JPH0355528A - Novel organic nonlinear optical material and method for converting light wavelength by using this material - Google Patents
Novel organic nonlinear optical material and method for converting light wavelength by using this materialInfo
- Publication number
- JPH0355528A JPH0355528A JP19162689A JP19162689A JPH0355528A JP H0355528 A JPH0355528 A JP H0355528A JP 19162689 A JP19162689 A JP 19162689A JP 19162689 A JP19162689 A JP 19162689A JP H0355528 A JPH0355528 A JP H0355528A
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- Prior art keywords
- nonlinear optical
- optical material
- compound
- acid adduct
- nonlinear
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Links
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- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 150000001787 chalcogens Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 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
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- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical class C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
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。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a nonlinear optical material suitable for use in various elements that utilize nonlinear optical effects, such as wavelength conversion elements. The present invention also relates to a method of converting optical 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
一を有した材料が注目を集めている。(Prior Art) In recent years, materials that have a nonlinear optical effect--a nonlinearity between polarization and electric field that appears when a strong optical electric field such as that of a laser beam is applied have 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。”Ｎ
ｏｎｌｉｎｅｒ Ｏｐｔｉｃａｌ Ｐｒｏｐｅｒｔｉｅ
ｓ ｏｆＯｒｇａｎｉｃ ａｎｄ Ｐｏｌｙｍｅｒｉｃ
Ｍａｔｅｒｉａｌ” ＡＣＳ ＳＹＭＰＯＳＩＵＭＳ
ＥＲＩＥＳ ２ ３ ３ Ｄａｖｉｄ Ｊ．Ｗｉｌ
ｌｉａｍｓ編（ＡｍｅｒｉｃａｎＣｈｅｍｉｃａｌ Ｓ
ｏｃｉｅｔｙ， １ ９ ８ ３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 nonlinear optical materials and are described in detail in, for example: ”N
onliner Optical Property
s of Organic and Polymeric
Material” ACS SYMPOSIUMS
ERIES 2 3 3 David J. Will
liams (American Chemical S
``Organic Nonlinear Optical Materials'' supervised by Masao Kato and Hachiro Nakanishi (CMC, published in 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。One of the applications of nonlinear optical materials is second harmonic generation (SHG) based on second-order nonlinear effects and wavelength conversion devices using sum frequency and difference frequency.
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べロプスカイト類である。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
れるようになった。The materials that have been practically used so far are inorganic velopskites represented by lithium niobate. However, in recent years, π containing an electron donating group and an electron withdrawing group has been developed.
Electronically conjugated organic compounds greatly exceed the aforementioned inorganic materials.
It has become known that it has various properties as a nonlinear optical material.
従って、この材料に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。Therefore, as an organic compound exhibiting a nonlinear optical response to be used in this material, the higher the nonlinear susceptibility in the molecular state, the more desirable it is.
しかしながら、２次の非線形光学材料として有用である
には、分子状態での性能のみでは不十分であり、集合状
態での分子配列に反転対称性の無いことが必須である。However, in order to be useful as a second-order nonlinear optical material, performance in the molecular state alone is insufficient, and it is essential that the molecular arrangement in the aggregate state has no inversion symmetry.
しかるに現状では分子配列を予測することは極めて困難
であり、また全有機化合物中での存在確率も高いもので
はない。However, currently it is extremely difficult to predict the molecular arrangement, and the probability of its existence among all organic compounds is not high.
（発明が解決しようとする課題）
従って本発明の第一の目的は、高い非線形応答性を示す
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) Therefore, the first object of the present invention is to provide an organic nonlinear optical material that exhibits high nonlinear responsiveness. The second purpose is to provide a method that utilizes the response related to optical wavelength conversion among 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、メソイオン化合
物又″はその酸付加物、好ましくは下記一般式（Ｉ）で
表わされる化合物又はそれらの酸付加物を非線形光学応
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 extensive research, the present inventors have found that a mesoionic compound or an acid adduct thereof, preferably a compound represented by the following general formula (I) or an acid adduct thereof. It has been found that the object of the present invention can be achieved by using as a nonlinear optically responsive compound.
一般式（Ｉ）
Ｒ３
（式中、
Ｘはカルコゲン原子又はＮ−Ｒ’
を表
わす。Ｒｌ 、Ｒｔ ，Ｒ＊は水素原子、アルキル基、
アリール基、を表わし、Ｒ１とＲ２とで環を形威しても
よい。Ｒ４はアリール基を表わす。）メソイオン化合物
は、シドノン（ａ）に代表される化合物群であり
シドノンなどのオキサジアゾール系化合物の他、オキサ
トリアゾール系化合物、チアゾール系化合物、ジチオー
ル系化合物などのオキソ型メソイオン化合物、シドノン
イミン系化合物、チアゾール系化合物、ジチオール系化
合物、などが知られており、これらに関しては、太田正
樹、加藤博著；日本化学雑誌、第８６巻、第７号、６６
１〜６７３頁に詳しい。General formula (I) R3 (wherein, X represents a chalcogen atom or N-R'. Rl, Rt, R* are hydrogen atoms, alkyl groups,
represents an aryl group, and R1 and R2 may form a ring. R4 represents an aryl group. ) Meso ion compounds are a group of compounds represented by sydone (a), and include oxadiazole compounds such as sydone, as well as oxo-type meso ion compounds such as oxatriazole compounds, thiazole compounds, and dithiol compounds, and sydone imine compounds. , thiazole compounds, dithiol compounds, etc. are known, and these are described in Masaki Ota and Hiroshi Kato; Nippon Kagaku Zasshi, Vol. 86, No. 7, 66.
Details on pages 1-673.
また一般式（Ｉ）で表わされるものの例を以下に示す。Further, examples of those represented by general formula (I) are shown below.
化合物１
化合物２
化合物３
化合物４
化合物５
化合物６
化合物７
化合物８
化合物９
ＣＨ．
Ｃ．Ｈ，
ＣＨ．
化合物ｌ３
化合物１４
１
ＣＨＩ
ｌ
ＣＨ，
ｌ
ＣＨ．
化合物１７
化合物１８
化合物ｌ９
化合物２０
ＣＨ．
１
ＣＨ．
Ｃ．Ｈ．
化合物２ｌ
Ｃ
．Ｈ２．
化合物２２
これらの化合物の合成は、前記の太田らの文献を参照し
て行なうことができる。Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 Compound 7 Compound 8 Compound 9 CH. C. H, CH. Compound 13 Compound 14 1 CHI l CH, l CH. Compound 17 Compound 18 Compound 19 Compound 20 CH. 1 CH. C. H. Compound 2l C. H2. Compound 22 These compounds can be synthesized with reference to the aforementioned document by Ota et al.
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。As will be clear from the Examples described below, the nonlinear optical material of the present invention is particularly useful as a material for wavelength conversion.
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つ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、光フリップフロップ回路等）、光変
調素子および位相共役光学素子等が挙げられる。However, the application of the nonlinear optical material of the present invention is not limited to wavelength conversion elements, but can be used for any element that utilizes nonlinear optical effects. Specific examples of optical elements using the nonlinear optical material of the present invention include optical bistable elements (optical storage elements,
Examples include optical pulse waveform control elements, optical limiters, differential amplification elements, optical transistors, A/D conversion elements, optical logic elements, optical multivibrators, optical flip-flop circuits, etc.), optical modulation elements, and phase conjugate optical elements.
本発明の化合物は、例えば粉末の形、宿主格子（ボリマ
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・プロジ
ェット膜など）、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 of the invention may be present, for example, in the form of a powder, in the form of molecular inclusions in a host lattice (bolimers, clathrates, solid solutions, liquid crystals), in the form of thin layers deposited on a support (Langmeer-Prodgett membranes), etc. It can be used as a nonlinear optical material in various forms such as single crystal form, solution form, etc.).
また本発明の化合物をペンダントの形でポリマー、ボリ
ジアセチレンなどに結合させて用いることもできる。The compound of the present invention can also be used in the form of a pendant bonded to a polymer, boridiacetylene, or the like.
これらの方法について詳しくは前述のＤ．Ｊ．Ｗｉｌｌ
ｉａｍｓ編の著作などに記載されている。For details on these methods, see D. above. J. Will
It is described in the works edited by Iams.
（実施例） 次に、本発明を実施例に基づいて詳しく説明する。(Example) Next, the present invention will be explained 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
， Ｋｕｒｔｚ）、ティー・ティー・ペリー（Ｔ． Ｔ
． Ｐｅｒｒｙ）著、ジャーナル オブ アプライド
フィジックス（Ｊ．Ａｐｐｌ．Ｐｈｙｓ．） ３ ９巻
、３７９８頁（１’９６８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った。Example Measurement of second harmonic generation was carried out by S.K. Kurz (S, K.
, Kurtz), T.T. Perry (T.T.
．． Perry), Journal of Applied
The test was carried out on the powder of the compound of the present invention according to the method described in J. Appl. Phys., Volume 3, 9, Page 3798 (published in 1'968).
第１図に示した装置により測定を行った。Measurements were carried out using the apparatus shown in FIG.
すなわち、測定は、バルスＹＡＧレーザー光（λ＝１，
０６４μｍ１ビーム径＃１叩φ、ビークハワ−＝ １
０ Ｍｗ／ｃｎｆ） ’ｊｒ：基本波ニ用イ、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。That is, the measurement is performed using pulsed YAG laser light (λ=1,
064 μm 1 beam diameter #1 stroke φ, beak height = 1
0 Mw/cnf) 'jr: Fundamental wave A. The intensity of the second harmonic was measured using the evaluation device shown in FIG.
測定は、尿素の第２高調波の強度との相対比較で行った
。また強度が弱い場合には目視による観測を行った。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主目
的であり、その強度比は比線形性の大きさの、参考値で
ある。The measurement was performed by relative comparison with the intensity of the second harmonic of urea. In addition, when the intensity was weak, visual observation was performed. In particular, in order to distinguish between the light emission (mainly yellow and red light emission) caused by two-photon absorption of the fundamental wave and the second harmonic, a spectrometer is installed.
Only the second harmonic was measured. Furthermore, the main purpose of powder method measurement is to determine the presence or absence of nonlinearity in the substance, and the intensity ratio is a reference value for the magnitude of specific linearity.
結果を表１に示した。The results are shown in Table 1.
（発明の効果）
これら粉末法により、ＳＨＧ活性を示した化合物は下記
に示す方法により、波長変換素子としての使用が可能で
ある。(Effects of the Invention) Compounds that exhibit SHG activity by these powder methods can be used as wavelength conversion elements by the method described below.
１．ファイバーのコア部分に上記化合物を単結晶化し、
クラッド材料としてガラスを用いた波長変換素子を作威
し、ＹＡＧレーザー光を入力しその第二高調波の発生が
可能である。さらに、他の方法として同様にして、導波
路型の波長変換素子を作成し、第二高調波の発生が可能
である。この時の位相整合方法には、チェレンコフ放射
方式を用いた。ただし、これらに限定されるだけでなく
、導波一導波の位相整合も可能である。波長変換波は第
二高調波に限定されるでけでなく、第三高調波、和およ
び差周波発生にも用いられる。1. The above compound is single-crystalized in the core part of the fiber,
It is possible to create a wavelength conversion element using glass as the cladding material, input YAG laser light, and generate its second harmonic. Furthermore, as another method, it is possible to create a waveguide type wavelength conversion element in the same manner and generate the second harmonic. The Cerenkov radiation method was used as the phase matching method at this time. However, the present invention is not limited to these, and phase matching between waveguides is also possible. Wavelength converted waves are not only limited to second harmonics, but can also be used for third harmonic, sum and difference frequency generation.
２．次に上記化合物を単結晶化し、そこからバルクの単
結晶を切り出し、ＹＡＧレーザー光を入力しその第二高
調波の発生が可能である。この時の位相整合方法には角
度位相整合を用いた。これらの、バルク単結晶はレーザ
ーのキャビティ外で用いられるだけでなく、ＬＤ励起固
体レーザー等の固体レーザーのキャビティ内で用いる事
で、波長変換効率を高めることが出来る。さらには、外
部共振器型のＬＤの共振器内に配置することでも、波長
変換効率を高めることが出来る。2. Next, the above compound is made into a single crystal, a bulk single crystal is cut out from the single crystal, and a YAG laser beam is input to generate the second harmonic. Angular phase matching was used as the phase matching method at this time. These bulk single crystals can be used not only outside the laser cavity, but also within the cavity of a solid-state laser such as an LD-pumped solid-state laser, thereby increasing the wavelength conversion efficiency. Furthermore, the wavelength conversion efficiency can also be increased by placing it within the resonator of an external resonator type LD.
以上の単結晶化には、ブリッジマン法、溶媒蒸発法等が
用いられる。The Bridgman method, solvent evaporation method, etc. are used for the above single crystallization.
波長変換波は第二高調波に限定されるだけでなく、第三
高調波、和差周波発生にも用いられる。The wavelength-converted wave is not limited to second harmonics, but can also be used to generate third harmonics and sum-difference frequencies.
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。Figure 1 shows a powder method measuring device, and the numbers in the figure indicate the following.
Claims (2)
形光学材料。(1) A nonlinear optical material consisting of a mesoionic compound or its acid adduct.
式（ I ）で表わされる化合物又はその酸付加物である
請求項（１）記載の非線形光学材料。 一般式（ I ） ▲数式、化学式、表等があります▼ （式中、Ｘはカルコゲン原子又はＮ−Ｒ＾４を表わす。 Ｒ＾１、Ｒ＾２、Ｒ＾３は水素原子、アルキル基、アリ
ール基、を表わし、Ｒ＾１とＲ＾２とで環を形成しても
よい。Ｒ＾４はアリール基を表わす。）（３）レーザー
光と非線形光学材料とを用いて光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) The nonlinear optical material according to claim (1), wherein the mesoionic compound or its acid adduct is a compound represented by the following general formula (I) or its acid adduct. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X represents a chalcogen atom or N-R^4. R^1, R^2, R^3 are hydrogen atoms, alkyl groups, aryl group, and R^1 and R^2 may form a ring. R^4 represents an aryl group.) (3) Conversion of optical wavelength using laser light and nonlinear optical material A method of converting light wavelength using the organic nonlinear optical material according to claim 1 as a nonlinear optical material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1191626A JP2729673B2 (en) | 1989-07-25 | 1989-07-25 | 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 |
|---|---|---|---|
| JP1191626A JP2729673B2 (en) | 1989-07-25 | 1989-07-25 | Novel organic nonlinear optical material and method of converting light wavelength using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0355528A true JPH0355528A (en) | 1991-03-11 |
| JP2729673B2 JP2729673B2 (en) | 1998-03-18 |
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ID=16277774
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1191626A Expired - Fee Related JP2729673B2 (en) | 1989-07-25 | 1989-07-25 | Novel organic nonlinear optical material and method of converting light wavelength using the same |
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| Country | Link |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01185527A (en) * | 1988-01-19 | 1989-07-25 | Ricoh Co Ltd | nonlinear optical materials |
| JPH02503481A (en) * | 1988-03-12 | 1990-10-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Zwitterionic NLO chromophore |
-
1989
- 1989-07-25 JP JP1191626A patent/JP2729673B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01185527A (en) * | 1988-01-19 | 1989-07-25 | Ricoh Co Ltd | nonlinear optical materials |
| JPH02503481A (en) * | 1988-03-12 | 1990-10-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Zwitterionic NLO chromophore |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2729673B2 (en) | 1998-03-18 |
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