JP2995273B2 - Organic nonlinear optical material - Google Patents
Organic nonlinear optical materialInfo
- Publication number
- JP2995273B2 JP2995273B2 JP3094961A JP9496191A JP2995273B2 JP 2995273 B2 JP2995273 B2 JP 2995273B2 JP 3094961 A JP3094961 A JP 3094961A JP 9496191 A JP9496191 A JP 9496191A JP 2995273 B2 JP2995273 B2 JP 2995273B2
- Authority
- JP
- Japan
- Prior art keywords
- nonlinear optical
- saccharin
- compound
- optical material
- present
- 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.)
- Expired - Lifetime
Links
- 230000003287 optical effect Effects 0.000 title claims description 26
- 239000000463 material Substances 0.000 title claims description 10
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 229940081974 saccharin Drugs 0.000 description 7
- 235000019204 saccharin Nutrition 0.000 description 7
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 4
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
Description
【０００１】[0001]
【産業上の利用分野】本発明は、優れた非線形光学効果
を有するサッカリン誘導体からなる非線形光学材料に関
する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a nonlinear optical material comprising a saccharin derivative having an excellent nonlinear optical effect.
【０００２】非線形光学材料は、レーザー光等の光を照
射した時にその光の波長変換や強度変調等の効果を有
し、光記録、情報処理、光通信等オプトエレクトロニク
ス分野に於て不可欠な材料として注目され、活発に研究
開発が行われている。[0002] Nonlinear optical materials have effects such as wavelength conversion and intensity modulation of light when irradiated with laser light or the like, and are indispensable materials in the field of optoelectronics such as optical recording, information processing and optical communication. The research and development are being actively conducted.
【０００３】[0003]
【従来の技術】従来、非線形光学材料としては、リン酸
二水素カリウム（KDP）やニオブ酸リチウム(LN)等の無
機結晶がレーザー光の光波長変換素子や光シャッター等
として実用化されているが、これらの無機結晶は操作性
が悪く、かつ非線形光学効果も十分ではない。一方、尿
素、２−メチル−４−ニトロアニリン(MNA)等のある種
の有機化合物は大きな非線形光学効果を有することが知
られている。しかしながら、これらの有機化合物の非線
形光学効果もまだ十分満足されるものではなく、また比
較的高い非線形光学効果を有するものは化合物自身かな
り着色しており、長波長吸収があり、使用波長領域が制
限されるという問題点があった。2. Description of the Related Art Conventionally, as a nonlinear optical material, inorganic crystals such as potassium dihydrogen phosphate (KDP) and lithium niobate (LN) have been put to practical use as an optical wavelength conversion element for laser light, an optical shutter, and the like. However, these inorganic crystals have poor operability and have insufficient nonlinear optical effects. On the other hand, certain organic compounds such as urea and 2-methyl-4-nitroaniline (MNA) are known to have large nonlinear optical effects. However, the nonlinear optical effects of these organic compounds are still not sufficiently satisfactory, and those having a relatively high nonlinear optical effect are considerably colored, have long-wavelength absorption, and the wavelength range used is limited. There was a problem that it was done.
【０００４】一方、種々のサッカリン誘導体は公知の化
合物であり、生理活性等の検討が行われている。しかし
ながら、尿素結合を有するサッカリンを光学材料として
検討した記載はなく、当然のことながら該化合物の非線
形光学活性については全く知られていない。On the other hand, various saccharin derivatives are known compounds, and their physiological activities and the like are being studied. However, there is no description of studying saccharin having a urea bond as an optical material, and, as a matter of course, there is no known nonlinear optical activity of the compound.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、高い非線形
光学効果を有し、かつ可視領域に吸収を持たない有機化
合物を提供することを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide an organic compound having a high nonlinear optical effect and having no absorption in the visible region.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、π電子共
役有機化合物が大きな非線形光学効果を有するという知
見に基づき、サッカリン誘導体の合成とその非線形光学
効果の測定を行ってきた。その結果、ある種の尿素結合
を有するサッカリン誘導体が高い非線形光学効果を有す
ることを見いだし本発明を完成するに至った。The present inventors have synthesized a saccharin derivative and measured the nonlinear optical effect based on the finding that a π-electron conjugated organic compound has a large nonlinear optical effect. As a result, they have found that a saccharin derivative having a certain urea bond has a high nonlinear optical effect, and have completed the present invention.
【０００７】すなわち、本発明は一般式〔Ｉ〕That is, the present invention provides a compound represented by the general formula [I]:
【０００８】[0008]
【化２】 で表されるサッカリン誘導体からなる非線形光学材料で
ある。Embedded image Is a nonlinear optical material comprising a saccharin derivative represented by
【０００９】本発明のサッカリン誘導体が高い非線形光
学活性を示す理由は明かではないが、例えば尿素結合に
置換した、塩素原子置換フェニル基及びサッカリン基に
よる効果的な分子内分極、及び反転対称性のない結晶構
造を有していることなどが考えられる。このことは、本
発明の化合物の類似化合物である、塩素原子を有しない
N’−(N’−フェニルカルバモイル)サッカリン等の非線
形光学活性は不活性であることからも推測できる。本発
明のサッカリン誘導体の製造方法は特に限定されず、如
何なる方法を用いてもよい。一般に好適に用いられる代
表的な製造方法としては、サッカリンとクロロフェニル
イソシアネートとを反応させることにより、目的とする
本発明のサッカリン誘導体を得ることができる。It is not clear why the saccharin derivatives of the present invention exhibit high non-linear optical activity. For example, effective intramolecular polarization by phenyl group and saccharin group substituted by urea bond, and inversion symmetry It is conceivable that it has no crystal structure. This means that it has no chlorine atom, which is an analog of the compound of the present invention.
The non-linear optical activity of N '-(N'-phenylcarbamoyl) saccharin and the like can be inferred from the fact that it is inactive. The method for producing the saccharin derivative of the present invention is not particularly limited, and any method may be used. Representative production method generally suitable for use in, by reacting a saccharin and chlorophenyl isocyanate, it is possible to obtain a service Kkarin derivative of the present invention of interest.
【００１０】[0010]
【発明の効果】本発明で提供するサッカリン誘導体は、
例えはＮｄ：YAGレーザー（１０６４ｎｍ）照射により
強い第二次高調波（５３２ｎｍの緑色光）を発生する。The saccharin derivative provided by the present invention is
For example, a strong second harmonic (green light of 532 nm) is generated by irradiation with an Nd: YAG laser (1064 nm).
【００１１】また、本発明で提供するサッカリン誘導体
は可視領域では透明な、無色の高融点の結晶である。す
なわち、本発明の化合物は単結晶としてだけでなく、フ
ィルム、ファイバー及び蒸着膜等種々の形態で使用する
ことができ、光波長変換素子、光スイッチング素子等の
素材用非線形光学材料として有用な化合物である。The saccharin derivative provided by the present invention is a colorless crystal having a high melting point which is transparent in the visible region. That is, the compound of the present invention can be used not only as a single crystal but also in various forms such as a film, a fiber, and a vapor-deposited film, and is a compound useful as a nonlinear optical material for a material such as an optical wavelength conversion element and an optical switching element. It is.
【００１２】[0012]
【実施例】以下製造例及び実施例により、本発明をさら
に具体的に説明するが、本発明はこれらの製造例及び実
施例に限定されるものではない。EXAMPLES The present invention will be described more specifically with reference to the following production examples and examples, but the present invention is not limited to these production examples and examples.
【００１３】製造例１ ナスフラスコにサッカリン（１．５ｇ）、３−クロロフ
ェニルイソシアネート(１．３ｇ)、及びエーテル（３０
ｍｌ）をいれ、５０℃にて2時間攪拌した。反応液を室
温に戻し、析出した固体をロ過しエーテルで洗浄した
後、乾燥することにより白色結晶のN−［N’−（３−ク
ロロフェニル)力ルバモイル］サッカリン（２．４ｇ）
を得た。収率は８６%であった。該化合物の融点は２２
９℃であり、化合物番号をＮｏ．１とする。Production Example 1 Saccharin (1.5 g), 3-chlorophenyl isocyanate (1.3 g), and ether (30
ml) and stirred at 50 ° C. for 2 hours. The reaction solution was returned to room temperature, and the precipitated solid was filtered, washed with ether, and dried to obtain white crystals of N- [N '-(3-chlorophenyl) caprubamoyl] saccharin (2.4 g).
I got The yield was 86%. The melting point of the compound is 22
9 ° C., and the compound number was No. Let it be 1.
【００１４】製造例２ ナスフラスコにサッカリン（１．５ｇ）、４−クロロフ
ェニルイソシアネート(１．３ｇ)、及びエーテル（３０
ｍｌ）をいれ、５０℃にて２時間攪拌した。反応液を室
温に戻し、析出した固体をロ過しエーテルで洗浄した
後、乾燥することにより白色結晶のN−[N’−(４−クロ
ロフェニル)カルバモイル]サッカリン（２．３ｇ）を得
た。収率は８４%であった。該化合物の融点は230℃であ
り、化合物番号をＮｏ．２とする。Production Example 2 Saccharin (1.5 g), 4-chlorophenylisocyanate (1.3 g), and ether (30
ml) and stirred at 50 ° C. for 2 hours. The reaction solution was returned to room temperature, the precipitated solid was filtered, washed with ether, and dried to obtain white crystals of N- [N '-(4-chlorophenyl) carbamoyl] saccharin (2.3 g). The yield was 84%. The melting point of the compound is 230 ° C., No. Compound No. Let it be 2.
【００１５】実施例1 製造例１及び２で合成した化合物を用いて、第２次高調
波発生（SHG）の測定を行った。該測定は、Ｋｕｒｔｚ
等により考案された粉末法の改良方法であり、単結晶が
発する高調波の強度を素早く、簡便に予測する方法であ
る。すなわち、光源には平均出力３．５WのQ−スイッチ
付きＮｄ：ＹＡＧレーザー(波長１０６４nm)のパルスを
用いた。レーザー光はレンズを通して集光し、ガラスに
挟んだ試料に、ガラス面に対して４５度の角度で入射し
た。発生した高調波は、ガラス面から５cmの距離におい
たＳＨ光のみを透過するフィルターを通して、フォトン
カウンティングヘッドにより検出した。尿素及び２−メ
チル−４−ニトロアニリンを標準試料としてＳＨＧを測
定し、尿素との強度比をもって試料の評価を行った。試
料の粉末には、メノウ乳鉢でできるかぎり均質に粉砕し
たものを使用した。その結果、化合物Ｎｏ．1のＳＨＧ
活性は尿素の５倍であり、化合物Ｎｏ．２のＳＨＧ活性
は尿素の４倍であった。Example 1 The compounds synthesized in Production Examples 1 and 2 were used to measure the second harmonic generation (SHG). The measurement was performed by Kurtz
It is a method of improving the powder method devised by the above-mentioned method and the like, and is a method of quickly and easily predicting the intensity of harmonics generated by a single crystal. That is, a pulse of an Nd: YAG laser (wavelength: 1064 nm) with a Q-switch having an average output of 3.5 W was used as a light source. The laser light was condensed through a lens and was incident on a sample sandwiched between glass at an angle of 45 degrees with respect to the glass surface. The generated harmonics were detected by a photon counting head through a filter that transmits only SH light at a distance of 5 cm from the glass surface. SHG was measured using urea and 2-methyl-4-nitroaniline as standard samples, and the samples were evaluated based on the intensity ratio with urea. As the powder of the sample, a powder crushed as homogeneously as possible in an agate mortar was used. As a result, Compound No. 1 SHG
The activity was 5 times that of urea, and Compound No. The SHG activity of 2 was 4 times that of urea.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 深谷 俊夫 茨木県つくば市東一丁目一番地 工業技 術院化学技術研究所内 (58)調査した分野(Int.Cl.6，ＤＢ名) G02F 1/35 504 C07D 333/42 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Toshio Fukaya Ichibanchi, Tsukuba, Ibaraki Pref. Industrial Research Institute, Institute of Chemical Technology (58) Field surveyed (Int.Cl. 6 , DB name) G02F 1/35 504 C07D 333/42 CA (STN) REGISTRY (STN)
Claims (1)
有機非線形光学材料。1. A compound of the general formula [I] An organic nonlinear optical material comprising a saccharin derivative represented by the following formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3094961A JP2995273B2 (en) | 1991-04-02 | 1991-04-02 | Organic nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3094961A JP2995273B2 (en) | 1991-04-02 | 1991-04-02 | Organic nonlinear optical material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04305629A JPH04305629A (en) | 1992-10-28 |
| JP2995273B2 true JP2995273B2 (en) | 1999-12-27 |
Family
ID=14124530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3094961A Expired - Lifetime JP2995273B2 (en) | 1991-04-02 | 1991-04-02 | Organic nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2995273B2 (en) |
-
1991
- 1991-04-02 JP JP3094961A patent/JP2995273B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04305629A (en) | 1992-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |