JPH04358132A - Nonlinear optical material - Google Patents
Nonlinear optical materialInfo
- Publication number
- JPH04358132A JPH04358132A JP13409491A JP13409491A JPH04358132A JP H04358132 A JPH04358132 A JP H04358132A JP 13409491 A JP13409491 A JP 13409491A JP 13409491 A JP13409491 A JP 13409491A JP H04358132 A JPH04358132 A JP H04358132A
- Authority
- JP
- Japan
- Prior art keywords
- tetralone
- nonlinear optical
- optical material
- compd
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 37
- 239000000463 material Substances 0.000 title claims abstract description 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- ASJHGJPQBYOWGU-UHFFFAOYSA-N 2-[(2,5-dimethoxyphenyl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1-one Chemical compound C1CC2=CC(OC)=CC=C2C(=O)C1=CC1=CC(OC)=CC=C1OC ASJHGJPQBYOWGU-UHFFFAOYSA-N 0.000 claims abstract description 5
- IAOURKOEPHIQSG-UHFFFAOYSA-N 2-[(2,4-dimethoxyphenyl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1-one Chemical compound C1CC2=CC(OC)=CC=C2C(=O)C1=CC1=CC=C(OC)C=C1OC IAOURKOEPHIQSG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 13
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- DYGMQSSRLXYBCP-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methylidene]-3,4-dihydronaphthalen-1-one Chemical compound C1=CC(OCC)=CC=C1C=C1C(=O)C2=CC=CC=C2CC1 DYGMQSSRLXYBCP-UHFFFAOYSA-N 0.000 abstract description 4
- GLUPCBJANWQOAQ-UHFFFAOYSA-N 2-[(4-methylsulfanylphenyl)methylidene]-3,4-dihydronaphthalen-1-one Chemical compound C1=CC(SC)=CC=C1C=C1C(=O)C2=CC=CC=C2CC1 GLUPCBJANWQOAQ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 abstract 1
- -1 benzaltetralone compound Chemical class 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
- OFAAPWXDZVKVFC-UHFFFAOYSA-N 2-[(3-fluorophenyl)methylidene]-3,4-dihydronaphthalen-1-one Chemical compound FC1=CC=CC(C=C2C(C3=CC=CC=C3CC2)=O)=C1 OFAAPWXDZVKVFC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MWRVIWQRUAVGJE-UHFFFAOYSA-N 2-[(4-bromophenyl)methylidene]-3,4-dihydronaphthalen-1-one Chemical compound C1=CC(Br)=CC=C1C=C1C(=O)C2=CC=CC=C2CC1 MWRVIWQRUAVGJE-UHFFFAOYSA-N 0.000 description 1
- OWFGMURBYHPNJK-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylidene]-3,4-dihydronaphthalen-1-one Chemical compound C1=CC(Cl)=CC=C1C=C1C(=O)C2=CC=CC=C2CC1 OWFGMURBYHPNJK-UHFFFAOYSA-N 0.000 description 1
- WHUMXSJINGHNDG-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1-one Chemical compound C1CC2=CC(OC)=CC=C2C(=O)C1=CC1=CC=C(Cl)C=C1 WHUMXSJINGHNDG-UHFFFAOYSA-N 0.000 description 1
- XZFPEYQKSLVXMN-UHFFFAOYSA-N 6-methoxy-2-[(4-methylphenyl)methylidene]-3,4-dihydronaphthalen-1-one Chemical compound C1CC2=CC(OC)=CC=C2C(=O)C1=CC1=CC=C(C)C=C1 XZFPEYQKSLVXMN-UHFFFAOYSA-N 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910017677 NH4H2 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004904 UV filter Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は光パラメトリック発振、
高調波発生、光スイッチング等の光信号処理システムに
おいて重要な新規な非線形光学材料に関するものである
。[Industrial Application Field] The present invention relates to optical parametric oscillation,
This paper relates to novel nonlinear optical materials that are important in optical signal processing systems such as harmonic generation and optical switching.
【０００２】0002
【従来の技術】光通信技術の重要な役割を占めると見ら
れる非線形光学材料は材料の非線形光応答性に基づき光
混合、パラメトリック発振、光高調波発生等の機能を発
揮するものであって、従来、ＫＨ２ＰＯ４、ＮＨ４Ｈ２
ＰＯ４等の無機結晶が用いられてきた。しかし、これら
の材料は潮解性、低い非線形感受率及び低い被破壊閾値
のために前述の用途の要求を満たすに至っていない。ま
た光スイッチングに利用出来る１次、２次の電気光学効
果は各々２次および３次の非線形光学効果と本質的に同
じ非線形分極から生じるものであるから同じ材料が使え
る可能性があるが、高周波数領域で無機材料はチャーピ
ングを生じる問題がある。π電子系の分極を利用した有
機非線形光学材料はその非線形光学定数が無機材料より
も大きいことや一般に潮解性もなく破壊閾値が高い等優
れているために各方面で幅広く研究、開発が進められて
いる。最近の成果について、例えば「ノンリニア・オプ
ティカル・プロパティズ・オブ・オーガニック・モレキ
ュールズ・アンド・クリスタルズ（Ｎｏｎｌｉｎｅａｒ
Ｏｐｔｉｃａｌ Ｐｒｏｐｅｒｔｉｅｓ ｏｆ
Ｏｒｇａｎｉｃ Ｍｏｌｅｃｕｌｅｓ ａｎｄ
Ｃｒｙｓｔａｌｓ）」Ｖｏｌ．１及びＶｏｌ．２、
Ｄ．Ｓ．Ｃｈｅｍｌａ、Ｊ．Ｚｙｓｓ編（１９８７年
Ａｃａｄｅｍｉｃ Ｐｒｅｓｓ社発行）に詳しく述
べられている。[Prior Art] Nonlinear optical materials, which are expected to play an important role in optical communication technology, exhibit functions such as optical mixing, parametric oscillation, and optical harmonic generation based on the nonlinear optical responsiveness of the material. Conventionally, KH2PO4, NH4H2
Inorganic crystals such as PO4 have been used. However, these materials do not meet the requirements of the aforementioned applications due to their deliquescent nature, low nonlinear susceptibility and low failure threshold. In addition, since the first-order and second-order electro-optic effects that can be used for optical switching arise from essentially the same nonlinear polarization as the second-order and third-order nonlinear optical effects, the same materials may be used, but it is possible to Inorganic materials have the problem of chirping in the frequency domain. Organic nonlinear optical materials that utilize the polarization of the π-electron system have been widely researched and developed in various fields because of their superior nonlinear optical constants, which are larger than those of inorganic materials, and which are generally non-deliquescent and have a high destruction threshold. ing. Regarding recent achievements, for example, "Nonlinear Optical Properties of Organic Molecules and Crystals"
Optical Properties of
Organic molecules and
Crystals)” Vol. 1 and Vol. 2,
D. S. Chemla, J. Zyss edition (1987)
(Published by Academic Press).
【０００３】しかしながら、半導体レーザのように出力
の小さなレーザで十分目的を達成しうる程度に大きな非
線形光学定数を持つ材料は見出されておらず、更に新規
な材料の開発が強く求められている。However, no material has been found that has a nonlinear optical constant large enough to achieve the purpose with a low-output laser like a semiconductor laser, and there is a strong need for the development of new materials. .
【０００４】0004
【発明が解決しようとする課題】本発明は大きい非線形
光学定数をもつ新規な有機非線形光学材料を提供するも
のである。SUMMARY OF THE INVENTION The present invention provides a novel organic nonlinear optical material having a large nonlinear optical constant.
【０００５】[0005]
【課題を解決するための手段】本発明は一般式（Ｉ）[Means for Solving the Problems] The present invention provides general formula (I)
【
化２】
（式中Ｚは炭素数１〜１０のアルキル基、炭素数１〜１
０のアルコキシ基、アリール基、ハロゲン原子またはア
ルキルチオ基であり、Ｙは水素原子または炭素数１〜５
のアルコキシ基であり、ｎは１〜５の整数であり、ｍは
１〜４の整数である）で示される化合物からなる非線形
光学材料およびこの化合物を含有する組成物からなる非
線形光学材料に関する。[
[Formula Z is an alkyl group having 1 to 10 carbon atoms, 1 to 1 carbon atoms]
0 alkoxy group, aryl group, halogen atom or alkylthio group, and Y is a hydrogen atom or a carbon number of 1 to 5
is an alkoxy group, n is an integer of 1 to 5, and m is an integer of 1 to 4) and a composition containing this compound.
【０００６】本発明においては上記の一般式（Ｉ）で示
されるベンザルテトラロン化合物が用いられるが、この
ベンザルテトラロン化合物は例えばオーガニックリアク
ション（Ｏｒｇａｎｉｃ Ｒｅａｃｔｉｏｎ）第１６
巻に詳しく述べられている方法により、α−テトラロン
と適当な置換基を有するベンズアルデヒドとのアルドー
ル型縮合により容易に合成出来る。[0006] In the present invention, a benzaltetralone compound represented by the above general formula (I) is used, and this benzaltetralone compound is, for example, organic reaction No. 16
It can be easily synthesized by aldol-type condensation of α-tetralone and benzaldehyde having an appropriate substituent according to the method described in detail in vol.
【０００７】上記の一般式（Ｉ）で示される化合物とし
ては例えば２−（２′，４′−ジメトキシベンザル）−
６−メトキシ−１−テトラロン、２−（２′，５′−ジ
メトキシベンザル）−６−メトキシ−１−テトラロン、
２−（４′−エトキシベンザル）−１−テトラロン、２
−（３′−フルオロベンザル）−１−テトラロン、２−
（４′−メチルチオベンザル）−１−テトラロン、２−
（４′−フェニルベンザル）−６−メトキシ−１−テト
ラロン、２−（４′−ブロモベンザル）−６−メトキシ
−１−テトラロン、２−（４′−クロロベンザル）−６
−メトキシ−１−テトラロン、２−（２′，４′−ジク
ロロベンザル）−６−メトキシ−１−テトラロン、２−
（４′−ブトキシベンザル）−１−テトラロン、２−（
４′−ブロモベンザル）−１−テトラロン、２−（４′
−クロロベンザル）−１−テトラロン、２−（２′，３
′，４′−トリメトキシベンザル）−１−テトラロン、
２−（４′−エトキシベンザル）−６−メトキシ−１−
テトラロン、２−（４′−メチルベンザル）−６−メト
キシ−１−テトラロン等がある。この中で好ましい化合
物としては、２−（２′，４′−ジメトキシベンザル）
−６−メトキシ−１−テトラロン、２−（２′，５′−
ジメトキシベンザル）−６−メトキシ−１−テトラロン
、２−（４′−エトキシベンザル）−１−テトラロン、
２−（４′−メチルチオベンザル）−１−テトラロンが
挙げられる。Examples of the compound represented by the above general formula (I) include 2-(2',4'-dimethoxybenzal)-
6-methoxy-1-tetralone, 2-(2',5'-dimethoxybenzal)-6-methoxy-1-tetralone,
2-(4'-ethoxybenzal)-1-tetralone, 2
-(3'-fluorobenzal)-1-tetralone, 2-
(4'-methylthiobenzal)-1-tetralone, 2-
(4'-phenylbenzal)-6-methoxy-1-tetralone, 2-(4'-bromobenzal)-6-methoxy-1-tetralone, 2-(4'-chlorobenzal)-6
-methoxy-1-tetralone, 2-(2',4'-dichlorobenzal)-6-methoxy-1-tetralone, 2-
(4'-butoxybenzal)-1-tetralone, 2-(
4'-bromobenzal)-1-tetralone, 2-(4'
-chlorobenzal)-1-tetralone, 2-(2',3
',4'-trimethoxybenzal)-1-tetralone,
2-(4'-ethoxybenzal)-6-methoxy-1-
Examples include tetralone, 2-(4'-methylbenzal)-6-methoxy-1-tetralone, and the like. Among these, a preferred compound is 2-(2',4'-dimethoxybenzal)
-6-methoxy-1-tetralone, 2-(2',5'-
dimethoxybenzal)-6-methoxy-1-tetralone, 2-(4'-ethoxybenzal)-1-tetralone,
2-(4'-methylthiobenzal)-1-tetralone is mentioned.
【０００８】また本発明になる非線形光学材料は上記の
一般式（Ｉ）で示される化合物を高分子化合物中に分散
あるいは溶解させた組成物であっても良い。高分子化合
物としては例えばメチル（メタ）アクリレート（メタア
クリレートまたはアクリレートを示す。以下同じ）、エ
チル（メタ）アクリレート、ｎ−ブチル（メタ）アクリ
レート、シクロヘキシル（メタ）アクリレート、（メタ
）アクリル酸、スチレン、ビニルトルエン、ジビニルベ
ンゼン、塩化ビニル、β−ヒドロキシエチル（メタ）ア
クリレート等の単量体のホモポリマまたはコポリマ、ポ
リエステル、ポリアミド、ポリウレタン、ポリカーボネ
ート、セルロースエステル、ポリエーテルなどが用いら
れる。一般式（Ｉ）で示される化合物と相当する単量体
を混合した後に熱又は光の作用によって重合せしめて組
成物としても良く、上記の高分子化合物と一般式（Ｉ）
で示される化合物とを適当な溶媒を用いて溶解混合させ
た後に溶媒を除去することによって組成物を得ても良い
。前者の場合には重合の最中にポーリングを行うことに
より、あるいは前者、後者ともに組成物を得た後にポー
リングを行うことにより非線形光学性能を向上させるこ
とも出来る。あるいは直流電場の存在下に上記の一般式
（Ｉ）で示される化合物を融点以上の温度に加熱し溶融
させた後に電場を保持しながら徐冷あるいは急冷するこ
とにより分子の配向方向が制御された非線形光学性能の
高い単結晶あるいは分子ガラスを得ることも出来る。The nonlinear optical material of the present invention may also be a composition in which the compound represented by the above general formula (I) is dispersed or dissolved in a polymer compound. Examples of polymer compounds include methyl (meth)acrylate (representing methacrylate or acrylate; the same applies hereinafter), ethyl (meth)acrylate, n-butyl (meth)acrylate, cyclohexyl (meth)acrylate, (meth)acrylic acid, and styrene. Homopolymers or copolymers of monomers such as , vinyltoluene, divinylbenzene, vinyl chloride, β-hydroxyethyl (meth)acrylate, polyesters, polyamides, polyurethanes, polycarbonates, cellulose esters, polyethers, etc. are used. A composition may be prepared by mixing the compound represented by general formula (I) and a corresponding monomer and then polymerizing the mixture by the action of heat or light.
A composition may be obtained by dissolving and mixing the compound represented by using an appropriate solvent and then removing the solvent. In the former case, the nonlinear optical performance can be improved by performing poling during polymerization, or in both the former and latter cases, by performing poling after obtaining the composition. Alternatively, the orientation direction of the molecules can be controlled by heating the compound represented by the general formula (I) above to a temperature above the melting point in the presence of a DC electric field to melt it, and then slowly or rapidly cooling it while maintaining the electric field. It is also possible to obtain single crystal or molecular glasses with high nonlinear optical performance.
【０００９】（作用）本発明の化合物においてはアクセ
プタ基としてカルボニル基をその構造中に有し、これら
がスチリルπ電子系と共役しているため、励起状態での
電荷移動により大きな双極子モーメントが生じ高い超分
極率を持ちこれによって高い非線形光学効果が得られる
。(Function) The compound of the present invention has a carbonyl group as an acceptor group in its structure, and since these are conjugated with the styryl π-electron system, a large dipole moment is generated due to charge transfer in the excited state. It has a high hyperpolarizability, which results in a high nonlinear optical effect.
【００１０】0010
【実施例】本発明をさらに実施例を用いて説明する。２
−（２′，４′−ジメトキシベンザル）−６−メトキシ
−１−テトラロン（化合物１）の合成２，４ジメトキシ
ベンズアルデヒド５．６６ｇ（３４．１ｍｍｏｌ）、α
−テトラロン６ｇ（３４．１ｍｍｏｌ）、メタノール２
０ｍｌおよび３５％ＮａＯＨ水溶液０．５ｍｌを１００
ｍｌのナス型フラスコに入れ、さらに沸石を一片加え冷
却用コンデンサをつけて約１時間加熱還流した。放置し
、析出した結晶を吸引濾別して集め、冷メタノールで洗
った後乾燥した。収量は５．１ｇ（１５．７ｍｍｏｌ、
４６．０％）であった。生成物の構造はｎｍｒ、ｉｒで
確認した。２−（３′−フルオロベンザル）−１−テト
ラロン（化合物２）、２−（２′，５′−ジメトキシベ
ンザル）−６−メトキシ−１−テトラロン（化合物３）
、２−（４′−エトキシベンザル）−１−テトラロン（
化合物４）、２−（４′−メチルチオベンザル）−１−
テトラロン（化合物５）、２−（２′４′−フェニルベ
ンザル）−６−メトキシ−１−テトラロン（化合物６）
も同様の方法で合成した。EXAMPLES The present invention will be further explained using examples. 2
Synthesis of -(2',4'-dimethoxybenzal)-6-methoxy-1-tetralone (compound 1) 2,4 dimethoxybenzaldehyde 5.66 g (34.1 mmol), α
-tetralone 6g (34.1mmol), methanol 2
0ml and 0.5ml of 35% NaOH aqueous solution to 100ml
The mixture was placed in a ml eggplant-shaped flask, a piece of zeolite was added, a cooling condenser was attached, and the mixture was heated under reflux for about 1 hour. After standing, the precipitated crystals were collected by suction filtration, washed with cold methanol, and then dried. The yield was 5.1g (15.7mmol,
46.0%). The structure of the product was confirmed by nmr and ir. 2-(3'-fluorobenzal)-1-tetralone (compound 2), 2-(2',5'-dimethoxybenzal)-6-methoxy-1-tetralone (compound 3)
, 2-(4'-ethoxybenzal)-1-tetralone (
Compound 4), 2-(4'-methylthiobenzal)-1-
Tetralone (Compound 5), 2-(2'4'-phenylbenzal)-6-methoxy-1-tetralone (Compound 6)
was also synthesized in a similar manner.
【００１１】比較例、実施例１〜２
化合物１および２の塩化メチレン溶液の吸収極大波長（
λｍａｘ）、融点（ｍ．ｐ．）と粉末法によって求めた
第２高調波発生効率（ＳＨＧ効率、尿素を１とした時の
第２高調波の強度比）の結果を表１に示す。粉末法の概
略は「ジャーナル・オブ・アブライド・フイジックス」
（Ｊｏｕｒｎａｌ ｏｆ ＡｐｐｌｉｅｄＰｈｙｓ
ｉｃｓ）Ｖｏｌ．３６（１９６８年）３７９８〜３８１
３頁に詳しく述べられている。粒径１００μｍ〜１２５
μｍに分級した試料粉末を無蛍光スライドガラス（マツ
ナミ硝子製）にはさみ、スペクトロレーザーシステム社
製パルスＮｄ：ＹＡＧレーザ（ＳＬ３０３型、最大出力
８５０ｍＪ、半値幅１５ｎｓ、パルス当たりの出力５０
ＭＷ、ビーム径９．５ｍｍ、波長１．０６４μｍ、繰返
し周波数１０Ｈｚ）により光照射した。発生した５３２
ｎｍの第２高調波の強度を赤外フィルタ、ＵＶフィルタ
を通して光電子増倍管により測定した。Comparative Examples, Examples 1 to 2 Maximum absorption wavelength of methylene chloride solutions of Compounds 1 and 2 (
Table 1 shows the results of the second harmonic generation efficiency (SHG efficiency, intensity ratio of the second harmonic when urea is set to 1) determined by the powder method. An overview of the powder method can be found in "Journal of Abrid Physics"
(Journal of Applied Phys.
ics) Vol. 36 (1968) 3798-381
It is detailed on page 3. Particle size 100μm~125
The sample powder classified into μm was sandwiched between non-fluorescent glass slides (manufactured by Matsunami Glass), and a pulsed Nd:YAG laser (Model SL303, maximum output 850 mJ, half-width 15 ns, output per pulse 50
Light irradiation was performed using MW, beam diameter of 9.5 mm, wavelength of 1.064 μm, and repetition frequency of 10 Hz). 532 occurred
The intensity of the second harmonic in nm was measured using a photomultiplier tube through an infrared filter and a UV filter.
【００１２】0012
【表１】[Table 1]
【００１３】実施例３〜６
上記の化合物３〜６について吸収極大波長と第２高調波
発生の有無を実施例１〜２と同じパルスＮｄ：ＹＡＧレ
ーザを用いて５３２ｎｍの緑色の光が発生するかどうか
を肉眼で判定した結果を表２に示す。Examples 3 to 6 For the above compounds 3 to 6, green light of 532 nm is generated using the same pulsed Nd:YAG laser as in Examples 1 to 2, with the maximum absorption wavelength and the presence or absence of second harmonic generation. Table 2 shows the results of visual judgment.
【００１４】[0014]
【表２】[Table 2]
【００１５】[0015]
【発明の効果】本発明により高い光学的非線形性を有す
る非線形光学材料を得ることができる。According to the present invention, a nonlinear optical material having high optical nonlinearity can be obtained.
Claims (10)
る非線形光学材料。 【化１】 （式中Ｚは炭素数１〜１０のアルキル基、炭素数１〜１
０のアルコキシ基、アリール基、ハロゲン原子またはア
ルキルチオ基であり、Ｙは水素原子または炭素数１〜５
のアルコキシ基であり、ｎは１〜５の整数であり、ｍは
１〜４の整数である）1. A nonlinear optical material comprising a compound represented by general formula (I). [Formula Z is an alkyl group having 1 to 10 carbon atoms, 1 to 1 carbon atoms]
0 alkoxy group, aryl group, halogen atom or alkylthio group, and Y is a hydrogen atom or a carbon number of 1 to 5
is an alkoxy group, n is an integer of 1 to 5, m is an integer of 1 to 4)
ル）−６−メトキシ−１−テトラロンからなる非線形光
学材料。2. A nonlinear optical material comprising 2-(2',4'-dimethoxybenzal)-6-methoxy-1-tetralone.
ル）−６−メトキシ−１−テトラロンからなる非線形光
学材料。3. A nonlinear optical material comprising 2-(2',5'-dimethoxybenzal)-6-methoxy-1-tetralone.
−テトラロンからなる非線形光学材料。[Claim 4] 2-(4'-ethoxybenzal)-1
- Nonlinear optical material consisting of tetralon.
１−テトラロンからなる非線形光学材料。[Claim 5] 2-(4'-methylthiobenzal)-
A nonlinear optical material consisting of 1-tetralone.
合物を含有する組成物からなる非線形光学材料。6. A nonlinear optical material comprising a composition containing the compound represented by the general formula (I) according to claim 1.
らなる非線形光学材料。7. A nonlinear optical material comprising a composition containing the compound of claim 2.
らなる非線形光学材料。8. A nonlinear optical material comprising a composition containing the compound according to claim 3.
らなる非線形光学材料。9. A nonlinear optical material comprising a composition containing the compound of claim 4.
からなる非線形光学材料。10. A nonlinear optical material comprising a composition containing the compound according to claim 5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13409491A JPH04358132A (en) | 1991-06-05 | 1991-06-05 | Nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13409491A JPH04358132A (en) | 1991-06-05 | 1991-06-05 | Nonlinear optical material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04358132A true JPH04358132A (en) | 1992-12-11 |
Family
ID=15120296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13409491A Pending JPH04358132A (en) | 1991-06-05 | 1991-06-05 | Nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04358132A (en) |
-
1991
- 1991-06-05 JP JP13409491A patent/JPH04358132A/en active Pending
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