JPS62222668A - Organic thin-film element - Google Patents
Organic thin-film elementInfo
- Publication number
- JPS62222668A JPS62222668A JP61066275A JP6627586A JPS62222668A JP S62222668 A JPS62222668 A JP S62222668A JP 61066275 A JP61066275 A JP 61066275A JP 6627586 A JP6627586 A JP 6627586A JP S62222668 A JPS62222668 A JP S62222668A
- Authority
- JP
- Japan
- Prior art keywords
- organic thin
- thin film
- molecules
- film
- active layer
- 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
- 239000010409 thin film Substances 0.000 title claims abstract description 79
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 2
- 238000010030 laminating Methods 0.000 claims 1
- 239000002120 nanofilm Substances 0.000 abstract description 8
- 239000000370 acceptor Substances 0.000 description 27
- 239000010408 film Substances 0.000 description 19
- 239000000758 substrate Substances 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 6
- 230000008859 change Effects 0.000 description 5
- 239000011368 organic material Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- -1 tetramethylphenylene diethylene Chemical group 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001661 cadmium Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Photovoltaic Devices (AREA)
- Light Receiving Elements (AREA)
Abstract
Description
【発明の詳細な説明】
［発明の目的］
（産業上の利用分野）
本発明は、有機薄膜を電子素子や光学素子の活性層とし
て用いた有機薄膜素子に関する。Detailed Description of the Invention [Object of the Invention] (Industrial Application Field) The present invention relates to an organic thin film device using an organic thin film as an active layer of an electronic device or an optical device.
（従来の技術）
近年、ラングミーア・プロジェット法（以下、ＬＢ法と
いう）に代表される有機分子の超薄膜形成技術の進展に
よシ、有機薄膜各種素子への応用技術開発が活発化して
いる。ダーラム（Ｄｕｈｒａｍ）大学のロパーツ（Ｇ、
Ｇ、 Ｒｏｂ・ｒｔｓ ）の、有機薄膜を用いたＭＩ
Ｓ累子の研究を代表として、この種の研究が各所で行わ
れている。しかし現状では、有機薄膜の性質を有効に利
用した新しい機能の素子は未だ実現されていない。(Conventional technology) In recent years, with the progress of ultra-thin film formation technology of organic molecules represented by the Langmeer-Prodgett method (hereinafter referred to as LB method), the development of applied technology to various organic thin film devices has become active. . Loparts (G) of Durham University
G, Rob・rts), MI using organic thin films
This type of research is being conducted in various places, with research by S. Yuko being a representative example. However, at present, no element with new functions that effectively utilizes the properties of organic thin films has yet been realized.
素子応用の面から見て有機材料の特性の中で特に注目さ
れるのは、分子間の電荷移動の現象である。有機材料に
は、イオン化ポテンシャルが小さく他の分子に電子を供
給して自らは正のイオン状態になり易いドナー性分子と
、電子親和力が大きく他の分子から電子を受取シ自らは
負のイオン状態になり易いアクセプタ性分子とがある。Among the characteristics of organic materials from the perspective of device applications, the phenomenon of intermolecular charge transfer is particularly noteworthy. Organic materials have donor molecules, which have a small ionization potential and easily become positive ions by supplying electrons to other molecules, and donor molecules, which have a large electron affinity and which accept electrons from other molecules and which themselves become negative ions. There are some acceptor molecules that are susceptible to
これら二種の分子間には電荷移動錯体と総称される化合
物が形成されることはよく知られている。例えは、ベレ
リンとテトラシアツキ７ノメタン（ＴＣＮＱ）との間の
化合物は電荷の移動しない中性分子からなる化合物であ
るが、テトラメチルフェニレンジｙｔン（ＴＭＰＤ）と
ＴＣＮＱではそれぞれ分子が正、負となりたイオン性の
化合物となる。また、テトラチアフルバレン（ＴＴＦ
）とクロラニルの場合のように、温度や圧力によって中
性からイオン性への転移が観測されることも知られてい
る。It is well known that a compound collectively called a charge transfer complex is formed between these two types of molecules. For example, the compound between belerin and tetracytoxy-7-methane (TCNQ) is a compound consisting of neutral molecules that do not transfer charges, but in tetramethylphenylene diethylene (TMPD) and TCNQ, the molecules are positive and negative, respectively. It becomes an ionic compound. In addition, tetrathiafulvalene (TTF
) and chloranil, it is also known that a transition from neutrality to ionicity is observed depending on temperature and pressure.
この様な有機材料の電荷移動の現象を素子の動作原理と
して応用する場合、電荷移動の効率、応答速度、制御性
等の電荷移動の特性そのものが優れていること、及び電
荷移動を起こすような材料、素子が容易に形成できるこ
と、等が要求される。When applying the phenomenon of charge transfer in organic materials as the operating principle of an element, it is important that the charge transfer characteristics themselves, such as charge transfer efficiency, response speed, and controllability, are excellent, and that the charge transfer phenomenon that causes charge transfer is excellent. Materials and elements that can be easily formed are required.
電荷移動錯体結晶については、結晶作成が極めて難しい
こと、および電荷移動を外部で制御することが難しいこ
と、等の問題がある。また、金属と有機分子膜の間の電
荷移動を光や電界により制御してスイッチング素子ある
いはメモリ素子に利用する試みもなされているが、これ
らの電荷移動の効率、応答速度、寿命等に大きな問題を
抱えている。この様に電荷移動の現象は、素子応用の可
能性が期待されつつも、現状では未だ実用に供されてい
ない。There are problems with charge transfer complex crystals, such as that it is extremely difficult to create the crystal and that it is difficult to control charge transfer externally. In addition, attempts have been made to control the charge transfer between metals and organic molecular films using light or electric fields and use them in switching devices or memory devices, but there are major problems with the efficiency of charge transfer, response speed, lifespan, etc. I am holding. Although the phenomenon of charge transfer is expected to have potential for device applications, it has not yet been put to practical use.
（発明が解決しようとする問題点）
以上のように有機薄膜は、新しい機能の素子への応用が
期待されながら、未だその様な素子は実現されていない
。(Problems to be Solved by the Invention) As described above, although organic thin films are expected to be applied to devices with new functions, such devices have not yet been realized.
本発明は上記の点に鑑みなされたもので、有機薄膜の電
荷移動現象を動作原理としてその電荷移動の効率向上を
図９、かつ信頼性向上を図りた有機薄膜素子を提供する
ことを目的とする。The present invention has been made in view of the above points, and aims to improve the efficiency of charge transfer using the charge transfer phenomenon of organic thin films as the operating principle, and to provide an organic thin film element with improved reliability. do.
［発明の構成コ
（問題点を解決するだめの手段）
本発明にかかる有機薄膜素子は、第１、第２の電極の間
に、ドナー性分子とアクセプタ性分子を含む有機薄膜を
活性層として設け、有機分子間の電荷移動現象を利用す
る素子である。具体的には、第１、第２の電極間に電圧
を印加した時の活性層の吸光率、伝導度特性、防電率、
膜内電位分布等の変化を利用する。この様な素子におい
て本発明は、活性層と第１．＄２の電極との間に絶縁性
有機薄膜を介在させたことを特徴とする。[Configuration of the Invention (Means for Solving the Problems)] The organic thin film device according to the present invention has an organic thin film containing donor molecules and acceptor molecules as an active layer between the first and second electrodes. This is an element that utilizes the phenomenon of charge transfer between organic molecules. Specifically, the absorbance of the active layer when a voltage is applied between the first and second electrodes, the conductivity characteristics, the electrical resistivity,
Utilizes changes in intramembrane potential distribution, etc. In such a device, the present invention provides an active layer and a first . The feature is that an insulating organic thin film is interposed between the $2 electrode and the $2 electrode.
ここで活性層は、ドナー性分子を含む第１の有機薄膜と
７クセブタ性分子を含む第２の有機薄膜の積層構造とし
てもよいし、ドナー性分子とアクセプタ性分子を共に含
む混合薄膜としてもよい。Here, the active layer may have a laminated structure of a first organic thin film containing donor molecules and a second organic thin film containing seven receptor molecules, or a mixed thin film containing both donor molecules and acceptor molecules. good.
また、ドナー性分子を含む第１の有機薄膜とアクセプタ
性分子を含む第２の有機薄膜の間に絶縁性有機薄膜を介
在させてもよいし、ドナー性分子を含む第１の有機薄膜
とアクセプタ性分子を含む第２の有機薄膜の積層構造を
繰返し積層した超格子構造としてもよい。更にこれらの
有機薄膜において、複数種のドナー性分子、複数種のア
クセプタ性分子を適宜組合わせることができる。Further, an insulating organic thin film may be interposed between the first organic thin film containing donor molecules and the second organic thin film containing acceptor molecules, or an insulating organic thin film may be interposed between the first organic thin film containing donor molecules and the acceptor molecules. The layered structure of the second organic thin film containing the organic molecules may be a superlattice structure in which layers are repeatedly layered. Furthermore, in these organic thin films, a plurality of types of donor molecules and a plurality of types of acceptor molecules can be appropriately combined.
本発明においては、有機薄膜の厚さを制御することも素
子特性上重要である。従って有機薄膜としては、ＬＢ法
によシ形成される単分子膜あるいはこれを複数層累積し
た超薄膜を用いることが好ましい。有機物質中を動く電
子または正孔は一般に半導体中のそれより速度は遅いが
、数Ｘ〜数１０スといった超薄膜を用いることにより、
十分高速度の電荷移動が可能であり、また実際にＬＢ法
によりその様な膜形成が可能である。In the present invention, controlling the thickness of the organic thin film is also important in terms of device characteristics. Therefore, as the organic thin film, it is preferable to use a monomolecular film formed by the LB method or an ultra-thin film obtained by stacking a plurality of monomolecular films. The speed of electrons or holes moving in organic materials is generally slower than that in semiconductors, but by using ultra-thin films of several times to several tens of times,
Charge transfer at a sufficiently high rate is possible, and such a film can actually be formed by the LB method.
（作用）
本発明の構成によれば、第１、第２の電極間に電圧を印
加することによシ、活性層としての有機薄膜のドナー性
分子とアクセプタ性分子間で電荷移動が生じ、これによ
フ活性層の吸光率、伝導度特性等が制御される。このと
き、活性層と第１、第２の電極との間に絶縁性有機薄膜
を介在させているため、電極と活性層との間の電荷移動
が阻止ないし抑制される。この結果活性層中のドナー性
分子とアクセプタ性分子間での電荷移動確率（効率）が
高いものとなる。また電極に金属を用いた場合、一般に
金属はそれ自身強いドナー性、アクセプタ性を示し、ま
た高い拡散能を示すため、ドナー性分子あるいはアクセ
プタ性分子と錯体を形成し易い。これは素子特性の劣化
の原因となる。(Function) According to the configuration of the present invention, by applying a voltage between the first and second electrodes, charge transfer occurs between donor molecules and acceptor molecules of the organic thin film as the active layer. This controls the absorbance, conductivity characteristics, etc. of the active layer. At this time, since the insulating organic thin film is interposed between the active layer and the first and second electrodes, charge transfer between the electrodes and the active layer is prevented or suppressed. As a result, the probability (efficiency) of charge transfer between donor molecules and acceptor molecules in the active layer becomes high. Furthermore, when a metal is used for the electrode, since the metal itself generally exhibits strong donor properties and acceptor properties, and also exhibits high diffusion ability, it is easy to form a complex with donor molecules or acceptor molecules. This causes deterioration of device characteristics.
この点本発明では活性層と電極の間に絶縁性有機薄膜を
介在させているため、活性層との化学反応を抑制するこ
とができ、素子の寿命特性を向上させることかできる。In this regard, in the present invention, since an insulating organic thin film is interposed between the active layer and the electrode, chemical reaction with the active layer can be suppressed, and the life characteristics of the element can be improved.
（実施例） 以下本発明の実施例を図面を参照して説明する。(Example) Embodiments of the present invention will be described below with reference to the drawings.
第１図は一実施例の有機薄膜素子である。図において、
１は第１の金属電極であジ、この上に絶縁性有機薄膜２
を介してドナー性分子を含む第１の有機薄膜（ドナー性
分子膜）３、アクセプタ性分子を含む第２の有機薄膜（
アクセプタ性分子膜）４が順次積層されて活性層が形成
され、更にこの上に絶縁性有機薄膜５を介して第２の金
属電極６が形成されている。FIG. 1 shows an example of an organic thin film device. In the figure,
1 is a first metal electrode, on which is an insulating organic thin film 2.
A first organic thin film containing donor molecules (donor molecule film) 3, a second organic thin film containing acceptor molecules (
An active layer is formed by sequentially stacking acceptor molecular films 4, and a second metal electrode 6 is further formed on this layer with an insulating organic thin film 5 interposed therebetween.
この素子の具体的な製造工程列は次の通りである。ポリ
ーＬ−７エニルアラニンを１＝５の体積比のソクロル酢
酸−クロロホルム溶液に約１１蜂曾の濃度となるように
溶解してＬＢ膜展開溶液を形成した。この製膜分子は１
３ ｄｙｎｅｒ７ら以上の表面圧で凝縮膜となることが
表面圧−分子占有面積曲線から知られた。ＬＨ膜形成装
置は市販の垂直引上は方式のものを用い、展開、累積に
先だって水相を−＝６．０に設定し、共存塩として２価
カドミウム塩を約０．０５ｍＭ添加し、水温を２０℃に
保った。The specific manufacturing process sequence for this device is as follows. An LB membrane developing solution was prepared by dissolving poly-L-7 enylalanine in a sochloroacetic acid-chloroform solution having a volume ratio of 1=5 to a concentration of about 11%. This film forming molecule is 1
It was known from the surface pressure-molecular occupied area curve that a condensed film was formed at a surface pressure of 3 dyner 7 or higher. A commercially available vertical pulling type LH film forming apparatus was used. Prior to development and accumulation, the aqueous phase was set to -=6.0, about 0.05mM of divalent cadmium salt was added as a coexisting salt, and the water temperature was was maintained at 20°C.
第１の金属電極１となるＢ膜を形成したガラス基板をこ
の水相に設置し、上記製膜分子を６００μ！トラニ、ト
法により展開して、表面圧を２０ｄｙｎＬＶｆｒＩｔに
設定して単分子膜を安定させた。そして引上げ速度７０
μｍｒｎ／ｍｉ ｎでこの基板を引上げ、単分子からな
るＬＢ膜を累積した。累積数は１０層とした。A glass substrate on which a B film, which will become the first metal electrode 1, has been formed is placed in this aqueous phase, and the above film-forming molecules are added to 600μ! The monomolecular film was stabilized by developing it by the Toranito method and setting the surface pressure at 20 dynLVfrIt. and pulling speed 70
This substrate was pulled up at μmrn/min to accumulate an LB film consisting of a single molecule. The cumulative number of layers was 10.
これが絶縁性有機薄膜２である。This is the insulating organic thin film 2.
ドナー性分子膜３としては、パラフェニレンジアミンと
ポリーＬ−フェニルアラニンを１：１に混合したものを
上記と同様の方法で１０層累積形成した。アクセプタ性
分子膜４としては、テトラシアノキノソメタンをポリー
Ｌ−フェニルアラニンと１：１に混合したものをやはり
同様の方法で１０層累積形成した。As the donor molecular film 3, 10 layers of a 1:1 mixture of para-phenylenediamine and poly-L-phenylalanine were formed in the same manner as above. As the acceptor molecular film 4, 10 layers of a mixture of tetracyanoquinosomethane and poly-L-phenylalanine in a ratio of 1:1 were formed in the same manner.
このようにして形成された活性層上に、先の絶縁性有機
薄膜２と同様の絶縁性有機薄膜５を形成した後、第２の
金属電極６としてＡｕ電極を形成した。After forming an insulating organic thin film 5 similar to the above-mentioned insulating organic thin film 2 on the active layer thus formed, an Au electrode was formed as the second metal electrode 6.
第２図はこのように構成された素子に、Ａｕ電極が正、
Ｕ電極側が負となる電圧を印加した時の、波長５００
ｎｍにおける吸光率の変化を示したものである。図には
、比較例として、第１図の絶縁性有機薄膜２および５を
省略した素子の特性を併せて示した。Figure 2 shows an element configured in this way with a positive Au electrode and
Wavelength 500 when applying a negative voltage to the U electrode side
It shows the change in absorbance in nm. The figure also shows, as a comparative example, the characteristics of an element in which the insulating organic thin films 2 and 5 of FIG. 1 are omitted.
図から明らかなようにこの実施例の素子では大きい吸光
率変化が認められる。これは比較例と具なシ、活性層と
電極の間に絶縁性有機薄膜を介在させた結果、ドナー性
分子とアクセプタ性分子間の電荷移動の効率が向上した
結果である。この様な吸光率の変化を、具体的な素子と
しては例えば光スイッチング素子あるいは表示素子等に
応用することができる。As is clear from the figure, a large change in absorbance is observed in the element of this example. This is a result of the fact that, as in the comparative example, the insulating organic thin film was interposed between the active layer and the electrode, and as a result, the efficiency of charge transfer between donor molecules and acceptor molecules was improved. Such a change in absorbance can be applied to specific devices such as optical switching devices or display devices.
第３図は他の実施例の有機薄膜素子である。第１図の実
施例と異なる点は、第１の金属電極１に代わって、Ｇａ
Ａｓ基板７を電極として用いていることである。ＧａＡ
ｓ基板７は、Ｓｌを１×１０１シマ添加したｎ型基板を
用いた。FIG. 3 shows an organic thin film device of another example. The difference from the embodiment shown in FIG. 1 is that instead of the first metal electrode 1, a Ga
The As substrate 7 is used as an electrode. GaA
As the s-substrate 7, an n-type substrate doped with 1×10 1 sl of Sl was used.
このＭＩＳ型素子は、逆バイアス約２ｖでキャノ４シタ
ンスの急激な変化が観測され、ＧａＡｇ基板７０表面が
反転したことが確認された。In this MIS type element, a rapid change in capacitance was observed at a reverse bias of about 2 V, and it was confirmed that the surface of the GaAg substrate 70 was reversed.
絶縁性有機薄膜２及び５を省略した他、この実施例と同
様に構成したＭＩＳ型素子では、明瞭なキャパシタンス
変化は認められなかった。In the MIS type device configured in the same manner as in this example except that the insulating organic thin films 2 and 5 were omitted, no clear change in capacitance was observed.
本発明は更に種々変形して実施することができる。第４
図は、第１図の構成における活性層部分に、ドナー性分
子とアクセプタ性分子を共に含む混合薄膜３４を用いた
ものである。第５図はドナー性分子膜３とアクセプタ性
分子膜５の間にも絶縁性有機薄膜８を介在させたもので
ある。更に第６図は、ドナー性分子膜３１＋３Ｍ＋・・
・とアクセプタ性分子膜４１ ＋ ４２ ＋・・・
を交互に例えばそれぞれを単分子膜として積層して超格
子構造の活性層としたものである。この様な構成として
も、第１図の素子と同様の特性が得られる。The present invention can be further modified and implemented in various ways. Fourth
The figure shows the structure of FIG. 1 in which a mixed thin film 34 containing both donor molecules and acceptor molecules is used in the active layer portion. In FIG. 5, an insulating organic thin film 8 is also interposed between the donor molecular film 3 and the acceptor molecular film 5. Furthermore, FIG. 6 shows a donor molecular film 31+3M+...
・and acceptor molecular film 41 + 42 +...
For example, each layer is laminated alternately as a monomolecular film to form an active layer with a superlattice structure. Even with such a configuration, characteristics similar to those of the device shown in FIG. 1 can be obtained.
本発明でのドナー性分子膜やアクセプタ性分子膜におい
て、ドナー性分子やアクセプタ性分子と混合して用いら
れる絶縁性分子、あるいは絶縁性分子膜に用いられる絶
縁性分子としては、以下のような分子が用いられる。In the donor molecule film and acceptor molecule film in the present invention, the insulating molecules used in combination with the donor molecule and acceptor molecule, or the insulating molecules used in the insulating molecule film, are as follows. molecules are used.
（１）下記一般式で表わされる置換可能な飽和及び不飽
和炭化水素誘導体
−Ｘ
ここで、Ｒは置換可能なＣＨ３（ＣＨ２）ｎ−あるいは
ＣＭ、＋ＣＨ２カ景ＣＨ２＝ ＣＨ２六ＨＣＨ２ｆ
（但し、ｎ及びｐ＋ｑ十）は８以上）からなる疎水基で
ある。またＸは親水基を表わし、−ＣＯＯＨｌ−ＯＨ，
−８ｏ、）ｌ。(1) Substitutable saturated and unsaturated hydrocarbon derivatives represented by the following general formula -X Here, R is substitutable CH3(CH2)n- or CM, +CH2 background CH2= CH26HCH2f
(where n and p+q10) are 8 or more). Moreover, X represents a hydrophilic group, -COOHl-OH,
-8o,)l.
−ＣＯＯＲ’、−ＮＨ２、−Ｎｅ（Ｒ’ ）５Ｙ−（Ｙ
ハハロｒ ン） ナトが挙げられる。-COOR', -NH2, -Ne(R')5Y-(Y
Ha ha ron) Nato is an example.
（２）種々の重合性分子
例えば、置換可能なアクリレート、メタクリレート、ビ
ニルエーテル、スチレン、ビニルアルコール、アクリル
アミド、アクリルなどのビニル重合体。あるいは、アラ
ニン、グルタメート、アクリレ−ト、などのα−アミノ
酸、ε−アミツカグロン酸等のα−アミノ酸以外のアミ
ノ酸。ヘキサメチレンジアミン等のジアミンと、ヘキサ
メチレンジアミン酸等のノカルゴン酸１；１混合物より
なるポリアミド重合体。(2) Various polymerizable molecules, such as vinyl polymers such as substitutable acrylates, methacrylates, vinyl ethers, styrene, vinyl alcohols, acrylamides, and acrylics. Alternatively, α-amino acids such as alanine, glutamate, acrylate, etc., and amino acids other than α-amino acids such as ε-amitsukagulonic acid. A polyamide polymer consisting of a 1:1 mixture of a diamine such as hexamethylene diamine and a nocargonic acid such as hexamethylene diamic acid.
これらの分子はそれ自身累積が可能な場合は単独で用い
ることができる。単独で製膜できないような分子は■で
示したような単独で製膜できる絶縁性分子と混合して用
いる。These molecules can be used alone if they themselves can be accumulated. Molecules that cannot be formed into a film by themselves are mixed with insulating molecules such as those shown in (3) that can be formed into a film by themselves.
ドナー性分子としては、以下に示すようなものを用い得
る。As the donor molecule, the following can be used.
（３） 以下のような構造式をもつフルバレン壓ドナ
ー
（４）以下のような構造式をもつ含Ｓ複素環型ドナー
Ｓｅ−８ｓ
Ｓｅ−８・
Ｔ・−Ｔ。(3) A fullvalene donor having the following structural formula. (4) An S-containing heterocyclic donor Se-8s Se-8·T·-T having the following structural formula.
ここでφはフェニル基を表わす。Here, φ represents a phenyl group.
（５）以下のような構造式をもつアミン型ドナーＮ−メ
チルアニリン
Ｈ２
テトラメチルベンジジン
（６）以下のような構造式をもつ金属化合物型す
０・・・■・・・０
０・・・■・・・Ｏ
（７）以下のような構造式をもつシアニン色素ドナー
ＲＲ
ＲＲ
ＭＩ Ｍ・（８）以
下のような構造式をもつ含Ｎ複素環型′ナー
Ｒフェノチアノン
（９）以下のような構造式をもつポリマー型ドナー
（３）から（９）に示したドナー性分子はその構造式の
ままでも、あるいはそれ全骨格として、 ＣＨ３（ＣＨ
２＋ｎ。(5) Amine-type donor N-methylaniline H2 having the following structural formula Tetramethylbenzidine (6) Metal compound-type donor having the following structural formula 0...■...0 0... ■・・・O (7) Cyanine dye donor RR RR MI M・(8) N-containing heterocyclic type 'ner R phenothianone having the following structural formula (9) As shown below. The donor molecules shown in (3) to (9) having structural formulas are CH3(CH
2+n.
ＣＨ，刊Ｈ２［ＣＨ２鑓ＣＨ２早ＣＨ２ｔ（ｎ及びｐ
＋ ｑ ＋ Ｌは８以上）からなる疎水基を有しｔ誘導
体でも、あるいは−ＣＯＯＨ、−ＯＨ。CH, published H2 [CH2 Yari CH2 early CH2t (n and p
+ q + L is 8 or more) and a t derivative, or -COOH, -OH.
−８ｏ、Ｈ、−ＣＯＯＲ’ 、 −ＮＨ２，−昶（
Ｒ’）３Ｙ″″ （Ｙはハロダン）からなる親水基を有
する誘導体でも、あるいはこれら疎水基と親水基を共に
有する誘導体でもよい。-8o, H, -COOR', -NH2, -昶(
It may be a derivative having a hydrophilic group such as R')3Y'''' (Y is halodane), or a derivative having both of these hydrophobic and hydrophilic groups.
アクセプタ性分子としては、以下に示すような分子を用
いることができる。As the acceptor molecule, the following molecules can be used.
αＱ 以下のような構造式をもつシアン化合物型アクセ
プタ
Ｆ
ＮＣＣＮ
αυ 以下のような構造式をもつキノン型アクセプタ
ｃｔ ｃｔ
ａり 以下のような構造式をもつニトロ化合物型アク
セグタ
αＱからα２に示したアクセプタ性分子はその構造式の
ままでも、あるいはそれを骨格として、ＣＨ３（ＣＨ２
＋ｎ、 ＣＨ３−ｅＣＨ２−）−（ＣＨ２−ＣＨ２早Ｃ
Ｈ２＃ （ｎ及びｐ＋ｑ＋ｔは８以上）からなる疎水基
を有しｔ誘導体でも、あるいは−ＣＯＯＨ、−ＯＨ、−
３ｏ３Ｈ。αQ Cyanide type acceptor with the following structural formula F NCCN αυ Quinone type acceptor with the following structural formula ct ct a nitro compound type acceptor with the following structural formula αQ to α2 Acceptors shown in αQ to α2 CH3 (CH2
+n, CH3-eCH2-)-(CH2-CH2 early C
H2# (n and p+q+t are 8 or more) with a hydrophobic group and a t derivative, or -COOH, -OH, -
3o3H.
−ＣＯＯＲ’ 、 −ＮＨ、−Ｎ”（Ｒつ、Ｙ−（Ｙは
〕・ロダン）からなる親水基を有する誘導体でも、ある
いはこれら疎水基と親水基を共に有する誘導体でもよい
。It may be a derivative having a hydrophilic group consisting of -COOR', -NH, -N" (R, Y- (Y is].rodan), or a derivative having both of these hydrophobic and hydrophilic groups.
［発明の効果］
以上述べたように本発明によれば、ドナー性分子とアク
セプタ性分子を含む有機薄膜を活性層として、電圧印加
によりドナー性分子とアクセプタ性分子１ｍ４１の電荷
移動を利用する有機薄膜素子において、各分子のイオン
化の確率を増大することができる。例えば、表示素子あ
るいは光学素子の場合には、電圧印加による吸光率、屈
折率の変化を大きくすることができ、ま之電子素子の場
合は電圧印加による伝導度、誘を率の変化を大きくする
ことができる。また本発明によれば、金属電極を用いた
場合にこれと活性層との化学反応を抑制して信頼性の旨
い素子を実現することができる。[Effects of the Invention] As described above, according to the present invention, an organic thin film containing donor molecules and acceptor molecules is used as an active layer, and an organic film that utilizes charge transfer between donor molecules and acceptor molecules 1m41 by applying a voltage. In thin film devices, the probability of ionization of each molecule can be increased. For example, in the case of display elements or optical elements, changes in absorbance and refractive index can be increased by applying voltage, and in the case of electronic devices, changes in conductivity and permittivity can be increased by applying voltage. be able to. Further, according to the present invention, when a metal electrode is used, a chemical reaction between the metal electrode and the active layer can be suppressed to realize a highly reliable element.
第１図は本発明の一実施例の有機薄膜素子を示す図、第
２図はその特性を比較例と共に示す図、第３図〜第６図
は他の実施例の有機薄膜素子を示す図である。
ｌ・・・第１の金属電極、２・・・絶縁性有機薄膜、３
・・・ドナー性分子展、４・・・アクセプタ性分子膜、
５・・・絶縁性有機薄膜、６・・・第２の金属電極、７
・・・ＧａＡａ基板、３４・・・混合薄膜、８・・・絶
縁性有機薄膜。
田願人代理人 弁理士 鈴 江 武 彦第１ＦＸＪ
０ １ ２ ３ 電圧
Ｉ￥ ２Ｍ
第 ３ Ｌニコ
第４と
第Ｓ ハFIG. 1 is a diagram showing an organic thin film device according to an example of the present invention, FIG. 2 is a diagram showing its characteristics together with comparative examples, and FIGS. 3 to 6 are diagrams showing organic thin film devices according to other examples. It is. l: first metal electrode, 2: insulating organic thin film, 3
... Donor property molecule exhibition, 4... Acceptor property molecule membrane,
5... Insulating organic thin film, 6... Second metal electrode, 7
. . . GaAa substrate, 34 . . . Mixed thin film, 8 . . . Insulating organic thin film. Tagani's agent Patent attorney Suzue Takehiko 1st FXJ 0 1 2 3 Voltage I ¥ 2M 3rd L Nico 4th and S C
Claims (8)
性分子を含む有機薄膜を有する活性層を挾んだ有機薄膜
素子において、前記活性層と第１、第２の電極との間に
絶縁性有機薄膜を介在させたことを特徴とする有機薄膜
素子。(1) In an organic thin film element in which an active layer having an organic thin film containing donor molecules and acceptor molecules is sandwiched between first and second electrodes, the active layer and the first and second electrodes are An organic thin film element characterized by having an insulating organic thin film interposed therebetween.
膜とアクセプタ性分子を含む第２の有機薄膜の積層構造
からなる特許請求の範囲第１項記載の有機薄膜素子。(2) The organic thin film device according to claim 1, wherein the active layer has a laminated structure of a first organic thin film containing donor molecules and a second organic thin film containing acceptor molecules.
を共に含む混合薄膜からなる特許請求の範囲第１項記載
の有機薄膜素子。(3) The organic thin film device according to claim 1, wherein the active layer is a mixed thin film containing both donor molecules and acceptor molecules.
膜とアクセプタ性分子を含む第２の有機薄膜の間に絶縁
性有機薄膜を介在させて構成されている特許請求の範囲
第１項記載の有機薄膜素子。(4) The active layer is constructed by interposing an insulating organic thin film between a first organic thin film containing donor molecules and a second organic thin film containing acceptor molecules. The organic thin film device described in .
膜とアクセプタ性分子を含む第２の有機薄膜の積層構造
が複数層繰返し積層されて超格子を構成する特許請求の
範囲第１項記載の有機薄膜素子。(5) The active layer constitutes a superlattice by repeatedly laminating multiple layers of a first organic thin film containing donor molecules and a second organic thin film containing acceptor molecules. The organic thin film device described in .
の範囲第１項記載の有機薄膜素子。(6) The organic thin film device according to claim 1, wherein the first and second electrodes are metal electrodes.
である特許請求の範囲第１項記載の有機薄膜素子。(7) The organic thin film device according to claim 1, wherein at least one of the first and second electrodes is a semiconductor.
膜は、ラングミュア・プロジェット法により形成された
ものである特許請求の範囲第１項記載の有機薄膜素子。(8) The organic thin film device according to claim 1, wherein the organic thin film and the insulating organic thin film constituting the active layer are formed by the Langmuir-Prodgett method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61066275A JPS62222668A (en) | 1986-03-25 | 1986-03-25 | Organic thin-film element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61066275A JPS62222668A (en) | 1986-03-25 | 1986-03-25 | Organic thin-film element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62222668A true JPS62222668A (en) | 1987-09-30 |
Family
ID=13311123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61066275A Pending JPS62222668A (en) | 1986-03-25 | 1986-03-25 | Organic thin-film element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62222668A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03116981A (en) * | 1989-09-29 | 1991-05-17 | Toshiba Corp | Organic thin film element |
| JPH0779005A (en) * | 1992-09-11 | 1995-03-20 | Res Dev Corp Of Japan | Organic superlattice optical response device |
| JPH0794690A (en) * | 1993-09-21 | 1995-04-07 | Toshiba Corp | Image sensor |
| JPH09221459A (en) * | 1996-02-15 | 1997-08-26 | Toshiba Corp | Charge transfer complex and organic thin film element |
| JP2001007366A (en) * | 1999-06-25 | 2001-01-12 | Sony Corp | Charge transfer heterojunction structure, and manufacture thereof |
| JP2003158254A (en) * | 2001-11-22 | 2003-05-30 | Nippon Hoso Kyokai <Nhk> | Photoconductive film and solid-state image pickup device |
| JP2003282934A (en) * | 2002-03-25 | 2003-10-03 | Japan Science & Technology Corp | Rapid response photoelectric current multiplying device formed of mixed thin film of heterologous organic semiconductor |
| JP2006073856A (en) * | 2004-09-03 | 2006-03-16 | Konica Minolta Medical & Graphic Inc | Photoelectric conversion element and radiation image detector |
| JP2006245616A (en) * | 2000-02-09 | 2006-09-14 | Cambridge Display Technol Ltd | Optoelectronic device |
| KR100714127B1 (en) | 2005-11-28 | 2007-05-02 | 한국전자통신연구원 | Molecular electronic device having organic conductive protective layer |
| WO2007108385A1 (en) * | 2006-03-20 | 2007-09-27 | Matsushita Electric Works, Ltd. | Organic thin film solar cell |
| JP2008153632A (en) * | 2006-12-15 | 2008-07-03 | Ind Technol Res Inst | Photovoltaic cell |
| JP2009117480A (en) * | 2007-11-02 | 2009-05-28 | Nippon Hoso Kyokai <Nhk> | Organic photoelectric conversion element, photosensor using the same, and color image pickup device |
| JP2014022525A (en) * | 2012-07-17 | 2014-02-03 | Nippon Hoso Kyokai <Nhk> | Organic photoelectric conversion element and light-receiving element including the same |
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1986
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03116981A (en) * | 1989-09-29 | 1991-05-17 | Toshiba Corp | Organic thin film element |
| JPH0779005A (en) * | 1992-09-11 | 1995-03-20 | Res Dev Corp Of Japan | Organic superlattice optical response device |
| JPH0794690A (en) * | 1993-09-21 | 1995-04-07 | Toshiba Corp | Image sensor |
| JPH09221459A (en) * | 1996-02-15 | 1997-08-26 | Toshiba Corp | Charge transfer complex and organic thin film element |
| JP2001007366A (en) * | 1999-06-25 | 2001-01-12 | Sony Corp | Charge transfer heterojunction structure, and manufacture thereof |
| JP2006245616A (en) * | 2000-02-09 | 2006-09-14 | Cambridge Display Technol Ltd | Optoelectronic device |
| JP2003158254A (en) * | 2001-11-22 | 2003-05-30 | Nippon Hoso Kyokai <Nhk> | Photoconductive film and solid-state image pickup device |
| JP2003282934A (en) * | 2002-03-25 | 2003-10-03 | Japan Science & Technology Corp | Rapid response photoelectric current multiplying device formed of mixed thin film of heterologous organic semiconductor |
| JP2006073856A (en) * | 2004-09-03 | 2006-03-16 | Konica Minolta Medical & Graphic Inc | Photoelectric conversion element and radiation image detector |
| KR100714127B1 (en) | 2005-11-28 | 2007-05-02 | 한국전자통신연구원 | Molecular electronic device having organic conductive protective layer |
| WO2007108385A1 (en) * | 2006-03-20 | 2007-09-27 | Matsushita Electric Works, Ltd. | Organic thin film solar cell |
| US9040817B2 (en) | 2006-03-20 | 2015-05-26 | Panasonic Corporation | Organic thin film solar cell |
| JP2008153632A (en) * | 2006-12-15 | 2008-07-03 | Ind Technol Res Inst | Photovoltaic cell |
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| JP2019096900A (en) * | 2012-08-09 | 2019-06-20 | ソニー株式会社 | Photoelectric conversion element, imaging device and optical sensor |
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| JP2021177567A (en) * | 2012-08-09 | 2021-11-11 | ソニーグループ株式会社 | Photoelectric conversion element, imaging device, and optical sensor |
| US11183654B2 (en) | 2012-08-09 | 2021-11-23 | Sony Corporation | Photoelectric conversion element, imaging device, and optical sensor |
| US10658430B2 (en) | 2015-11-12 | 2020-05-19 | Panasonic Intellectual Property Management Co., Ltd. | Photosensor |
| US11228725B2 (en) | 2015-11-12 | 2022-01-18 | Panasonic Intellectual Property Management Co., Ltd. | Photosensor |
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