JPS63216033A - Organic nonlinear optical material - Google Patents
Organic nonlinear optical materialInfo
- Publication number
- JPS63216033A JPS63216033A JP4871387A JP4871387A JPS63216033A JP S63216033 A JPS63216033 A JP S63216033A JP 4871387 A JP4871387 A JP 4871387A JP 4871387 A JP4871387 A JP 4871387A JP S63216033 A JPS63216033 A JP S63216033A
- Authority
- JP
- Japan
- Prior art keywords
- nonlinear optical
- optical material
- group
- organic nonlinear
- org
- 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.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 39
- 239000000463 material Substances 0.000 title claims abstract description 27
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 230000004044 response Effects 0.000 abstract description 5
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 238000012546 transfer Methods 0.000 abstract description 3
- 230000021615 conjugation Effects 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 230000007547 defect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- -1 ethyl-hydroxyethylamino group Chemical group 0.000 description 2
- 230000015654 memory Effects 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- KAJALVWKFPQZOO-UHFFFAOYSA-N (4-azaniumylphenyl)-ethyl-(2-hydroxyethyl)azanium;sulfate Chemical compound OS(O)(=O)=O.OCCN(CC)C1=CC=C(N)C=C1 KAJALVWKFPQZOO-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LKZPHJNKIKZCMQ-UHFFFAOYSA-N 2-nitro-3-(2-phenylethenyl)aniline Chemical compound NC1=CC=CC(C=CC=2C=CC=CC=2)=C1[N+]([O-])=O LKZPHJNKIKZCMQ-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- 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、光双安定素子などの非線形光学素子用素材と
して有用な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 useful as a material for nonlinear optical elements such as optical bistable elements.
三次の非線形光学材料は、第三高調波発生（以下、ＴＨ
Ｇと略す）による周波数変換機能を有しているほか、光
双安定現象を利用した元スイッチ、元メモリへの応用な
どが可能であるため、将来の光素子の中心素材として、
活発な研究開発が進められている。なかでも、有機非線
形光学材料は、（１１ＫＤＰ−ＬｉＮｂＯｓ ！どの無
機強誘電体結晶に比べ、非線形光学定数が大きい、（２
）ガリウムーヒ素などの無機半導体に比べ応答速度が速
い、（３）高速応答・室温動作が確認されている塩化第
一銅（ＣｕＣｔ）では困難なμｍオーダーの薄膜化が容
易なこと、など従来の材料では同時に満たされることの
なかった要求条件をすべて満足する可能性全稈めており
、活発な材料探索が進められている。Third-order nonlinear optical materials are used for third-harmonic generation (hereinafter referred to as TH).
In addition to having a frequency conversion function (abbreviated as G), it can also be applied to original switches and original memories using the optical bistable phenomenon, so it will be used as a central material for future optical devices.
Active research and development is underway. Among them, organic nonlinear optical materials include (11KDP-LiNbOs!), which has a large nonlinear optical constant compared to any inorganic ferroelectric crystal.
) It has a faster response speed than inorganic semiconductors such as gallium-arsenide, and (3) It is easy to make thin films on the μm order, which is difficult to do with cuprous chloride (CuCt), which has been confirmed to have high-speed response and room temperature operation. There is every possibility of satisfying all of the requirements that have not been met simultaneously with other materials, and active material searches are underway.
現在、三次の効果の大きい有機非線形元学材料ハ、■ポ
リジアセチレン〔特に、ＰＴＳ：２゜４−へキサジイン
−１，６−ビス（ｐ−トルエンスルホナート）〕、ポリ
アセチレンに代表されるπ共役高分子系と、■アミノニ
トロスチルベン（特に、ＤＥＡＮＳ ： Ｎ、Ｎ−ジエ
チル−４−アミノ−４′−二トロスチルベン）に代表さ
れる、ドナー・アクセプターを非対称に置換した低分子
系の２種に分類できる０
〔発明が解決しようとする問題点〕
■のπ共役高分子系の非線形性は、価電子帯の自由電子
の分極を根源としているため、無機半導体と極めて類似
した欠点、すなわち、狭いバンドギャップに基づい念共
鳴効果による応答速度の低下から逃れられない。■ドナ
ー・アクセプター非対称置換低分子系は、現状（ＤＥＡ
ＮＳ）以上に効果を大きくしようとすると分子内電荷移
動による吸収帯の長波長化によって、■と同様の欠点を
露呈する０更に、結晶が非対称中心構造をとるものの一
部は、二次効果の混在によって、非線形動作の信頼性に
問題を生じる。At present, organic nonlinear materials with large third-order effects are being developed. There are two types: high-molecular systems and low-molecular systems in which the donor and acceptor are asymmetrically substituted, such as (1) aminonitrostilbene (especially DEANS: N,N-diethyl-4-amino-4'-nitrostilbene). 0 [Problems to be Solved by the Invention] The nonlinearity of the π-conjugated polymer system in (2) is rooted in the polarization of free electrons in the valence band, so it has drawbacks that are very similar to those of inorganic semiconductors, namely: Due to the narrow bandgap, it is impossible to escape from a decrease in response speed due to the telephonic resonance effect. ■ Donor-acceptor asymmetrically substituted low-molecular systems are currently available (DEA
If you try to make the effect larger than NS), the wavelength of the absorption band will become longer due to intramolecular charge transfer, exposing the same drawbacks as in ■0.Furthermore, some of the crystals with an asymmetric center structure are affected by secondary effects. The mixture causes problems with the reliability of nonlinear operation.
本発明の目的は、上記従来技術の欠点を克服し、高速・
高効率の光非線形応答を示す有機非線形光学材料を提供
することにある０
〔問題点を解決するための手段〕
本発明を概説すれば、本発明は有機非線形光学材料に関
する発明であって、下記一般式ｌ：（ただし、Ｄは電子
供与性基を示す）で表されることを特徴とする０
本発明による有機非線形光学材料の主要な特徴は、吸収
の長波長化全抑制して応答速度の低下を防いでいる上に
、従来になく大きな三次の非線形光学効果を有する点で
ある。これは、非線形光学効果を太きくしようとすると
、を共役の拡大や電荷移動の増大による吸収の長波長化
を伴うという従来技術の欠点を、比較的長いπ共役系（
２２「電子系のテレフタル−ビス−アニリン： ＴＢＡ
）の分子両端に、ドナー性の強い分極基金対称置換する
ことによって解決したものである。The purpose of the present invention is to overcome the drawbacks of the above-mentioned prior art, and to
An object of the present invention is to provide an organic nonlinear optical material exhibiting highly efficient optical nonlinear response. The organic nonlinear optical material according to the present invention is characterized by being represented by the general formula l: (wherein D represents an electron-donating group). This feature not only prevents a decrease in the optical density but also has a larger third-order nonlinear optical effect than ever before. This eliminates the drawback of the conventional technology that attempting to increase the nonlinear optical effect results in longer absorption wavelengths due to conjugation expansion and charge transfer.
22 “Electronic terephthal-bis-aniline: TBA
) was solved by symmetrically substituting polarized funds with strong donor properties at both ends of the molecule.
本発明の有機非線形光学材料は、従来から報告例のある
ようなドナー・アクセプターを非対称に置換した低分子
系とは異なり、基底状態での分極が小さい上、励起状態
の電子雲が対称中心構造をとることに特徴がある。した
がって、本発明の有機非線形光学材料は本質的には二次
の非線形光学効果を発現しない材料であるから、二次の
非線形光学効果の混在によって、非線形光学素子の動作
が影響を受けることもない。The organic nonlinear optical material of the present invention differs from conventionally reported low-molecular-weight systems in which donors and acceptors are asymmetrically substituted.In addition, the polarization in the ground state is small, and the electron cloud in the excited state has a symmetric center structure. It is characterized by taking Therefore, since the organic nonlinear optical material of the present invention is essentially a material that does not exhibit a second-order nonlinear optical effect, the operation of the nonlinear optical element will not be affected by the presence of the second-order nonlinear optical effect. .
本発明の有機非線形光学材料は、前記一般式１式％
ここで、基りは、アミン基、モノあるいはジアルキルア
ミノ基、モノあるいはジ（ヒドロキシアルキル）アミン
基が代表的である。The organic nonlinear optical material of the present invention has the general formula 1. Here, the group is typically an amine group, a mono- or dialkylamino group, or a mono- or di(hydroxyalkyl)amine group.
例えば、ドナー（Ｄ）がジアルキルアミノ基である場合
、ジエチルアミノ基とジメチルアミノ基とでは、ドナー
性に優９、平面共役構造金とシやすいジエチルアミノ基
のほうが、大きな非線形光学効果を発現する。更に、フ
レキシビリティの増大により、溶解性が高く、溶融結晶
化に適した融点を示す。エチル−ヒドロキシエチルアミ
ノ基ドナーにすると、溶解性は、更に向上する。Ｄがジ
メチルアミノ基の材料’ｉＤＭ−ＴＥＡ、 ドナーＤ
がジエチルアミノ基の材料全ＤＥ−ＴＥＡ、Ｄがエチル
−ヒドロキシエチルアミノ基の材料’１ＥＯＥ−ＴＥＡ
と略称する。For example, when the donor (D) is a dialkylamino group, between a diethylamino group and a dimethylamino group, the diethylamino group has superior donor properties9, and the diethylamino group, which is more easily bonded to planar conjugated gold, exhibits a greater nonlinear optical effect. Furthermore, due to increased flexibility, it exhibits high solubility and a melting point suitable for melt crystallization. When the ethyl-hydroxyethylamino group donor is used, the solubility is further improved. Material in which D is a dimethylamino group 'iDM-TEA, Donor D
All DE-TEA is a diethylamino group material, '1EOE-TEA is a material where D is an ethyl-hydroxyethylamino group.
It is abbreviated as.
以下、前記一般式Ｉで表される化合物の製造例金示すが
、これらに限定されない。Examples of the production of the compound represented by the general formula I are shown below, but the invention is not limited thereto.
製造例１、ＤＥ−ＴＢＡの合成
Ｎ、Ｎ−ジエチル−ｐ−フ二二レンジアミン（＆６ｆ、
２２ｍｍｏｌ） のベンゼン−エタノール（１：１）
溶液に、テレフタルアルデヒド（１，３ｆ、 １０
ｍｍｏｌ ） のエタノール溶液と触媒量のベンゼン
スルホン酸を加え、室温で１時間かくはんした。更に、
油浴上で、３時間、加熱還流した０反応液を室温まで冷
し、生底物を完全に析出させた後、これをろ取、冷エタ
ノールにて充分洗浄した。メチルシクロヘキサン二〇−
ジクロロベンゼン（１：１）混合溶媒を用いて再結晶し
、橙色うろこ状結晶（２，６ｙ ）ｋ得た。融点：２２
７℃。第１図に、溶融結晶化薄膜のＵＶ−ＶＩＳスペク
トルを示す。すなわち第１図は本発明による有機非線形
光学材料：ＤＥ−ＴＢＡ（７）溶融結晶化薄膜のＵＶ−
Ｖ工Ｓスペクトル全波長（ｎｍ、横軸）と吸光度（任意
単位、縦軸）との関係で示したグラフである。Production Example 1, Synthesis of DE-TBA N,N-diethyl-p-phenyl diamine (&6f,
22 mmol) of benzene-ethanol (1:1)
Add terephthalaldehyde (1,3f, 10
mmol) of ethanol solution and a catalytic amount of benzenesulfonic acid were added, and the mixture was stirred at room temperature for 1 hour. Furthermore,
The 0 reaction solution was heated under reflux on an oil bath for 3 hours and cooled to room temperature to completely precipitate the raw bottom material, which was collected by filtration and thoroughly washed with cold ethanol. Methylcyclohexane 20-
Recrystallization was performed using a dichlorobenzene (1:1) mixed solvent to obtain orange scaly crystals (2,6y)k. Melting point: 22
7℃. FIG. 1 shows the UV-VIS spectrum of the melt-crystallized thin film. That is, FIG. 1 shows the UV radiation of a melt-crystallized thin film of an organic nonlinear optical material according to the present invention: DE-TBA (7).
It is a graph showing the relationship between the total wavelength (nm, horizontal axis) and absorbance (arbitrary unit, vertical axis) of the V engineering S spectrum.
第１図から明らかなように、上記薄膜は長波長領域（約
７００ ｎｍ以上）に吸収を持たない。As is clear from FIG. 1, the thin film described above has no absorption in the long wavelength region (about 700 nm or more).
製造例２、ＤＭ−ＴＥＡの合成
Ｎ、 Ｎ−ジメチル−ｐ−フェニレンジアミン（五〇
？ 、 ２２ ｍｍｏｌ ） ノ工ｆｉ ／ ｋ溶
液ＶＣ、テレフタルアルデヒド（１，３ｔ、 １０ ｍ
ｍｏｌ ）のエタノール溶液と触媒量のベンゼンスルホ
ン酸を加え、室温で１時間かくはんし念０更に、油浴上
で、３時間、加熱還流した。析出物をろ取、冷エタノー
ルにて充分洗浄したのち、０−ジクロロベンゼンより再
結晶し橙色の結晶（２−２？）を得た。融点＝３００℃
以上。Production Example 2, Synthesis of DM-TEA N, N-dimethyl-p-phenylenediamine (50
? , 22 mmol) engineering fi/k solution VC, terephthalaldehyde (1,3 t, 10 m
mol) of ethanol solution and a catalytic amount of benzenesulfonic acid were added, stirred at room temperature for 1 hour, and then heated under reflux on an oil bath for 3 hours. The precipitate was collected by filtration, thoroughly washed with cold ethanol, and then recrystallized from 0-dichlorobenzene to obtain orange crystals (2-2?). Melting point = 300℃
that's all.
製造例３、ＥＯＥ−ＴＥＡの合成
硫酸−４−アミノ−Ｎ−（β−ヒドロキシエチル）−Ｎ
−エチルアニリン（９，５Ｆ、３３ｍｍｏ’ｌ ）
のエタノール−水（１：１）溶液に、水酸化す） ＩＪ
ウム水溶液を加え、弱酸性にすると均一溶液となるから
、この溶液にテレフタルアルデヒド（２，２Ｆ、１６ｍ
ｍｏｌ） のエタノール溶ｔｔ−加え室温で３時間、
更に、油浴上で１時間加熱還流した。反応液を室温まで
冷却し、生成物を析出させ、これをろ取、冷エタノール
−水（１ｅ４）混合溶媒更に冷水で充分洗浄した。得ら
れた粗結晶はエタノール−水（１：１）混合溶媒から再
結晶し、橙色結晶５．５１を得た。Production Example 3, Synthesis of EOE-TEA Sulfuric acid-4-amino-N-(β-hydroxyethyl)-N
-Ethylaniline (9,5F, 33mmol)
IJ
A homogeneous solution is obtained by adding an aqueous solution of terephthalaldehyde (2.2 F, 16 m
mol) of ethanol solution was added at room temperature for 3 hours.
Furthermore, the mixture was heated under reflux on an oil bath for 1 hour. The reaction solution was cooled to room temperature to precipitate a product, which was collected by filtration and thoroughly washed with a cold ethanol-water (1e4) mixed solvent and then with cold water. The obtained crude crystals were recrystallized from an ethanol-water (1:1) mixed solvent to obtain 5.51 orange crystals.
融点＝１１３〜１１５℃。Melting point = 113-115°C.
以下、本発明を実ハ例によフ更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０
実施例１〜３
製造例１〜３で得られた化合物について非線形光学特性
を測定した。Hereinafter, the present invention will be explained in more detail with reference to actual examples.
The present invention is not limited to these examples.0 Examples 1 to 3 Nonlinear optical properties of the compounds obtained in Production Examples 1 to 3 were measured.
ＴＨＧ測定の方法は、以下に述べる通りである。光源に
は、Ｎｄ ： ＹＡＧレーザ−（波長１．０６μｍ 、
ｊ ＯＨｚ −５０ＭＷ／ｃｍ” ） ｋ用い、可視
光をカットした後、レンズで集光したビームを試料に照
射し、試料より放射された元をモノクロメータに通して
、ＴＨＧ元（（Ｌ３５ μｍ）のみの強度をホトマルで
検知した。測定試料は、ＤＭ−ＴＥＡ、ＤＥ−ＴＥＡ％
ＥＯＥ−’Ｉ’ＢＡｔ−１０５〜１２０μｍの粒径に粉
砕したものを用いた。更に、観測される’Ｉ’ＨＧ光が
、尿素や純粋に三次の効果のみによること全確認するた
めに、同一試料の第二高調波発生（以下、５Ｈ（）と略
す）についても測定した。その結果を下記表１に示す。The method of THG measurement is as described below. The light source was a Nd:YAG laser (wavelength: 1.06 μm,
After cutting off visible light, the sample is irradiated with a beam focused by a lens, and the source emitted from the sample is passed through a monochromator to obtain the THG source ((L35 μm) The intensity of
EOE-'I'BAt-ground to a particle size of 105 to 120 μm was used. Furthermore, in order to fully confirm that the observed 'I'HG light was due to urea or purely third-order effects, the second harmonic generation (hereinafter abbreviated as 5H()) of the same sample was also measured. The results are shown in Table 1 below.
なお、比較資料として、尿素、ＭＮＡ及びＤＥＡＮＳの
結果を併記した。In addition, the results of urea, MNA, and DEANS are also listed as comparative data.
以上説明したように、本発明の有機非線形光学材料は、
従来になく大きな三次の非線光学効果を有するので、こ
れ全利用した光学素子、例えば光双安定性素子、元スイ
ッチ、元メモリなど将来の元通信用光集積素子の中心素
材として利用できる。As explained above, the organic nonlinear optical material of the present invention is
Since it has a larger third-order nonlinear optical effect than ever before, it can be used as a core material for future optical integrated devices for communication, such as optical devices that fully utilize this, such as optical bistable devices, original switches, and original memories.
第１図は、本発明による有機非線形光学材料：ＤＥ−Ｔ
ＥＡ＋７）溶融結晶化薄膜０ＵＶ−ＶＩＳスペクトル図
である。
特許出願人 日本電信電話株式会社
同 東し株式会社FIG. 1 shows an organic nonlinear optical material according to the present invention: DE-T.
EA+7) is a 0UV-VIS spectrum diagram of a melted crystallized thin film. Patent applicant Nippon Telegraph and Telephone Corporation Toshi Co., Ltd.
Claims (1)
特徴とする有機非線形光学材料。 ２、該基Ｄが、アミノ基である特許請求の範囲第１項記
載の有機非線形光学材料。 ３、該基Ｄが、モノ又はジアルキルアミノ基である特許
請求の範囲第１項又は第２項記載の有機非線形光学材料
。 ４、該基Ｄが、モノ又はジ（ヒドロキシアルキル）アミ
ノ基である特許請求の範囲第１項又は第２項記載の有機
非線形光学材料。[Scope of Claims] 1. Characterized by being represented by the following general formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] (However, D represents an electron-donating group) Organic nonlinear optical materials. 2. The organic nonlinear optical material according to claim 1, wherein the group D is an amino group. 3. The organic nonlinear optical material according to claim 1 or 2, wherein the group D is a mono- or dialkylamino group. 4. The organic nonlinear optical material according to claim 1 or 2, wherein the group D is a mono- or di(hydroxyalkyl)amino group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4871387A JPH0660984B2 (en) | 1987-03-05 | 1987-03-05 | Organic nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4871387A JPH0660984B2 (en) | 1987-03-05 | 1987-03-05 | Organic nonlinear optical material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63216033A true JPS63216033A (en) | 1988-09-08 |
| JPH0660984B2 JPH0660984B2 (en) | 1994-08-10 |
Family
ID=12810946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4871387A Expired - Fee Related JPH0660984B2 (en) | 1987-03-05 | 1987-03-05 | Organic nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0660984B2 (en) |
-
1987
- 1987-03-05 JP JP4871387A patent/JPH0660984B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0660984B2 (en) | 1994-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Naseema et al. | Synthesis, characterization and studies on the nonlinear optical parameters of hydrazones | |
| JPH0377923A (en) | Organic nonlinear optical material | |
| JPS63216033A (en) | Organic nonlinear optical material | |
| JPH0193720A (en) | Organic nonlinear optical material | |
| JPS62136601A (en) | Organic nonlinear optical material | |
| JPH03140927A (en) | Organic nonlinear optical material | |
| JP2530725B2 (en) | Organic nonlinear optical material | |
| JPH03230127A (en) | Aromatic nonlinear optical material | |
| JPH07117672B2 (en) | Nonlinear optical organic material | |
| EP0487019B1 (en) | Use of a nonlinear optical compound | |
| JPH01130136A (en) | Organic nonlinear optical material | |
| JPS63267924A (en) | Organic nonlinear optical material | |
| EP0355326A2 (en) | Nonlinear optical material | |
| JPH0795175B2 (en) | Organic nonlinear optical material and nonlinear optical device | |
| JPH0432822A (en) | Nonlinear optical material containing aromatic ring | |
| JPH03259126A (en) | Novel aromatic nonlinear optical material | |
| JPH01130135A (en) | Organic nonlinear optical material | |
| JPH0335021A (en) | Preparation of organic polymer material showing non-linear optical characteristic | |
| JPH02285329A (en) | Nonlinear optical material | |
| JPH0498224A (en) | Nonlinear optical material | |
| JPH02243644A (en) | New organic compound | |
| JPH06130435A (en) | Organic nonlinear optical material | |
| JPH02196759A (en) | New organic compound | |
| JPH0498225A (en) | Nonlinear optical material | |
| JPH05173208A (en) | Organic non-linear optical material |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |