JP2698092B2 - Nonlinear optical film - Google Patents
Nonlinear optical filmInfo
- Publication number
- JP2698092B2 JP2698092B2 JP63095410A JP9541088A JP2698092B2 JP 2698092 B2 JP2698092 B2 JP 2698092B2 JP 63095410 A JP63095410 A JP 63095410A JP 9541088 A JP9541088 A JP 9541088A JP 2698092 B2 JP2698092 B2 JP 2698092B2
- Authority
- JP
- Japan
- Prior art keywords
- nonlinear optical
- polymer
- optical film
- conjugated polymer
- polymer chain
- 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
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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
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- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【発明の詳細な説明】 〔概要〕 非線形光学効果を利用した各種のオプティカルデバイ
スに適用可能な非線形光学膜に係り、特には共役ポリマ
ーからなる有機非線形光学膜に関し、非線形光学定数の
著しい向上を可能にすることを目的とし、 共役ポリマーからなる非線形光学膜において、前記共
役ポリマー中のポリマー鎖の所々に束縛励起子が形成さ
れるように構成し、又は前記共役ポリマー中のポリマー
鎖の所々に、前記共役ポリマーを構成するモノマー分子
とは異なるモノマー分子が組み込まれるように構成し、
又は前記共役ポリマー中のポリマー鎖の所々で共役結合
が切断されるように構成する。DETAILED DESCRIPTION OF THE INVENTION [Summary] The present invention relates to a non-linear optical film applicable to various optical devices utilizing a non-linear optical effect, and particularly to an organic non-linear optical film made of a conjugated polymer. In a nonlinear optical film made of a conjugated polymer, a constrained exciton is formed at each part of the polymer chain in the conjugated polymer, or at each part of the polymer chain in the conjugated polymer, It is configured such that a monomer molecule different from the monomer molecule constituting the conjugated polymer is incorporated,
Alternatively, the conjugated polymer is configured so that a conjugated bond is cleaved at various points in the polymer chain.
本発明は、非線形光学効果を利用した各種のオプティ
カルデバイスに適用可能な非線形光学膜に係り、特には
共役ポリマーからなる有機非線形光学膜に関する。The present invention relates to a nonlinear optical film applicable to various optical devices utilizing a nonlinear optical effect, and more particularly to an organic nonlinear optical film made of a conjugated polymer.
従来、例えばポリジアセチレンに代表される共役ポリ
マーからなる非線形光学膜が知られている。この種の非
線形光学膜においては、共役ポリマー鎖に存在する自由
励起子に起因した半値幅0.05〜0.1eVの励起子吸収が生
じることから、比較的大きな３次非線形光学定数｜X(3)
｜〜10-10〜10-8esuが得られていた。Conventionally, a nonlinear optical film made of a conjugated polymer represented by, for example, polydiacetylene has been known. In this type of nonlinear optical film, since the exciton absorption with a half width of 0.05 to 0.1 eV due to the free excitons present in the conjugated polymer chain occurs, a relatively large third-order nonlinear optical constant | X (3)
| ~ 10 -10 ~ 10 -8 esu had been obtained.
上記従来の非線形光学膜は、上述したように比較的大
きな３次非線形光学定数を示すが、この程度の定数で
は、非双安定素子等のオールオプティカル（All−Optic
al）デバイスを実現するのにはまだ不十分である。The above-described conventional nonlinear optical film exhibits a relatively large third-order nonlinear optical constant as described above, but with such a constant, an all-optical material such as a non-bistable element or the like can be used.
al) Not enough to realize the device.
本発明は、上記問題に鑑み、非線形光学定数の著しい
向上を可能にすることを目的とする。The present invention has been made in view of the above problems, and has as its object to enable a remarkable improvement in the nonlinear optical constant.
共役ポリマーからなる非線形光学膜において、上記共
役ポリマー中のポリマー鎖の所々に束縛励起子が形成さ
れるように構成する。In the nonlinear optical film made of a conjugated polymer, a constrained exciton is formed at each part of the polymer chain in the conjugated polymer.
又は、上記共役ポリマー中のポリマー鎖の所々に、上
記共役ポリマーを構成するモノマー分子とは異なるモノ
マー分子が組み込まれるように構成し、又は上記共役ポ
リマー中のポリマー鎖の所々で共役結合が切断されるよ
うに構成する。Alternatively, a configuration is adopted in which a monomer molecule different from a monomer molecule constituting the conjugated polymer is incorporated into a portion of the polymer chain in the conjugated polymer, or a conjugated bond is cleaved at portions of the polymer chain in the conjugated polymer. It is configured so that:
共役ポリマー中に存在する自由励起子がポリマー鎖の
所々で束縛励起子化されると、励起子がポリマー鎖と垂
直な２方向だけでなくポリマー鎖方向にも束縛されて、
３次元的な束縛中心が形成されるため、吸収の振動子強
度が著しく増大し、かつ、光吸収スペクトルが先鋭化す
る。このことから、非線形光学定数が飛躍的に向上す
る。When free excitons present in the conjugated polymer are bound to exciton at some points in the polymer chain, the excitons are bound not only in two directions perpendicular to the polymer chain but also in the polymer chain direction,
Since a three-dimensional bound center is formed, the oscillator strength of absorption is significantly increased, and the light absorption spectrum is sharpened. From this, the nonlinear optical constant is dramatically improved.
また、共役ポリマー中のポリマー鎖の所々に、共役ポ
リマーを構成するモノマー分子とは異なるモノマー分子
が混入したり、あるいはポリマー鎖の共役結合が切断さ
れた場合も、明らかにポリマー鎖の状態が変化し、ポリ
マー鎖中に束縛中心が形成される。このようにして得ら
れる束縛中心も３次元的な束縛中心となるため、非線形
光学定数の著し向上が可能になる。Also, when a polymer molecule different from the monomer molecule constituting the conjugated polymer is mixed into the polymer chain in the conjugated polymer or the conjugated bond of the polymer chain is broken, the state of the polymer chain is obviously changed. Thus, a binding center is formed in the polymer chain. The constraint center thus obtained is also a three-dimensional constraint center, so that the nonlinear optical constant can be significantly improved.
以下、本発明の実施例について、図面を参照しながら
説明する。Hereinafter, embodiments of the present invention will be described with reference to the drawings.
第１図は、本発明の非線形光学膜の一実施例の分子構
造を示す図である。ここでは、ジアセチレン（一般構造
式Ｒ−Ｃ≡Ｃ−Ｃ≡Ｃ−Ｒ′もしくはＲ−Ｃ≡Ｃ−Ｃ≡
Ｃ−Ｒ）をポリマー化してなるポリジアセチレン膜を例
にとって述べる。FIG. 1 is a diagram showing the molecular structure of one embodiment of the nonlinear optical film of the present invention. Here, diacetylene (general structural formula RC—CC—C—R ′ or RC—CC—C}
A polydiacetylene film obtained by polymerizing C—R) will be described as an example.
第１図において、膜を構成する各ジアセチレン分子は
膜厚方向に重合されていて、膜厚方向に沿った一次元の
共役ポリマー鎖が形成されている。このポリマー鎖の所
々（一点鎖線で示す箇所）に、母体を構成するジアセチ
レン分子（構造式Ｒ−Ｃ≡Ｃ−Ｃ≡Ｃ−Ｒ′）とは異な
る種類のジアセチレン分子（構造式Ｒ″−Ｃ≡Ｃ−Ｃ≡
Ｃ−Ｒ）が組み込まれている。ここで、２つの側鎖
Ｒ″とＲとは互いに異なっていてもよく、あるいは同
じものであってもよい。上記２種類のジアセチレン分子
の量的割合は任意であり、例えば1:1であってもよい。In FIG. 1, each diacetylene molecule constituting the film is polymerized in the film thickness direction, and a one-dimensional conjugated polymer chain is formed along the film thickness direction. In some parts of the polymer chain (points indicated by the dashed line), diacetylene molecules (structural formula R ″) of a type different from the diacetylene molecule (structural formula R—C≡C—C—C—R ′) that constitutes the base. -C {CC}
C-R) are incorporated. Here, the two side chains R ″ and R may be different from each other or may be the same. The quantitative ratio of the two kinds of diacetylene molecules is arbitrary, for example, 1: 1. There may be.
このように構成された非線形光学膜では、上記の異な
る分子の組み込まれた箇所に不純物中心ができる。する
と、ポリマー鎖中の電子もしくはホールが上記不純物中
心付近に３次元的に束縛され、束縛励起子が形成され
る。この束縛励起子準位により、吸収の振動子強度が約
10〜1000倍増加し、且つ光吸収スペクトルが先鋭化する
ため、三次非線形光学定数｜X(3)従来より２〜８桁も増
大する。In the nonlinear optical film configured as described above, an impurity center is formed at a portion where the different molecules are incorporated. Then, electrons or holes in the polymer chain are three-dimensionally bound to the vicinity of the impurity center, and bound excitons are formed. Due to this bound exciton level, the oscillator strength of absorption is about
Increases from 10 to 1000 times, and the light absorption spectrum is sharpened, third-order nonlinear optical constant | X (3) is also increased conventionally 2-8 digits.
本実施例の非線形光学膜を作製するには、まず、例え
ばアセトンやクロロホルム等の有機溶媒中に、上述した
母体を構成するジアセチレンと、不純物中心となるジア
セチレンとを適宜の割合で混合溶解する。そして、この
溶液から、既知の溶媒蒸発法やシア（Shear）法等によ
り上記ジアセチレンの単結晶を育成し、これに紫外線を
照射したり熱を加えてポリマー化させることにより、上
記構成のポリジアセチレン膜が得られる。In order to fabricate the nonlinear optical film of this embodiment, first, in an organic solvent such as acetone or chloroform, the above-mentioned diacetylene constituting the base and the diacetylene serving as the impurity center are mixed and dissolved at an appropriate ratio. I do. From this solution, the diacetylene single crystal is grown by a known solvent evaporation method, a shear method, or the like, and is irradiated with ultraviolet light or heated to polymerize, thereby obtaining a polydiethylene having the above structure. An acetylene film is obtained.
その他の作製方法としては、先に本発明者によって提
案されたドライな方法（特願昭62−323832号参照）を利
用できる。即ち、上述した複数種類のジアセチレンを真
空チャンバ内で同時にガス化して基板に到達させ、この
基板上で隣接する各分子を結合もしくは吸着させて膜成
長を行う。この際、ジアセチレン分子のガス化される量
を各種類毎に調整することにより、膜中のそれぞれの構
成分子の割合を容易に制御できる。As another manufacturing method, a dry method previously proposed by the present inventors (see Japanese Patent Application No. 62-323382) can be used. That is, a plurality of the above-described diacetylenes are simultaneously gasified in a vacuum chamber to reach a substrate, and adjacent molecules are bonded or adsorbed on the substrate to grow a film. At this time, the ratio of each constituent molecule in the film can be easily controlled by adjusting the amount of gasified diacetylene molecules for each type.
第２図は、本発明の他の実施例の分子構造を示す図で
ある。FIG. 2 is a diagram showing a molecular structure of another embodiment of the present invention.
同図において、ポリマー鎖の所々（一点鎖線で示す箇
所）に、第１図のジアセチレン分子（構造式Ｒ−Ｃ≡Ｃ
−Ｃ≡Ｃ−Ｒ′）の代わりに、別のジアセチレン分子
（構造式Ｒ″−Ｃ≡Ｃ−Ｃ≡Ｃ−Ｒ′又はＲ−Ｃ≡Ｃ−
Ｃ≡Ｃ−Ｒ″）が組み込まれている。即ち、前記実施例
において組み込まれたジアセチレン分子は、母体を構成
するジアセチレン分子の両方の側鎖Ｒ、Ｒ′をこれとは
異なる側鎖Ｒ″、Ｒで置き換えたものであったが、第
２図においてはＲとＲ′のいずれか一方を別の側鎖Ｒ″
で置き換えたものである。このような構成からなる膜で
あっても、前述したと同様な方法で作製することがで
き、同様な作用及び効果が得られる。In the figure, the diacetylene molecule (structural formula RC—C 式 C) of FIG.
—C≡C—R ′), another diacetylene molecule (structural formula R ″ —C≡C—C−C—R ′ or R—C≡C—
In other words, the diacetylene molecule incorporated in the above-mentioned example is obtained by replacing both side chains R and R 'of the diacetylene molecule constituting the parent with a different side chain. In FIG. 2, one of R and R 'is replaced with another side chain R ".
Is replaced by Even a film having such a configuration can be manufactured by the same method as described above, and the same operation and effect can be obtained.
第３図は、本発明の更に他の実施例の分子構造を示す
図である。FIG. 3 is a view showing a molecular structure of still another embodiment of the present invention.
同図においては、１つのジアセチレン分子（構造式Ｒ
−Ｃ≡Ｃ−Ｃ≡Ｃ−Ｒ′）と、第１図に示したと同様な
もう１つのジアセチレン分子（構造式Ｒ″−Ｃ≡Ｃ−Ｃ
≡Ｃ−Ｒ）とが、ポリマー鎖の方向に沿って周期的に
分布している。このような構成は、例えば前述したドラ
イな方法において、真空チャンバ内でガス化されるジア
セチレン分子の種類を交互に切り換えながら膜成長を行
うことにより、極めて制御性良く得られる。このような
同期分布構造により、不純物中心の周期分布が実現され
るので、いわゆる超格子と同様な構造が得られ、よって
束縛励起子の生成を一段と効率良く行うことができる。In the figure, one diacetylene molecule (structural formula R
-C≡CC≡CR ′) and another diacetylene molecule similar to that shown in FIG. 1 (structural formula R ″ -C 図 CC)
(C—R) are periodically distributed along the direction of the polymer chain. Such a configuration can be obtained with very good controllability, for example, by performing film growth while alternately switching the type of diacetylene molecules to be gasified in the vacuum chamber in the above-described dry method. With such a synchronous distribution structure, a periodic distribution of impurity centers is realized, so that a structure similar to a so-called superlattice can be obtained, so that bound excitons can be generated more efficiently.
なお第３図において、構造式Ｒ″−Ｃ≡Ｃ−Ｃ≡Ｃ−
Ｒのジアセチレン分子の代わりに、第２図に示したと
同様な構造式きＲ″−Ｃ≡Ｃ−Ｃ≡Ｃ−Ｒ′もしくはＲ
−Ｃ≡Ｃ−Ｃ≡Ｃ−Ｒ″のジアセチレン分子を用いても
よい。In FIG. 3, the structural formula R ″ -C≡CC≡C-
In place of the diacetylene molecule of R, a structural formula similar to that shown in FIG.
A diacetylene molecule of —C≡CC−CR ”may be used.
又、上述した各実施例においては、ポリマー鎖の所々
に異なる種類のジアセチレン分子を組み込んでポリマー
鎖の状態を変化させる（特には不純物中心を形成する）
ようにしたが、この代わりに、ポリマー鎖における共役
結合の一部を切断して欠陥を作るようにしてもよい。こ
の場合、上記欠陥が束縛中心として作用し、よって束縛
励起子が形成されるので、前記実施例と同様に三次非線
形光学定数｜X(3)｜の飛躍的増大が可能になる。Also, in each of the above-described embodiments, different kinds of diacetylene molecules are incorporated into the polymer chain to change the state of the polymer chain (particularly to form impurity centers).
Alternatively, a defect may be created by cutting a part of the conjugate bond in the polymer chain. In this case, the above-mentioned defect acts as a bound center, and a bound exciton is formed, so that the third-order nonlinear optical constant | X (3) | can be dramatically increased as in the above-described embodiment.
上記ポリマー鎖の切断は、前述したような既知の方法
でポリジアセチレン膜を作製した後、これにイオン注入
やボンバードメントを施すこと等により行う。なお、前
述したドライな方法を利用した場合、成膜時に紫外線等
の光を交互にオン、オフさせれば、オン時には共役結合
ができ、オフ時には共役結合ができないことから、ポリ
マー鎖方向に沿って周期的に切断した構造が得られる。
このような周期分布を持たせれば、第３図の場合と同様
に、束縛励起子の生成を一段と効率良く行うことがで
き、非線形光学定数も一層大きくなる。The cutting of the polymer chain is performed by preparing a polydiacetylene film by a known method as described above and then performing ion implantation or bombardment on the film. When the above-mentioned dry method is used, if light such as ultraviolet rays is alternately turned on and off at the time of film formation, a conjugate bond can be formed at the time of on and a conjugate bond cannot be formed at the time of off. And a periodically cut structure is obtained.
With such a periodic distribution, as in the case of FIG. 3, bound excitons can be generated more efficiently, and the nonlinear optical constant is further increased.
なお、これまでに述べた各実施例において使用可能な
ジアセチレン（ジアセチレン系化合物）分子の一例を第
４図（ａ）〜（ｃ）に示す。なお、同図（ｃ）は、側鎖
ＲとＲ′に電子供与性のドナー基（−NH2，−NMe2）も
しくは電子受容性のアクセプタ基（−NO2，−CN）を用
いた例である。なお、上記ドナー基やアクセプタ基を用
いる場合、結合時の反応を緩和するために、中間にベン
ゼン環のような共役結合を介して付与するようにしても
よい。但し、使用可能なジアセチレンは第４図に示す物
質に限定されない。FIGS. 4 (a) to 4 (c) show examples of diacetylene (diacetylene-based compound) molecules which can be used in each of the embodiments described above. FIG. 3C shows an example in which an electron-donating donor group (—NH 2 , —NMe 2 ) or an electron-accepting acceptor group (—NO 2 , —CN) is used for the side chains R and R ′. It is. In the case where the above-mentioned donor group or acceptor group is used, it may be provided via a conjugate bond such as a benzene ring in the middle in order to moderate the reaction at the time of bonding. However, usable diacetylene is not limited to the substances shown in FIG.
又、本発明はジアセチレン系化合物に限らず、各種の
有機材料を使用できる。例えば、共役ポリマーを構成す
る分子が、第５図に示すようなポリマーの構成単位であ
るモノマー分子のいずれかであってもよい。特に、同図
中で※印を付した物質は剛直な構造を有しており、吸収
スペクトルの先鋭化を助長するのに有効である。この他
には、液晶ポリマーを用いることもでき、あるいは複数
の構成分子からなるポリマーアロイであって、この中に
アロイを構成する分子とは異なる種類の分子をドープし
たものを用いることもできる。Further, the present invention is not limited to diacetylene-based compounds, and various organic materials can be used. For example, the molecules constituting the conjugated polymer may be any of the monomer molecules which are the constituent units of the polymer as shown in FIG. In particular, the substances marked with * in the figure have a rigid structure, and are effective in promoting sharpening of the absorption spectrum. In addition, a liquid crystal polymer may be used, or a polymer alloy composed of a plurality of constituent molecules, which is doped with a different kind of molecule from the molecules constituting the alloy may be used.
以上説明したように、本発明によれば、振動子強度の
増大と光吸収スペクトルの先鋭化を可能にして、非線形
光学定数の飛躍的な向上を実現することができる。従っ
て、従来の有機非線形光学膜では困難であったオールオ
プティカルデバイスへの応用が可能になる。As described above, according to the present invention, it is possible to increase the oscillator strength and sharpen the light absorption spectrum, thereby achieving a dramatic improvement in the nonlinear optical constant. Therefore, application to all-optical devices, which has been difficult with conventional organic nonlinear optical films, becomes possible.
更に、異なる分子の組み込み箇所やポリマー鎖の切断
箇所がポリマー鎖の方向に沿って周期分布をもつように
すれば、非線形光学定数を更に向上させることができ
る。Furthermore, if the incorporation points of different molecules or the break points of the polymer chains have a periodic distribution along the direction of the polymer chains, the nonlinear optical constant can be further improved.
第１図は本発明の非線形光学膜の一実施例の分子構造を
示す図、 第２図は本発明の非線形光学膜の他の実施例の分子構造
を示す図、 第３図は本発明の非線形光学膜の更に他の実施例の分子
構造を示す図、 第４図（ａ）〜（ｃ）は上記各実施例において使用可能
なジアセチレン系化合物の一例を示す図、 第５図は本発明において使用可能な、ジアセチレン系化
合物以外の有機材料の一例を示す図である。FIG. 1 is a diagram showing a molecular structure of one embodiment of the nonlinear optical film of the present invention, FIG. 2 is a diagram showing a molecular structure of another embodiment of the nonlinear optical film of the present invention, and FIG. FIGS. 4 (a) to 4 (c) are diagrams showing an example of a diacetylenic compound which can be used in each of the above embodiments, and FIG. It is a figure which shows an example of the organic material other than a diacetylene type compound which can be used in this invention.
Claims (6)
て、前記共役ポリマー中のポリマー鎖の所々に束縛励起
子が形成されていることを特徴とする非線形光学膜。1. A nonlinear optical film comprising a conjugated polymer, wherein constrained excitons are formed at various portions of a polymer chain in the conjugated polymer.
て、前記共役ポリマー中のポリマー鎖の所々に、前記共
役ポリマーを構成するモノマー分子とは異なるモノマー
分子が組み込まれていることを特徴とする非線形光学
膜。2. A nonlinear optical film comprising a conjugated polymer, wherein a monomer molecule different from a monomer molecule constituting the conjugated polymer is incorporated in each of the polymer chains in the conjugated polymer. film.
て、前記共役ポリマー中のポリマー鎖の所々で共役結合
が切断されていることを特徴とする非線形光学膜。3. A nonlinear optical film comprising a conjugated polymer, wherein a conjugate bond is broken at various positions of polymer chains in the conjugated polymer.
ー鎖の方向に周期的に分布していることを特徴とする請
求項１に記載の非線形光学膜。4. The nonlinear optical film according to claim 1, wherein the positions where the bound excitons are formed are periodically distributed in the direction of the polymer chain.
が、前記ポリマー鎖の方向に周期的に分布していること
を特徴とする請求項２に記載の非線形光学膜。5. The nonlinear optical film according to claim 2, wherein the incorporation points of the different monomer molecules are periodically distributed in the direction of the polymer chain.
鎖の方向に周期的に分布していることを特徴とする請求
項３に記載の非線形光学膜。6. The nonlinear optical film according to claim 3, wherein the cut points of the conjugate bond are periodically distributed in the direction of the polymer chain.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63095410A JP2698092B2 (en) | 1988-04-20 | 1988-04-20 | Nonlinear optical film |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63095410A JP2698092B2 (en) | 1988-04-20 | 1988-04-20 | Nonlinear optical film |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01267529A JPH01267529A (en) | 1989-10-25 |
| JP2698092B2 true JP2698092B2 (en) | 1998-01-19 |
Family
ID=14136907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63095410A Expired - Lifetime JP2698092B2 (en) | 1988-04-20 | 1988-04-20 | Nonlinear optical film |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2698092B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2918235B2 (en) * | 1989-01-31 | 1999-07-12 | 富士通株式会社 | Nonlinear optical material |
| US6716947B1 (en) * | 2002-10-15 | 2004-04-06 | Korea Institute Of Science And Technology | Method for preparing dimethyl dipropargylmalonate polymer containing six-membered ring structure |
| JP5485608B2 (en) * | 2008-07-30 | 2014-05-07 | 日本製紙株式会社 | Phenolsulfonic acid ester, developer and heat-sensitive recording material |
-
1988
- 1988-04-20 JP JP63095410A patent/JP2698092B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| SOLID STATE COMMUNICATIONS=1987 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01267529A (en) | 1989-10-25 |
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