JPH0740105B2 - Non-linear optical element - Google Patents
Non-linear optical elementInfo
- Publication number
- JPH0740105B2 JPH0740105B2 JP5655586A JP5655586A JPH0740105B2 JP H0740105 B2 JPH0740105 B2 JP H0740105B2 JP 5655586 A JP5655586 A JP 5655586A JP 5655586 A JP5655586 A JP 5655586A JP H0740105 B2 JPH0740105 B2 JP H0740105B2
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- JP
- Japan
- Prior art keywords
- linear optical
- optical element
- och
- optical effect
- weight
- 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.)
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Description
【発明の詳細な説明】 〔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新規化合物及び
それらの新規化合物を含む非線形光学効果に優れた化合
物群を素子として用いることを特徴とする非線形光学素
子に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] The present invention is characterized by using a novel compound having an excellent nonlinear optical effect and a group of compounds having an excellent nonlinear optical effect including these novel compounds as an element. Non-linear optical element.
レーザー光等の光を物質に照射した時に生ずる二次、三
次等の高調波の発生、カー効果、パラメトリック発振等
の現象は非線形光学効果として知られている。Phenomena such as generation of secondary and tertiary harmonics, Kerr effect, and parametric oscillation that occur when a material is irradiated with light such as laser light are known as nonlinear optical effects.
この非線形光学効果は光の波長変換、強度変調等の効果
を有し、短波長レーザ光の発生、情報処理、光通信等に
応用されるものであり、従ってこれらの目的に適した優
れた非線形光学効果を有し、かつ耐久性に優れた素子材
料の開発が望まれている。This non-linear optical effect has effects such as wavelength conversion and intensity modulation of light, and is applied to the generation of short-wavelength laser light, information processing, optical communication, etc. Therefore, it is an excellent non-linear optical element suitable for these purposes. Development of an element material having an optical effect and excellent in durability is desired.
従来、いくつかの無機化合物、例えばリン酸二水素カリ
ウム（KDP）、ニオブ酸リチウム（LiNbO3）等が非線形
光学材料として用いられている。しかし、これら無機化
合物における非線形光学効果は顕著ではない。また、い
くつかの有機化合物、例えば尿素、２−メチル−４−ニ
トロアニリン（NMA）等は、無機化合物と比較して大き
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は光損傷の閾値が高くな
く、非線形光学材料としての問題点を有している。Conventionally, some inorganic compounds such as potassium dihydrogen phosphate (KDP) and lithium niobate (LiNbO 3 ) have been used as nonlinear optical materials. However, the nonlinear optical effect in these inorganic compounds is not remarkable. Also, some organic compounds, such as urea and 2-methyl-4-nitroaniline (NMA), are known to have a large non-linear optical effect as compared with inorganic compounds. However, these organic compounds do not have a high threshold for optical damage, and have a problem as a nonlinear optical material.
本発明者等は一群のベンゼン環を有する共役オレフィン
化合物が非線形光学効果を示し、かつ高い光損傷閾値を
有することを見出した。The present inventors have found that a conjugated olefin compound having a group of benzene rings exhibits a non-linear optical effect and has a high photodamage threshold.
本発明者等は、この発見に基づきカルボニル基を共役系
に有する非対称な共役オレフィン化合物の一群、即ちカ
ルコンを合成し、その非線形光学効果を評価した。その
結果、一群のカルコンが高い非線形光学効果を有するこ
とを見出し、本発明を完成するに至った。Based on this finding, the present inventors synthesized a group of asymmetric conjugated olefin compounds having a carbonyl group in a conjugated system, that is, chalcone, and evaluated its nonlinear optical effect. As a result, they have found that a group of chalcones have a high nonlinear optical effect, and completed the present invention.
即ち本発明は、下記の一般式（Ｉ） （但し式中、X1,X2,Y1,Y2は各々 X1＝−OCH3,−OH X2＝−OCH3 Y1＝Ｈ又は−NO2,−Cl Y2＝Ｈ又は−OCH3,−Cl の中から選ばれた基を示す。） で示される非線形光学効果を有するカルコン化合物、及
び下記一般式（Ｉ） （但し式中、X1,X2,Y1,Y2は各々 X1＝−OCH3,−OH X2＝−OCH3 Y1＝Ｈ又は−NO2,−Cl Y2＝Ｈ又は−OCH3,−Cl の中から選ばれた基を示す。） で示されるカルコン化合物の結晶からなり、その非線形
光学効果を利用する非線形光学素子を提供するものであ
る。That is, the present invention provides the following general formula (I) (In the formula, X 1 , X 2 , Y 1 , and Y 2 are respectively X 1 = -OCH 3 , -OH X 2 = -OCH 3 Y 1 = H or -NO 2 , -Cl Y 2 = H or-. A group selected from OCH 3 and —Cl), and a chalcone compound having a nonlinear optical effect represented by the following general formula (I) (In the formula, X 1 , X 2 , Y 1 , and Y 2 are respectively X 1 = -OCH 3 , -OH X 2 = -OCH 3 Y 1 = H or -NO 2 , -Cl Y 2 = H or-. A group selected from OCH 3 and —Cl 2) is formed, and a non-linear optical element utilizing the non-linear optical effect thereof is provided.
以下本発明を実施例について説明する。まず、本発明の
新規なカルコン化合物の合成例を示す。The present invention will be described below with reference to examples. First, a synthesis example of the novel chalcone compound of the present invention will be shown.
本発明に規定する非線形光学効果を有するカルコン化合
物は以下に示す方法により合成、精製した。The chalcone compound having a nonlinear optical effect defined in the present invention was synthesized and purified by the method shown below.
合成例 １ ２′,4,4′−トリメトキシカルコンは、４−メトキシベ
ンズアルデヒド1.4重量部と、２′,4′−ジメトキシア
セトフェノン1.8重量部をエタノール中において水酸化
ナトリウムを触媒とする公知の方法で合成した（Kauffm
ann et al.,Chem.Ber.,46,3796（1913））。得られた粗
結晶はエタノールより再結晶し、融点88℃の粉末結晶1.
6重量部を得た。Synthesis example 1 2 ', 4,4'-Trimethoxychalcone was synthesized by a known method using 1.4 parts by weight of 4-methoxybenzaldehyde and 1.8 parts by weight of 2', 4'-dimethoxyacetophenone in ethanol using sodium hydroxide as a catalyst. (Kauffm
ann et al., Chem. Ber., 46 , 3796 (1913)). The obtained crude crystals were recrystallized from ethanol and powder crystals with a melting point of 88 ° C 1.
6 parts by weight were obtained.
合成例 ２ ２′,4′−ジメトキシ−３−ニトロカルコンは、２′,
4′−ジメトキシアセトフェノン1.8重量部と３−ニトロ
ベンズアルデヒド1.5重量部を用い、公知の手順で合成
した（松岡，日本化学雑誌，80,61（1959））。Synthesis example 2 2 ', 4'-dimethoxy-3-nitrochalcone is 2',
It was synthesized by a known procedure using 1.8 parts by weight of 4'-dimethoxyacetophenone and 1.5 parts by weight of 3-nitrobenzaldehyde (Matsuoka, Nippon Kagaku Shimbun, 80 , 61 (1959)).
反応生成物を水中に注ぎ、生じた沈澱生成物を濾過した
後、エタノールより再結晶することにより融点153〜154
℃の粉末を37％の収率で得た。The reaction product was poured into water, and the resulting precipitated product was filtered and then recrystallized from ethanol to give a melting point of 153-154.
C powder was obtained with a yield of 37%.
合成例 ３ ２′,4′−ジメトキシ−３−クロロカルコンは、２′,
4′−ジメトキシアセトフェノン1.0重量部と、３−クロ
ロベンズアルデヒド1.0重量部を20重量部のエタノール
に溶解し、水酸化バリウム８水塩を1.0重量部加え、55
〜60℃で15分間撹拌した。得られた生成物を水中に注
ぎ、沈澱物を濾過する。粗結晶を希塩酸で洗浄すること
により、融点79〜80℃の微結晶を51％の収率で得た。Synthesis example 3 2 ', 4'-dimethoxy-3-chlorochalcone is 2',
1.0 parts by weight of 4'-dimethoxyacetophenone and 1.0 parts by weight of 3-chlorobenzaldehyde were dissolved in 20 parts by weight of ethanol, and 1.0 part by weight of barium hydroxide octahydrate was added.
Stir for 15 minutes at ~ 60 ° C. The product obtained is poured into water and the precipitate is filtered. The crude crystals were washed with diluted hydrochloric acid to obtain fine crystals with a melting point of 79-80 ° C in a yield of 51%.
合成例 ４ ２′−ヒドロキシ−４′−メトキシ−４−クロロカルコ
ンは、４−クロロ−２′,4′−ジメトキシカルコン1.0
重量部を20重量部の48％臭化水素酸中に懸濁させ、15〜
20分間加熱還流して得た。Synthesis example 4 2'-Hydroxy-4'-methoxy-4-chlorochalcone is 4-chloro-2 ', 4'-dimethoxychalcone 1.0
Parts by weight in 20 parts by weight of 48% hydrobromic acid,
It was obtained by heating under reflux for 20 minutes.
同様な方法で反応する他の化合物、例えば ２′−ヒドロキシカルコン等の合成が可能である。Other compounds that react in a similar manner, such as It is possible to synthesize 2'-hydroxychalcone and the like.
冷却後、生成した粗結晶を濾過、水洗し、エタノールか
ら再結晶する。反応収率は55％、融点は125〜126℃であ
った。After cooling, the generated crude crystals are filtered, washed with water and recrystallized from ethanol. The reaction yield was 55%, and the melting point was 125 to 126 ° C.
第１図に非線形光学効果のうちの一種である高調波発生
効率の測定法を示す。これはKurtz等によって考案され
た測定法（参考文献;J.Appl.Phys.,39,2,3798（196
8））の改良法であり、結晶の有する高調波発生効率を
微細結晶である粉末を用いて測定する簡便法である。第
１図において光源１は繰り返し速度10Hz、パルス幅10n
s、ピーク出力10MW、波長1.06μｍのNd:YAGレーザーで
ある。レーザー光はフィルター７を用いて減光した後、
試料２を置いた衝立に垂直に入射した。この測定法にお
いては、粉末試料を用いているため乱反射の効率によ
り、単結晶を用いた場合と異なって、発生した高調波は
全方向に拡がる。この高調波を入射光に対して45゜、試
料から50cmの位置においた分光器３に入射する。この
時、集光レンズ４を用いて高調波を分光器のスリット位
置に集光した。分光器を通すことにより、基本波と高調
波とを分離し、またその波長から二次高調波と三次高調
波とを確認した。光強度は、分光器の出射スリット位置
に取り付けた光電子増倍管５で検出し、その電気信号の
強度をオシロスコープ６に出力することにより観測し
た。多結晶状態の試料は乳鉢で均一な粉末となるように
砕いた。入射光強度の変動が見掛け上の高調波変換効率
に影響を与えないよう、入射光強度をモニターしながら
補正処理を行った。FIG. 1 shows a method of measuring the harmonic generation efficiency, which is one of the nonlinear optical effects. This is a measurement method devised by Kurtz et al. (Reference; J. Appl. Phys., 39, 2 , 3798 (196
It is an improved method of 8)) and is a simple method to measure the harmonic generation efficiency of a crystal by using a fine crystal powder. In Fig. 1, the light source 1 has a repetition rate of 10 Hz and a pulse width of 10 n.
s, peak output 10 MW, wavelength 1.06 μm Nd: YAG laser. After the laser light is dimmed using the filter 7,
The sample 2 was vertically incident on the screen. In this measuring method, since a powder sample is used, the generated harmonic waves spread in all directions due to the efficiency of diffuse reflection, unlike the case of using a single crystal. The higher harmonic wave is incident on the spectroscope 3 at a position of 45 ° with respect to the incident light and 50 cm from the sample. At this time, the harmonics were condensed at the slit position of the spectroscope using the condenser lens 4. The fundamental wave and the harmonics were separated by passing through a spectroscope, and the second harmonic and the third harmonic were confirmed from the wavelengths. The light intensity was detected by the photomultiplier tube 5 attached to the exit slit position of the spectroscope, and the intensity of the electric signal was output to the oscilloscope 6 for observation. The polycrystalline sample was crushed in a mortar to give a uniform powder. The correction process was performed while monitoring the incident light intensity so that the fluctuation of the incident light intensity does not affect the apparent harmonic conversion efficiency.
高調波変換効率の絶対値を粉末法の結果より求めること
は困難であるため、よく研究されている尿素を標準とし
て用い、それとの相対値として評価した。Since it is difficult to obtain the absolute value of the harmonic conversion efficiency from the results of the powder method, urea, which has been well studied, was used as a standard and evaluated as a relative value.
測定結果の例を第１表に示す。Table 1 shows an example of the measurement results.
第１表に示すように、実施例で示した一連の化合物は、
従来用いられている非線形物質であるリン酸二水素カリ
ウム（KDP）と比較し、100倍の変換効率を示すことがわ
かった。 As shown in Table 1, the series of compounds shown in the examples are
It was found that the conversion efficiency was 100 times higher than that of potassium dihydrogen phosphate (KDP), which is a conventionally used nonlinear substance.
本発明の非線形光学素子は、従来の材料と比較し、第二
高調波変換効率が約100倍であることにより、従来の材
料の1/100の大きさで従来と同等の波長変換素子が可能
となり、光演算素子のマイクロチップ化が可能となる等
の極めて優れた効果を奏する。The non-linear optical element of the present invention has a second harmonic conversion efficiency that is about 100 times that of conventional materials, which makes it possible to use wavelength conversion elements that are 1/100 the size of conventional materials and equivalent to conventional ones. Therefore, it is possible to obtain an extremely excellent effect such as making the optical operation element into a microchip possible.
第１図は実施例に使用した非線形光学効果測定装置の概
略図、第２図はこの試料部分の拡大図である。 １……光源Nd:YAGレーザー ２……試料粉末 ３……分光器 ４……集光レンズ ５……光電子増倍管 ６……オシロスコープ ７……フィルターFIG. 1 is a schematic view of a non-linear optical effect measuring device used in Examples, and FIG. 2 is an enlarged view of this sample portion. 1 …… Light source Nd: YAG laser 2 …… Sample powder 3 …… Spectroscope 4 …… Condenser lens 5 …… Photomultiplier tube 6 …… Oscilloscope 7 …… Filter
Claims (1)
合物の結晶からなり、その非線形光学効果を利用する非
線形光学素子。 （但し式中、X1,X2,Y1,Y2は各々 X1＝−OCH3,−OH X2＝−OCH3 Y1＝Ｈ又は−NO2,−Cl Y2＝Ｈ又は−OCH3,−Cl の中から選ばれた基を示す。）1. A non-linear optical element comprising a crystal of a chalcone compound represented by the following general formula (I) and utilizing its non-linear optical effect. (In the formula, X 1 , X 2 , Y 1 , and Y 2 are respectively X 1 = -OCH 3 , -OH X 2 = -OCH 3 Y 1 = H or -NO 2 , -Cl Y 2 = H or-. A group selected from OCH 3 and -Cl is shown.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5655586A JPH0740105B2 (en) | 1986-03-14 | 1986-03-14 | Non-linear optical element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5655586A JPH0740105B2 (en) | 1986-03-14 | 1986-03-14 | Non-linear optical element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6323136A JPS6323136A (en) | 1988-01-30 |
| JPH0740105B2 true JPH0740105B2 (en) | 1995-05-01 |
Family
ID=13030356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5655586A Expired - Lifetime JPH0740105B2 (en) | 1986-03-14 | 1986-03-14 | Non-linear optical element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0740105B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0833562B2 (en) * | 1987-07-23 | 1996-03-29 | 日本油脂株式会社 | Non-linear optical material |
| DE3889723T2 (en) * | 1987-07-23 | 1994-09-08 | Nippon Oils & Fats Co Ltd | NON-LINEAR OPTICAL MATERIAL. |
| JPH02176633A (en) * | 1988-12-28 | 1990-07-09 | Nippon Oil & Fats Co Ltd | Organic nonlinear optical element |
| AU2012222074A1 (en) * | 2011-02-25 | 2013-09-12 | National Institutes Of Health | Chalcone derivatives as Nrf2 activators |
| CN112870363B (en) * | 2021-04-03 | 2022-02-18 | 兰州大学第一医院 | Application of human PCID2 protein in preparation or screening of antitumor drugs and compound with antitumor activity |
-
1986
- 1986-03-14 JP JP5655586A patent/JPH0740105B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6323136A (en) | 1988-01-30 |
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