JP5805361B2 - Luminescent material and method for producing light emitting element - Google Patents
Luminescent material and method for producing light emitting element Download PDFInfo
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本発明は、発光波長を容易に調節することが可能で、かつ、偏光発光素子を容易に作製することが可能な新規な有機発光性材料、および、これらの材料を用いて作製した偏光発光素子に関するものである。 The present invention relates to a novel organic light-emitting material capable of easily adjusting the emission wavelength and capable of easily producing a polarized light-emitting element, and a polarized light-emitting element produced using these materials It is about.
発光素子のひとつとして有機エレクトロルミネッセンス（以下ＥＬと呼ぶ）素子が注目されている。有機ＥＬ素子は有機材料に注入された電子と正孔の再結合により生じた励起子によって発光する発光素子であり、液晶ディスプレイやプラズマディスプレイに次ぐ次世代のフラットパネルディスプレイとしてはもちろん、液晶ディスプレイの面発光光源としても注目されており活発に開発が行われている。 As one of the light emitting elements, an organic electroluminescence (hereinafter referred to as EL) element has attracted attention. An organic EL element is a light emitting element that emits light by excitons generated by recombination of electrons and holes injected into an organic material. Of course, it is a next-generation flat panel display next to liquid crystal displays and plasma displays. It is also attracting attention as a surface emitting light source and is being actively developed.
一般的な白色光は、赤色（Ｒ）、緑色（Ｇ）、青色（Ｂ）の３原色の光が含まれる。これに対して、白色ＬＥＤランプ、白色有機ＥＬランプは、青色の光と黄色蛍光体、または青色と黄色の光によって白色光を得ている。このような白色ランプを用いると、赤色の光が含まれていないため演色性が低いという問題がある。演色性を高める方法として、光の３原色であるＲＧＢの３つの発光材料を組み合わせて使う方法があり、材料開発が進んでいる。しかし、発光波長は材料の分子構造に大きく依存しており、各色の発光材料を自在に選定するのが大変難しく、特に有機ＥＬ材料の開発で大きな問題となっている。また、有機ＥＬ素子を液晶ディスプレイの面発光光源として用いる場合、光源側の偏光板を光が通過する時に、偏光子の吸収軸方向の光をほとんど吸収してしまうために少なくとも５０％の光量の損失があり、光利用効率が悪くなるという問題があった。 General white light includes light of three primary colors of red (R), green (G), and blue (B). On the other hand, white LED lamps and white organic EL lamps obtain white light by blue light and yellow phosphor, or blue and yellow light. When such a white lamp is used, there is a problem that the color rendering property is low because red light is not included. As a method for improving color rendering, there is a method of using three light emitting materials of RGB, which are the three primary colors of light, in combination, and material development is progressing. However, the emission wavelength greatly depends on the molecular structure of the material, and it is very difficult to freely select the light emitting material of each color, which is a big problem especially in the development of organic EL materials. Further, when the organic EL element is used as a surface emitting light source of a liquid crystal display, when light passes through the polarizing plate on the light source side, most of light in the absorption axis direction of the polarizer is absorbed, so that the amount of light is at least 50%. There was a problem that there was a loss and the light utilization efficiency deteriorated.
そこで、有機発光性材料の分子配向を制御することにより偏光発光を得る試みがなされている。分子配向を制御する方法として水面展開法、ＬＢ法、摩擦転写法、配向膜を使用するラビング法などが開発されている。有機発光性材料の分子配向を制御した発光層からなる偏光発光素子では液晶パネルに直接直線偏光を供給することが可能である、または、偏光発光素子の偏光方向と光源側の偏光板の吸収軸方向を直交させることにより偏光板による光損失を大幅に改善することができる。
偏光発光の例として、特許文献１にはポリアミック酸に１軸性の有機発光性材料を混合して、それを水面展開法やＬＢ法により作成する方法が開示されている。特許文献２には、ポリシランを透明体表面に一方向に押圧摩擦展延する方法が開示されている。非特許文献１にはラビング処理した配向膜上に成膜した有機発光性材料を含む発光層を用いた素子が偏光発光する旨が記載されている。
しかしながら、これらの有機発光性材料では有機発光性材料に特有の発光波長が決まっており、発光色の調整が困難であること、また、水面展開法やＬＢ法では生産性が悪く、ラビング処理した配向膜ではラビング処理による静電気や塵の発生、ラビング斑が生じる、有機発光性材料が液晶性を有している必要があり、有機発光性材料の選択に制限があるという問題があった。Thus, attempts have been made to obtain polarized light emission by controlling the molecular orientation of the organic light emitting material. As a method for controlling the molecular orientation, a water surface development method, an LB method, a friction transfer method, a rubbing method using an alignment film, and the like have been developed. In a polarized light emitting device composed of a light emitting layer in which the molecular orientation of an organic light emitting material is controlled, linearly polarized light can be directly supplied to the liquid crystal panel, or the polarization direction of the polarized light emitting device and the absorption axis of the polarizing plate on the light source side By making the directions orthogonal, the optical loss due to the polarizing plate can be greatly improved.
As an example of polarized light emission, Patent Document 1 discloses a method in which a polyamic acid is mixed with a uniaxial organic light-emitting material and is prepared by a water surface development method or an LB method. Patent Document 2 discloses a method in which polysilane is rubbed and pressed in one direction on the surface of a transparent body. Non-Patent Document 1 describes that an element using a light-emitting layer containing an organic light-emitting material formed on a rubbing-treated alignment film emits polarized light.
However, in these organic light emitting materials, the light emission wavelength peculiar to the organic light emitting material is determined, and it is difficult to adjust the emission color. In addition, the water surface development method and the LB method are not productive, and are rubbed. In the alignment film, there is a problem that static electricity and dust are generated by rubbing treatment, rubbing spots are generated, the organic light emitting material needs to have liquid crystal properties, and selection of the organic light emitting material is limited.
本発明は以上の事柄を鑑みてなされたものであり、その目的は、発光性材料の発光波長が容易に調整することが可能であり、かつ、偏光発光素子の生産性を向上させることが可能な有機発光性材料を提供することである。 The present invention has been made in view of the above matters, and the object thereof is to easily adjust the emission wavelength of the luminescent material and to improve the productivity of the polarized light-emitting device. An organic light emitting material is provided.
本願発明の発明者らは、上記した課題について検討したところ、水素結合性置換基を少なくとも１つ以上有する水素結合性発光性分子と、水素結合性置換基を少なくとも１つ以上有する水素結合性化合物とからなり、前記水素結合性発光性分子と前記水素結合性化合物が分子間水素結合により自己組織化した超分子からなることを特徴とする有機発光性材料を見出し、かつ、水素結合性化合物の膜に直線偏光光を照射した後、または、直線偏光光を照射してから熱処理した後、この膜上に水素結合性発光性分子の層を形成して熱処理することを特徴とする製法で作製した偏光発光素子によって上記課題を解決することができることを見出し、本願発明を完成するに至った。 The inventors of the present invention have studied the above-described problems. As a result, a hydrogen-bonding luminescent molecule having at least one hydrogen-bonding substituent and a hydrogen-bonding compound having at least one hydrogen-bonding substituent An organic light-emitting material characterized in that the hydrogen-bonding light-emitting molecule and the hydrogen-bonding compound are composed of supramolecules that are self-assembled by intermolecular hydrogen bonding; and Prepared by a manufacturing method characterized by forming a layer of hydrogen-bonding light-emitting molecules on the film and then heat-treating it after irradiating the film with linearly polarized light or after heat treatment after irradiating with linearly polarized light It has been found that the above-mentioned problems can be solved by the polarized light emitting element, and the present invention has been completed.
本発明により、有機発光性材料の発光色が容易に調整可能となり、水素結合性化合物の膜に直線偏光光を照射する工程と膜上に水素結合性発光性分子の層を形成し熱処理する工程によって作製される偏光発光素子は、水面展開法やＬＢ法に比べて製造工程が簡単になると共に、ラビング処理による静電気や塵の発生、ラビング斑が生じるという問題がなくなり生産性を向上できる。これにより従来技術の問題点を解決することができる。 According to the present invention, the emission color of the organic light-emitting material can be easily adjusted, and a step of irradiating the film of hydrogen bonding compound with linearly polarized light and a step of forming a layer of hydrogen bonding light-emitting molecules on the film and performing a heat treatment The polarized light-emitting device manufactured by the method can be manufactured more easily than the water surface development method and the LB method, and can be improved in productivity by eliminating problems such as generation of static electricity and dust and rubbing spots due to rubbing treatment. Thereby, the problems of the prior art can be solved.
以下に、本発明の詳細を説明する。
本発明の有機発光性材料は、水素結合性置換基を少なくとも１つ以上有する水素結合性発光性分子と、水素結合性置換基を少なくとも１つ以上有する水素結合性化合物とからなり、前記水素結合性発光性分子と前記水素結合性化合物とが分子間水素結合により自己組織化した超分子からなることを特徴とする有機発光性材料である。Details of the present invention will be described below.
The organic light-emitting material of the present invention comprises a hydrogen-bonding light-emitting molecule having at least one hydrogen-bonding substituent and a hydrogen-bonding compound having at least one hydrogen-bonding substituent, and the hydrogen bond An organic light-emitting material, wherein the light-emitting molecule and the hydrogen bonding compound are composed of supramolecules self-assembled by intermolecular hydrogen bonding.
水素結合性発光性分子とは、フルオレン、ポリアセチレンやアントラセンなどを発光性コアとし、コアに対して水素結合性置換基を有する分子構造をした分子であり、水素結合性分子とは水素結合性置換基を有する化合物のことである。
発光性コアには分子に異方性を有している必要があればよく、ここで例示した化合物に特に限定されることはない。また、水素結合性発光性分子は液晶性を有していてもよく、有していなくてもよい。A hydrogen-bonding light-emitting molecule is a molecule having a luminescent core of fluorene, polyacetylene, anthracene, etc., and a molecular structure having a hydrogen-bonding substituent on the core. It is a compound having a group.
The light emitting core only needs to have molecular anisotropy, and is not particularly limited to the compounds exemplified here. Further, the hydrogen-bonding light-emitting molecule may or may not have liquid crystallinity.
また、水素結合性置換基の例としてカルボキシル基、水酸基、スルホン酸基、アミノ基などがあげられるが水素結合を形成する置換基であればこれらの置換基に特に制限されることはない。
水素結合性発光性分子と水素結合性分子を混合するとお互いの水素結合性置換基により分子間に水素結合が形成され超分子構造を形成することができる。Examples of the hydrogen bonding substituent include a carboxyl group, a hydroxyl group, a sulfonic acid group, and an amino group, but the substituent is not particularly limited as long as the substituent forms a hydrogen bond.
When a hydrogen-bonding light-emitting molecule and a hydrogen-bonding molecule are mixed, a hydrogen bond is formed between the molecules by the mutual hydrogen-bonding substituents, and a supramolecular structure can be formed.
水素結合性発光性分子は単独でも発光可能であるが、水素結合性発光性分子と水素結合性化合物が超分子を形成することで、水素結合性発光性分子の単独時と比べて発光波長が変化する性質を有していることがわかり、混合する水素結合性化合物の種類や酸性度を調節することにより発光波長を調整できることが可能となった。 A hydrogen-bonding light-emitting molecule can emit light alone, but the hydrogen-bonding light-emitting molecule and the hydrogen-bonding compound form a supramolecule, so that the emission wavelength is longer than that of a hydrogen-bonding light-emitting molecule alone. It was found that it has a changing property, and it became possible to adjust the emission wavelength by adjusting the kind and acidity of the hydrogen bonding compound to be mixed.
水素結合性化合物に高分子の水素結合性化合物を用いた場合、水素結合性化合物の膜をガラス基板上に製膜し、その膜に直線偏光光を照射後、または直線偏光光を照射して熱処理した後、膜上に水素結合性発光性分子の層を形成して加熱処理することで偏光発光素子を容易に作製することができる。
特に光反応性高分子の側鎖末端にカルボキシル基などの水素結合性置換基を有する水素結合性化合物では側鎖がカルボキシル基の分子間水素結合により擬似架橋して液晶性メソゲンコアを形成している。この水素結合性化合物に直線偏光光を照射して加熱すると、水素結合により擬似架橋している液晶性メソゲン側鎖が一軸方向に配向するという特性を有している。その際、一軸配向する方向は用いる材料によって異なり、直線偏光光の電界ベクトル方向に対して平行、または、垂直方向に配向する。
一軸配向した水素結合性化合物の膜上に水素結合性発光性分子層を形成すると、形成後、水素結合性発光性分子は配向しておらず、発光色も水素結合性発光性分子単独時の発光波長と変わらない。しかしながら、一軸配向した水素結合性化合物膜と水素結合性発光性分子層を接触させた状態で加熱することにより、一軸配向した水素結合性化合物の水素結合基間に水素結合性発光性分子が取り込まれ、水素結合性発光性分子と水素結合性化合物の間に水素結合による超分子が形成され発光波長が変化し、かつ、水素結合性発光性分子を一軸配向させることができ、偏光発光素子を容易に作製することが可能となった。
一般の配向膜では発光性分子に液晶性が必要であるが、本願発明では、発光性分子は液晶性を有していてもよいし、液晶性を有していなくても配向するのが特徴である。When a high molecular weight hydrogen bonding compound is used as the hydrogen bonding compound, a film of the hydrogen bonding compound is formed on a glass substrate, and the film is irradiated with linearly polarized light or irradiated with linearly polarized light. After the heat treatment, a polarized light-emitting element can be easily manufactured by forming a layer of hydrogen-bonding light-emitting molecules on the film and performing heat treatment.
In particular, in the case of a hydrogen bonding compound having a hydrogen bonding substituent such as a carboxyl group at the end of the side chain of the photoreactive polymer, the side chain is pseudo-crosslinked by intermolecular hydrogen bonding of the carboxyl group to form a liquid crystalline mesogenic core. . When this hydrogen bonding compound is irradiated with linearly polarized light and heated, the liquid crystalline mesogen side chain that is pseudo-crosslinked by hydrogen bonding has a characteristic that it is aligned in a uniaxial direction. At this time, the direction of uniaxial orientation differs depending on the material used, and the orientation is parallel or perpendicular to the electric field vector direction of linearly polarized light.
When a hydrogen-bonded luminescent molecule layer is formed on a uniaxially oriented hydrogen-bonded compound film, the hydrogen-bonded luminescent molecules are not oriented after the formation, and the emission color is the same as when the hydrogen-bonded luminescent molecules are alone. Same as the emission wavelength. However, by heating the uniaxially oriented hydrogen bonding compound film and the hydrogen bonding luminescent molecule layer in contact with each other, the hydrogen bonding luminescent molecules are taken in between the hydrogen bonding groups of the uniaxially oriented hydrogen bonding compound. In addition, a supramolecule due to hydrogen bonding is formed between the hydrogen-bonding light-emitting molecule and the hydrogen-bonding compound, the emission wavelength is changed, and the hydrogen-bonding light-emitting molecule can be uniaxially oriented. It became possible to produce it easily.
In general alignment films, the light-emitting molecules must have liquid crystallinity. However, in the present invention, the light-emitting molecules may have liquid crystallinity or may be aligned even without liquid crystallinity. It is.
本発明の実施例において用いた化合物に関する合成方法を以下に示す。
（発光性分子１）
９Ｈ−フルオレンと１−ブロモヘキサンをアルカリ条件下で加熱することにより、９，９−ジヘキシル−フルオレンを合成した。９，９−ジヘキシル−フルオレンとパラホルムアルデヒドと臭化水素を酢酸中で加熱することにより２，７−ビス（ブロモメチル）−９，９−ジヘキシル−フルオレンを合成した。２，７−ビス（ブロモメチル）−９，９−ジヘキシル−フルオレンとトリメチルシリルシアニドとテトラブチルアンモニウムフルオライドをアセトニトリル中、窒素雰囲気下で反応させ、２，２‘−（９，９−ジヘキシルフルオレン−２，７−ジイル）ジアセトニトリルを合成した。２，２‘−（９，９−ジヘキシルフルオレン−２，７−ジイル）ジアセトニトリルと４−ピリジンカルボキシアルデヒド、カリウムｔ−ブトキシドをテトラヒドロフラン中で反応させ、発光性分子１を合成した。A synthesis method relating to the compound used in the examples of the present invention is shown below.
(Luminescent molecule 1)
9,9-dihexyl-fluorene was synthesized by heating 9H-fluorene and 1-bromohexane under alkaline conditions. 2,7-bis (bromomethyl) -9,9-dihexyl-fluorene was synthesized by heating 9,9-dihexyl-fluorene, paraformaldehyde and hydrogen bromide in acetic acid. 2,7-bis (bromomethyl) -9,9-dihexyl-fluorene, trimethylsilylcyanide and tetrabutylammonium fluoride were reacted in acetonitrile under a nitrogen atmosphere to obtain 2,2 ′-(9,9-dihexylfluorene- 2,7-Diyl) diacetonitrile was synthesized. 2,2 ′-(9,9-dihexylfluorene-2,7-diyl) diacetonitrile was reacted with 4-pyridinecarboxaldehyde and potassium t-butoxide in tetrahydrofuran to synthesize luminescent molecule 1.
（化合物１）
４−ヒドロキシ−安息香酸と１−ブロモドデカンをアルカリ条件下で加熱することにより、４−ドデシルオキシ−安息香酸を合成した。(Compound 1)
4-Dodecyloxy-benzoic acid was synthesized by heating 4-hydroxy-benzoic acid and 1-bromododecane under alkaline conditions.
（重合体１）
ｐ−クマル酸と６−クロロ−１−ヘキサノールをアルカリ条件下で加熱することにより、４−（６−ヒドロキシヘキシルオキシ）桂皮酸を合成した。この生成物に、メタクリル酸を大過剰加えてエステル化反応させ、４−メタクリロイルオキシヘキシルオキシ桂皮酸を合成した。この生成物をテトラヒドロフラン中に溶解し、反応開始剤としてアゾビスイソブチロニトリルを添加して重合することにより重合体１を得た。
以下、本発明を実施例を用いて具体的に説明する。(Polymer 1)
4- (6-Hydroxyhexyloxy) cinnamic acid was synthesized by heating p-coumaric acid and 6-chloro-1-hexanol under alkaline conditions. A large excess of methacrylic acid was added to this product for esterification to synthesize 4-methacryloyloxyhexyloxycinnamic acid. This product was dissolved in tetrahydrofuran, polymerized by adding azobisisobutyronitrile as a reaction initiator, and polymerized.
Hereinafter, the present invention will be specifically described with reference to examples.
（実施例１）
水素結合性発光性分子として発光性分子１と、水素結合性化合物として化合物１とポリメタクリル酸メチルをテトラヒドロフランに溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは４９１ｎｍであった。(Example 1)
A light-emitting molecule 1 as a hydrogen-bonding light-emitting molecule, a compound 1 and polymethyl methacrylate as a hydrogen-bonding compound were dissolved in tetrahydrofuran, and then spin-coated on a glass substrate to produce a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 491 nm.
（実施例２）
水素結合性発光性分子として発光性分子１と、水素結合性化合物としてコハク酸とポリメタクリル酸メチルをテトラヒドロフランに溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは５０８ｎｍであった。(Example 2)
A light-emitting molecule 1 as a hydrogen-bonding light-emitting molecule and succinic acid and polymethyl methacrylate as hydrogen-bonding compounds were dissolved in tetrahydrofuran, and then spin-coated on a glass substrate to produce a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 508 nm.
（実施例３）
水素結合性発光性分子として発光性分子１と、水素結合性化合物としてテレフタル酸とポリメタクリル酸メチルをテトラヒドロフランに溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは５１０ｎｍであった。(Example 3)
A luminescent molecule 1 as a hydrogen-bonding luminescent molecule and terephthalic acid and polymethyl methacrylate as hydrogen-bonding compounds were dissolved in tetrahydrofuran, and then spin-coated on a glass substrate to produce a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 510 nm.
（実施例４）
水素結合性発光性分子として発光性分子１と、水素結合性化合物としてフタル酸とポリメタクリル酸メチルをテトラヒドロフランに溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは５４０ｎｍであった。Example 4
A light-emitting molecule 1 as a hydrogen-bonding light-emitting molecule and phthalic acid and polymethyl methacrylate as hydrogen-bonding compounds were dissolved in tetrahydrofuran, and then spin-coated on a glass substrate to produce a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 540 nm.
（実施例５）
水素結合性発光性分子として発光性分子１と、水素結合性化合物としてマロン酸とポリメタクリル酸メチルをテトラヒドロフランに溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは５４３ｎｍであった。(Example 5)
Luminescent molecule 1 as a hydrogen bonding luminescent molecule and malonic acid and polymethyl methacrylate as hydrogen bonding compounds were dissolved in tetrahydrofuran and spin coated on a glass substrate to prepare a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 543 nm.
（実施例６）
水素結合性発光性分子として発光性分子１と、水素結合性化合物としてシュウ酸とポリメタクリル酸メチルをテトラヒドロフランに溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは５５７ｎｍであった。(Example 6)
A light-emitting molecule 1 as a hydrogen-bonding light-emitting molecule and oxalic acid and polymethyl methacrylate as hydrogen-bonding compounds were dissolved in tetrahydrofuran, and then spin-coated on a glass substrate to produce a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 557 nm.
（実施例７）
水素結合性発光性分子として発光性分子１と、水素結合性化合物としてカンファースルホン酸とポリメタクリル酸メチルをテトラヒドロフランに溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは５５５ｎｍであった。(Example 7)
A light-emitting molecule 1 as a hydrogen-bonding light-emitting molecule and camphorsulfonic acid and polymethyl methacrylate as hydrogen-bonding compounds were dissolved in tetrahydrofuran and spin-coated on a glass substrate to prepare a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 555 nm.
（実施例８）
重合体１をテトラヒドロフランに溶解し、スピンコーターを用いてガラス基板上に０．３μｍの厚みで塗布した。塗布面に高圧水銀灯からの光をグランテーラープリズムにより直線偏光性に変換して照射した。次に発光性分子１をクロロホルムに溶解し該基材上にスピンコーターを用いて塗布した。該基材を１６５℃に加熱して室温まで冷却した。このようにして作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは５０８ｎｍであり、その光は偏光性を有していた。(Example 8)
Polymer 1 was dissolved in tetrahydrofuran and applied to a glass substrate with a thickness of 0.3 μm using a spin coater. The coated surface was irradiated with light from a high-pressure mercury lamp converted to linear polarization by a Grand Taylor prism. Next, the luminescent molecule 1 was dissolved in chloroform and coated on the substrate using a spin coater. The substrate was heated to 165 ° C. and cooled to room temperature. When the film thus produced was irradiated with 365 nm light, the maximum wavelength λmax of the fluorescence spectrum was 508 nm, and the light had polarization.
（比較例１）
水素結合性発光性分子として発光性分子１とポリメタクリル酸メチルをテトラヒドロフラン溶解した後、ガラス基板上にスピンコートして薄膜を作製した。作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは４６０ｎｍであった。(Comparative Example 1)
A luminescent molecule 1 and polymethyl methacrylate were dissolved in tetrahydrofuran as hydrogen-bonding luminescent molecules and then spin-coated on a glass substrate to prepare a thin film. The maximum wavelength λmax of the fluorescence spectrum when the produced film was irradiated with 365 nm light was 460 nm.
（比較例２）
特許３９４５７９０に記載の水素結合性置換基を有さない直線偏光性の光と熱処理により複屈折性を示す材料をテトラヒドロフランに溶解し、スピンコーターを用いてガラス基板上に０．３μｍの厚みで塗布した。塗布面に高圧水銀灯からの光をグランテーラープリズムにより直線偏光性に変換して照射した。次に発光性分子１をクロロホルムに溶解し該基材上にスピンコーターを用いて塗布した。該基材を１２０℃に加熱して室温まで冷却した。このようにして作製したフィルムに３６５ｎｍの光を照射したときの蛍光スペクトルの極大波長λｍａｘは４６０ｎｍであり、その光は偏光性を有していなかった。(Comparative Example 2)
A material exhibiting birefringence is dissolved in tetrahydrofuran by linearly polarized light having no hydrogen bonding substituent described in Patent 3945790 and heat treatment, and applied to a glass substrate with a thickness of 0.3 μm using a spin coater. did. The coated surface was irradiated with light from a high-pressure mercury lamp converted to linear polarization by a Grand Taylor prism. Next, the luminescent molecule 1 was dissolved in chloroform and coated on the substrate using a spin coater. The substrate was heated to 120 ° C. and cooled to room temperature. When the film produced in this manner was irradiated with 365 nm light, the maximum wavelength λmax of the fluorescence spectrum was 460 nm, and the light had no polarization.
Claims (5)
前記水素結合性化合物は、化学式６で表される化合物、または、化学式８で表される繰り返し単位を１種以上含む、単独重合体あるいは共重合体であり、
前記水素結合性発光性分子と前記水素結合性化合物が分子間水素結合により自己組織化した超分子からなることを特徴とする有機発光性材料。
素数７〜２６のフェニルアルキル基、フェニル基、フェノキシ基、およびアルキル基置換フェニル基からなる群より選ばれた１種であり、
Ｒ３、Ｒ４、Ｒ５、Ｒ６は、それぞれ単独に、水素原子およびシアノ基からなる群より選ばれた１種であり、
Ｒ７〜Ｒ１２は、それぞれ単独に、水素原子、アルキル基、アルキルオキシ基およびハロゲン原子からなる群より選ばれた１種であり、
Ｒ１３〜Ｒ２０は、それぞれ単独に、水素原子、アルキル基、およびアルキルオキシ基からなる群より選ばれた１種である。
Ｙはアルキル基およびアルコキシル基からなる群より選ばれた１種であり、
ｌ＝０または１、ｋ＝０または１、
Ｚ＝なし，Ｏ，ＣＨ２，ＣＯＯまたはＯＣＯ、
Ｒ１〜Ｒ８は、それぞれ単独に、水素原子、アルキル基、アルコキシル基およびハロゲン原子からなる群より選ばれた１種であり、
Ｒ９、Ｒ１０はそれぞれ、水素原子である。
ｎ＝０〜２０、ｍ＝０または１（ただし、ｎ＝０の場合、ｍ＝０）、ｋ＝０または１、ｃ＝０または１、ｐ＝２以上の整数、
Ｙ＝なし，Ｏ，ＣＨ２，ＣＯＯまたはＯＣＯ、
Ｒ１は水素原子またはメチル基であり、
Ｒ２〜Ｒ９は、それぞれ単独に、水素原子、アルキル基、アルコキシル基およびハロゲン原子からなる群より選ばれた１種であり、Ｒ１０、Ｒ１１はそれぞれ水素原子である。 A hydrogen-bonding luminescent molecule represented by Chemical Formula 1 and a hydrogen-bonding compound;
The hydrogen bonding compound is a compound represented by Chemical Formula 6 or a homopolymer or copolymer containing one or more repeating units represented by Chemical Formula 8,
An organic light-emitting material comprising the supramolecule in which the hydrogen-bonding light-emitting molecule and the hydrogen-bonding compound are self-assembled by intermolecular hydrogen bonding.
R 3 , R 4 , R 5 , R 6 are each independently one type selected from the group consisting of a hydrogen atom and a cyano group,
R 7 to R 12 are each independently one type selected from the group consisting of a hydrogen atom, an alkyl group, an alkyloxy group, and a halogen atom,
R 13 to R 20 are each independently one type selected from the group consisting of a hydrogen atom, an alkyl group, and an alkyloxy group.
Y is one selected from the group consisting of an alkyl group and an alkoxyl group,
l = 0 or 1, k = 0 or 1,
Z = none, O, CH 2 , COO or OCO,
R 1 to R 8 are each independently one type selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxyl group, and a halogen atom,
R 9 and R 10 are each a hydrogen atom.
n = 0 to 20, m = 0 or 1 (where n = 0, m = 0), k = 0 or 1, c = 0 or 1, p = 2 or greater integer,
Y = none, O, CH 2 , COO or OCO,
R 1 is a hydrogen atom or a methyl group,
R 2 to R 9 are each independently one type selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxyl group, and a halogen atom, and R 10 and R 11 are each a hydrogen atom.
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