JP2574697B2 - Novel organic nonlinear optical material and method of converting light wavelength using the same - Google Patents
Novel organic nonlinear optical material and method of converting light wavelength using the sameInfo
- Publication number
- JP2574697B2 JP2574697B2 JP528889A JP528889A JP2574697B2 JP 2574697 B2 JP2574697 B2 JP 2574697B2 JP 528889 A JP528889 A JP 528889A JP 528889 A JP528889 A JP 528889A JP 2574697 B2 JP2574697 B2 JP 2574697B2
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- JP
- Japan
- Prior art keywords
- nonlinear optical
- optical material
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- same
- light wavelength
- Prior art date
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- 230000003287 optical effect Effects 0.000 title claims description 35
- 239000000463 material Substances 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000005259 measurement Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- -1 1,3-butadienyl group Chemical group 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000010219 correlation analysis Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005556 structure-activity relationship Methods 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- XDJAAZYHCCRJOK-UHFFFAOYSA-N 4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1 XDJAAZYHCCRJOK-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 101100276976 Drosophila melanogaster Drak gene Proteins 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000009022 nonlinear effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000015 polydiacetylene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は波長変換素子等の非線形光学効果を利用する
各種素子に用いるに適した非線形光学材料に関する。ま
た、非線形光学材料を用いた光波長の変換方法に関す
る。Description: TECHNICAL FIELD The present invention relates to a nonlinear optical material suitable for use in various devices utilizing a nonlinear optical effect such as a wavelength conversion device. Further, the present invention relates to a method for converting a light wavelength using a nonlinear optical material.
（従来の技術） 近年、非線形光学効果−レーザー光のような強い光電
界を与えたときに表われる、分極と電界との間の非線形
性−を有した材料が注目を集めている。(Prior Art) In recent years, a material having a nonlinear optical effect-nonlinearity between polarization and an electric field, which appears when a strong optical electric field such as laser light is applied-has attracted attention.
かかる材料は、一般に非線形光学材料として知られて
おり、例えば次のものなどに詳しく記載されている。
“Nonliner Optical Properties of Organic and Polym
eric Material"ACS SYMPOSIUM SERIES 233 David J.Wil
liams編（American Chemical Society、1983年刊）、
「有機非線形光学材料」加藤正雄、中西八郎監修（シー
・エム・シー社、1985年刊）。Such materials are generally known as non-linear optical materials and are described in detail, for example, in:
“Nonliner Optical Properties of Organic and Polym
eric Material "ACS SYMPOSIUM SERIES 233 David J. Wil
liams (American Chemical Society, 1983),
"Organic Nonlinear Optical Materials", edited by Masao Kato and Hachiro Nakanishi (CMC, 1985).
非線形光学材料の用途の１つに、２次の非線形効果に
基づいた第２高調波発生（SHG）および和周波、差周波
を用いた波長変換デバイスがある。これまで実用上用い
られているものは、ニオブ酸リチウムに代表される無機
質のペロブスカイト類である。しかし近年になり、電子
供与基および電子吸引基を有するπ電子共役系有機化合
物は前述の無機質を大きく上回る、非線形光学材料とし
ての諸性能を有していることが知られるようになつた。One of the applications of the nonlinear optical material is a second harmonic generation (SHG) based on a second-order nonlinear effect and a wavelength conversion device using a sum frequency and a difference frequency. Until now, inorganic perovskites represented by lithium niobate have been practically used. However, in recent years, it has become known that a π-electron conjugated organic compound having an electron donating group and an electron withdrawing group has various properties as a nonlinear optical material, which greatly exceeds the above-mentioned inorganic substances.
従つて、この材料の用いるべき非線形光学応答を示す
有機化合物としては、まず分子状態での非線形感受率が
高いもの程望ましい。このような性質の発現にはπ電子
共役鎖の長い化合物が有用であることが知られており、
前述の文献にも種々記載されているが、それらの化合物
においては自明の如く吸収極大波長が長波長化し、例え
ば青色光の透過率の低下を招き、第２高調波としての青
色光の発生に障害となる。このことは、ｐ−ニトロアニ
リン誘導体においても生じており、第２高調波発生の効
率にその波長の透過率の影響が大きいことは、Alain Az
ma他著、Proceedings of SPIE、400巻、New Optieal
Materials,（1983）186頁第４図より明らかである。Therefore, as the organic compound exhibiting a nonlinear optical response to be used by this material, it is preferable that the material has a higher nonlinear susceptibility in a molecular state. It is known that a compound having a long π electron conjugated chain is useful for expressing such properties,
Although various descriptions are given in the above-mentioned documents, in these compounds, the absorption maximum wavelength becomes longer as is self-evident, for example, causing a decrease in the transmittance of blue light and causing the generation of blue light as a second harmonic. It is an obstacle. This also occurs in the p-nitroaniline derivative, and the effect of the transmittance at that wavelength on the efficiency of second harmonic generation is large.
Ma et al., Proceedings of SPIE, 400 volumes, New Optieal
Materials, (1983), page 186, FIG.
従つて青色光に対する透過率の高い非線形光学材料の
出現が望まれている。従来、ニトロアニリンのベンゼン
核の炭素原子を窒素原子などで置き換えることが検討さ
れて来たが必ずしも満足のいく結果は得られていない。Therefore, the emergence of a nonlinear optical material having a high transmittance for blue light is desired. Conventionally, it has been studied to replace the carbon atom of the benzene nucleus of nitroaniline with a nitrogen atom or the like, but a satisfactory result has not always been obtained.
また、本願出願人はより優れた方法について、特開昭
62−210430号広報および特開昭62−210432号公報にて開
示した。しかしながら、更に高い非線形光学応答性を示
し、且つ青色光透過性に優れた化合物の出現が求められ
ている。In addition, the applicant of the present application has disclosed a
This is disclosed in Japanese Patent Application Publication No. 62-210430 and JP-A-62-210432. However, there is a demand for a compound exhibiting even higher nonlinear optical response and having excellent blue light transmittance.
（発明が解決しようとする課題） 従つて本発明の第一の目的は、高い非線形応答性を示
し、且つ青色光透過性に優れた有機非線形光学材料を提
供することにある。第二の目的は非線形応答性のうち光
波長の変換に関する応答性を利用した方法を提供するこ
とにある。(Problems to be Solved by the Invention) Accordingly, a first object of the present invention is to provide an organic nonlinear optical material which exhibits high nonlinear response and excellent blue light transmittance. A second object is to provide a method that utilizes the response related to light wavelength conversion among the nonlinear responses.
（課題を解決するための手段） 本発明者らは、鋭意研究を重ねた結果、下記一般式
（Ｉ）で表わされる化合物を非線形光学応答性化合物と
して用いることにより、本発明の目的が達成可能なこと
を見出した。(Means for Solving the Problems) As a result of intensive studies, the present inventors have achieved the object of the present invention by using a compound represented by the following general formula (I) as a nonlinear optically responsive compound. I found something.
一般式（Ｉ） （式中、Ｑは、テトラゾール環と共役とする多重結合を
含む基を表わす。Ｒは、水素原子、アルキル基、アリー
ル基を表わす。） Ｑで表わされる、多重結合を含む基としては、例えば
置換あるいは無置換のビニル基、置換あるいは無置換の
1,3−ブタジエニル基、置換あるいは無置換のフエニル
基、置換あるいは無置換のナフチル基、置換あるいは無
置換のピリジル基が挙げられる。これらのうちでは、電
子供与性基で置換された上述の基が好ましく、特に電子
供与性基で置換されたフエニル基およびピリジル基が好
ましい。General formula (I) (In the formula, Q represents a group containing a multiple bond conjugated to a tetrazole ring. R represents a hydrogen atom, an alkyl group, or an aryl group.) Examples of the group containing a multiple bond represented by Q include, for example, Substituted or unsubstituted vinyl, substituted or unsubstituted
Examples thereof include a 1,3-butadienyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted pyridyl group. Of these, the above groups substituted with an electron donating group are preferred, and phenyl and pyridyl groups substituted with an electron donating group are particularly preferred.
Ｒで表わされる基は水素原子、アルキル基、アリール
基であるが、アルキル基としては例えば、メチル基、エ
チル基、ヒドロキシエチル基、プロピル基、イソプロピ
ル基、ドデシル基が挙げられる。アリール基としては、
フエニル基、３−メチルフエニル基、４−クロロフエニ
ル基、２−ナフチル基が挙げられる。これらのうち、炭
素数６以下のものが好ましく、特に水素原子が好まし
い。The group represented by R is a hydrogen atom, an alkyl group, or an aryl group. Examples of the alkyl group include a methyl group, an ethyl group, a hydroxyethyl group, a propyl group, an isopropyl group, and a dodecyl group. As the aryl group,
Examples include a phenyl group, a 3-methylphenyl group, a 4-chlorophenyl group, and a 2-naphthyl group. Among them, those having 6 or less carbon atoms are preferable, and a hydrogen atom is particularly preferable.
なお、上述の電子供与性基としては置換基定数σ＋が
負の置換基を指す。The electron donating group described above refers to a substituent having a negative substituent constant σ + .
置換基定数は、構造活性相関懇話会編「化学の領域」
増刊122号の「薬物の構造活性相関−ドラツクデザイン
と作用機作研究への指針」95〜111頁 南江堂社刊やコ
ルビン・ハンシユ（Corwin・Hansch）、アルバート・レ
オ（Albert・Leo）著、「サブステイチユーアント・コ
ンスタンツ・フオー・コーリレーシヨン・アナリシス・
イン・ケミストリー・アンド・バイオロジー」（Substi
tuent Constants for Correlation Analysis in Chemis
try and Biology）69〜161頁 ジヨン・ワイリー・アン
ド・サンズ（John Wiley and Sons）社刊に示された値
を表わす。Substituent constants can be found in `` Chemical Fields '', edited by Structure-Activity Relationship Society
Supplement No. 122, “Structure-Activity Relationships of Drugs-Guidelines for Drak Design and Mode of Action Studies”, pp. 95-111, published by Nankodo Co., and by Corwin Hansch, Albert Leo, "Substantiate Your Constants For Correlation Analysis
In Chemistry and Biology "(Substi
tuent Constants for Correlation Analysis in Chemis
try and Biology, pp. 69-161 Represents the values given in the publication of John Wiley and Sons.
以下に本発明に用いられる化合物の具体例を示すが、
本発明の範囲はこれらのみに限られるものではない。The following shows specific examples of the compound used in the present invention,
The scope of the present invention is not limited only to these.
これらの化合物の合成は、スキーム１に従つて合成す
ることができる。 These compounds can be synthesized according to Scheme 1.
合成例１（化合物１の合成） DMF100ml中にｐ−メトキシベンゾニトリル27.1g（0.2
ml）、アジ化ナトリウム14.3g（0.22mol）及び塩化アン
モニウム1.2g（0.022mol）を加え、反応温度を100℃に
保ちながら７時間加熱撹拌した。反応終了後、DMFを減
圧留去した後水および濃塩酸を加えて酸性にし、得られ
た固体を過し、水／メタノールにて再結晶すると化合
物１が得られた。 Synthesis Example 1 (Synthesis of Compound 1) 27.1 g (0.2 g) of p-methoxybenzonitrile in 100 ml of DMF
ml), 14.3 g (0.22 mol) of sodium azide and 1.2 g (0.022 mol) of ammonium chloride, and the mixture was heated and stirred for 7 hours while maintaining the reaction temperature at 100 ° C. After completion of the reaction, DMF was distilled off under reduced pressure, and the mixture was acidified by adding water and concentrated hydrochloric acid. The obtained solid was filtered and recrystallized from water / methanol to obtain Compound 1.
収量5.2g 収率14.8％ 合成例２（化合物６の合成） DMF100ml中に４−シアノピリジン20.8g（0.2mol）、
アゾ化ナトリウム14.3g（0.22mol）及び塩化アンモニウ
ム1.2g（0.022mol）を加え、反応温度を100℃に保ちな
がら4.5時間加熱撹拌した。Yield 5.2 g Yield 14.8% Synthesis Example 2 (Synthesis of Compound 6) 4-cyanopyridine 20.8 g (0.2 mol) in DMF 100 ml,
14.3 g (0.22 mol) of sodium azide and 1.2 g (0.022 mol) of ammonium chloride were added, and the mixture was heated and stirred for 4.5 hours while maintaining the reaction temperature at 100 ° C.
反応終了後、DMFを減圧留去し、水および濃塩酸を加
えてpH5にし、得られた固体を取し、水にて再結晶す
ると化合物６が得られた。After completion of the reaction, DMF was distilled off under reduced pressure, and water and concentrated hydrochloric acid were added to adjust the pH to 5. The obtained solid was collected and recrystallized with water to obtain Compound 6.
収量22g 収率74.8％ 後述の実施例より明らかなように、本発明の非線形光
学材料は波長変換用の材料として特に有用なものであ
る。しかしながら本発明の非線形光学材料の用途は波長
変換素子にかぎられるものではなく、非線形光学効果を
利用するものであればいかなる素子にも使用可能であ
る。本発明の非線形光学材料が用いられうる素子の具体
例として、波長変換素子以外に、光双安定素子（光記憶
素子、光パルス波形制御素子、光リミター、微分増幅素
子、光トランジスター、A/D変換素子、光論理素子、光
マルチバイブレーター、光フリツプフロツプ回路等）、
光変調素子および位相共役光学素子等が挙げられる。Yield: 22 g Yield: 74.8% As is clear from the examples described below, the nonlinear optical material of the present invention is particularly useful as a material for wavelength conversion. However, the application of the nonlinear optical material of the present invention is not limited to the wavelength conversion element, but can be used for any element utilizing the nonlinear optical effect. Specific examples of the device in which the nonlinear optical material of the present invention can be used include, besides the wavelength conversion device, an optical bistable device (optical storage device, optical pulse waveform control device, optical limiter, differential amplifier device, optical transistor, A / D Conversion element, optical logic element, optical multivibrator, optical flip-flop circuit, etc.),
An optical modulation element, a phase conjugate optical element, and the like can be given.
本発明の化合物は、例えば粉末の形、宿主格子（ポリ
マー、包接化合物、固溶体、液晶）中の分子の包有物の
形、支持体上に沈積した薄層の形（ラングミーア・ブロ
ジエツト膜など）、単結晶の形、溶液の形等、種々の形
で非線形光学材料として用いることができる。The compounds according to the invention can be used, for example, in the form of powders, in the form of inclusions of molecules in the host lattice (polymers, clathrates, solid solutions, liquid crystals), in the form of thin layers deposited on supports (Langmea-Blodgett membranes, etc.). ), In the form of a single crystal, in the form of a solution, etc., it can be used as a nonlinear optical material.
また本発明の化合物をペンダントの形でポリマー、ポ
リジアセチレンなどに結合させて用いることもできる。Further, the compound of the present invention can be used by binding to a polymer, polydiacetylene or the like in a pendant form.
これらの方法について詳しくは前述のD.J.Williams編
の著作などに記載されている。Details of these methods are described in the above-mentioned work by DJ Williams.
（実施例） 次に、本発明を実施例に基づいて詳しく説明する。(Examples) Next, the present invention will be described in detail based on examples.
実施例 第２高調波発生の測定をエス・ケー・クルツ（S.K.Ku
rts）、テイー・テイー・ペリー（T.T.Perry）著、ジヤ
ーナル オブ アプライド フイジツクス（J.Appl.Phy
s.）39巻3798頁（1968年刊）中に記載されている方法に
準じて、本発明の化合物の粉末に対して行なつた。Example 2nd harmonic generation measurement was performed by SKKu
rts), TTPerry, Journal of Applied Physics (J.Appl.Phy)
s.) 39, p. 3798 (1968) was carried out on a powder of the compound of the present invention.
第１図に示した装置により測定を行つた。 The measurement was performed by the apparatus shown in FIG.
すなわち、測定は、パルスYAGレーザー光（λ＝1.064
μｍ、ビーム径≒1mmφ、ピークパワー≒10Mw/cm2）を
基本波に用い、第１図に示す評価装置にて、その第２高
調波の強度を測定した。測定は、尿素の第２高調波の強
度との相対比較で行つた。また強度が弱い場合には目視
による観測を行つた。特に、基本波の２光子吸収による
発光（おもに黄、赤の発光）と第２高調波とを区別する
ために、分光器を入れ、第２高調波のみを測定する様に
した。さらに粉末法の測定は、その物質の非線形性の有
無を判断することが注目的であり、その強度比は非線形
性の大きさの、参考値である。That is, the measurement was performed using pulsed YAG laser light (λ = 1.064).
μm, a beam diameter of ≒ 1 mmφ, and a peak power of ≒ 10 Mw / cm 2 ) were used as fundamental waves, and the intensity of the second harmonic was measured by the evaluation apparatus shown in FIG. The measurement was performed by a relative comparison with the intensity of the second harmonic of urea. When the intensity was weak, visual observation was performed. In particular, in order to distinguish between the emission due to two-photon absorption of the fundamental wave (mainly yellow and red emission) and the second harmonic, a spectroscope was put in and only the second harmonic was measured. Further, in the measurement by the powder method, it is noteworthy to judge the presence or absence of nonlinearity of the substance, and the intensity ratio is a reference value of the magnitude of the nonlinearity.
結果を表１に示した。 The results are shown in Table 1.
第１図に粉末法の測定装置を示すが、図中の番号は下記
を示す。 1:粉末試料、2:基本波カツトフイルター 3:分光器、4:フオトマル、5:アンプ （11）：波長1.064μｍ、（12）:0.532μｍFIG. 1 shows a measuring apparatus of the powder method, and the numbers in the figure indicate the following. 1: powder sample, 2: fundamental wave cut filter 3: spectroscope, 4: photometric, 5: amplifier (11): wavelength 1.064 μm, (12): 0.532 μm
Claims (2)
ら成る非線形光学材料 一般式（Ｉ） （式中、Ｑは、テトラゾール環を共役する多重結合を含
む基を表わす。Ｒは、水素原子、アルキル基、アリール
基を表わす。）1. A nonlinear optical material comprising a compound represented by the following general formula (I): (In the formula, Q represents a group containing a multiple bond that conjugates a tetrazole ring. R represents a hydrogen atom, an alkyl group, or an aryl group.)
波長の変換を行なう際に、非線形光学材料として請求項
（１）記載の有機非線形光学材料を用いる光波長の変換
方法2. A method for converting an optical wavelength using an organic nonlinear optical material according to claim 1, wherein the optical wavelength is converted using a laser beam and a nonlinear optical material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP528889A JP2574697B2 (en) | 1989-01-12 | 1989-01-12 | Novel organic nonlinear optical material and method of converting light wavelength using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP528889A JP2574697B2 (en) | 1989-01-12 | 1989-01-12 | Novel organic nonlinear optical material and method of converting light wavelength using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02184829A JPH02184829A (en) | 1990-07-19 |
| JP2574697B2 true JP2574697B2 (en) | 1997-01-22 |
Family
ID=11607054
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP528889A Expired - Fee Related JP2574697B2 (en) | 1989-01-12 | 1989-01-12 | Novel organic nonlinear optical material and method of converting light wavelength using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2574697B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5874593A (en) * | 1994-05-16 | 1999-02-23 | Sumitomo Chemical Company, Limited | Production process and intermediate of tetrazole compound |
| WO2002021948A1 (en) | 2000-09-12 | 2002-03-21 | Filligent Limited | Tobacco smoke filter |
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1989
- 1989-01-12 JP JP528889A patent/JP2574697B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02184829A (en) | 1990-07-19 |
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