon atoms; an optionally substituted benzoyl group; an acryloyl group or a methacryloyl group; R 2 and R 3 each independently represent a hydrogen atom; fluorine, chlorine, Halogen atoms such as iodine; methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, hexyl group, octyl group, 2-ethylhexyl group, lauryl group, stearyl group A linear or branched alkyl group having 1 to 18 carbon atoms which may be substituted; Substitution of ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, lauryloxy group, stearyloxy group, etc. A linear or branched alkoxy group having 1 to 18 carbon atoms which may be substituted; hydroxyl group; amino group; monomethylamino group, dimethylamino group, monoethylamino group, diethylamino group, monopropylamino group, dipropylamino group, C1-C4 linear or branched amino group which may be substituted such as monoisopropylamino group, diisopropylamino group, etc .; nitro group; carboxyl group; methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl Group, isobutoxy A straight chain having 1 to 8 carbon atoms of an alkyl group which may be substituted, such as a rubonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, hexyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group or the like; A branched alkyloxycarbonyl group; a hydroxyalkyl group having 1 to 8 carbon atoms such as a hydroxyethyl group, a hydroxybutyl group, and a hydroxyoctyl group; an alkyl group represented by -R 4 OCOR 5 in the following (Chemical Formula 2 to Chemical Formula 5 ) An alkylcarbonyloxyalkyl group having 2 to 9 carbon atoms in total; a carboxyalkyl group having 1 to 3 carbon atoms in an alkyl group such as a carboxyethyl group or a carboxypropyl group; -R in the following (Chemical Formula 6 to Chemical Formula 8) 6 COOR 7 alkyloxy in which the total number of carbon atoms of the alkyl group represented by 7 is 2 to 10 Carbonyl alkyl group; aryl group such as phenyl group, benzyl group, tolyl group, xylyl group; acyl group such as formyl group, acetyl group, propionyl group, butyryl group, benzoyl group; sulfo group; cyano group; acryloyloxymethyl group, Examples thereof include an acryloyloxyalkyl group having 1 to 2 carbon atoms in an alkyl group such as an acryloyloxyethyl group; a methacryloyloxyalkyl group having 1 to 2 carbon atoms in an alkyl group such as a methacryloyloxymethyl group and a methacryloyloxyethyl group.
アルキルカルボニルオキシアルキル基(−R4OCOR5)
アルキルオキシカルボニルアルキル基(−R6COOR7)
上記の一般式(1)の置換基の中でも好ましくは、R1がホルミル基、炭素数2〜8のアルキルカルボニル基、ベンゾイル基、アクリロイル基またはメタクリロイル基であり、R2が炭素数1〜4のアルキル基、アルキル基の炭素数の合計が2〜9のアルキルカルボニルオキシアルキル基、アルキル基の炭素数が1〜2のアクリロイルオキシアルキル基またはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基であり、R3が水素原子である。 Among the substituents of the general formula (1), R 1 is preferably a formyl group, an alkylcarbonyl group having 2 to 8 carbon atoms, a benzoyl group, an acryloyl group, or a methacryloyl group, and R 2 has 1 to 4 carbon atoms. Alkyl group, an alkylcarbonyloxyalkyl group having 2 to 9 carbon atoms in total, an acryloyloxyalkyl group having 1 to 2 carbon atoms, or a methacryloyloxyalkyl alkyl group having 1 to 2 carbon atoms And R 3 is a hydrogen atom.
加えて、上記の一般式(1)の置換基のR1とR2の関係については、R1とR2が上記それぞれの選択肢のうちから選ばれることを前提として、R1がアクリロイル基もしくはメタクリロイル基であるか、そうでなければR2がアルキル基の炭素数が1〜2のアクリロイルオキシアルキル基もしくはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基であるか、あるいはR1がアクリロイル基もしくはメタクリロイル基であって、かつR2がアルキル基の炭素数が1〜2のアクリロイルオキシアルキル基もしくはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基であるという関係にあることが好ましい。 In addition, regarding the relationship between R 1 and R 2 of the substituent of the above general formula (1), R 1 is an acryloyl group or R 1 and R 2 on the assumption that R 1 and R 2 are selected from the respective options. Is a methacryloyl group, or R 2 is an acryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group or a methacryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group, or R 1 is It may be an acryloyl group or a methacryloyl group, and R 2 may be an acryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group or a methacryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group. preferable.
本発明のベンゾトリアゾール誘導体化合物一般式(1)としては、例えば、次に示すものを挙げることができる。N−{2−[2−(2−ヒドロキシ−5−メチルフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}アセトアミド、N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}アセトアミド、N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}−2−エチルヘキサンアミド、N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}ベンズアミド、N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}アクリルアミド、N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}メタクリルアミド、3−{5−[6−(2−エチルヘキサンアミド)−1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル] −2H−ベンゾトリアゾール−2−イル}−4−ヒドロキシフェネチル 2−エチルヘキサノエート、4−ヒドロキシ−3−[5−(6−メタクリルアミド−1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル) −2H−ベンゾトリアゾール−2−イル]フェネチル メタクリレート、3−[5−(6−アセトアミド−1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル)−2H−ベンゾトリアゾール−2−イル]−4−ヒドロキシフェネチル メタクリレート、3−{5−[6−(2−エチルヘキサンアミド)−1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル] −2H−ベンゾトリアゾール−2−イル}−4−ヒドロキシフェネチル メタクリレート。 As benzotriazole derivative compound general formula (1) of this invention, the following can be mentioned, for example. N- {2- [2- (2-hydroxy-5-methylphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H-benzo [de] isoquinoline-6 -Yl} acetamide, N- {2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H- Benzo [de] isoquinolin-6-yl} acetamide, N- {2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2 , 3-Dihydro-1H-benzo [de] isoquinolin-6-yl} -2-ethylhexanamide, N- {2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzo Triazol-5-yl] -1,3-dioxo-2,3-dihydro-1H-benzo [de] isoquinolin-6-yl} benzamide, N- {2- [2- (5-tert-butyl-2-] Hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H-benzo [de] isoquinolin-6-yl} acrylamide, N- {2- [2- (5 -Tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H-benzo [de] isoquinolin-6-yl} methacrylamide, 3- {5- [6- (2-Ethylhexanamide) -1,3-dioxo-1H-benzo [de] isoquinolin-2 (3H) -yl] -2H-benzotriazol-2-yl -4-hydroxyphenethyl 2-ethylhexanoate, 4-hydroxy-3- [5- (6-methacrylamido-1,3-dioxo-1H-benzo [de] isoquinolin-2 (3H) -yl) -2H -Benzotriazol-2-yl] phenethyl methacrylate, 3- [5- (6-acetamido-1,3-dioxo-1H-benzo [de] isoquinolin-2 (3H) -yl) -2H-benzotriazole-2- Yl] -4-hydroxyphenethyl methacrylate, 3- {5- [6- (2-ethylhexanamide) -1,3-dioxo-1H-benzo [de] isoquinolin-2 (3H) -yl] -2H-benzo Triazol-2-yl} -4-hydroxyphenethyl methacrylate.
本発明である一般式(1)のベンゾトリアゾール誘導体化合物は、下記(化9〜化14)に示した反応式を経て合成することができる。なおXはハロゲン原子を表す。ただし本発明のベンゾトリアゾール誘導体化合物は、下記合成方法による合成物に限られるものではない。
本発明のベンゾトリアゾール誘導体化合物の重合体は一般式(1)におけるR1がホルミル基、炭素数2〜8のアルキルカルボニル基、ベンゾイル基、アクリロイル基またはメタクリロイル基であり、R2が炭素数1〜4のアルキル基、アルキル基の炭素数の合計が2〜9のアルキルカルボニルオキシアルキル基、アルキル基の炭素数が1〜2のアクリロイルオキシアルキル基またはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基であり、R3が水素原子であるとともに、R1がアクリロイル基もしくはメタクリロイル基であるか、および/またはR2がアルキル基の炭素数が1〜2のアクリロイルオキシアルキル基もしくはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基であるベンゾトリアゾール誘導体化合物の単独重合体であり、または前記ベンゾトリアゾール誘導体化合物と不飽和二重結合を有する化合物との共重合体である。 In the polymer of the benzotriazole derivative compound of the present invention, R 1 in the general formula (1) is a formyl group, an alkylcarbonyl group having 2 to 8 carbon atoms, a benzoyl group, an acryloyl group, or a methacryloyl group, and R 2 has 1 carbon atom. -4 alkyl group, alkylcarbonyloxyalkyl group having 2 to 9 carbon atoms in total, alkyl group acryloyloxyalkyl group having 1 to 2 carbon atoms, or methacryloyl alkyl group having 1 to 2 carbon atoms An oxyalkyl group, R 3 is a hydrogen atom, R 1 is an acryloyl group or a methacryloyl group, and / or R 2 is an acryloyloxyalkyl group or an alkyl group having 1 to 2 carbon atoms in the alkyl group Benzotriazole derivative, which is a methacryloyloxyalkyl group having 1 to 2 carbon atoms A homopolymer of body compound, or a copolymer of said benzotriazole derivative compound and an unsaturated compound having a double bond.
共重合体とする場合の共重合対象となる化合物は、具体的には、例えばメチル(メタ)アクリレート、エチル(メタ)アクリレート、プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート等の(メタ)アクリル酸アルキルエステル類;グリシジル(メタ)アクリレート等のエポキシ基含有の不飽和単量体;(メタ)アクリルアミド、ダイアセトンアクリルアミド、ジメチルアクリルアミド、N‐イソプロピルアクリルアミド、ヒドロキシエチルアクリルアミド、N,N'−ジメチルアミノエチル(メタ)アクリレート、アクリロイルモルホリン、2−ビニルピリジン、4−ビニルピリジン、1−ビニルイミダゾール、N−ビニルカルバゾール、(4−ビニルフェニル)−ジフェニルアミン等の含窒素不飽和単量体;塩化ビニル、塩化ビニリデン等のハロゲン元素含有の不飽和単量体;スチレン、α−メチルスチレン、ビニルトルエン等の芳香族不飽和単量体;酢酸ビニル等のビニルエステル;ビニルエーテル;(メタ)アクリロニトリル等の不飽和シアン化合物単量体;4−(メタ)アクリロイルオキシ−2,2,6,6− テトラメチルピペリジン、4−(メタ)アクリロイルアミノ−2,2,6,6−テトラメチルピペリジン、4−(メタ)アクリロイルオキシ−1,2,2,6,6−ペンタメチルピペリジン、4−(メタ)アクリロイルアミノ−1,2,2,6,6−ペンタメチルピペリジン、4−シアノ−4−(メタ)アクリロイルアミノ−2,2,6,6−テトラメチルピペリジン、4−クロトノイルオキシ−2,2,6,6−テトラメチルピペリジン、4−クロトノイルアミノ−2,2,6,6‐テトラメチルピペリジン、1−(メタ)アクリロイル−4−(メタ)アクリロイルアミノ−2,2,6,6−テトラメチルピペリジン、1−(メタ)アクリロイル−4−シアノ−4−(メタ)アクリロイルアミノ−2,2,6,6−テトラメチルピペリジン、1−クロトノイル−4−クロトノイルオキシ−2,2,6,6−テトラメチルピペリジン等の光安定性単量体;ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、カプロラクトン変性ヒドロキシ(メタ)アクリレート等の水酸基含有単量体;(メタ)アクリル酸、クロトン酸、イタコン酸、マレイン酸、無水マレイン酸等のカルボキシル基含有不飽和単量体;ビニルスルホン酸、スチレンスルホン酸、スルホエチル(メタ)アクリレート等のスルホン酸基含有不飽和単量体;2−(メタ)アクリロイルオキシエチルアシッドホスフェート、2−(メタ)アクリロイルオキシプロピルアシッドホスフェート、2−(メタ)アクリロイルオキシ−3−クロロプロピルアシッドホスフェート、2−メタクリロイルオキシエチルフェニルリン酸等の酸性リン酸エステル系不飽和単量体等が挙げられるが、特に限定されるものではなく、共重合体に要求される種々の物性を付与し、必要な物性を損なわない化合物であればよい。また、一種類のみを用いてもよく、また、二種類以上を適宜混合して用いてもよい。 Specific examples of the compound to be copolymerized in the case of a copolymer include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, and butyl (meth) acrylate. , (Meth) acrylic acid alkyl esters such as isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate; glycidyl (meth) acrylate Epoxy group-containing unsaturated monomers such as (meth) acrylamide, diacetone acrylamide, dimethylacrylamide, N-isopropylacrylamide, hydroxyethyl acrylamide, N, N′-dimethylaminoethyl (meth) acrylate , Acryloylmorpholine, 2-vinylpyridine, 4-vinylpyridine, 1-vinylimidazole, N-vinylcarbazole, (4-vinylphenyl) -diphenylamine and other nitrogen-containing unsaturated monomers; vinyl chloride, vinylidene chloride, etc. Halogen-containing unsaturated monomers; aromatic unsaturated monomers such as styrene, α-methylstyrene and vinyltoluene; vinyl esters such as vinyl acetate; vinyl ether; unsaturated cyanide compounds such as (meth) acrylonitrile alone 4- (meth) acryloyloxy-2,2,6,6-tetramethylpiperidine, 4- (meth) acryloylamino-2,2,6,6-tetramethylpiperidine, 4- (meth) acryloyloxy -1,2,2,6,6-pentamethylpiperidine, 4- (meth) acryloylamino-1 2,2,6,6-pentamethylpiperidine, 4-cyano-4- (meth) acryloylamino-2,2,6,6-tetramethylpiperidine, 4-crotonoyloxy-2,2,6,6- Tetramethylpiperidine, 4-crotonoylamino-2,2,6,6-tetramethylpiperidine, 1- (meth) acryloyl-4- (meth) acryloylamino-2,2,6,6-tetramethylpiperidine, 1 -(Meth) acryloyl-4-cyano-4- (meth) acryloylamino-2,2,6,6-tetramethylpiperidine, 1-crotonoyl-4-crotonoyloxy-2,2,6,6-tetramethyl Light-stable monomers such as piperidine; hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, caprolactone-modified hydroxy Hydroxyl group-containing monomers such as (meth) acrylate; carboxyl group-containing unsaturated monomers such as (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, maleic anhydride; vinyl sulfonic acid, styrene sulfonic acid, sulfoethyl Sulfonic acid group-containing unsaturated monomers such as (meth) acrylate; 2- (meth) acryloyloxyethyl acid phosphate, 2- (meth) acryloyloxypropyl acid phosphate, 2- (meth) acryloyloxy-3-chloropropyl Acid phosphates, acidic phosphate ester unsaturated monomers such as 2-methacryloyloxyethylphenyl phosphoric acid, and the like are mentioned, but there is no particular limitation, and various physical properties required for the copolymer are imparted. Any compound that does not impair the necessary physical properties may be used. Further, only one type may be used, or two or more types may be appropriately mixed and used.
重合体を得る際の重合方法は、特に限定されるものではなく、従来公知の種々の重合方法、例えば、ラジカル重合、イオン重合による連鎖重合反応を用いた溶液重合法、塊状(バルク)重合法、懸濁(パール)重合法、光重合法等を採用することができる。 The polymerization method for obtaining the polymer is not particularly limited, and various conventionally known polymerization methods, for example, solution polymerization method using chain polymerization reaction by radical polymerization, ion polymerization, bulk polymerization method, etc. Suspension (pearl) polymerization method, photopolymerization method and the like can be employed.
溶液重合法を採用して重合体を得る場合において用いることができる溶媒としては、具体的には、例えば、トルエン、キシレン、その他の高沸点の芳香族系溶媒;酢酸エチル、酢酸ブチル、セロソルブアセテート等のエステル系溶媒;メチルエチルケトン、メチルイソブチルケトン等のケトン系溶媒;メタノール、エタノール、2−プロパノール等のアルコール系溶媒等が挙げられるが、特に限定されるものではない。これら溶媒は、一種類のみを用いてもよく、また、二種類以上を適宜混合して用いてもよい。また、溶媒の使用量は、特に限定されるものではない。 Specific examples of solvents that can be used in the case of obtaining a polymer by adopting the solution polymerization method include, for example, toluene, xylene, and other high-boiling aromatic solvents; ethyl acetate, butyl acetate, cellosolve acetate. Ester solvents such as: methyl solvents such as methyl ethyl ketone and methyl isobutyl ketone; alcohol solvents such as methanol, ethanol, 2-propanol, and the like, but are not particularly limited. Only one kind of these solvents may be used, or two or more kinds may be appropriately mixed and used. Moreover, the usage-amount of a solvent is not specifically limited.
塊状(バルク)重合法を採用して重合体を得る場合において用いることができる重合開始剤としては、後述に列記する重合開始剤が挙げられる。 Examples of the polymerization initiator that can be used in the case of obtaining a polymer by employing a bulk polymerization method include the polymerization initiators listed below.
懸濁(パール)重合法を採用して重合体を得る場合において用いることができる分散剤としては、具体的には、例えば、ポリビニルアルコール、 ポリ(メタ)アクリル酸またはその塩、スチレンとマレイン酸共重合体の塩、α−メチルスチレンとアクリル酸共重合体の塩、ポリビニルピロリドン、ポリ(メタ)アクリルアミド、メチルセルロース、エチルセルロース、ヒドロキシメチルセルロース、ヒドロキシエチルセルロース、ヒドロキシプロピルメチルセルロース、ヒドロキシブチルメチルセルロース、カルボキシメチルセルロース、ゼラチン、デンプン、トラガント、ペクチン、グルー、アルギン酸またはその塩等の高分子界面活性剤;ポリエチレンオキサイド、ポリプロピレンオキサイド等のポリオキシアルキレン系分散剤;ポリオキシエチレン−アルキルエーテル、ポリオキシエチレン−アルキルフェノール、ポリオキシエチレン−多価アルコールエステル、多価アルコールと脂肪酸とのエステル、オキシエチレン・オキシプロピレンブロック縮合物等の非イオン系界面活性剤等が挙げられる。また、これら分散剤は、一種類のみを用いてもよく、また、二種類以上を適宜混合して用いてもよい。また、分散剤の使用量は、特に限定されるものではない。 Specific examples of the dispersant that can be used in the case of obtaining a polymer by employing the suspension (pearl) polymerization method include, for example, polyvinyl alcohol, poly (meth) acrylic acid or a salt thereof, styrene and maleic acid Salt of copolymer, salt of α-methylstyrene and acrylic acid copolymer, polyvinylpyrrolidone, poly (meth) acrylamide, methylcellulose, ethylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylmethylcellulose, hydroxybutylmethylcellulose, carboxymethylcellulose, gelatin , Starch, tragacanth, pectin, glue, alginic acid or a salt thereof; polyoxyalkylene dispersants such as polyethylene oxide and polypropylene oxide; Shiechiren - alkyl ether, polyoxyethylene - alkyl phenols, polyoxyethylene - polyol esters, esters of polyhydric alcohols and fatty acids, a nonionic surfactant such as oxyethylene-oxypropylene block condensates thereof. Moreover, these dispersing agents may use only one type, and may mix and use two or more types suitably. Moreover, the usage-amount of a dispersing agent is not specifically limited.
また、溶液重合法、塊状重合法、懸濁重合法を採用して重合体を得る際には、重合開始剤を用いることができる。重合開始剤としては、具体的には、例えば、 2,2'−アゾビス−(2−メチルブチロニトリル) 、2,2'−アゾビスイソブチロニトリル、1,1’ −アゾビス(シクロヘキサン−1−カルボニトリル)、ベンゾイルパーオキサイド、ジ−t− ブチルパーオキサイド、t−ブチルパーオキシ−2−エチルヘキサノエート等の油溶性のラジカル重合開始剤;過硫酸アンモニウム、過硫酸カリウム、過硫酸ナトリウム、t−ブチルパーオキサイド、2,2−アゾビス[2−(2−イミダゾリン−2−イル)プロパン]・二塩酸塩、2,2−アゾビス[2−(2−イミダゾリン−2−イル)プロパン]・二硫酸・二水和物、2,2−アゾビス(2−アミジノプロパン)・二塩酸塩 、2,2−アゾビス〔N−(2−カルボキシエチル)−2−メチルプロピオンアミジン]水和物、2,2−アゾビス{2−[1−(2−ヒドロキシエチル)−2−イミダゾリン−2−イル]プロパン}・二塩酸塩、2,2−アゾビス[2−(2−イミダゾリン−2−イル)プロパン]、2,2−アゾビス(1−イミノ−1−ピロリジノ−2−エチルプロパン)・二塩酸塩、2、2−アゾビス{2−メチル−N−[1,1−ビス(ヒドロキシメチル)−2−ヒドロキシエチル]プロピオンアミド}、2,2−アゾビス[2−メチル−N−(2−ヒドロキシエチル)プロピオンアミド]、2,2−アゾビス(N−ヒドロキシエチルイソブチルアミド)、4,4−アゾビス(4−シアノペンタン酸)等の水溶性のラジカル重合開始剤;過硫酸塩類や有機過酸化物類の重合開始剤にナトリウムスルホオキシレートホルムアルデヒド、亜硫酸水素ナトリウム、亜硫酸水素アンモニウム、チオ硫酸ナトリウム、チオ硫酸アンモニウム、過酸化水素、ヒドロキシメタンスルフィン酸ナトリウム、L−アスコルビン酸、およびその塩、第一銅塩、第一鉄塩などの還元剤を重合開始剤に組み合わせて用いるレドックス系開始剤;ベンゾフェノン、N,N′−テトラアルキル−4,4′−ジアミノベンゾフェノン、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−ブタノン−1、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノ−プロパノン−1、4,4′−ビス(ジメチルアミノ)ベンゾフェノン(ミヒラーケトン)、4,4′−ビス(ジエチルアミノ)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等の芳香族ケトン類、アルキルアントラキノン、フェナントレンキノン等のキノン類、ベンゾイン、アルキルベンゾイン等のベンゾイン化合物、ベンゾインアルキルエーテル、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、ベンジルジメチルケタール等のベンジル誘導体、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、2,4−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等の2,4,5−トリアリールイミダゾール二量体、N−フェニルグリシン、N−フェニルグリシン誘導体、9−フェニルアクリジン等のアクリジン誘導体、1,2−オクタンジオン,1−[4−(フェニルチオ)−,2−(o−ベンゾイルオキシム)]等のオキシムエステル類、7−ジエチルアミノ−4−メチルクマリン等のクマリン系化合物、2,4−ジエチルチオキサントン等のチオキサントン系化合物、2,4,6−トリメチルベンゾイル−ジフェニル−ホスフィンオキサイド等のアシルホスフィンオキサイド系化合物等の光(主として紫外線)開裂型ラジカル重合開始剤が挙げられるが、特に限定されるものではない。また、これら重合開始剤は、一種類のみを用いてもよく、また、二種類以上を適宜混合して用いてもよい。また、重合開始剤の使用量は、特に限定されるものではない。 In addition, when a polymer is obtained by employing a solution polymerization method, a bulk polymerization method, or a suspension polymerization method, a polymerization initiator can be used. Specific examples of the polymerization initiator include 2,2′-azobis- (2-methylbutyronitrile), 2,2′-azobisisobutyronitrile, 1,1′-azobis (cyclohexane- 1-carbonitrile), benzoyl peroxide, di-t-butyl peroxide, oil-soluble radical polymerization initiators such as t-butylperoxy-2-ethylhexanoate; ammonium persulfate, potassium persulfate, sodium persulfate , T-butyl peroxide, 2,2-azobis [2- (2-imidazolin-2-yl) propane] dihydrochloride, 2,2-azobis [2- (2-imidazolin-2-yl) propane] Disulfuric acid dihydrate, 2,2-azobis (2-amidinopropane) dihydrochloride, 2,2-azobis [N- (2-carboxyethyl) -2-methylpropion Midine] hydrate, 2,2-azobis {2- [1- (2-hydroxyethyl) -2-imidazolin-2-yl] propane} dihydrochloride, 2,2-azobis [2- (2- Imidazolin-2-yl) propane], 2,2-azobis (1-imino-1-pyrrolidino-2-ethylpropane) dihydrochloride, 2,2-azobis {2-methyl-N- [1,1- Bis (hydroxymethyl) -2-hydroxyethyl] propionamide}, 2,2-azobis [2-methyl-N- (2-hydroxyethyl) propionamide], 2,2-azobis (N-hydroxyethylisobutyramide) Water-soluble radical polymerization initiators such as 4,4-azobis (4-cyanopentanoic acid); polymerization initiators of persulfates and organic peroxides, sodium sulfooxylate formaldehyde, sodium hydrogensulfite As a polymerization initiator, a reducing agent such as sodium, ammonium bisulfite, sodium thiosulfate, ammonium thiosulfate, hydrogen peroxide, sodium hydroxymethanesulfinate, L-ascorbic acid, and salts thereof, cuprous salts, ferrous salts, etc. Redox initiators used in combination; benzophenone, N, N′-tetraalkyl-4,4′-diaminobenzophenone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2- Methyl-1- [4- (methylthio) phenyl] -2-morpholino-propanone-1,4,4'-bis (dimethylamino) benzophenone (Michler ketone), 4,4'-bis (diethylamino) benzophenone, 4-methoxy Aromatic ketones such as -4'-dimethylaminobenzophenone, alkyl Quinones such as anthraquinone and phenanthrenequinone, benzoin compounds such as benzoin and alkylbenzoin, benzoin ether compounds such as benzoin alkyl ether and benzoin phenyl ether, benzyl derivatives such as benzyldimethyl ketal, 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, 2,4-di (p-methoxyphenyl) -5-phenylimidazole dimer, 2- (2,4-dimethoxyphenyl)- 2,4, such as 4,5-diphenylimidazole dimer 5-triarylimidazole dimer, N-phenylglycine, N-phenylglycine derivative, acridine derivative such as 9-phenylacridine, 1,2-octanedione, 1- [4- (phenylthio)-, 2- (o -Benzoyloxime)], coumarin compounds such as 7-diethylamino-4-methylcoumarin, thioxanthone compounds such as 2,4-diethylthioxanthone, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide Examples thereof include, but are not particularly limited to, light (mainly ultraviolet) cleavage type radical polymerization initiators such as acylphosphine oxide compounds. Moreover, these polymerization initiators may use only 1 type, and may mix and use 2 or more types suitably. Moreover, the usage-amount of a polymerization initiator is not specifically limited.
反応温度は、特に限定されるものではないが、室温〜200℃の範囲が好ましく、50℃〜150℃の範囲がより好ましい。尚、反応時間は、反応温度、或いは、用いる単量体組成物の組成や重合開始剤の種類等に応じて、重合反応が完結するように、適宜設定すればよい。 Although reaction temperature is not specifically limited, The range of room temperature-200 degreeC is preferable, and the range of 50 degreeC-150 degreeC is more preferable. The reaction time may be appropriately set so that the polymerization reaction is completed according to the reaction temperature, the composition of the monomer composition to be used, the kind of the polymerization initiator, or the like.
光重合法を採用して重合体を得る場合において共重合対象となる化合物は、前述の他に分子内に2個以上のエチレン性不飽和基を有する(メタ)アクリレートなどが挙げられる。分子内に2個以上のエチレン性不飽和基を有する(メタ)アクリレートとしては、例えば、1,3−ブタンジオールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,9−ノナンジオールジ(メタ)アクリレート、1,10−デカンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ビスフェノールAジ(メタ)アクリレート、トリシクロデカンジメタノールジ(メタ)アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールジ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、トリス(2−アクリロキシエチル)イソシアヌレート、グリセリントリ(メタ)アクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、及びこれらのエチレンオキシドまたはプロピレンオキシドまたはε−カプロラクトン変性(メタ)アクリレート、エポキシ(メタ)アクリレート、ウレタン(メタ)アクリレート、ポリエステル(メタ)アクリレートなどを挙げることができる。これらは単独で用いてもよいし、または2種以上を組わせて用いてもよい。 In the case of obtaining a polymer by employing the photopolymerization method, the compound to be copolymerized includes (meth) acrylate having two or more ethylenically unsaturated groups in the molecule in addition to the above. Examples of the (meth) acrylate having two or more ethylenically unsaturated groups in the molecule include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,9 -Nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, bisphenol A di ( (Meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, hydroxypivalic acid neopentyl glycol di (meth) acrylate, trimethylolethane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (2-a Riloxyethyl) isocyanurate, glycerin tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (Meth) acrylate, and ethylene oxide or propylene oxide or ε-caprolactone modified (meth) acrylate, epoxy (meth) acrylate, urethane (meth) acrylate, polyester (meth) acrylate, and the like can be given. These may be used alone or in combination of two or more.
光重合法を採用して重合体を得る場合において用いる光重合開始剤としては、活性エネルギー線の照射によって光重合開始作用を示す公知の光重合開始剤のいずれもが使用できる。例えば、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン、1−ヒドロキシ−シクロヘキシル−フェニル−ケトン、2−ヒドロキシ−2−メチル−1−フェニル−プロパン−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、2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]−フェニル}−2−メチル−プロパン−1−オン、フェニルグリオキシリックアシッドメチルエステル、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、2−ジメチルアミノ−2−(4−メチル−ベンジル)−1−(4−モルフォリン−4−イル−フェニル)−ブタン−1−オン、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などを挙げることができ、また、ベンゾフェノンおよび/または2−イソプロピルチオキサントンと重合促進剤の2−エチルヘキシル−4−ジメチルアミノベンゾエートおよび/またはエチル−4−ジメチルアミノベンゾエートといった組み合わせも使用できる。本発明で、これらの光重合開始剤を単独で用いてもよいし、または2種以上を組み合わせて用いてもよい。 As a photopolymerization initiator used when a photopolymerization method is employed to obtain a polymer, any of known photopolymerization initiators that exhibit a photopolymerization initiating action upon irradiation with active energy rays can be used. For example, 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1- [ 4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) ) -Benzyl] -phenyl} -2-methyl-propan-1-one, phenylglyoxylic acid methyl ester, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2-dimethylamino-2- (4-methyl-benzene) And (zyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, and the like. A combination of 2-isopropylthioxanthone and the polymerization accelerators 2-ethylhexyl-4-dimethylaminobenzoate and / or ethyl-4-dimethylaminobenzoate can also be used. In the present invention, these photopolymerization initiators may be used alone or in combination of two or more.
そのうちでも、1−ヒドロキシ−シクロヘキシル−フェニル−ケトン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オンおよび/または2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]−フェニル}−2−メチル−プロパン−1−オンが、硬化膜の黄変が少なく、表面硬化性に優れる点から好ましく用いられる。 Among them, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one and / or 2-hydroxy-1- {4- [ 4- (2-Hydroxy-2-methyl-propionyl) -benzyl] -phenyl} -2-methyl-propan-1-one is preferably used from the viewpoint of little yellowing of the cured film and excellent surface curability.
波長変換材料はフィルムに配合したり、フィルム表面または中間層に成膜して、波長変換フィルムとして使用されることが多く、本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体も同様に、波長変換フィルムに使用できる。本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を使用できるフィルムの樹脂素材は特に限定されるわけではないが、例えば、ポリエチレン、ポリプロピレン、ポリブテン、ポリペンテン、ポリ−3−メチルブチレン、ポリメチルペンテンなどのα−オレフィン重合体またはエチレン−酢酸ビニル共重合体、エチレン−プロピレン共重合体などのポリオレフィン、ポリ塩化ビニル、ポリ臭化ビニル、ポリフッ化ビニル、塩素化ポリエチレン、塩素化ポリプロピレン、臭素化ポリエチレン、塩化ゴム、塩化ビニル−酢酸ビニル共重合体、塩化ビニル−エチレン共重合体、塩化ビニル−プロピレン共重合体、塩化ビニル−スチレン共重合体、塩化ビニル−イソブチレン共重合体、塩化ビニル−塩化ビニリデン共重合体、塩化ビニル−スチレン−無水マレイン酸三元共重合体、塩化ビニル−スチレン−アクリロニトリル三元共重合体、塩化ビニル−ブタジエン共重合体、塩化ビニル−イソブチレン共重合体、塩化ビニル−塩素化プロピレン共重合体、塩化ビニル−塩化ビニリデン−酢酸ビニル三元共重合体、塩化ビニル−アクリル酸エステル共重合体、塩化ビニル−マレイン酸エステル共重合体、塩化ビニル−メタクリル酸エステル共重合体、塩化ビニル−アクリロニトリル共重合体、内部可塑性ポリ塩化ビニルなどの含ハロゲン合成樹脂、石油樹脂、クマロン樹脂、ポリスチレン、スチレンと他の単量体(無水マレイン酸、ブタジエン、アクリロニトリルなど)との共重合体、アクリロニトリル−ブタジエン−スチレン樹脂、アクリル酸エステル−ブタジエン−スチレン樹脂、メタクリル酸エステル−ブタジエン−スチレン樹脂などのスチレン系樹脂、ポリ酢酸ビニル、ポリビニルアルコール、ポリビニルホルマール、ポリビニルブチラール、アクリル樹脂、メタクリレート樹脂、ポリアクリロニトリル、ポリフェニレンオキシド、ポリカーボネート、変性ポリフェニレンオキシド、ポリアセタール、フェノール樹脂、尿素樹脂、メラミン樹脂、エポキシ樹脂、シリコン樹脂、ポリエチレンテレフタレート、強化ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリスルホン系樹脂、ポリエーテルスルホン、ポリフェニレンスルフィド、ポリエーテルケトン、ポリエーテルイミド、ポリオキシベンゾイル、ポリイミド、ポリマレイミド、ポリアミドイミド、アルキド樹脂、アミノ樹脂、ビニル樹脂、水溶性樹脂、粉体塗料用樹脂、ポリアミド樹脂、ポリウレタン樹脂、不飽和ポリエステル樹脂等を挙げることができる。 The wavelength conversion material is often used as a wavelength conversion film by blending into a film or forming a film on a film surface or an intermediate layer, and the benzotriazole derivative compound of the present invention and a polymer having them are also similar. Can be used for wavelength conversion film. Although the resin material of the film which can use the benzotriazole derivative compound of this invention and the polymer which has them is not necessarily limited, For example, polyethylene, polypropylene, polybutene, polypentene, poly-3-methylbutylene, polymethyl Α-Olefin polymer such as pentene or polyolefin such as ethylene-vinyl acetate copolymer, ethylene-propylene copolymer, polyvinyl chloride, polyvinyl bromide, polyvinyl fluoride, chlorinated polyethylene, chlorinated polypropylene, brominated Polyethylene, chlorinated rubber, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-propylene copolymer, vinyl chloride-styrene copolymer, vinyl chloride-isobutylene copolymer, vinyl chloride-chloride Vinylidene copolymer, chloride Nyl-styrene-maleic anhydride terpolymer, vinyl chloride-styrene-acrylonitrile terpolymer, vinyl chloride-butadiene copolymer, vinyl chloride-isobutylene copolymer, vinyl chloride-chlorinated propylene copolymer , Vinyl chloride-vinylidene chloride-vinyl acetate terpolymer, vinyl chloride-acrylic acid ester copolymer, vinyl chloride-maleic acid ester copolymer, vinyl chloride-methacrylic acid ester copolymer, vinyl chloride-acrylonitrile copolymer Polymers, halogen-containing synthetic resins such as internal plastic polyvinyl chloride, petroleum resins, coumarone resins, polystyrene, copolymers of styrene and other monomers (maleic anhydride, butadiene, acrylonitrile, etc.), acrylonitrile-butadiene- Styrene resin, acrylic ester-butadiene-styrene Styrene resin such as lene resin, methacrylate ester-butadiene-styrene resin, polyvinyl acetate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, acrylic resin, methacrylate resin, polyacrylonitrile, polyphenylene oxide, polycarbonate, modified polyphenylene oxide, polyacetal, Phenol resin, urea resin, melamine resin, epoxy resin, silicone resin, polyethylene terephthalate, reinforced polyethylene terephthalate, polybutylene terephthalate, polysulfone resin, polyethersulfone, polyphenylene sulfide, polyetherketone, polyetherimide, polyoxybenzoyl, polyimide , Polymaleimide, polyamideimide, alkyd resin, amino resin, vinyl Fat, water-soluble resins, powder coating resins, polyamide resins, polyurethane resins and unsaturated polyester resins.
本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を波長変換フィルムに使用する場合、波長変換材料としては本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体のみ、あるいは他の波長変換材料と組合せて使用できる。本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体以外の波長変換機能を有する化合物としては、一般に市場で入手できるもので紫外線領域に励起帯を有し可視光領域に発光ピークを有するものあれば特に限定されない。例えば、ペリレン誘導体、クマリン誘導体、有機金属錯体、ピラン誘導体、スチルベン誘導体、アクリドン誘導体、オキサゾン誘導体、キナクリドン誘導体、ベンゾオキサゾール誘導体、ポリフルオレン誘導体、ポリフェニレンビニレン誘導体等、一般的な低分子蛍光材料、低分子リン光材料、ポリマー発光材料等が用いられる。これらの発光材料は、一種類のみを用いてもよく、また、二種類以上を適宜混合して用いてもよい。 When the benzotriazole derivative compound of the present invention and the polymer having them are used for a wavelength conversion film, the wavelength conversion material includes only the benzotriazole derivative compound of the present invention and the polymer having them, or other wavelength conversion materials. Can be used in combination with The compounds having a wavelength conversion function other than the benzotriazole derivative compounds of the present invention and the polymers having them are generally available on the market and have an excitation band in the ultraviolet region and an emission peak in the visible region. If it does not specifically limit. For example, general low-molecular fluorescent materials such as perylene derivatives, coumarin derivatives, organometallic complexes, pyran derivatives, stilbene derivatives, acridone derivatives, oxazone derivatives, quinacridone derivatives, benzoxazole derivatives, polyfluorene derivatives, polyphenylene vinylene derivatives, etc. A phosphorescent material, a polymer light emitting material, or the like is used. These light emitting materials may be used alone or in a suitable mixture of two or more.
本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体をフィルムに配合する場合、樹脂に対して少なすぎると十分な発光が得られず、また、多すぎると濃度消光が起こるため、0.001〜20重量%、好ましくは0.01〜10重量%の範囲で使用されることが好ましい。 When the benzotriazole derivative compound of the present invention and the polymer having them are blended in a film, if the amount is too small relative to the resin, sufficient light emission cannot be obtained, and if too large, concentration quenching occurs. It is preferably used in the range of -20% by weight, preferably 0.01-10% by weight.
本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体をフィルムに成膜する方法として、例えば、湿式塗布法が挙げられる。湿式塗布法は複雑な工程を必要とせず、製造コストが低く、大面積化が容易という利点があり、湿式塗布法として、例えば、インクジェット法、スピンコート法やディップコート法がある。湿式塗布法を行うには波長変換材料を有機溶媒に溶解させる必要があり、有機溶媒に溶解しやすい波長変換材料を用いることが望ましい。本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体は、有機溶媒に溶解しやすく、例えばスピンコート法によって、波長変換膜を形成することができる。 Examples of a method for forming a film of the benzotriazole derivative compound of the present invention and a polymer having them into a film include a wet coating method. The wet coating method does not require a complicated process, has an advantage that the manufacturing cost is low and the area can be easily increased, and examples of the wet coating method include an inkjet method, a spin coating method, and a dip coating method. In order to perform the wet coating method, it is necessary to dissolve the wavelength conversion material in an organic solvent, and it is desirable to use a wavelength conversion material that is easily dissolved in the organic solvent. The benzotriazole derivative compound of the present invention and the polymer having them can be easily dissolved in an organic solvent, and a wavelength conversion film can be formed by, for example, a spin coating method.
本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を湿式塗布法によりフィルムに成膜する際、ベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を溶解させる有機溶媒として、ペンタン、ヘキサン、ヘプタン等の脂肪族炭化水素;ベンゼン、トルエン、キシレン等の芳香族炭化水素;シクロヘキサン、メチルシクロヘキサン等の脂環式炭化水素;石油エーテル、石油ベンジン等の石油系溶媒;四塩化炭素、クロロホルム、1,2−ジクロロエタン等のハロゲン化炭化水素;エチルエーテル、イソプロピルエーテル、アニソール、ジオキサン、テトラヒドロフラン等のエーテル;アセトン、メチルイソブチルケトン、メチルエチルケトン、シクロヘキサノン、アセトフェノン、イソフォロン等のケトン;酢酸エチル、酢酸ブチル等のエステル;ジメチルホルムアミド、ジメチルアセトアミド等のアミド;アセトニトリル;ジメチルスルフォキシド;クロロベンゼン、ジクロロベンゼン等のハロゲン化ベンゼン等が挙げられる。これらは一種類のみを用いてもよく、また、二種類以上を適宜混合して用いてもよい。 When the benzotriazole derivative compound of the present invention and a polymer having them are formed into a film by a wet coating method, an organic solvent for dissolving the benzotriazole derivative compound and the polymer having them is pentane, hexane, heptane, etc. Aliphatic hydrocarbons; aromatic hydrocarbons such as benzene, toluene and xylene; alicyclic hydrocarbons such as cyclohexane and methylcyclohexane; petroleum solvents such as petroleum ether and petroleum benzine; carbon tetrachloride, chloroform, and 1.2 -Halogenated hydrocarbons such as dichloroethane; ethers such as ethyl ether, isopropyl ether, anisole, dioxane, tetrahydrofuran; ketones such as acetone, methyl isobutyl ketone, methyl ethyl ketone, cyclohexanone, acetophenone, isophorone; And esters such as dimethylformamide and dimethylacetamide; acetonitrile; dimethyl sulfoxide; and halogenated benzenes such as chlorobenzene and dichlorobenzene. Only one kind of these may be used, or two or more kinds may be appropriately mixed and used.
本発明のベンゾトリアゾール誘導体化合物を有する重合体は、単独で波長変換フィルムにすることができる。例えば、フィルムや硝子板の表面に成膜し、波長変換フィルムを剥がし取ることで得られる。 The polymer having the benzotriazole derivative compound of the present invention can be made into a wavelength conversion film alone. For example, it can be obtained by forming a film on the surface of a film or glass plate and peeling off the wavelength conversion film.
本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を使用できる太陽電池は特に限定されるわけではないが、例えば、単結晶シリコン太陽電池、多結晶シリコン太陽電池、リボンシリコン太陽電池、球状シリコン太陽電池、薄膜シリコン太陽電池、ヘテロ接合太陽電池、CIGS系太陽電池、CdTe太陽電池、色素増感太陽電池、有機半導体太陽電池、ヘロブスカイト太陽電池を挙げることができる。 The solar cell that can use the benzotriazole derivative compound of the present invention and the polymer having them is not particularly limited, and examples thereof include a single crystal silicon solar cell, a polycrystalline silicon solar cell, a ribbon silicon solar cell, and a spherical silicon. A solar cell, a thin film silicon solar cell, a heterojunction solar cell, a CIGS solar cell, a CdTe solar cell, a dye-sensitized solar cell, an organic semiconductor solar cell, and a herbskite solar cell can be exemplified.
本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を太陽電池に用いる方法として、本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体を用いた波長変換フィルムを太陽電池に取り付ける方法、太陽電池部材であるフロントシート、バックシート、封止材等に配合または成膜する方法が挙げられる。 As a method for using a benzotriazole derivative compound of the present invention and a polymer having them in a solar cell, a method for attaching a wavelength conversion film using the benzotriazole derivative compound of the present invention and a polymer having them to a solar cell, Examples thereof include a method of blending or forming a film with a battery member such as a front sheet, a back sheet, and a sealing material.
以下に本発明で実施したベンゾトリアゾール誘導体化合物、及びその重合体の合成法と特性を示す。ただし本発明は、以下の実施様態のみに限られるものではない。 The synthesis method and characteristics of the benzotriazole derivative compound and its polymer carried out in the present invention are shown below. However, the present invention is not limited to the following embodiments.
(実施例1)
[中間体;6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンの合成]
Example 1
[Intermediate; 6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1H-benzo [de] isoquinoline-1,3 (2H) -Synthesis of dione]
500mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、2−アミノ−4−tert−ブチルフェノール15.2g(0.0920モル)、水200ml、62.5%硫酸45.2g(0.2880モル)を入れて混合し、3〜7℃で36%亜硝酸ナトリウム水溶液18.6g(0.0970モル)を2時間かけて滴下し、同温度で2時間撹拌してジアゾニウム塩水溶液を得た。1000mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、m−フェニレンジアミン10.0g(0.0925モル)、水100ml、62.5%硫酸7.2g(0.0459モル)を入れて混合し、炭酸ナトリウム31.0g(0.2925モル)を徐々に加えながらジアゾニウム塩水溶液を5〜10℃で4時間かけて滴下し、5〜15℃で12時間撹拌して、4−tert−ブチル−2−(2,4−ジアミノフェニルジアゼニル)フェノールのスラリー液を得た。このスラリー液にトルエン200mlを仕込み、70〜75℃で静置して下層部の水層を分離して除去し、水100mlで水洗してトルエンを減圧回収した。回収物にイソプロピルアルコール150ml、水50ml、25%アンモニア水溶液40ml、硫酸銅五水和物30.0g(0.1202モル)を仕込み、80℃で24時間撹拌後に150ml回収し、20℃に冷却して析出している結晶をろ過、水洗、乾燥し、粗製の2−(5−アミノー2H−ベンゾトリアゾール−2−イル)−4−tert−ブチルフェノールを21.1g得た。 A 500 ml four-necked flask is equipped with a condenser with a ball, a thermometer, and a stirring device, 15.2 g (0.0920 mol) of 2-amino-4-tert-butylphenol, 200 ml of water, 45.2 g of 62.5% sulfuric acid ( 0.2880 mol) was added and mixed, and 18.6 g (0.0970 mol) of 36% aqueous sodium nitrite solution was added dropwise at 3 to 7 ° C. over 2 hours, followed by stirring at the same temperature for 2 hours and an aqueous diazonium salt solution. Got. A 1000-ml four-necked flask is equipped with a condenser with a ball, a thermometer, and a stirrer, 10.0 g (0.0925 mol) of m-phenylenediamine, 100 ml of water, 7.2 g of 62.5% sulfuric acid (0.0459 mol). The diazonium salt aqueous solution was added dropwise at 5 to 10 ° C. over 4 hours while gradually adding 31.0 g (0.2925 mol) of sodium carbonate, and stirred at 5 to 15 ° C. for 12 hours. A slurry solution of -tert-butyl-2- (2,4-diaminophenyldiazenyl) phenol was obtained. To this slurry liquid, 200 ml of toluene was charged and allowed to stand at 70 to 75 ° C., and the lower aqueous layer was separated and removed, washed with 100 ml of water, and toluene was recovered under reduced pressure. The recovered product was charged with 150 ml of isopropyl alcohol, 50 ml of water, 40 ml of 25% ammonia aqueous solution and 30.0 g (0.1202 mol) of copper sulfate pentahydrate, and after stirring at 80 ° C. for 24 hours, 150 ml was collected and cooled to 20 ° C. The precipitated crystals were filtered, washed with water and dried to obtain 21.1 g of crude 2- (5-amino-2H-benzotriazol-2-yl) -4-tert-butylphenol.
500mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、粗製の2−(5−アミノー2H−ベンゾトリアゾール−2−イル)−4−tert−ブチルフェノールを21.1g、イソプロピルアルコール50ml、水100ml、硫化ナトリウム九水和物24.0g(0.0999モル)を仕込み、80〜90℃で1時間撹拌後に同温度でろ過して不溶解分を除去した。ろ液から50ml回収後、塩酸でpH6に調整し、沈殿物をろ過、水洗、乾燥し、結晶を12.8g得た。この結晶12.8gを0.5mmHg、250℃で蒸留して蒸留オイルを9.2g得た。この蒸留オイル9.2g、トルエン80ml、活性炭1.0gを玉付きコンデンサー、温度計、撹拌装置を取り付けた200mlの4つ口フラスコに仕込み、90℃で1時間撹拌後に同温度でろ過して活性炭を除去し、トルエンを減圧回収してイソプロピルアルコール20mlを仕込み、析出している結晶をろ過し、イソプロピルアルコールで洗浄して乾燥し、2−(5−アミノー2H−ベンゾトリアゾール−2−イル)−4−tert−ブチルフェノールを8.3g得た。 A 500 ml four-necked flask is equipped with a condenser with a ball, a thermometer and a stirrer, and 21.1 g of crude 2- (5-amino-2H-benzotriazol-2-yl) -4-tert-butylphenol, 50 ml of isopropyl alcohol 100 ml of water and 24.0 g (0.0999 mol) of sodium sulfide nonahydrate were charged, stirred at 80 to 90 ° C. for 1 hour and then filtered at the same temperature to remove insoluble matters. After collecting 50 ml from the filtrate, the pH was adjusted to 6 with hydrochloric acid, and the precipitate was filtered, washed with water and dried to obtain 12.8 g of crystals. 12.8 g of this crystal was distilled at 0.5 mmHg and 250 ° C. to obtain 9.2 g of distilled oil. 9.2 g of this distilled oil, 80 ml of toluene and 1.0 g of activated carbon were charged into a 200 ml four-necked flask equipped with a condenser with a ball, a thermometer and a stirrer, stirred at 90 ° C. for 1 hour, filtered at the same temperature and activated carbon. The toluene was recovered under reduced pressure, and 20 ml of isopropyl alcohol was added. The precipitated crystals were filtered, washed with isopropyl alcohol and dried to give 2- (5-amino-2H-benzotriazol-2-yl)- 8.3 g of 4-tert-butylphenol was obtained.
100mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、2−(5−アミノー2H−ベンゾトリアゾール−2−イル)−4−tert−ブチルフェノールを5.0g(0.0177モル)、酢酸30ml、4−ニトロ−1,8−ナフタル酸無水物4.0g(0.0164モル)を仕込み、118℃で48時間還流撹拌した。20℃に冷却し、析出している結晶をろ過、水洗、乾燥して、2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −6−ニトロ−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを4.6g得た。 A condenser with a ball, a thermometer and a stirrer were attached to a 100 ml four-necked flask, and 5.0 g (0.0177 mol) of 2- (5-amino-2H-benzotriazol-2-yl) -4-tert-butylphenol 30 ml of acetic acid and 4.0 g (0.0164 mol) of 4-nitro-1,8-naphthalic anhydride were charged and stirred at 118 ° C. for 48 hours under reflux. After cooling to 20 ° C., the precipitated crystals were filtered, washed with water and dried to give 2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -6- 4.6 g of nitro-1H-benzo [de] isoquinoline-1,3 (2H) -dione was obtained.
200mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −6−ニトロ−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを4.6g、エタノール80ml、塩化スズ12.0g(0.0633モル)、塩酸12mlを仕込み、83℃で2時間還流撹拌した。5℃に冷却し、析出している結晶をろ過、水洗、乾燥して、6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを3.4g得た。収率13%(2−アミノ−4−tert−ブチルフェノールから)であった。 A 200 ml four-necked flask was equipped with a ball condenser, a thermometer, and a stirring device, and 2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -6-nitro -1H-benzo [de] isoquinoline-1,3 (2H) -dione (4.6 g), ethanol (80 ml), tin chloride (12.0 g, 0.0633 mol), and hydrochloric acid (12 ml) were charged, and the mixture was refluxed and stirred at 83 ° C. for 2 hours. . After cooling to 5 ° C., the precipitated crystals were filtered, washed with water and dried to give 6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl. ] 3.4 g of -1H-benzo [de] isoquinoline-1,3 (2H) -dione was obtained. The yield was 13% (from 2-amino-4-tert-butylphenol).
(実施例2)
[化合物(a);N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}アセトアミドの合成]
[Compound (a); N- {2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H -Synthesis of Benzo [de] isoquinolin-6-yl} acetamide]
100mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを1.5g(0.0031モル)、無水酢酸60mlを仕込み、60℃で24時間撹拌した。20℃に冷却し、析出している結晶をろ過、水洗、乾燥して、化合物(a)を1.2g得た。収率74%(6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンから)であった。融点は300℃以上。 A condenser with a ball, a thermometer, and a stirrer were attached to a 100 ml four-necked flask, and 6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl]. 1.5 g (0.0031 mol) of -1H-benzo [de] isoquinoline-1,3 (2H) -dione and 60 ml of acetic anhydride were charged and stirred at 60 ° C. for 24 hours. The mixture was cooled to 20 ° C., and the precipitated crystals were filtered, washed with water and dried to obtain 1.2 g of compound (a). Yield 74% (6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1H-benzo [de] isoquinoline-1,3 (2H ) -From dione). Melting point is 300 ° C or higher.
また、HPLC分析により、化合物(a)の純度を測定した。
<測定条件>
装置:L−2130((株)日立ハイテクノロジーズ製)
使用カラム:SUMIPAX ODS A−212 6.0×150mm 5μm
カラム温度:40℃
移動相: メタノール/水=95/5
流速:1.0ml/min
検出:UV250nm
<測定結果>
HPLC純度:99.5%
なお、以下の実施例3〜4も本実施例と同様の測定条件でHPLC測定を行った。
Moreover, the purity of the compound (a) was measured by HPLC analysis.
<Measurement conditions>
Device: L-2130 (manufactured by Hitachi High-Technologies Corporation)
Column used: SUMPAX ODS A-212 6.0 × 150 mm 5 μm
Column temperature: 40 ° C
Mobile phase: methanol / water = 95/5
Flow rate: 1.0 ml / min
Detection: UV250nm
<Measurement results>
HPLC purity: 99.5%
The following Examples 3 to 4 were also subjected to HPLC measurement under the same measurement conditions as in this example.
また、化合物(a)のNMR測定を行った結果、上記構造を支持する結果が得られた。
測定条件は次のとおりである。
<測定条件>
装置:JEOL ECX-400
共振周波数:400MHz(1H−NMR)
溶媒:DMSO−d6
1H−NMRの内部標準物質として、テトラメチルシランを用い、ケミカルシフト値はδ値(ppm)、カップリング定数はHertzで示した。またsはsinglet、dはdoublet、tはtriplet、ddはdouble doublet、mはmultipletの略とする。以下の実施例すべてにおいても同様である。得られたNMRスペクトルの内容は以下のとおりである。なお、以下の実施例3、4、6,7も本実施例と同様の測定条件でNMR測定を行った。
δ=10.48(s,1H,N−H),10.31(s,1H,phenol−OH),8.80(d,1H,J=8.7Hz,naphthalene−H),8.58(d,1H,J=7.3Hz,naphthalene−H),8.53(d,1H,J=8.3Hz,naphthalene−H),8.38(d,1H,J=8.3Hz,naphthalene−H),8.17(s,1H,benzotriazol−H),8.15(d,1H,J=1.9Hz,benzotriazol−H),7.96(dd,1H,naphthalene−H),7.74(d,1H,J=2.4Hz,benzotriazol−H),7.54(d,1H,J=8.8Hz,benzene−H),7.51(d,1H,J=8.7Hz,benzene−H),7.12(d,1H,J=8.8Hz,benzene−H),2.32(s,3H,CH3−H),1.32(s,9H,C(CH3)3−H)
Moreover, as a result of conducting NMR measurement of the compound (a), a result supporting the above structure was obtained.
The measurement conditions are as follows.
<Measurement conditions>
Equipment: JEOL ECX-400
Resonant frequency: 400 MHz (1H-NMR)
Solvent: DMSO-d6
Tetramethylsilane was used as an internal standard of 1H-NMR, the chemical shift value was represented by δ value (ppm), and the coupling constant was represented by Hertz. Also, s is a singlet, d is a doublet, t is a triplet, dd is a double doublet, and m is a short of multiplet. The same applies to all the following examples. The contents of the obtained NMR spectrum are as follows. In the following Examples 3, 4, 6, and 7, NMR measurement was performed under the same measurement conditions as in this example.
δ = 10.48 (s, 1H, NH), 10.31 (s, 1H, phenol-OH), 8.80 (d, 1H, J = 8.7 Hz, naphthalene-H), 8.58 (D, 1H, J = 7.3 Hz, naphthalene-H), 8.53 (d, 1H, J = 8.3 Hz, naphthalene-H), 8.38 (d, 1H, J = 8.3 Hz, naphthalene) -H), 8.17 (s, 1H, benzotriazole-H), 8.15 (d, 1H, J = 1.9 Hz, benzotriazole-H), 7.96 (dd, 1H, naphthalene-H), 7 .74 (d, 1H, J = 2.4 Hz, benzotriazole-H), 7.54 (d, 1H, J = 8.8 Hz, benzene-H), 7.51 (d, 1H, J = .7 Hz, benzene-H), 7.12 (d, 1H, J = 8.8 Hz, benzene-H), 2.32 (s, 3H, CH3-H), 1.32 (s, 9H, C ( CH3) 3-H)
(実施例3)
[化合物(b);N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}ベンズアミドの合成]
[Compound (b); N- {2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H -Synthesis of Benzo [de] isoquinolin-6-yl} benzamide]
300mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを1.8g(0.0038モル)、N−メチルピロリドン40ml、無水安息香酸6.0g(0.0265モル)、炭酸カリウム4.0g(0.0289モル)を仕込み、200℃で24時間還流撹拌した。N−メチルピロリドンを減圧回収し、トルエン200mlを仕込み、20℃に冷却し、析出している結晶をろ過、水洗、乾燥して、結晶を1.0g得た。この結晶1.0g、活性炭0.2g、トルエン200mlを玉付きコンデンサー、温度計、撹拌装置を取り付けた300mlの4つ口フラスコに仕込み、110℃で1時間撹拌後に同温度でろ過して活性炭を除去し、トルエン50mlを減圧回収し、5℃に冷却し、析出している結晶をろ過し、トルエンで洗浄後に乾燥して、化合物(b)を0.6g得た。収率27%(6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンから)であった。融点は268℃、HPLC純度96.3%であった。 A 300 ml four-necked flask was equipped with a ball condenser, a thermometer, and a stirrer, and 6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl]. 1.8 g (0.0038 mol) of 1H-benzo [de] isoquinoline-1,3 (2H) -dione, 40 ml of N-methylpyrrolidone, 6.0 g (0.0265 mol) of benzoic anhydride, potassium carbonate 4 0.0 g (0.0289 mol) was charged and stirred at 200 ° C. for 24 hours under reflux. N-methylpyrrolidone was recovered under reduced pressure, charged with 200 ml of toluene and cooled to 20 ° C., and the precipitated crystals were filtered, washed with water and dried to obtain 1.0 g of crystals. 1.0 g of this crystal, 0.2 g of activated carbon, and 200 ml of toluene were charged into a 300 ml four-necked flask equipped with a condenser with a ball, a thermometer, and a stirrer, stirred at 110 ° C. for 1 hour and filtered at the same temperature to obtain activated carbon. After removing 50 ml of toluene under reduced pressure and cooling to 5 ° C., the precipitated crystals were filtered, washed with toluene and dried to obtain 0.6 g of compound (b). Yield 27% (6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1H-benzo [de] isoquinoline-1,3 (2H ) -From dione). The melting point was 268 ° C. and the HPLC purity was 96.3%.
また、化合物(b)のNMR測定を行った結果、上記構造を支持する結果が得られた。得られたNMRスペクトルの内容は以下のとおりである。
δ=10.94(s,1H,N−H),10.31(s,1H,phenol−OH),8.68(d,1H,J=8.7Hz,naphthalene−H),8.60(d,2H,J=8.0Hz,naphthalene−H),8.21(s,1H,benzotriazol−H),8.19(d,1H,J=5.0Hz,naphthalene−H),8.18(d,1H,J=2.5Hz,benzotriazol−H),8.15(d,2H,J=8.4Hz,benzene−H),7.94(dd,1H,naphthalene−H),7.75(d,1H,J=2.4Hz,benzotriazol−H),7.66(t,3H,benzene−H),7.57(d,1H,J=9.2Hz,benzene−H),7.51(d,1H,J=8.8Hz,benzene−H),7.13(d,1H,J=8.8Hz,benzene−H),1.33(s,9H,C(CH3)3−H)
Further, as a result of NMR measurement of the compound (b), a result supporting the above structure was obtained. The contents of the obtained NMR spectrum are as follows.
δ = 10.94 (s, 1H, NH), 10.31 (s, 1H, phenol-OH), 8.68 (d, 1H, J = 8.7 Hz, naphthalene-H), 8.60. (D, 2H, J = 8.0 Hz, naphthalene-H), 8.21 (s, 1H, benzotriazole-H), 8.19 (d, 1H, J = 5.0 Hz, naphthalene-H), 8. 18 (d, 1H, J = 2.5 Hz, benzotriazole-H), 8.15 (d, 2H, J = 8.4 Hz, benzene-H), 7.94 (dd, 1H, naphthalenes-H), 7 .75 (d, 1H, J = 2.4 Hz, benzotriazole-H), 7.66 (t, 3H, benzene-H), 7.57 (d, 1H, J = 9.2 Hz, benzen) -H), 7.51 (d, 1H, J = 8.8 Hz, benzene-H), 7.13 (d, 1H, J = 8.8 Hz, benzene-H), 1.33 (s, 9H, C (CH3) 3-H)
(実施例4)
[化合物(c);N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}メタクリルアミドの合成
[Compound (c); N- {2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H Synthesis of -benzo [de] isoquinolin-6-yl} methacrylamide
1000mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを2.4g(0.0050モル)、トルエン500ml、メタクリル酸クロライド3.6ml、ピリジン25mlを仕込み、60〜65℃で2時間撹拌した。同温度でろ過して不溶解分を除去し、水300mlで洗浄後にトルエンを減圧回収し、メタノール30mlを仕込んで析出している結晶を15℃でろ過し、メタノールで洗浄して乾燥し、結晶を0.4g得た。この結晶をメタノールでリパルプ洗浄し、化合物(c)を0.3g得た。収率11%(6−アミノ−2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル] −1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンから)であった。融点は254℃、HPLC純度95.0%であった。 A 1000 ml four-necked flask was equipped with a condenser with a ball, a thermometer, and a stirring device, and 6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl]. -1H-benzo [de] isoquinoline-1,3 (2H) -dione 2.4 g (0.0050 mol), toluene 500 ml, methacrylic acid chloride 3.6 ml and pyridine 25 ml were charged at 60 to 65 ° C. for 2 hours. Stir. The insoluble matter was removed by filtration at the same temperature. After washing with 300 ml of water, toluene was recovered under reduced pressure. 30 ml of methanol was added, and the precipitated crystals were filtered at 15 ° C., washed with methanol and dried. 0.4g was obtained. The crystals were repulped with methanol to obtain 0.3 g of compound (c). Yield 11% (6-amino-2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1H-benzo [de] isoquinoline-1,3 (2H ) -From dione). The melting point was 254 ° C. and the HPLC purity was 95.0%.
また、化合物(c)のNMR測定を行った結果、上記構造を支持する結果が得られた。得られたNMRスペクトルの内容は以下のとおりである。
δ=10.43(s,1H,N−H),10.32(s,1H,phenol−OH),8.58(d,1H,J=7.6Hz,naphthalene−H),8.57(d,1H,J=8.6Hz,naphthalene−H),8.55(d,1H,J=8.1Hz,naphthalene−H),8.18(s,1H,benzotriazol−H),8.16(d,1H,J=4.4Hz,benzotriazol−H),8.09(d,1H,J=8.2Hz,naphthalene−H),7.93(dd,1H,naphthalene−H),7.75(d,1H,J=2.4Hz,benzotriazol−H),7.56(d,1H,J=9.2Hz,benzene−H),7.51(d,1H,J=8.8Hz,benzene−H),7.12(d,1H,J=8.7Hz,benzene−H),6.11(s,1H,C=CH2−H),5.70(s,1H,C=CH2−H),2.08(s,3H,CH3−H),1.32(s,9H,C(CH3)3−H)
Further, as a result of conducting NMR measurement of the compound (c), a result supporting the above structure was obtained. The contents of the obtained NMR spectrum are as follows.
δ = 10.43 (s, 1H, NH), 10.32 (s, 1H, phenol-OH), 8.58 (d, 1H, J = 7.6 Hz, naphthalene-H), 8.57 (D, 1H, J = 8.6 Hz, naphthalene-H), 8.55 (d, 1H, J = 8.1 Hz, naphthalene-H), 8.18 (s, 1H, benzotriazole-H), 8. 16 (d, 1H, J = 4.4 Hz, benzotriazol-H), 8.09 (d, 1H, J = 8.2 Hz, naphthalene-H), 7.93 (dd, 1H, naphthalene-H), 7 .75 (d, 1H, J = 2.4 Hz, benzotriazol-H), 7.56 (d, 1H, J = 9.2 Hz, benzene-H), 7.51 (d, 1H, J = .8 Hz, benzene-H), 7.12 (d, 1H, J = 8.7 Hz, benzene-H), 6.11 (s, 1H, C = CH2-H), 5.70 (s, 1H, C = CH2-H), 2.08 (s, 3H, CH3-H), 1.32 (s, 9H, C (CH3) 3-H)
(実施例5)
[中間体;6−アミノ−2−{2−[2−ヒドロキシ−5−(2−ヒドロキシエチル)フェニル]−2H−ベンゾトリアゾール−5−イル}−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンの合成]
(Example 5)
[Intermediate; 6-amino-2- {2- [2-hydroxy-5- (2-hydroxyethyl) phenyl] -2H-benzotriazol-5-yl} -1H-benzo [de] isoquinoline-1,3 Synthesis of (2H) -dione]
2−アミノ−4−tert−ブチルフェノールを2−アミノ−4−(2−ヒドロキシエチル)フェノールにした以外は実施例1と同様にして、6−アミノ−2−{2−[2−ヒドロキシ−5−(2−ヒドロキシエチル)フェニル]−2H−ベンゾトリアゾール−5−イル}−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを収率34%(2−アミノ−4−(2−ヒドロキシエチル)フェノールから)で得た。 6-amino-2- {2- [2-hydroxy-5] In the same manner as in Example 1 except that 2-amino-4-tert-butylphenol was changed to 2-amino-4- (2-hydroxyethyl) phenol. -(2-hydroxyethyl) phenyl] -2H-benzotriazol-5-yl} -1H-benzo [de] isoquinoline-1,3 (2H) -dione in a yield of 34% (2-amino-4- (2 -Hydroxyethyl) from phenol).
(実施例6)
[化合物(d);3−{5−[6−(2−エチルヘキサンアミド)−1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル] −2H−ベンゾトリアゾール−2−イル}−4−ヒドロキシフェネチル 2−エチルヘキサノエートの合成]
[Compound (d); 3- {5- [6- (2-ethylhexanamide) -1,3-dioxo-1H-benzo [de] isoquinolin-2 (3H) -yl] -2H-benzotriazole-2 -Il} -4-hydroxyphenethyl Synthesis of 2-ethylhexanoate]
200mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、6−アミノ−2−{2−[2−ヒドロキシ−5−(2−ヒドロキシエチル)フェニル]−2H−ベンゾトリアゾール−5−イル}−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを3.3g、トルエン20ml、2−エチルヘキサン酸110ml、メタンスルホン酸0.7gを仕込み、130℃で32時間還流脱水した。20℃に冷却し、析出している結晶をろ過し、トルエンで洗浄後に乾燥し、結晶を5.0g得た。この結晶をメチルエチルケトンで再結晶し、ついでイソプロピルアルコールで再結晶し、化合物(d)を0.7g得た。収率14%(6−アミノ−2−{2−[2−ヒドロキシ−5−(2−ヒドロキシエチル)フェニル]−2H−ベンゾトリアゾール−5−イル}−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンから)であった。融点は220℃であった。 A 200 ml four-necked flask was equipped with a ball condenser, a thermometer, and a stirring device, and 6-amino-2- {2- [2-hydroxy-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole-5. -Il} -1H-benzo [de] isoquinoline-1,3 (2H) -dione (3.3 g), toluene (20 ml), 2-ethylhexanoic acid (110 ml) and methanesulfonic acid (0.7 g) were charged and refluxed at 130 ° C. for 32 hours. Dehydrated. After cooling to 20 ° C., the precipitated crystals were filtered, washed with toluene and dried to obtain 5.0 g of crystals. The crystals were recrystallized from methyl ethyl ketone and then recrystallized from isopropyl alcohol to obtain 0.7 g of compound (d). Yield 14% (6-amino-2- {2- [2-hydroxy-5- (2-hydroxyethyl) phenyl] -2H-benzotriazol-5-yl} -1H-benzo [de] isoquinoline-1, 3 (2H) -dione). The melting point was 220 ° C.
また、HPLC分析により、化合物(d)の純度を測定した。
<測定条件>
装置:L−2130((株)日立ハイテクノロジーズ製)
使用カラム:SUMIPAX ODS A−212 6.0×150mm 5μm
カラム温度:40℃
移動相: メタノール/水=9/1
流速:1.0ml/min
検出:UV250nm
<測定結果>
HPLC純度:96.8%
Moreover, the purity of the compound (d) was measured by HPLC analysis.
<Measurement conditions>
Device: L-2130 (manufactured by Hitachi High-Technologies Corporation)
Column used: SUMPAX ODS A-212 6.0 × 150 mm 5 μm
Column temperature: 40 ° C
Mobile phase: methanol / water = 9/1
Flow rate: 1.0 ml / min
Detection: UV250nm
<Measurement results>
HPLC purity: 96.8%
また、化合物(d)のNMR測定を行った結果、上記構造を支持する結果が得られた。得られたNMRスペクトルの内容は以下のとおりである。
δ=10.46(s,1H,N−H),10.40(s,1H,phenol−OH),8.70(d,1H,J=8.8Hz,naphthalene−H),8.58(d,1H,J=7.3Hz,naphthalene−H),8.55(d,1H,J=8.2Hz,naphthalene−H),8.29(d,1H,J=8.2Hz,naphthalene−H),8.15(m,2H,benzotriazol−H),7.98(dd,1H,naphthalene−H),7.73(d,1H,J=2.1Hz,benzotriazol−H),7.55(d,1H,J=9.2Hz,benzene−H),7.35(d,1H,J=8.5Hz,benzene−H),7.11(d,1H,J=8.5Hz,benzene−H),4.29(m,2H,benzene−C−CH2−H),2.94(m,2H,benzene−CH2−H),2.72(m,1H,>CH−C−H),2.19(m,1H,>CH−C−H),1.36(m,8H,>C−CH2−H),0.98(t,8H,CH2−CH2−H),0.75(t,12H,CH3−H)
Further, as a result of conducting NMR measurement of the compound (d), a result supporting the above structure was obtained. The contents of the obtained NMR spectrum are as follows.
δ = 10.46 (s, 1H, NH), 10.40 (s, 1H, phenol-OH), 8.70 (d, 1H, J = 8.8 Hz, naphthalene-H), 8.58 (D, 1H, J = 7.3 Hz, naphthalene-H), 8.55 (d, 1H, J = 8.2 Hz, naphthalene-H), 8.29 (d, 1H, J = 8.2 Hz, naphthalene) -H), 8.15 (m, 2H, benzotriazole-H), 7.98 (dd, 1H, naphthalene-H), 7.73 (d, 1H, J = 2.1 Hz, benzotriazole-H), 7 .55 (d, 1H, J = 9.2 Hz, benzene-H), 7.35 (d, 1H, J = 8.5 Hz, benzene-H), 7.11 (d, 1H, J = 8.5 Hz) benzene-H), 4.29 (m, 2H, benzene-C-CH2-H), 2.94 (m, 2H, benzene-CH2-H), 2.72 (m, 1H,> CH-C- H), 2.19 (m, 1H,> CH-CH), 1.36 (m, 8H,> C-CH2-H), 0.98 (t, 8H, CH2-CH2-H), 0.75 (t, 12H, CH3-H)
(実施例7)
[化合物(e);4−ヒドロキシ−3−[5−(6−メタクリルアミド−1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル)−2H−ベンゾトリアゾール−2−イル]フェネチル メタクリレートの合成
[Compound (e); 4-hydroxy-3- [5- (6-methacrylamide-1,3-dioxo-1H-benzo [de] isoquinolin-2 (3H) -yl) -2H-benzotriazole-2- Of yl] phenethyl methacrylate
100mlの4つ口フラスコに玉付きコンデンサー、温度計、撹拌装置を取り付け、6−アミノ−2−{2−[2−ヒドロキシ−5−(2−ヒドロキシエチル)フェニル]−2H−ベンゾトリアゾール−5−イル}−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンを2.2g、N−メチルピロリドン10ml、メタクリロイルクロリド7.0g、炭酸カリウム0.8gを仕込み、55〜65℃で24時間撹拌した。20℃に冷却し、析出している結晶をろ過し、トルエンで洗浄後に乾燥し、結晶を1.1g得た。この結晶をトルエンで再結晶して化合物(e)を0.3g得た。収率11%(6−アミノ−2−{2−[2−ヒドロキシ−5−(2−ヒドロキシエチル)フェニル]−2H−ベンゾトリアゾール−5−イル}−1H−ベンゾ[de]イソキノリン−1,3(2H)−ジオンから)であった。融点は242℃であった。 A condenser with a ball, a thermometer, and a stirrer were attached to a 100 ml four-necked flask, and 6-amino-2- {2- [2-hydroxy-5- (2-hydroxyethyl) phenyl] -2H-benzotriazole-5. -Il} -1H-benzo [de] isoquinoline-1,3 (2H) -dione (2.2 g), N-methylpyrrolidone (10 ml), methacryloyl chloride (7.0 g), and potassium carbonate (0.8 g) were charged at 55 to 65 ° C. Stir for 24 hours. After cooling to 20 ° C., the precipitated crystals were filtered, washed with toluene and dried to obtain 1.1 g of crystals. This crystal was recrystallized from toluene to obtain 0.3 g of compound (e). Yield 11% (6-amino-2- {2- [2-hydroxy-5- (2-hydroxyethyl) phenyl] -2H-benzotriazol-5-yl} -1H-benzo [de] isoquinoline-1, 3 (2H) -dione). The melting point was 242 ° C.
また、HPLC分析により、化合物(e)の純度を測定した。
<測定条件>
装置:L−2130((株)日立ハイテクノロジーズ製)
使用カラム:SUMIPAX ODS A−212 6.0×150mm 5μm
カラム温度:40℃
移動相: アセトニトリル/水=6/4
流速:1.0ml/min
検出:UV250nm
<測定結果>
HPLC純度:96.0%
Further, the purity of the compound (e) was measured by HPLC analysis.
<Measurement conditions>
Device: L-2130 (manufactured by Hitachi High-Technologies Corporation)
Column used: SUMPAX ODS A-212 6.0 × 150 mm 5 μm
Column temperature: 40 ° C
Mobile phase: Acetonitrile / water = 6/4
Flow rate: 1.0 ml / min
Detection: UV250nm
<Measurement results>
HPLC purity: 96.0%
また、化合物(e)のNMR測定を行った結果、上記構造を支持する結果が得られた。得られたNMRスペクトルの内容は以下のとおりである。
δ=10.44(s,1H,N−H),10.42(s,1H,phenol−OH),8.58(d,1H,J=8.2Hz,naphthalene−H),8.57(d,1H,J=8.6Hz,naphthalene−H),8.56(d,1H,J=8.6Hz,naphthalene−H),8.17(s,1H,benzotriazol−H),8.16(d,1H,J=8.5Hz,benzotriazol−H),8.09(d,1H,J=8.1Hz,benzotriazol−H),7.93(dd,1H,naphthalene−H),7.75(s,1H,benzene−H),7.57(d,1H,J=9.2Hz,naphthalene−H),7.37(d,1H,J=8.3Hz,benzene−H),7.13(d,1H,J=8.5Hz,benzene−H),6.11(s,1H,C=CH2−H),6.02(s,1H,C=CH2−H),5.71(s,1H,C=CH2−H),5.67(s,1H,C=CH2−H),4.33(m,2H,benzene−C−CH2−H),2.98(m,2H,benzene−CH2−H),2.08(s,3H,CH3−H),1.87(s,3H,CH3−H)
In addition, as a result of NMR measurement of the compound (e), a result supporting the above structure was obtained. The contents of the obtained NMR spectrum are as follows.
δ = 10.44 (s, 1H, NH), 10.42 (s, 1H, phenol-OH), 8.58 (d, 1H, J = 8.2 Hz, naphthalene-H), 8.57. (D, 1H, J = 8.6 Hz, naphthalene-H), 8.56 (d, 1H, J = 8.6 Hz, naphthalene-H), 8.17 (s, 1H, benzotriazole-H), 8. 16 (d, 1H, J = 8.5 Hz, benzotriazole-H), 8.09 (d, 1H, J = 8.1 Hz, benzotriazole-H), 7.93 (dd, 1H, naphthalene-H), 7 .75 (s, 1H, benzene-H), 7.57 (d, 1H, J = 9.2 Hz, naphthalenes-H), 7.37 (d, 1H, J = 8.3 Hz, be zene-H), 7.13 (d, 1H, J = 8.5 Hz, benzene-H), 6.11 (s, 1H, C = CH2-H), 6.02 (s, 1H, C = CH2) -H), 5.71 (s, 1H, C = CH2-H), 5.67 (s, 1H, C = CH2-H), 4.33 (m, 2H, benzene-C-CH2-H). 2.98 (m, 2H, benzene-CH2-H), 2.08 (s, 3H, CH3-H), 1.87 (s, 3H, CH3-H)
(実施例8)
[重合体(a);N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}メタクリルアミドを有する重合体]
(Example 8)
[Polymer (a); N- {2- [2- (5-tert-butyl-2-hydroxyphenyl) -2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro- Polymer with 1H-benzo [de] isoquinolin-6-yl} methacrylamide]
ジムロート冷却器、水銀温度計、撹拌装置を取り付けた50mlフラスコに、実施例4で得られた化合物(c);N−{2−[2−(5−tert−ブチル−2−ヒドロキシフェニル)−2H−ベンゾトリアゾール−5−イル]−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル}メタクリルアミドを0.5g、トリプロピレングリコールジアクリレート[新中村化学工業株式会社製「APG−200」]を4.5g、ウレタンアクリレート[新中村化学工業株式会社製「UA−160TM」]を4.0g、エトキシ化ペンタエリスリトールテトラアクリレート[新中村化学工業株式会社製「ATM−4E」]を1.0g、および、光重合開始剤として[1−ヒドロキシ−シクロヘキシル−フェニル−ケトン(チバスペシャリティケミカルズ株式会社製「イルガキュア184」]を0.3g仕込み、40℃〜50℃で1時間撹拌行い、光硬化性樹脂組成物10.3gを得た。得られた光硬化性樹脂組成物を、バーコーターNo.4を用いてポリエステルフィルム(パナック社製「ルミラー125T60」、厚み=125μm)に塗布し、空気雰囲気下で、高圧水銀ランプ(ウシオ電機株式会社製「UVL−7000N」)を使用して、光量500mJ/cm2で紫外線を照射し、光重合させて膜厚15〜20μmの重合体膜を有するポリエステルフィルムを作製。重合体膜をポリエステルフィルムからキャストし、重合体(a)をフィルム状態で得た。 The compound (c) obtained in Example 4; N- {2- [2- (5-tert-butyl-2-hydroxyphenyl)-in a 50 ml flask equipped with a Dimroth condenser, a mercury thermometer, and a stirring device. 0.5 g of 2H-benzotriazol-5-yl] -1,3-dioxo-2,3-dihydro-1H-benzo [de] isoquinolin-6-yl} methacrylamide, tripropylene glycol diacrylate [Shin Nakamura Chemical "APG-200" manufactured by Kogyo Co., Ltd., 4.0 g of urethane acrylate ["UA-160TM" manufactured by Shin-Nakamura Chemical Co., Ltd.], ethoxylated pentaerythritol tetraacrylate [manufactured by Shin-Nakamura Chemical Co., Ltd. 1.0 g of “ATM-4E” and [1-hydroxy-cyclohexyl-phenyl-ketone as a photopolymerization initiator 0.3 g of “Irgacure 184” manufactured by Ciba Specialty Chemicals Co., Ltd.] was charged and stirred at 40 ° C. to 50 ° C. for 1 hour to obtain 10.3 g of a photocurable resin composition. Is applied to a polyester film (“Lumirror 125T60” manufactured by Panac Co., Ltd., thickness = 125 μm) using a bar coater No. 4, and a high-pressure mercury lamp (“UVL-7000N” manufactured by USHIO INC.) Is applied in an air atmosphere. Use to produce a polyester film having a polymer film having a film thickness of 15 to 20 μm by irradiating with ultraviolet rays at a light quantity of 500 mJ / cm 2 and photopolymerizing the polymer film from the polyester film to obtain the polymer (a). Obtained in film form.
(比較例1)
従来の一般的な青色発光材料であり、ナフタルイミド誘導体である化合物(f);N−[2−(4−tert−ブチルフェニル)−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル]アセトアミドを実施例1〜2と同様の方法で合成した。 Compound (f) which is a conventional general blue light-emitting material and is a naphthalimide derivative; N- [2- (4-tert-butylphenyl) -1,3-dioxo-2,3-dihydro-1H-benzo [De] isoquinolin-6-yl] acetamide was synthesized in the same manner as in Examples 1-2.
[溶液の吸収及び発光特性]
上記の実施例及び比較例により得られた化合物(a)〜(f)のメタノール溶液での吸収及び発光特性を表1に示す。
[Solution absorption and emission characteristics]
Table 1 shows the absorption and emission characteristics of the compounds (a) to (f) obtained in the above Examples and Comparative Examples in methanol solutions.
[波長変換フィルムの作製]
上記の実施例及び比較例で得られた化合物(a)、(b)、(d)、(f)それぞれと、ポリメタクリル酸メチル及び溶媒を、表2で示す比率で混合し、波長変換材料を有した樹脂組成物を得た。得られた波長変換材料を有した樹脂組成物を、バーコーターNo.4を用いてガラス板(セントラル社製「フロートガラス板」、厚み=2mm)に塗布し、加熱乾燥90℃を2分、120℃を3分の順で行った後、減圧乾燥40℃を24時間実施して溶媒を除去。膜厚3〜4μmの波長変換材料を有するフィルムを得た。
[Production of wavelength conversion film]
Each of the compounds (a), (b), (d), (f) obtained in the above Examples and Comparative Examples, polymethyl methacrylate and a solvent are mixed at a ratio shown in Table 2 to obtain a wavelength conversion material. A resin composition having was obtained. The resin composition having the obtained wavelength conversion material was used as a bar coater No. 4 was applied to a glass plate (“float glass plate” manufactured by Central Co., Ltd., thickness = 2 mm), heat-dried 90 ° C. for 2 minutes, and 120 ° C. for 3 minutes in this order, and then vacuum-dried at 40 ° C. for 24 minutes. Run for hours to remove solvent. A film having a wavelength conversion material having a thickness of 3 to 4 μm was obtained.
[フィルムの吸収及び発光特性]
上記で得られた化合物(a)、(b)、(d)、(f)のフィルムでの吸収及び発光特性を表3に示す。また、実施例8で得られた重合体(a)の吸収及び発光特性も同様に表3に示す。
[Absorption and emission characteristics of film]
Table 3 shows the absorption and emission characteristics of the compounds (a), (b), (d), and (f) obtained above. The absorption and emission characteristics of the polymer (a) obtained in Example 8 are also shown in Table 3.
[耐光性]
上記の実施例により得られた化合物(a)、(b)、(d)、(f)のフィルムの、紫外線照射による耐光性を表4に示す。
[Light resistance]
Table 4 shows the light resistance of the films of the compounds (a), (b), (d), and (f) obtained by the above-described examples by ultraviolet irradiation.
表1及び3より、従来の一般的な青色発光材料である化合物(f)は、10000以上のモル吸光係数を示し、溶液で80%以上、フィルムで50%以上の蛍光量子効率を示すことから、優れた波長変換性をもつと言えるが、表4より、紫外線照射で吸光度及び蛍光量子効率が大きく低下したことから、耐光性が不十分で長期使用が困難な問題があることがわかる。本発明品は、従来品の2倍程度である約30000のモル吸光係数を示し、溶液で40%程度、フィルムで20%程度の蛍光量子効率を示すことから、優れた波長変換性をもつと言え、さらに紫外線照射による吸光度及び蛍光量子効率の低下が少ないことから、優れた耐光性をもち、長期使用が可能であることから、有用な波長変換材料であることがわかる。なお、実施例及び比較例により得られた化合物の吸収スペクトル、発光スペクトル、励起スペクトル、蛍光量子効率、及び耐光性の測定条件は次の通りである。 From Tables 1 and 3, the compound (f), which is a conventional general blue light-emitting material, exhibits a molar extinction coefficient of 10,000 or more, and exhibits a fluorescence quantum efficiency of 80% or more in solution and 50% or more in film. Although it can be said that it has an excellent wavelength conversion property, it can be seen from Table 4 that the absorbance and the fluorescence quantum efficiency are greatly reduced by ultraviolet irradiation, and thus there is a problem that light resistance is insufficient and long-term use is difficult. The product of the present invention exhibits a molar extinction coefficient of about 30,000, which is about twice that of the conventional product, and exhibits a fluorescence quantum efficiency of about 40% for the solution and about 20% for the film. In other words, since the decrease in absorbance and fluorescence quantum efficiency due to ultraviolet irradiation is small, it has excellent light resistance and can be used for a long period of time. In addition, the measurement conditions of the absorption spectrum of the compound obtained by the Example and the comparative example, the emission spectrum, the excitation spectrum, the fluorescence quantum efficiency, and light resistance are as follows.
<溶液の吸収スペクトル測定条件>
装置:UV−2450((株)島津製作所製)
測定波長:250〜 500nm
溶媒:メタノール
濃度:10ppm
セル:1cm石英
<Measurement conditions of absorption spectrum of solution>
Apparatus: UV-2450 (manufactured by Shimadzu Corporation)
Measurement wavelength: 250-500 nm
Solvent: Methanol Concentration: 10ppm
Cell: 1cm quartz
<フィルムの吸収スペクトル測定条件>
装置: U−3900H((株)日立ハイテクサイエンス製)
測定波長:310〜510nm
<Conditions for measuring absorption spectrum of film>
Apparatus: U-3900H (manufactured by Hitachi High-Tech Science Co., Ltd.)
Measurement wavelength: 310-510 nm
<溶液の発光スペクトル、励起スペクトル及び蛍光量子効率測定条件>
装置:FP−8500(日本分光(株)製)及び
測定波長:200〜 850nm
溶媒:メタノール
濃度:10ppm
セル:1cm石英
<Measurement conditions of emission spectrum, excitation spectrum and fluorescence quantum efficiency of solution>
Apparatus: FP-8500 (manufactured by JASCO Corporation) and measurement wavelength: 200 to 850 nm
Solvent: Methanol Concentration: 10ppm
Cell: 1cm quartz
<フィルムの発光スペクトル、励起スペクトル及び蛍光量子効率測定条件>
装置:FP−8500(日本分光(株)製)
測定波長:200〜 850nm
<Film emission spectrum, excitation spectrum and fluorescence quantum efficiency measurement conditions>
Apparatus: FP-8500 (manufactured by JASCO Corporation)
Measurement wavelength: 200 to 850 nm
<耐光性測定条件>
装置:スーパーキセノンウェザーメーター SX−75(スガ試験機(株))
照射照度:60W/m2
照射時間:24時間
ブラックパネル温度:63℃
槽内湿度:50%
<Light resistance measurement conditions>
Equipment: Super Xenon Weather Meter SX-75 (Suga Test Instruments Co., Ltd.)
Irradiance: 60W / m2
Irradiation time: 24 hours Black panel temperature: 63 ° C
Humidity in the tank: 50%
本発明のベンゾトリアゾール誘導体化合物、及びそれらを有する重合体は、モル吸光係数及び蛍光量子効率が大きく、優れた波長変換性を示す。また、紫外線の照射による劣化が少なく、優れた耐光性を示すことから、長期使用が可能であり、波長変換材料、波長変換フィルム及び太陽電池として、好適に利用できる。 The benzotriazole derivative compound of the present invention and the polymer having them have a large molar extinction coefficient and fluorescence quantum efficiency, and exhibit excellent wavelength conversion properties. In addition, since it is less deteriorated by irradiation with ultraviolet rays and exhibits excellent light resistance, it can be used for a long time and can be suitably used as a wavelength conversion material, a wavelength conversion film, and a solar cell.
Claims (9)
[式中R1はホルミル基、炭素数2〜18のアルキルカルボニル基、置換されていてもよいベンゾイル基、アクリロイル基またはメタクリロイル基を表し、R2及びR3はそれぞれ独立して、水素原子、ハロゲン原子、炭素数1〜18のアルキル基、炭素数1〜18のアルコキシ基、ヒドロキシル基、アミノ基、炭素数1〜4の直鎖または分鎖のモノ置換アミノ基、炭素数1〜4の直鎖または分鎖のジ置換アミノ基、ニトロ基、カルボキシル基、アルキル基の炭素数が1〜8のアルキルオキシカルボニル基、炭素数1〜8のヒドロキシアルキル基、アルキル基の炭素数の合計が2〜9のアルキルカルボニルオキシアルキル基、アルキル基の炭素数が1〜3のカルボキシアルキル基、アルキル基の炭素数の合計が2〜10のアルキルオキシカルボニルアルキル基、アリール基、アシル基、スルホ基、シアノ基、アルキル基の炭素数が1〜2のアクリロイルオキシアルキル基またはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基を表す。] A benzotriazole derivative compound represented by the following general formula (1):
[Wherein R 1 represents a formyl group, an alkylcarbonyl group having 2 to 18 carbon atoms, an optionally substituted benzoyl group, an acryloyl group or a methacryloyl group, and R 2 and R 3 each independently represent a hydrogen atom, A halogen atom, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyl group, an amino group, a linear or branched mono-substituted amino group having 1 to 4 carbon atoms, and an alkyl group having 1 to 4 carbon atoms The total of carbon number of linear or branched di-substituted amino group, nitro group, carboxyl group, alkyloxycarbonyl group having 1 to 8 carbon atoms, hydroxyalkyl group having 1 to 8 carbon atoms, alkyl group. An alkylcarbonyloxyalkyl group having 2 to 9 carbon atoms, a carboxyalkyl group having 1 to 3 carbon atoms in the alkyl group, and an alkyloxyalkyl having 2 to 10 carbon atoms in total. Boniruarukiru group, an aryl group, an acyl group, a sulfo group, a cyano group, methacryloyloxy alkyl group having a carbon number of 1-2 acryloyloxy alkyl group or an alkyl group having carbon atoms in the alkyl group 1-2. ]
かつ、R1がアクリロイル基もしくはメタクリロイル基であるか、および/またはR2がアルキル基の炭素数が1〜2のアクリロイルオキシアルキル基もしくはアルキル基の炭素数が1〜2のメタクリロイルオキシアルキル基である請求項1記載のベンゾトリアゾール誘導体化合物。 R 1 in the general formula (1) is a formyl group, an alkylcarbonyl group having 2 to 8 carbon atoms, a benzoyl group, an acryloyl group or a methacryloyl group, and R 2 is a carbon atom having 1 to 4 carbon atoms or an alkyl group. An alkylcarbonyloxyalkyl group having a total number of 2 to 9, an acryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group, or a methacryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group, and R 3 is hydrogen Is an atom,
R 1 is an acryloyl group or a methacryloyl group, and / or R 2 is an acryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group or a methacryloyloxyalkyl group having 1 to 2 carbon atoms in the alkyl group. The benzotriazole derivative compound according to claim 1.
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