JPH01207724A - Organic nonlinear optical material - Google Patents
Organic nonlinear optical materialInfo
- Publication number
- JPH01207724A JPH01207724A JP3341588A JP3341588A JPH01207724A JP H01207724 A JPH01207724 A JP H01207724A JP 3341588 A JP3341588 A JP 3341588A JP 3341588 A JP3341588 A JP 3341588A JP H01207724 A JPH01207724 A JP H01207724A
- Authority
- JP
- Japan
- Prior art keywords
- halogen
- acceptor
- type
- visible absorption
- nonlinearity
- 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 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 230000009102 absorption Effects 0.000 abstract description 18
- 238000010521 absorption reaction Methods 0.000 abstract description 18
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 239000004065 semiconductor Substances 0.000 abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 230000006866 deterioration Effects 0.000 abstract description 3
- 230000009103 reabsorption Effects 0.000 abstract description 3
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 18
- 150000001555 benzenes Chemical class 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- YBADLXQNJCMBKR-UHFFFAOYSA-N (4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-N 0.000 description 1
- FTTIAVRPJGCXAC-UHFFFAOYSA-N 2-methyl-4-nitro-1-oxidopyridin-1-ium Chemical compound CC1=CC([N+]([O-])=O)=CC=[N+]1[O-] FTTIAVRPJGCXAC-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- HVVNJUAVDAZWCB-YFKPBYRVSA-N [(2s)-pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1 HVVNJUAVDAZWCB-YFKPBYRVSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BWOVZCWSJFYBRM-UHFFFAOYSA-N carbononitridic isocyanate Chemical compound O=C=NC#N BWOVZCWSJFYBRM-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229910052739 hydrogen Chemical group 0.000 description 1
- 239000001257 hydrogen Chemical group 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- -1 prolinol (NPP>) Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
Landscapes
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、光情報処理や光通信などで用いられる有機非
線形光学材料に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an organic nonlinear optical material used in optical information processing, optical communication, etc.
［従来の技術］
オプトエレクトロニクス分野の新素子として、非線形光
学素子の実現を目指した材料探索研究が数多くなされて
おり、近年、π電子共役系を有する右は化合物は、分子
自体の性能の大きざおよび高速の光応答性から注目され
ている。[Prior art] Many materials exploration studies have been conducted with the aim of realizing nonlinear optical elements as new elements in the field of optoelectronics.In recent years, compounds with π-electron conjugated systems have been developed to It is attracting attention because of its fast photoresponsiveness.
特に、２次の光非線形性を有する材料については、種々
の化合物系で検討されており、また総説的な解説も数多
くある。（１）ＡＣ３ｓｙｍｐｏｓｉｕｍｓｅｒｉｅｓ
２３３（１９８３）、 ２）Ｄ、Ｊ、Ｗｉｌｌｉａｍ
ｓ Ａｎａｅｗ、Ｃｈｅｍ。In particular, materials with second-order optical nonlinearity have been studied using various compound systems, and there are many general explanations. (1) AC3symposium series
233 (1983), 2) D. J. William
s Anaew, Chem.
Ｉｎｔ、Ｅｄ、Ｅｎａｌ、２３ ｐ６９０ （１９８４
）など。）π電子共役系を有する有機化合物の光非線形
性は、レーザー光入射時のπ電子のゆらぎに起因するも
のとされており、このゆらぎを大きくするため、π電子
共役系にドナー性、アクセプター性の置換基を導入する
ことが従来の分子設計指針であった。Int, Ed, Enal, 23 p690 (1984
)Such. ) The optical nonlinearity of organic compounds with a π-electron conjugated system is said to be caused by the fluctuation of π-electrons when laser light is incident, and in order to increase this fluctuation, donor and acceptor properties are added to the π-electron conjugated system. The conventional molecular design guideline was to introduce substituents.
しかし、上記分子設計指針による化合物、すなわち、π
電子共役系にドナー性、アクセプター性の置換基を導入
した化合物は、分子間で強く双極子−双極子相互作用す
るため、多くの場合、２分子の双極子が打ち消し合う構
造である中心対称性の結晶を形成し、２次の光非線形性
を発現しない。However, the compound according to the above molecular design guideline, i.e., π
Compounds in which donor and acceptor substituents are introduced into an electronically conjugated system have strong dipole-dipole interactions between molecules, so in many cases they have a central symmetry structure in which the dipoles of the two molecules cancel each other out. crystal, and does not exhibit second-order optical nonlinearity.
従来の研究では、結晶の中心対称性を崩し２次の光非線
形性を発現させるために、光学活性な置換基や水素結合
形成性の置＠基をπ電子共役系に導入するという試みが
なされて来た。In previous research, attempts have been made to introduce optically active substituents and hydrogen bond-forming substituents into the π-electron conjugated system in order to break the central symmetry of the crystal and develop second-order optical nonlinearity. I came.
すでに膨大な数の有機化合物について検討され、２−メ
チル−４−ニトロアニリン（ＭＮＡ） 、Ｎ。A huge number of organic compounds have already been investigated, including 2-methyl-4-nitroaniline (MNA), N.
Ｎ−ジメチル−２−アセチルアミノ−４−ニトロアニリ
ン（ＤＡＮ＞、Ｎ−（４−ニトロフェニル）−（し）−
プロリノール（ＮＰＰ＞などのベンゼン誘導体では、Ｎ
ｄ：ＹＡＧレーザの波長（λ・１．０６μｍ）で比較的
大きな光非線形性が見い出された。N-dimethyl-2-acetylamino-4-nitroaniline (DAN>, N-(4-nitrophenyl)-(shi)-
In benzene derivatives such as prolinol (NPP>), N
A relatively large optical nonlinearity was found at the wavelength of the d:YAG laser (λ·1.06 μm).
しかし、これらのベンゼン誘導体はアミノ基とニトロ基
の様に強いドナー性基と強いアクセプター性基を有して
いるため光非線形性は比較的大きいが、可視吸収も長波
長までおる。従って、これらの化合物を用いて半導体レ
ーザ光（λ＝０，８〜０゜９μｍ）を透過型で波長変換
する場合には、化合物自身による第二高調波の再吸収に
よって化合物劣化や変換効率の低下等の問題があった。However, since these benzene derivatives have strong donor groups and strong acceptor groups such as amino groups and nitro groups, their optical nonlinearity is relatively large, but their visible absorption extends to long wavelengths. Therefore, when transmitting wavelength conversion of semiconductor laser light (λ = 0.8 to 0.9 μm) using these compounds, reabsorption of the second harmonic by the compound itself may cause deterioration of the compound or decrease in conversion efficiency. There were problems such as decline.
ざらに長いπ電子共役系を有しているため、分子光非線
形性をベンゼン誘導体よりさらに大きくできるスチルベ
ン誘導体等は、アミノ基とニトロ基の様に強いドナー性
基と強いアクセプター性基を導入すると、双極子モーメ
ントも大きくなるため、結晶状態での分子間双極子−双
極子相互作用が強くなって中心対称性となる傾向が強く
、また可視吸収もざらに長波長化する。従って、Ｎｄ：
ＹＡＧレーザ波長においては、上記ベンゼン誘導体程度
の光非線形性の発現すら観測されていない。Stilbene derivatives, which have a relatively long π-electron conjugated system and can exhibit even greater molecular optical nonlinearity than benzene derivatives, can be used by introducing strong donor groups and strong acceptor groups, such as amino and nitro groups. , since the dipole moment also increases, the intermolecular dipole-dipole interaction in the crystalline state becomes stronger, and there is a strong tendency for central symmetry to occur, and the visible absorption wavelength also becomes roughly longer. Therefore, Nd:
At the YAG laser wavelength, even the expression of optical nonlinearity comparable to that of the benzene derivatives described above has not been observed.
可視吸収の短波長化を考慮し、分子設計されている例と
しては、２−メチル−４−ニトロピリジン−Ｎ−オキシ
ド（ＰＯＭ＞とＮ−［２−（５−二トロピリジル）］−
（Ｌ）−プロリノール（ＰＮＰ）が挙げられる。しかし
、ＰＯＭは光非線形性が小さく、またＰＮＰは短波長化
が不十分な上、結晶性にも問題がある。Examples of molecules whose molecules are designed with short wavelengths of visible absorption in mind are 2-methyl-4-nitropyridine-N-oxide (POM> and N-[2-(5-nitropyridyl)]-
(L)-prolinol (PNP) is mentioned. However, POM has small optical nonlinearity, and PNP is insufficiently shortened in wavelength and also has problems with crystallinity.
［発明が解決しようとする課題］
かかる従来技術により、かなり手広く材料探索がなされ
、比較的大きな光非線形性を発現する材料は見い出され
ているが、可視吸収が長波長側にあり、透過型、すなわ
ち基本波（半導体レーザ光）が材料中を伝搬し、第二高
調波も少なくとも材料を一部透過する構成で、半導体レ
ーザを波長変換するに適当な材料は未だ見い出されてい
ない状況にある。[Problems to be Solved by the Invention] According to the prior art, materials have been extensively searched and materials that exhibit relatively large optical nonlinearity have been found, but the visible absorption is on the long wavelength side, and the materials are not transparent or transparent. That is, the fundamental wave (semiconductor laser light) propagates through the material, and the second harmonic also transmits at least a portion of the material, and a material suitable for wavelength conversion of a semiconductor laser has not yet been found.
本発明の目的は、透過型で半導体レーザを波長変換する
ための大きな光非線形性と短波長側の可視吸収を有する
有機非線形光学材料を提供することにある。An object of the present invention is to provide an organic nonlinear optical material having large optical nonlinearity and visible absorption on the short wavelength side for wavelength conversion of a transmission type semiconductor laser.
［課題を解決するための手段］
上記目的を達成するため、本発明は、下記の構成を有す
る。[Means for Solving the Problems] In order to achieve the above object, the present invention has the following configuration.
「下記一般式（Ｉ）からなることを特徴とする有機非線
形光学材料。"An organic nonlinear optical material characterized by comprising the following general formula (I).
（Ａはアクセプター性基、Ｘはハロゲンを示す。）一般
に、分子光非線形性はπ電子共役系の長さと母骨格に導
入するドナー性基、アクセプター性基の強さに比例する
。(A represents an acceptor group and X represents a halogen.) Generally, molecular optical nonlinearity is proportional to the length of the π-electron conjugated system and the strength of the donor group and acceptor group introduced into the parent skeleton.
従って、前記の様に、一般にスチルベン誘導体はベンゼ
ン誘導体と比較し、同じ置換基を導入したものでは分子
光非線形性は大きくなるが次の問題が生じる。Therefore, as described above, stilbene derivatives generally have greater molecular optical nonlinearity than benzene derivatives when the same substituents are introduced, but the following problem occurs.
（１）双極子モーメントが大きくなり、結晶は中心対称
性となり易い。(1) The dipole moment becomes large, and the crystal tends to become centrosymmetric.
（２）可視吸収が長波長化する。(2) Visible absorption becomes longer wavelength.
そこで、本発明ではπ電子母骨格に導入するドナー性基
をハロゲンにすることにより、上記問題点を解決した。Therefore, in the present invention, the above-mentioned problem was solved by using halogen as the donor group introduced into the π-electron host skeleton.
ハロゲンには、σ電子に関してアクセプター性、π電子
に関してドナー性という特異な性質がある。Halogen has a unique property of being an acceptor for σ electrons and a donor for π electrons.
従って、本発明の化合物の場合、双極子モーメントは大
きくならず、また有機材料の光非線形性の起源であるπ
電子のフレキシビリティ−は保持されるので分子光非線
形性もベンゼン誘導体に強いドナー性基を導入した場合
に比較して小さくならずに済む。Therefore, in the case of the compound of the present invention, the dipole moment is not large, and π is the origin of optical nonlinearity in organic materials.
Since electronic flexibility is maintained, molecular optical nonlinearity does not become smaller than when a strong donor group is introduced into a benzene derivative.
また、可視吸収は既知のベンゼン誘導体より短波長側と
なるので、半導体レーザ光（λ＝０．８〜０゜９μｍ）
を波長変換する場合などにも第二高調波の再吸収による
化合物劣化や変換効率の低下などの問題を起こさない。In addition, since visible absorption is on the shorter wavelength side than known benzene derivatives, semiconductor laser light (λ = 0.8 to 0°9 μm)
Even when converting wavelengths, problems such as compound deterioration and reduction in conversion efficiency due to reabsorption of second harmonics do not occur.
この点が本発明による化合物の既知化合物との差異であ
り、特筆すべき特徴である。This point is a difference between the compound according to the present invention and known compounds, and is a noteworthy feature.
アクセプター基としては、ｕａｍｍｅｔの置換基定数を
用いると、σｐ＞０．２程度のもので、例えば、ニトロ
、トリフルオロメチル、シアノ、イソシアネート、アル
デヒド、アミド、カルボン酸メチル、カルボン酸エチル
などが挙げられる。中でも、ニトロ基が、強い共鳴効果
を有しているので、化合物の光非線形性を大きくする上
で有用である。As the acceptor group, using the substituent constant of uammet, σp>0.2 or so, such as nitro, trifluoromethyl, cyano, isocyanate, aldehyde, amide, methyl carboxylate, ethyl carboxylate, etc. It will be done. Among them, the nitro group has a strong resonance effect and is therefore useful in increasing the optical nonlinearity of the compound.
本発明においては、ハロゲンであれば適用できるが、中
でもアクセプター性基がニトロ基である場合、ハロゲン
として臭素を導入すると、半導体レーザを波長変換する
上で要求される短波長側の可視吸収と大きな光非線形性
が最もよく実現できる。In the present invention, any halogen can be applied, but especially when the acceptor group is a nitro group, introducing bromine as a halogen will increase the visible absorption on the short wavelength side required for wavelength conversion of a semiconductor laser. Optical nonlinearity is best realized.
また、化合物の一部または全てが重水素化されているこ
とが好ましい。化合物の重水素化は、近赤外吸収のシフ
ト効果などがあるが、重水素化していない化合物と同様
の可視吸収と非線形光学効果を有する。Further, it is preferable that part or all of the compound is deuterated. Deuterated compounds have a near-infrared absorption shift effect, but they have visible absorption and nonlinear optical effects similar to those of non-deuterated compounds.
［実施例］
ｐ−ブロモベンズアルデヒド３．７ＣＪ （２０ｍｍｏ
ｆ）とｐ−ニトロフェニル酢酸３．６２ｏ （２０ｍｍ
ｏｌ）をピペリジン’ｌＱｍｌ中に加え、反応温度１２
０℃で約４ ｈｒ、還流する。[Example] p-bromobenzaldehyde 3.7CJ (20mmo
f) and p-nitrophenylacetic acid 3.62o (20mm
ol) was added to piperidine'lQml, and the reaction temperature was 12
Reflux at 0° C. for about 4 hr.
ピペリジンをロータリーエバポレータで除去した俊、反
応混合物をシリカゲルのカラムクロマトグラフィーにか
ける。展開溶媒はクロロホルムを用いる。ＴＬＣで目的
物層を確認し、その層の溶媒を除去した後、ベンゼンで
再結晶すると薄黄色の結晶が得られる。（目的物生成量
３．９２ｇ、収率６４．５％）
同定はＩＲおよび元素分析により行なった。After removing the piperidine using a rotary evaporator, the reaction mixture is subjected to column chromatography on silica gel. Chloroform is used as the developing solvent. After confirming the target layer by TLC and removing the solvent from the layer, recrystallization with benzene yields pale yellow crystals. (Amount of target product produced: 3.92 g, yield: 64.5%) Identification was performed by IR and elemental analysis.
次に、化合物の光非線形性を調べるために５ＨＧ（第２
高調波発生）を粉末法（Ｓ、に、にＵｒｔＺ、 Ｔ、
Ｔ。Next, in order to investigate the optical nonlinearity of the compound, 5HG (second
harmonic generation) to the powder method (S, to, UrtZ, T,
T.
ｐｅｒｒｙ、 Ｊ、＾１）ｐｌ、Ｐｈｙｓ ３９３７９
Ｂ （１９６６））により測定した。測定に用いた光源
は、Ｎｄ：ＹＡＧレーザーで、試料は乳鉢により１０μ
ｍ以下に粉砕したものを使用した。紫外可視スペクトル
の測定は、石英セルにエタノール溶液を充填し、行なっ
た。perry, J, ^1) pl, Phys 39379
B (1966)). The light source used for the measurement was a Nd:YAG laser, and the sample was placed in a mortar at 10 μm.
It was used after being crushed to a size smaller than m. The measurement of the ultraviolet-visible spectrum was performed by filling a quartz cell with an ethanol solution.
５）−ＩＧおよび可視吸収の吸収端の測定結果を表１に
示す。5) Table 1 shows the measurement results of the absorption edges of -IG and visible absorption.
本発明によるＢＮＳは既知化合物の中では最大のＳＨＧ
が報告されているＮＰＰと同等の光非線形性を有し、し
かも可視吸収の吸収端はＰＯＭと同等であった。BNS according to the present invention has the largest SHG among known compounds.
It had optical nonlinearity equivalent to that of NPP, which has been reported, and the absorption edge of visible absorption was equivalent to that of POM.
表１．有機非線形光学化合物のＳＨＧとｕｖｃｕｔ−ｏ
ｆｆ （λ： １．０６μｍ）
［発明の効果］
本発明により、大きな光非線形性と短波長側の可視吸収
を有し、半導体レーザの波長変換を透過型で可能とする
高性能の有機非線形光学材料を提供することができる。Table 1. Organic nonlinear optical compounds SHG and uvcut-o
ff (λ: 1.06 μm) [Effects of the Invention] The present invention provides high-performance organic nonlinear optics that has large optical nonlinearity and visible absorption on the short wavelength side and enables wavelength conversion of semiconductor lasers in a transmission type. material can be provided.
Claims (1)
機非線形光学材料。 ▲数式、化学式、表等があります▼（ I ） （Ａはアクセプター性基、Ｘはハロゲンを示す。）（２
）アクセプター性基がニトロ基であることを特徴とする
請求項（１）記載の有機非線形光学材料。 （３）ハロゲンが臭素であることを特徴とする請求項（
１）記載の有機非線形光学材料。[Claims] (1) An organic nonlinear optical material characterized by comprising the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (A represents an acceptor group and X represents a halogen.) (2
2.) The organic nonlinear optical material according to claim 1, wherein the acceptor group is a nitro group. (3) A claim characterized in that the halogen is bromine (
1) The organic nonlinear optical material described above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3341588A JPH01207724A (en) | 1988-02-15 | 1988-02-15 | Organic nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3341588A JPH01207724A (en) | 1988-02-15 | 1988-02-15 | Organic nonlinear optical material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01207724A true JPH01207724A (en) | 1989-08-21 |
Family
ID=12385944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3341588A Pending JPH01207724A (en) | 1988-02-15 | 1988-02-15 | Organic nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01207724A (en) |
-
1988
- 1988-02-15 JP JP3341588A patent/JPH01207724A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| THE JOURNAL OF CHEMICAL PHYSICS=1977 * |
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