JPH03204623A - Organic nonlinear optical material - Google Patents
Organic nonlinear optical materialInfo
- Publication number
- JPH03204623A JPH03204623A JP32390A JP32390A JPH03204623A JP H03204623 A JPH03204623 A JP H03204623A JP 32390 A JP32390 A JP 32390A JP 32390 A JP32390 A JP 32390A JP H03204623 A JPH03204623 A JP H03204623A
- Authority
- JP
- Japan
- Prior art keywords
- group
- nonlinear optical
- optical material
- groups
- organic nonlinear
- 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 27
- 239000000463 material Substances 0.000 title claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- KYPOHTVBFVELTG-UHFFFAOYSA-N but-2-enedinitrile Chemical group N#CC=CC#N KYPOHTVBFVELTG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 10
- 230000007935 neutral effect Effects 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- PTBNNFFSVCLJBS-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-oxopropanal Chemical compound COC1=CC=C(C(=O)CC=O)C=C1 PTBNNFFSVCLJBS-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、第二高調波発生、光情報処理、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 (Field of Industrial Application) The present invention relates to an organic nonlinear optical material used in second harmonic generation, optical information processing, optical communication, etc.
（従来の技術および問題点）
オプトエレクトロニクスの分野において、非線形光学効
果を利用した新素子の探索が広くなされている。例えば
、二次の非線形光学効果を利用することにより、半導体
レーザーの波長の短波長化などができ光記録の高密度が
可能である。そのための材料として有機化合物が安定性
、非線形光学定数の大きさ、結晶の得やすさなどの点で
注目を集めている。(Prior Art and Problems) In the field of optoelectronics, there has been a wide search for new elements that utilize nonlinear optical effects. For example, by utilizing the second-order nonlinear optical effect, the wavelength of a semiconductor laser can be shortened, and high-density optical recording is possible. Organic compounds are attracting attention as materials for this purpose due to their stability, large nonlinear optical constants, and ease of obtaining crystals.
二次の非線形光学材料としては、ベンゼン誘導体を中心
に一連の報告があり、 （ＡＣ５ＳＹＭＰＯ５ＩＵＭ
５ＥＲＩＥＳ ２３３ （１９８３））、光学活
性な置換基や水素結合を形成しやすいような置換基を導
入し結晶の対称性をくずし非線形光学効果を発現させた
試みもある。As for second-order nonlinear optical materials, there have been a series of reports centering on benzene derivatives (AC5SYMPO5IUM
5ERIES 233 (1983)), there have also been attempts to introduce optically active substituents or substituents that are likely to form hydrogen bonds to break the symmetry of the crystal and produce nonlinear optical effects.
しかしながら、これらの材料は吸収端が長波長であるた
め一般的な半導体レーザーでは使用できないという欠点
を有している。However, these materials have the disadvantage that they cannot be used in general semiconductor lasers because their absorption edges are at long wavelengths.
一方、尿素、ＫＤＰなどの材料が透明性に優れた非線形
光学材料として知られているが、これらの材料は非線形
光学定数が小さく ＳＨＧ能が小さいためハイパワーレ
ーザーなどの波長変換素子としてしか実用化されていな
い。On the other hand, materials such as urea and KDP are known as nonlinear optical materials with excellent transparency, but these materials have small nonlinear optical constants and low SHG ability, so they are only practical for wavelength conversion elements such as high-power lasers. It has not been.
また、結晶状態においては結晶の対称性がくずれていな
いため、第二高調波が発生しない化合物もあるが、これ
らの材料をポリマー中に分散させポーリング処理を行な
うことにより導波路型第二高調波発生素子を作ろうとす
る試みもなされている。しかしながら、この方法も、透
明域が広く、非線形光学定数が大きな材料がないため実
用化されていない。In addition, there are some compounds that do not generate second harmonics because the symmetry of the crystal is not disrupted in the crystalline state, but by dispersing these materials in polymers and performing a poling process, waveguide-type second harmonics can be generated. Attempts have also been made to create generator elements. However, this method has not been put to practical use because there is no material with a wide transparent region and a large nonlinear optical constant.
（発明が解決しようとする問題点）
本発明の課題は、広い波長範囲で使用可能で、大きな非
線形光学定数を有する非線形光学材料を発明することに
ある。(Problems to be Solved by the Invention) An object of the present invention is to invent a nonlinear optical material that can be used in a wide wavelength range and has a large nonlinear optical constant.
（課題を解決するための手段）
上記目的を解決するため、鋭意探索し下記式（１）で示
される有機非線形光学材料を見いだした。(Means for Solving the Problems) In order to solve the above object, we conducted an intensive search and found an organic nonlinear optical material represented by the following formula (1).
式（１）
（上式中、Ａ１、Ａ２、Ａ３、Ａ４、Ａ５、Ｂ１、Ｂ２
、Ｂ３、Ｂ４、Ｂ５は水素原子、フッ素原子、塩素原子
、アルキル基、アルコキシ基、アミノ基、アルキルアミ
ノ基、ジアルキルアミノ基、ニトロ基、シアノ基、ジシ
アノエチレン基のいずれかを示す。）
ＡＩ、Ａ２、Ａ３、Ａ４、Ａ５、Ｂ１、Ｂ２、Ｂ３、Ｂ
４、Ｂ５の取りうる置換基はいろいろとありうるが、Ａ
Ｉ、Ａ２、Ａ３、Ａ４、Ａ５のいずれか一つ以上が電子
吸引基である場合には、Ｂ１、Ｂ２、Ｂ３、Ｂ４、Ｂ５
のいずれか一つ以上が中性基、又は電子供与基であるこ
とが望ましく、Ａ１、Ａ２、Ａ３、Ａ４、Ａ５のいずれ
か一つ以上が電子供与基である場合には、Ｂ１、Ｂ２、
Ｂ３、Ｂ４、Ｂ５のいずれか一つ以上が中性基、又は電
子吸引基であることが望ましい。Formula (1) (In the above formula, A1, A2, A3, A4, A5, B1, B2
, B3, B4, and B5 each represent a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group, an alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a nitro group, a cyano group, or a dicyanoethylene group. ) AI, A2, A3, A4, A5, B1, B2, B3, B
4. There are various possible substituents for B5, but A
When any one or more of I, A2, A3, A4, A5 is an electron-withdrawing group, B1, B2, B3, B4, B5
It is desirable that at least one of A1, A2, A3, A4, A5 is an electron donating group, B1, B2,
It is desirable that at least one of B3, B4, and B5 is a neutral group or an electron-withdrawing group.
ここで、中性基は、水素原子、アルキル基を示し、電子
供与基は、アルコキシ基、アミノ基、アルキルアミノ基
、ジアルキルアミノ基を示し、電子吸引基はニトロ基、
シアノ基、ジシアノエチレン基を意味する。Here, the neutral group represents a hydrogen atom or an alkyl group, the electron-donating group represents an alkoxy group, an amino group, an alkylamino group, or a dialkylamino group, and the electron-withdrawing group represents a nitro group,
It means a cyano group or a dicyanoethylene group.
本発明の非線形光学材料は、以下の実施例に示すように
吸収端が短波長にあるうえ、大きな非線形光学定数を有
している。本発明の化合物のなかには結晶状態では第二
高調波を発生しないものもあるがこれらの化合物でもポ
リマーに分散しポーリング処理をすることにより非線形
光学材料として使用することができる。The nonlinear optical material of the present invention has an absorption edge at a short wavelength and has a large nonlinear optical constant, as shown in the following examples. Some of the compounds of the present invention do not generate second harmonics in a crystalline state, but even these compounds can be used as nonlinear optical materials by dispersing them in a polymer and subjecting them to poling treatment.
（実施例）
以下、本発明を実施例によりさらに具体的に説明するが
、本発明はこれら実施例に限定されない。(Examples) Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
１− （４−ｔ−ブチルフェニル）−３−（４−メトキ
シフェニル）−１，３−プロパンジオン１００ｍ ｇを
乳鉢中で良くすりつぶしスライドガラスにはさんだ。Example 1 100 mg of 1-(4-t-butylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione was thoroughly ground in a mortar and sandwiched between glass slides.
この試料にパルスエネルギー５０ｍＪ、繰り返し１０ｐ
ｐｓのＮｄ；ＹＡＧレーザー光を照射し発生した第二高
調波発生を光電子増倍管で検知しその強度を測定した。This sample was given a pulse energy of 50 mJ and repeated 10 p.
The second harmonic generated by irradiation with ps Nd;YAG laser light was detected with a photomultiplier tube, and its intensity was measured.
尿素の第二高調波の強度を１とした時にの１− （４−
ｔ−ブチルフェニル）−３−（４−メトキシフェニル）
−１，３−プロパンジオン第二高調波の強度は１４であ
った。1- (4-
t-butylphenyl)-3-(4-methoxyphenyl)
The intensity of the -1,3-propanedione second harmonic was 14.
このように１− （４−ｔ−ブチルフェニル’）−３−
（４−メトキシフェニル） −１，３−プロパンジオン
は尿素に比べ大きなＳＨＧ能を持っていることが証明さ
れた。In this way, 1-(4-t-butylphenyl')-3-
It was demonstrated that (4-methoxyphenyl)-1,3-propanedione has greater SHG ability than urea.
０．５重量％のエタノール溶液を調製し吸収スベクトル
を測定することにより吸収端を求めたところ吸収端は４
０５ ｎｍだった。The absorption edge was determined by preparing a 0.5% by weight ethanol solution and measuring the absorption vector, and the absorption edge was 4.
It was 0.05 nm.
同様の方法で２−メチル−４−ニトロアニリンの吸収端
を求めたところ４５８ ｎｍだった。このように１−
（４−ｔ−ブチルフェニル）−３−（４−メトキシフェ
ニル）−１，３−プロパンジオンは吸収端が短く非線形
光学材料として有用であることが証明された。The absorption edge of 2-methyl-4-nitroaniline was determined to be 458 nm using a similar method. Like this 1-
(4-t-Butylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione has a short absorption edge and has been proven to be useful as a nonlinear optical material.
（発明の効果）
本発明によれば、吸収端が短く、高いＳＨＧ能を持つ有
機非線形光学材料を提供することができる。(Effects of the Invention) According to the present invention, an organic nonlinear optical material having a short absorption edge and high SHG ability can be provided.
持許出顎人口。！その素株式会社Protruding jaw population. ! Sonomoto Co., Ltd.
Claims (2)
、Ｂ３、Ｂ４、Ｂ５は水素原子、フッ素原子、塩素原子
、アルキル基、アルコキシ基、アミノ基、アルキルアミ
ノ基、ジアルキルアミノ基、ニトロ基、シアノ基、ジシ
アノエチレン基のいずれかを示す。）で示される化合物
からなる有機非線形光学材料。(1) General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the above formula, A1, A2, A3, A4, A5, B1, B2
, B3, B4, and B5 each represent a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group, an alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a nitro group, a cyano group, or a dicyanoethylene group. ) An organic nonlinear optical material consisting of a compound shown in
Ｂ２、Ｂ４、Ｂ５が水素原子、Ａ３が炭素数１〜５の直
鎖または分岐したアルコキシ基、Ｂ３が炭素数１〜５の
直鎖または分岐したアルキル基、である有機非線形光学
材料。(2) A1, A2, A4, A5, B1 in general formula (1),
An organic nonlinear optical material in which B2, B4, and B5 are hydrogen atoms, A3 is a straight chain or branched alkoxy group having 1 to 5 carbon atoms, and B3 is a straight chain or branched alkyl group having 1 to 5 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32390A JPH03204623A (en) | 1990-01-05 | 1990-01-05 | Organic nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32390A JPH03204623A (en) | 1990-01-05 | 1990-01-05 | Organic nonlinear optical material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03204623A true JPH03204623A (en) | 1991-09-06 |
Family
ID=11470697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32390A Pending JPH03204623A (en) | 1990-01-05 | 1990-01-05 | Organic nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03204623A (en) |
-
1990
- 1990-01-05 JP JP32390A patent/JPH03204623A/en active Pending
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