JP2507902B2 - Sulfur-containing organic third-order nonlinear optical material - Google Patents
Sulfur-containing organic third-order nonlinear optical materialInfo
- Publication number
- JP2507902B2 JP2507902B2 JP3074738A JP7473891A JP2507902B2 JP 2507902 B2 JP2507902 B2 JP 2507902B2 JP 3074738 A JP3074738 A JP 3074738A JP 7473891 A JP7473891 A JP 7473891A JP 2507902 B2 JP2507902 B2 JP 2507902B2
- Authority
- JP
- Japan
- Prior art keywords
- light
- sulfur
- containing organic
- order nonlinear
- nonlinear optical
- 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 30
- 239000000463 material Substances 0.000 title claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 17
- 229910052717 sulfur Inorganic materials 0.000 title claims description 17
- 239000011593 sulfur Substances 0.000 title claims description 17
- 150000002894 organic compounds Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000523 sample Substances 0.000 description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Description
【０００１】本発明は、三次非線形光学材料に関し、さ
らに詳しくは特定の含硫黄有機化合物を含有する三次非
線形光学材料に関する。The present invention relates to a third-order nonlinear optical material, and more particularly to a third-order nonlinear optical material containing a specific sulfur-containing organic compound.
【０００２】ある種の有機化合物などの材料が三次非線
形光学特性を示すことは、知られており、これらの材料
は、一般に非線形媒質とも呼ばれている。しかしなが
ら、公知の有機化合物分子は、一般に可視光波長域にお
ける吸収が大きく且つ大きな三次の分子超分極率（或い
は三次の超分子分極率）を示さないので、三次非線形光
学材料としての有用性が低い。従って、三次非線形光学
効果が大きい実用的な材料の実現が切望されている。It is known that materials such as certain organic compounds exhibit third-order nonlinear optical characteristics, and these materials are also generally called nonlinear media. However, known organic compound molecules generally have a large absorption in the visible light wavelength range and do not exhibit a large third-order molecular hyperpolarizability (or third-order supramolecular polarizability), and thus have low utility as a third-order nonlinear optical material. . Therefore, realization of a practical material having a large third-order nonlinear optical effect is desired.
【０００３】本発明者らは、三次非線形光学材料として
の効果に優れた材料を求めて研究を重ねた結果、シアノ
コバラミン（ビタミンＢ１２）が優れた性能を示すこと
を見出し、この知見に基いてすでに特許出願を行なって
いる（特願平２−２４２３５号）。The inventors of the present invention have found that cyanocobalamin (vitamin B 12 ) exhibits excellent performance as a result of repeated research for a material excellent in the effect as a third-order nonlinear optical material, and based on this finding. A patent application has already been filed (Japanese Patent Application No. 2-24235).
【０００４】本発明者は、さらに研究を重ねた結果、含
硫黄有機化合物であるトリチア［５］ヘテロヘリセン
（或いは［５］チアヘリセン）およびテトラチア［７］
ヘテロヘリセン（或いは［７］チアヘリセン）が、可視
光波長域における吸収を殆ど示さず、且つ大きな三次の
分子超分極率を有しており、三次非線形光学材料として
優れた効果を奏することを見出した。しかしながら、こ
れらの化合物は、例えばベンゼン溶液の濃度が２％以下
程度と溶媒或いは他のマトリックスへの溶解性乃至混和
性が低いという難点がある。また、トリチア［５］ヘテ
ロヘリセンの場合には、溶液状態において、レーザー光
の様な高強度の光に対して耐光性が低いという問題点も
存在する。As a result of further studies, the present inventor has found that sulfur-containing organic compounds, trithia [5] heterohelicene (or [5] thiahelicene) and tetrathia [7].
It was found that heterohelicene (or [7] thiahelicene) exhibits almost no absorption in the visible light wavelength range and has a large third-order molecular hyperpolarizability, and thus exhibits an excellent effect as a third-order nonlinear optical material. . However, these compounds have a problem that the concentration of the benzene solution is, for example, about 2% or less and the solubility or miscibility in the solvent or other matrix is low. In addition, in the case of trithia [5] heterohelicene, there is also a problem that the solution has a low light resistance to high-intensity light such as laser light.
【０００５】本発明者は、引き続き研究を重ねた結果、
さらに他の特定の含硫黄有機化合物が、三次非線形光学
材料としての優れた性能を備えているのみならず、溶解
度および耐光性にも優れていることを見出した。すなわ
ち、本発明は、下記の含硫黄有機系三次非線形光学材料
を提供するものである： 一般式The present inventor, as a result of continuing research,
It was also found that other specific sulfur-containing organic compounds not only have excellent performance as a third-order nonlinear optical material, but also have excellent solubility and light resistance. That is, the present invention provides the following sulfur-containing organic third-order nonlinear optical material:
【化２】 （ただしｎ＝１〜３であって且つｍ＝１〜４であるか或
いはｎ＝１であって且つｍ＝０である）で示される含硫
黄有機化合物の少なくとも１種を含有する含硫黄有機系
三次非線形光学材料。Embedded image (Provided that n = 1 to 3 and m = 1 to 4 or n = 1 and m = 0), the sulfur-containing organic compound contains at least one sulfur-containing organic compound. -Based third-order nonlinear optical materials.
【０００６】本発明において、上記一般式で示される含
硫黄有機化合物は、ジチア［３］ヘテロヘリセン、２−
アルキルジチア［３］ヘテロヘリセン、２−アルキルト
リチア［５］ヘテロヘリセンおよび２−アルキルテトラ
チア［７］ヘテロヘリセンである。これらの化合物は、
ベンゼンなどの溶媒に溶解した溶液状態；ポリメチルメ
タクリレート、ポリスチレンなどの透明樹脂にドープし
た状態；蒸着膜、単結晶などの固体状態などの種々の形
態で使用される。溶液中でのこれら化合物の濃度は、通
常０．０５〜４重量％（以下単に“％”とする）程度で
あり、より好ましくは、２〜４％程度である。In the present invention, the sulfur-containing organic compound represented by the above general formula is dithia [3] heterohelicene, 2-
Alkyldithia [3] heterohelicene, 2-alkyltrithia [5] heterohelicene and 2-alkyltetrathia [7] heterohelicene. These compounds are
It is used in various forms such as a solution state dissolved in a solvent such as benzene; a state in which a transparent resin such as polymethylmethacrylate or polystyrene is doped; a vapor-deposited film, a solid state such as a single crystal. The concentration of these compounds in the solution is usually about 0.05 to 4% by weight (hereinafter simply referred to as "%"), and more preferably about 2 to 4%.
【０００７】溶媒としては、上記一般式で示される含硫
黄有機化合物を溶解し得るものであれば特に限定されな
い。具体的には、ベンゼン、ジクロルメタン、ジオキサ
ンなどが挙げられる。The solvent is not particularly limited as long as it can dissolve the sulfur-containing organic compound represented by the above general formula. Specific examples include benzene, dichloromethane, dioxane and the like.
【０００８】以下図面を参照しつつ、本発明の含硫黄有
機系三次非線形光学材料の分子超分極率を評価する為に
使用した縮退四光波混合法について説明する。The degenerate four-wave mixing method used for evaluating the molecular hyperpolarizability of the sulfur-containing organic third-order nonlinear optical material of the present invention will be described below with reference to the drawings.
【０００９】図１は、縮退四光波混合法による測定光学
系を示す模式図である。Ｎｄ・ＹＡＧレーザー（１）を
出た円偏光の波長１０６４ｎｍのパルス光（定格出力
１．１Ｊ／ハ゜ルス ）をスリット（２）を介してＫＤ＊Ｐ
光学結晶（３）に導き、波長５３２ｎｍでパルス幅約７
ｎｓの光を得る。従って、ＫＤ＊Ｐ光学結晶（３）を出
る光には、波長１０６４ｎｍの光と波長５３２ｎｍの光
とが混在するので、波長１０６４ｎｍの光を赤外線吸収
フィルター（４）で吸収除去し、測定には、残った波長
５３２ｎｍの光を使用する。赤外線吸収フィルター
（４）を通過した波長５３２ｎｍの光は、半透鏡
（５１）により２分割される。その一方の光は、さらに
他の半透鏡（５２）により２分割され、一方の光は、全
反射鏡（６１）で反射された後、λ／４板（８１）によ
り紙面に垂直な方向に偏光され、ポンプ光（Ｐ１）とし
て５ＴＨおよび／または７ＴＨを含む試料（９）に照射
される。半透鏡（５２）により２分割された他の一方の
光は、全反射鏡（６２）で反射された後、λ／４板（８
２）により紙面に垂直な方向に偏光され、ポンプ光（Ｐ
２）として５ＴＨおよび／また７ＴＨを含む試料（９）
に照射される。半透鏡（５１）により２分割された他方
の光は、ＮＤフィルター（７１）により１／１０に減力
され、半透鏡（５３）により再度２分割される。半透鏡
（５３）により分割された一方の光は、λ／４板
（８３）により紙面に垂直な方向に偏光され、プローブ
光（Ｐｒ）として５ＴＨおよび／また７ＴＨを含む試料
（９）に照射される。半透鏡（５３）により分割された
他の一方の光は、ＮＤフィルター（７２）により１／１
０００に減力された後、全反射鏡（６５）で反射され、
ストリークカメラ（10）に導入され、参照光（Ｒ）とし
て検出される。図示の装置においては、ポンプ光
（Ｐ１）、ポンプ光（Ｐ２）およびプローブ光（Ｐｒ）
の光路長は、半透鏡（５１）を基点として、試料（９）
までの各光路長差が２ｍｍ以下となるように配置されて
いる。FIG. 1 is a schematic diagram showing a measuring optical system by the degenerate four-wave mixing method. Circularly polarized pulsed light with a wavelength of 1064 nm (rated output 1.1 J / pulse) emitted from an Nd / YAG laser (1) is passed through the slit (2) to KD * P.
Lead to optical crystal (3), pulse width about 7 at wavelength 532nm
Get ns of light. Therefore, since the light exiting the KD * P optical crystal (3) contains the light having the wavelength of 1064 nm and the light having the wavelength of 532 nm, the light having the wavelength of 1064 nm is absorbed and removed by the infrared absorption filter (4) and the measurement is performed. , Using the remaining light having a wavelength of 532 nm. The light having a wavelength of 532 nm that has passed through the infrared absorption filter (4) is split into two by the semi-transparent mirror (5 1 ). While the light is divided into two parts by yet another half mirror (5 2), one light is reflected by the total reflection mirror (6 1), lambda / 4 plate (8 1) perpendicular to the paper surface The sample (9) polarized in different directions and containing 5TH and / or 7TH as pump light (P 1 ) is irradiated. Another one of the lights 2 divided by half mirror (5 2) is reflected by the total reflection mirror (6 2), lambda / 4 plate (8
2 ) is polarized in the direction perpendicular to the paper surface, and the pump light (P
Samples containing 5TH and / or 7TH as 2 ) (9)
Is irradiated. The other light split into two by the semi-transparent mirror (5 1 ) is reduced to 1/10 by the ND filter (7 1 ) and split into two again by the semi-transparent mirror (5 3 ). One of the light beams split by the semi-transparent mirror (5 3 ) is polarized by the λ / 4 plate (8 3 ) in a direction perpendicular to the paper surface, and contains 5 TH and / or 7 TH as probe light (Pr) (9) Is irradiated. The other one of the lights split by the semi-transparent mirror (5 3 ) is 1/1 by the ND filter (7 2 ).
After being reduced to 000, it is reflected by the total reflection mirror (6 5 ),
It is introduced into the streak camera (10) and detected as reference light (R). In the illustrated apparatus, pump light (P 1 ), pump light (P 2 ) and probe light (Pr)
The optical path length of the sample (9) is based on the semi-transparent mirror (5 1 ).
Are arranged so that the respective optical path length differences up to are 2 mm or less.
【００１０】この様な状態で、ポンプ光（Ｐ１）、ポン
プ光（Ｐ２）およびプローブ光（Ｐｒ）が同時に試料
（９）に照射されると、信号光（Ｓ）として試料からの
光が発生する。この信号光（Ｓ）は、λ／４板（８３）
および半透鏡（５３）を経て、全反射鏡（６３）および
（６４）により反射されて、ストリークカメラ（10）に
導入される。図示の光学系における試料（９）上でのポ
ンプ光（Ｐ１）、ポンプ光（Ｐ２）およびプローブ光
（Ｐｒ）の強度比は、Ｐ１：Ｐ２：Ｐｒ＝１０：１０：
１である。ストリークカメラ（10）に導入された信号光
（Ｓ）および参照光（Ｒ）の強度は、ストリークカメラ
（10）内で空間分布面積として、信号光面積（ＡＳ）お
よび参照光面積（ＡＲ）で表わされる。In such a state, when the pump light (P 1 ), the pump light (P 2 ) and the probe light (Pr) are simultaneously applied to the sample (9), the light from the sample is emitted as the signal light (S). Occurs. This signal light (S) is a λ / 4 plate (8 3 ).
After passing through the semi-transparent mirror (5 3 ), the light is reflected by the total reflection mirrors (6 3 ) and (6 4 ) and introduced into the streak camera (10). The intensity ratio of the pump light (P 1 ), the pump light (P 2 ), and the probe light (Pr) on the sample (9) in the illustrated optical system is P 1 : P 2 : Pr = 10: 10:
It is 1. The intensities of the signal light (S) and the reference light (R) introduced into the streak camera (10) are the spatial distribution area in the streak camera (10) as the signal light area (A S ) and the reference light area (A R). ).
【００１１】本発明の含硫黄有機系三次非線形光学材料
は、高速スイッチ、光論理素子、光メモリー、位相補正
素子、位相共役鏡、画像伝送材料などとして有用であ
る。The sulfur-containing organic third-order nonlinear optical material of the present invention is useful as a high-speed switch, an optical logic element, an optical memory, a phase correction element, a phase conjugate mirror, an image transmission material and the like.
【００１２】[0012]
【発明の効果】本発明によれば、下記の様な顕著な効果
が達成される。 （イ）溶媒に対する溶解性およびマトリックスに対する
混和性に優れているので、高性能の三次非線形光学材料
が得られる。 （ロ）光の損傷が小さい。 （ハ）使用状態でも、媒体の交換が可能である。 （ニ）レーザー光の様な強い光に対しても優れた耐光性
を発揮する。According to the present invention, the following remarkable effects are achieved. (A) A high-performance third-order nonlinear optical material can be obtained because it has excellent solubility in a solvent and miscibility with a matrix. (B) Light damage is small. (C) The medium can be exchanged even in the state of use. (D) It exhibits excellent light resistance against strong light such as laser light.
【００１３】以下に実施例を示し、本発明の特徴とする
ところをより一層明確にする。Examples will be shown below to further clarify the characteristics of the present invention.
【００１４】実施例１〜４および参考例１〜４ 図１に示す形式の測定光学系を使用して、本発明による
含硫黄有機化合物の三次非線形光学材料としての性能を
調べた。各化合物は、濃度２〜４％のベンゼン溶液とし
て厚さ１mmの石英セルに入れて図１の（９）の位置に置
き、それから発生する光を検出することにより行なっ
た。信号光および参照光の波長は、５３２ｎｍであっ
た。なお、各実施例で使用した化合物は、以下の通りで
ある。 実施例１…ジチア［３］ヘテロヘリセン（前記一般式に
おいて、ｎ＝１，ｍ＝０） 実施例２…２−メチルジチア［３］ヘテロヘリセン（前
記一般式において、ｎ＝１，ｍ＝１） 実施例３…２−メチルトリチア［５］ヘテロヘリセン
（前記一般式において、ｎ＝２，ｍ＝１） 実施例４…２−メチルテトラチア［７］ヘテロヘリセン
（前記一般式において、ｎ＝３，ｍ＝１）Examples 1 to 4 and Reference Examples 1 to 4 Using a measuring optical system of the type shown in FIG. 1, the performance of the sulfur-containing organic compound according to the present invention as a third-order nonlinear optical material was investigated. Each compound was placed as a benzene solution having a concentration of 2 to 4% in a quartz cell having a thickness of 1 mm, placed at the position (9) in FIG. 1, and the light generated from it was detected. The wavelengths of the signal light and the reference light were 532 nm. The compounds used in each example are as follows. Example 1 ... Dithia [3] heterohelicene (n = 1, m = 0 in the general formula) Example 2 2-Methyldithia [3] heterohelicene (n = 1, m = 1 in the general formula) Example 3 ... 2-Methyltrithia [5] heterohelicene (n = 2, m = 1 in the general formula) Example 4 ... 2-Methyltetrathia [7] heterohelicene (n = 3 in the general formula) m = 1)
【００１５】試料から発生する比光強度は、光学系にお
ける光検出器であるストリークカメラ内の信号光面積
（ＡＳ）と参照光面積（ＡＲ）との比、Ｉ＝ＡＳ／ＡＲ
で表した。各化合物の溶液の比光強度をＩＳとし、ベン
ゼンのみの比光強度をＩｂとすると、各化合物部分から
の比光強度は、Ｉｈ＝ＩＳ−Ｉｂとして得られる。この
比光強度Ｉｈと同一の光学系で得た標準試料としての二
硫化炭素の比光強度Ｉｃおよび二硫化炭素の三次非線形
感受率χ（３）ｃを用いて、比較法により各化合物の三
次非線形感受率χ（３）ｈを求めた。そしてこの
χ（３）ｈを単位体積中の分子数で除し、さらに局所電
場の補正を施した後、ａ．ｕ．単位（アトミックユニッ
ト）に変換して三次の分子超分極率を得た。なお、二硫
化炭素の三次非線形感受率χ（３）ｃは、１．７×１０
-12 ｅｓｕとした。（文献：日本化学会第５９春季年会
講演予稿集，P545,3E134,1990 年）結果を下記第１表に
示す。溶解性は、ベンゼンに対するものである。なお、
第１表には、参考例１、２、３および４として、ベンゼ
ン、二硫化炭素、トリチア［５］ヘテロヘリセンおよび
テトラチア［７］ヘテロヘリセンについての結果をそれ
ぞれ示す。The specific light intensity generated from the sample is I = A S / A R , which is the ratio of the signal light area (A S ) and the reference light area (A R ) in the streak camera which is the photodetector in the optical system.
It was expressed by. When the specific light intensity of the solution of each compound is I S and the specific light intensity of benzene alone is I b , the specific light intensity from each compound portion is obtained as I h = I S −I b . The specific light intensity I c of carbon disulfide as a standard sample obtained by the same optical system as this specific light intensity I h and the third-order nonlinear susceptibility χ ( 3 ) c of carbon disulfide were used to compare each compound. The third-order nonlinear susceptibility χ ( 3 ) h of Then, after dividing this χ ( 3 ) h by the number of molecules in a unit volume and further correcting the local electric field, a. u. By converting into units (atomic units), a third-order molecular hyperpolarizability was obtained. The third-order nonlinear susceptibility χ ( 3 ) c of carbon disulfide is 1.7 × 10.
-12 esu. (Reference: Proceedings of the 59th Annual Meeting of the Chemical Society of Japan, P545, 3E134, 1990) The results are shown in Table 1 below. Solubility is with respect to benzene. In addition,
Table 1 shows the results for benzene, carbon disulfide, trithia [5] heterohelicene and tetrathia [7] heterohelicene as Reference Examples 1, 2, 3 and 4, respectively.
【００１６】 第 １ 表試 料 三次分子超分極率（ａ．ｕ．） 溶 解 性 耐光性 実施例１ ７．３×１０5 ２％以上 良好 実施例２ ５．５×１０5 〃 〃 実施例３ ２．３×１０6 〃 〃 実施例４ ７．２×１０6 〃 〃 参考例１ ２．７×１０4 − − 参考例２ １．３×１０5 − − 参考例３ ８．９×１０6 ２％以下 不良 参考例４ １．８×１０7 １％以下 良好Table 1Sample fee Tertiary molecule hyperpolarizability (au) Solubility Light resistance Example 1 7.3 × 10Five2% or more Good Example 2 5.5 × 10Five〃 〃 Example 3 2.3 × 106〃 〃 Example 4 7.2 × 106〃 〃 Reference example 1 2.7 × 10Four--Reference Example 2 1.3 × 10Five--Reference Example 3 8.9 × 1062% or less Defect Reference example 4 1.8 × 1071% or less good
【００１７】第１表に示す結果から、本発明による含硫
黄有機化合物は、ベンゼンに比して１〜２桁大きい三次
分子超分極率を備えていることが明らかである。また、
古くから大きな非線形性を示す化合物として知られ、標
準物質として良く使用されている二硫化炭素に比して
も、同等乃至２桁近く大きい三次分子超分極率を備えて
いることが明らかである。さらに、本発明による含硫黄
有機化合物は、トリチア［５］ヘテロヘリセンおよびテ
トラチア［７］ヘテロヘリセンと同等の三次の分子超分
極率値を有しているのみならず、これら化合物よりも優
れた溶解性を備え、また耐光性にも優れている。From the results shown in Table 1, it is clear that the sulfur-containing organic compound according to the present invention has a third-order molecular hyperpolarizability that is one to two orders of magnitude higher than that of benzene. Also,
It is clear that even if compared with carbon disulfide, which has long been known as a compound exhibiting a large non-linearity and is often used as a standard substance, it has a third-order molecular hyperpolarizability equal to or higher than that of nearly two orders of magnitude. Furthermore, the sulfur-containing organic compound according to the present invention not only has a third-order molecular hyperpolarizability value equivalent to that of trithia [5] heterohelicene and tetrathia [7] heterohelicene, but also has a better solubility than these compounds. It also has excellent light resistance and light resistance.
【００１８】[0018]
【図面の簡単な説明】[Brief description of drawings]
【図１】本発明による含硫黄有機系三次非線形光学材料
の分子超分極率を調べるために使用した縮退四光波混合
法による測定光学系の概要を示す模式図である。FIG. 1 is a schematic diagram showing an outline of a measurement optical system by a degenerate four-wave mixing method used for investigating a molecular hyperpolarizability of a sulfur-containing organic third-order nonlinear optical material according to the present invention.
（１）…Ｎｄ・ＹＡＧレーザー （２）…スリット （３）…ＫＤ＊Ｐ光学結晶 （４）…赤外線吸収フィルター （５１）〜（５３）…半透鏡 （６１）〜（６５）…５３２ｎｍ用全反射鏡 （７１）〜（７２）…ＮＤフィルター （８１）〜（８３）…λ／４板 （９）…試料 （10）…ストリークカメラ （Ｐ１）…ポンプ光 （Ｐ２）…ポンプ光 （Ｐｒ）…プローブ光 （Ｓ）…信号光 （Ｒ）…参照光(1) ... Nd · YAG laser (2) ... slit (3) ... KD * P optical crystal (4) ... infrared absorption filter (5 1) to (3) ... half mirror (6 1) to (6 5) ... 532 nm for total reflection mirror (7 1) ~ (7 2 ) ... ND filter (8 1) ~ (8 3 ) ... λ / 4 plate (9) ... sample (10) ... streak camera (P 1) ... pump light (P 2 ) ... Pump light (Pr) ... Probe light (S) ... Signal light (R) ... Reference light
───────────────────────────────────────────────────── フロントページの続き (72)発明者 山田 紘一 東京都板橋区前野町６−10−４−108 (72)発明者 川面 博司 埼玉県川越市小堤289−13 (56)参考文献 特開 平５−27282（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Koichi Yamada 6-10-4-108 Maeno-cho, Itabashi-ku, Tokyo (72) Inventor Hiroshi Kawami 289-13 Kotsumi, Kawagoe-shi, Saitama (56) References 5-27282 (JP, A)
Claims (1)
いはｎ＝１であって且つｍ＝０である）で示される含硫
黄有機化合物の少なくとも１種を含有する含硫黄有機系
三次非線形光学材料。1. A compound of the general formula (Provided that n = 1 to 3 and m = 1 to 4 or n = 1 and m = 0), the sulfur-containing organic compound contains at least one sulfur-containing organic compound. -Based third-order nonlinear optical materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3074738A JP2507902B2 (en) | 1991-03-13 | 1991-03-13 | Sulfur-containing organic third-order nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3074738A JP2507902B2 (en) | 1991-03-13 | 1991-03-13 | Sulfur-containing organic third-order nonlinear optical material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0553161A JPH0553161A (en) | 1993-03-05 |
| JP2507902B2 true JP2507902B2 (en) | 1996-06-19 |
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|---|---|---|---|
| JP3074738A Expired - Lifetime JP2507902B2 (en) | 1991-03-13 | 1991-03-13 | Sulfur-containing organic third-order nonlinear optical material |
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| US6017470A (en) * | 1995-08-21 | 2000-01-25 | The Trustees Of Columbia University In The City Of New York | Substituted [6]helicene compounds that show enhanced nonlinear optical rotatory power and uses thereof |
| KR101511072B1 (en) * | 2009-03-20 | 2015-04-10 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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| JPH0553161A (en) | 1993-03-05 |
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