JPS63210919A - Organic nonlinear optical material - Google Patents
Organic nonlinear optical materialInfo
- Publication number
- JPS63210919A JPS63210919A JP4471587A JP4471587A JPS63210919A JP S63210919 A JPS63210919 A JP S63210919A JP 4471587 A JP4471587 A JP 4471587A JP 4471587 A JP4471587 A JP 4471587A JP S63210919 A JPS63210919 A JP S63210919A
- Authority
- JP
- Japan
- Prior art keywords
- nonlinear optical
- optical
- materials
- positive integer
- electron
- 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.)
- Pending
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 38
- 239000000463 material Substances 0.000 title claims abstract description 27
- 239000000126 substance Substances 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- JQDVJEDWLMLZOR-UHFFFAOYSA-N n-(6-nitronaphthalen-2-yl)acetamide Chemical compound C1=C([N+]([O-])=O)C=CC2=CC(NC(=O)C)=CC=C21 JQDVJEDWLMLZOR-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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）
この発明は光混合、光パラメトリック或は高調波発生な
ど光信号処理において重要な、非線形光学効果が大きい
新規な有機非線形光学材料に関するものである。[Detailed Description of the Invention] (Industrial Application Field) This invention relates to a new organic nonlinear optical material that has a large nonlinear optical effect and is important in optical signal processing such as optical mixing, optical parametric, and harmonic generation. .
（従来の技術）
最近、系外からの人力光に対し、入力光以外の成分の光
を発生する物質かいわゆる非線形光学材料として注目さ
れている。これは、振動数の異なる２種の入射光の和の
振動数の光を発生する光混合、入射光が振動数の異なる
２種の光となる光パラメトリック、或は入射光の二次又
は三次の高調波への変換なと、光信号処理用材料として
重要な役割を演するためである。(Prior Art) Recently, materials that generate light components other than the input light in response to human-powered light from outside the system, or so-called nonlinear optical materials, have attracted attention. This is light mixing that generates light whose frequency is the sum of two types of incident light with different frequencies, optical parametric where the incident light becomes two types of light with different frequencies, or secondary or tertiary of the incident light. This is because it plays an important role as an optical signal processing material by converting it into harmonics.
従来、この神の材料としてＫＨ２ＰＯ，又はＬ＋ＮｂＯ
３なとの無機の強誘電性結晶が知られており、最近はこ
れらの無機結晶より非線形係数が大きい２−メチル−４
−ニトロアニリン（ＭＮＡ）なとの有機物も知られてお
り、又、特開昭６１−６０６３８号公報にも有機非線形
光学材料が開示されている。Conventionally, KH2PO or L+NbO was used as this divine material.
Inorganic ferroelectric crystals such as 2-methyl-4 are known, and recently 2-methyl-4 has a larger nonlinear coefficient than these inorganic crystals.
- Organic substances such as nitroaniline (MNA) are also known, and organic nonlinear optical materials are also disclosed in Japanese Patent Application Laid-Open No. 61-60638.
（発明が解決しようとする問題点）
しかしながら、特に有機非線形光学材料について具体的
なデバイス化には尚、研究が必要とされており、ＭＮＡ
のような材料の非線形光学定数は無機非線形光学結晶に
比べれば大きいが、まだその絶対値は小さく、更に大き
い非線形光学定数を有する材料の出現か望まれている。(Problems to be solved by the invention) However, research is still required to develop specific devices, especially for organic nonlinear optical materials, and MNA
Although the nonlinear optical constants of such materials are larger than those of inorganic nonlinear optical crystals, their absolute values are still small, and it is hoped that materials with even larger nonlinear optical constants will emerge.
従って、この発明は以上述へた非線形光学定数か小さい
という欠点を除去し、従来のものより大幅に大きい非線
形光学定数を有する有機非線形光学材料を提供すること
を目的とする。Therefore, it is an object of the present invention to eliminate the above-mentioned disadvantage of having a small nonlinear optical constant, and to provide an organic nonlinear optical material having a significantly larger nonlinear optical constant than conventional materials.
（問題点を解決するための手段）
そこで、上記目的を達成すへく、有機化合物分子のいか
なる構造が非線形光学特性を与えるかを理論的に検討し
、特に三次の非線形感受率γに着目して更に検討を加え
た結果、２．６位置にそわぞれ電子吸引基と電子供与基
を有するナフタレン及びその誘導体が大きいγ値を持つ
ことを知見し、この発明を達成するに至った。(Means for solving the problem) Therefore, in order to achieve the above objective, we theoretically investigated what structure of organic compound molecules gives nonlinear optical properties, and in particular, we focused on the third-order nonlinear susceptibility γ. As a result of further investigation, it was found that naphthalene and its derivatives, which have an electron-withdrawing group and an electron-donating group at the 2.6 position, have a large γ value, leading to the achievement of the present invention.
従って、この発明の有機非線形光学材料は、次の一般式
（上記式中のＲは、 Ｃｍ Ｈ２＋ｍ＋１、− ＣＨ
２Ｃｍ Ｈ２ＩＩｌ＋１−０Ｘ ０又はて表わされる基
、Ｒ′及びＲ″はそれぞれ−Ｈ又は−Ｃ、ＢＨ２ａａ＋
１、 （ＣＨ２）ｍ Ｃ０ＯＨ或はＣｏ （ＣＨ２
）−−＋ ＣＨ３で表わされる基、但しｍは正の整数、
ｎはＯ＜ｎ＜２ｍ＋１を満足する正の整数、Ｘはハロゲ
ン原子を表わす）で示されることを特徴とする。Therefore, the organic nonlinear optical material of the present invention has the following general formula (R in the above formula is Cm H2+m+1, -CH
2Cm H2III+1-0X 0 or the group represented by R' and R'' are respectively -H or -C, BH2aa+
1, (CH2)m C0OH or Co (CH2
)--+ group represented by CH3, where m is a positive integer,
n is a positive integer satisfying O<n<2m+1, and X represents a halogen atom).
（作用）
π電子化合物が強い電界によって大きく分極することは
既に知られている。又−ＮＯ２などの電子吸引基及び−
ＮＦ２や−Ｎ（ＣＨ３）２などの電子供与基を付けるこ
とにより分極が更に促進されることも判っている。π電
子系が大きければ大きい程その分極が大きくなることは
明らかである。しかしながら、この発明の式（１）及び
（２）で示されるナフタレンの２．６位に電子吸引基と
電ｒ供４基をそれぞれ有することにより、それらの化合
物は既知の有機非線形光学材料を大幅に凌駕する非線形
光学定数を有する。(Function) It is already known that π-electron compounds are significantly polarized by a strong electric field. Also, electron-withdrawing groups such as -NO2 and -
It has also been found that polarization can be further promoted by adding electron-donating groups such as NF2 or -N(CH3)2. It is clear that the larger the π-electron system, the greater its polarization. However, by having an electron-withdrawing group and an electron-donating group at the 2.6-position of the naphthalene represented by the formulas (1) and (2) of this invention, these compounds are significantly superior to known organic nonlinear optical materials. It has a nonlinear optical constant exceeding .
このように、この発明の非線形光学材料は、従来のこの
種材料より著しく優れた非線形光学特性を有し、又化学
的に安定であり、光関連部品材料として広範囲の用途に
適用されることが考えられる。As described above, the nonlinear optical material of the present invention has significantly superior nonlinear optical properties than conventional materials of this kind, and is chemically stable, so it can be applied to a wide range of applications as a material for optical-related parts. Conceivable.
（実施例） 次にこの発明を実施例により説明する。(Example) Next, the present invention will be explained with reference to examples.
火旌圀
式（Ｉ）
で示される２−アセチルアミノ−６−ニトロナフタレン
（化合物Ｉ）Ｉｇを１００ｃｍ３のジオキサンに溶解し
、次に示す測定法により三次の非線形感受率γを測定し
たところ、１．ＯＸ ｔｏ−’ｅ ｓ ｕが得られた。Ig of 2-acetylamino-6-nitronaphthalene (compound I) represented by the formula (I) was dissolved in 100 cm3 of dioxane, and the third-order nonlinear susceptibility γ was measured using the measurement method shown below. ．． OX to-'e su was obtained.
瀝定直訴
式（１）又は（２）の化合物をジオキサン又はテトラヒ
ドロフラン（溶媒は化合物を溶解するものなら種類を問
わない）に溶解し、これを０．９ｍｍ厚のセルに入れ、
これに５１４．５ｎｍのアルゴンレーザービーム（径１
．５ ｍｍ）をあてる。Dissolve the compound of formula (1) or (2) in dioxane or tetrahydrofuran (any solvent can be used as long as it dissolves the compound), and place this in a 0.9 mm thick cell.
In addition to this, a 514.5 nm argon laser beam (diameter 1
．． 5 mm).
光の強度を徐々に強くし、自己集束効果の起り始める時
の光の強度Ｐｔｈを測定する。次に測定セルの厚さを変
えて同様の測定を行い、話導された次式■に基づき式■
よりγを求める。The light intensity is gradually increased, and the light intensity Pth at which the self-focusing effect begins to occur is measured. Next, we performed similar measurements by changing the thickness of the measurement cell, and based on the following formula
Find γ.
ｐＬｈｌ／２ ＝ Ｐｅ、ｌ／２ ＋Ａ／Ｌ ・、 、
・、 ・・■ここで
Ｐ ｃ、＝ ５．７６３ λ２ ε。ｃ／４π２ γ
・・・・■但しｐ ｃｒはセル長さの逆数（１／Ｌ）を
横軸に、Ｐｔｈの平方根を縦軸にとり、測定データをプ
ロットした特性線（直線）のせつ片、Ａは比例定数、λ
は光の波長、ε。は真空の誘電率、Ｃは光の速度である
。pLhl/2 = Pe, l/2 +A/L ・, ,
・, ・・■Here, P c, = 5.763 λ2 ε. c/4π2 γ
・・・・■ However, p cr is the peak of the characteristic line (straight line) plotting the measured data with the horizontal axis representing the reciprocal of the cell length (1/L) and the vertical axis representing the square root of Pth, and A is the constant of proportionality. ,λ
is the wavelength of light, ε. is the dielectric constant of vacuum, and C is the speed of light.
又、第１Ｏ頁〜第１４頁に示す一連の化合物■→πにつ
いてγを測定し、その結果を別表１に示す。In addition, γ was measured for a series of compounds ■→π shown on pages 10 to 14, and the results are shown in Attached Table 1.
この結果より全ての化合物についてγ値は１．０〜１．
５ Ｘ １０−’ｅ ｓ ｕの範囲に入ることが確認さ
れた。この値は従来より知られている代表的な非線形光
学材料であるジアセチレン重合体のγの値（８５００±
５０００） ｘ １Ｏ−Ｉ３ｅ ｓ ｕに比べ約１００
倍大である。From this result, the γ value for all compounds was 1.0 to 1.
It was confirmed that it falls within the range of 5 x 10-'e su. This value corresponds to the γ value (8500±
5000) x 100 compared to 1O-I3e s u
It is twice as large.
（発明の効果）
以上説明してきたように、この発明の有機非線形光学材
料は、前記式（１）及び（２）で示される構造を有する
化合物から成ることにより、従来のものに比べ、はるか
に大きい非線形光学定数を有し、かつ安定な実用性の高
い材料であり、高性能の光スィッチ、光シャッタ、光双
安定素子等のＨ３
Ｈ３
（ＣＨ２）２ＣＨ３
（ＣＨ２）３Ｃ８３
Ｃ８２Ｃ１１２ＣＱ
ＣＨ２ＣＨ２Ｃ９
ＣＨ３
ＣＨ３
ＣＨ３
ＣＨ３
Ｈ３(Effects of the Invention) As explained above, the organic nonlinear optical material of the present invention is composed of a compound having the structures represented by the above formulas (1) and (2), and therefore has a much greater effect than conventional materials. It has a large nonlinear optical constant, is a stable and highly practical material, and is used for high performance optical switches, optical shutters, optical bistable devices, etc. H3
Claims (1)
２Ｃ、Ｈ２、、３−ｎＸｎ又は ▲数式、化学式、表等があります▼ で表わされる基、Ｒ′及びＲ″はそれぞれ−Ｈ又は−Ｃ
＿ｍＨ＿２＿ｍ＿＋＿１、−（ＣＨ＿２）＿ｍＣＯＯＨ
或は−ＣＯ（ＣＨ＿２）＿ｍ＿−＿１ＣＨ＿３で表わさ
れる基、但しｍは正の整数、ｎは０＜ｎ＜２ｍ＋１を満
足する正の整数、Ｘはハロゲン原子を表わす）で示され
ることを特徴とする有機非線形光学材料。(1) The following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼... (1) or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼... (2) (R in the above formula is -C_mH_2_m_+_1, -CH
The group represented by 2C, H2,, 3-nXn or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, R' and R'' are respectively -H or -C
_mH_2_m_+_1, -(CH_2)_mCOOH
or a group represented by -CO(CH_2)_m_-_1CH_3, where m is a positive integer, n is a positive integer satisfying 0<n<2m+1, and X represents a halogen atom). organic nonlinear optical materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4471587A JPS63210919A (en) | 1987-02-27 | 1987-02-27 | Organic nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4471587A JPS63210919A (en) | 1987-02-27 | 1987-02-27 | Organic nonlinear optical material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63210919A true JPS63210919A (en) | 1988-09-01 |
Family
ID=12699117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4471587A Pending JPS63210919A (en) | 1987-02-27 | 1987-02-27 | Organic nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63210919A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4913836A (en) * | 1988-12-05 | 1990-04-03 | Hoechst Celanese Corp. | Side chain liquid crystalline polymers exhibiting nonlinear optical response |
-
1987
- 1987-02-27 JP JP4471587A patent/JPS63210919A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4913836A (en) * | 1988-12-05 | 1990-04-03 | Hoechst Celanese Corp. | Side chain liquid crystalline polymers exhibiting nonlinear optical response |
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