JPH10182651A - Pyridophenoxazine-metal chelate compound - Google Patents
Pyridophenoxazine-metal chelate compoundInfo
- Publication number
- JPH10182651A JPH10182651A JP8357304A JP35730496A JPH10182651A JP H10182651 A JPH10182651 A JP H10182651A JP 8357304 A JP8357304 A JP 8357304A JP 35730496 A JP35730496 A JP 35730496A JP H10182651 A JPH10182651 A JP H10182651A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- metal chelate
- chelate compound
- group
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規な金属キレー
ト化合物に関し、詳しくは有機溶媒に対する溶解性が高
く、塗布によるコーティングが可能で、しかも耐光性に
優れた、光記録媒用記録材料として有用なピリドフェノ
オキサジン金属キレート化合物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel metal chelate compound, and more particularly, it is useful as a recording material for an optical recording medium having high solubility in an organic solvent, coating by coating, and excellent light resistance. Pyridophenoxazine metal chelate compound.
【０００２】[0002]
【従来の技術】従来、有機色素薄膜を記録層とする記録
媒体において、該有機色素薄膜にフタロシアニン化合物
を使用したもの（例えば特開昭５８−１８３２９６号公
報その他）、シアニン系色素を使用したもの（例えば特
開昭５７−８２０９３号公報その他）、あるいはフェナ
レン系色素、ナフトキノン系色素などを使用したものが
知られている。たゞ、フタロシアニン化合物は、熱、光
等に対する安定性が極めて高いため、情報記録感度が低
く記録に時間を要するし、また有機溶剤への溶解性が乏
しく、従来は蒸着法しか薄膜化はできず生産性が悪いと
いう難点を有している。フェナレン系色素又はナフトキ
ノン系色素は、蒸着させやすい利点を有する反面、反射
率が低いという欠点がある。シアニン系色素は、塗布に
よるコーティングが容易であるという利点を有する反
面、耐光性に劣り、再生光による劣化を起こすという欠
点がある。2. Description of the Related Art Conventionally, a recording medium having an organic dye thin film as a recording layer, a phthalocyanine compound used in the organic dye thin film (for example, Japanese Patent Application Laid-Open No. 58-183296 and others), and a cyanine dye is used. (For example, JP-A-57-82093 and others), or those using a phenalene dye, a naphthoquinone dye or the like are known. However, phthalocyanine compounds have extremely high stability to heat, light, etc., and therefore have low information recording sensitivity and require time for recording, and have poor solubility in organic solvents. And has the disadvantage of low productivity. Phenalene dyes or naphthoquinone dyes have the advantage of being easy to deposit, but have the disadvantage of low reflectivity. Cyanine dyes have the advantage of being easy to coat by application, but have the disadvantage that they are inferior in light resistance and deteriorate by reproduction light.
【０００３】加えて、近年、従来の光ディスクで使用さ
れてきた波長域より短波長に発振波長（６３０〜７２０
ｎｍ）を有する半導体レーザーが実用化されはじめてい
る。更に、基板上に有機色素、金属反射層、保護層を順
次積層してなるＣＤ−Ｒ媒体は、そのＣＤ規格を満足す
るには高い反射率を必要とし、そのため再生波長域（７
７０〜８３０ｎｍ）に高い屈折率を有し、且つ安定性の
高い有機色素の開発が必要である。In addition, in recent years, the oscillation wavelength (630 to 720) has been shortened to a wavelength shorter than the wavelength range used in conventional optical disks.
nm) are being put to practical use. Furthermore, a CD-R medium in which an organic dye, a metal reflective layer, and a protective layer are sequentially laminated on a substrate requires a high reflectance to satisfy the CD standard.
It is necessary to develop an organic dye having a high refractive index (70 to 830 nm) and high stability.
【０００４】[0004]
【発明が解決しようとする課題】従って、本発明は有機
溶媒に対する溶解性が高く、塗布によるコーティングが
可能で、しかも耐光性に優れた、光記録媒用記録材料と
して有用な、新規な化合物を提供することを目的とす
る。Accordingly, the present invention provides a novel compound which has high solubility in an organic solvent, can be coated by coating, and has excellent light resistance and is useful as a recording material for an optical recording medium. The purpose is to provide.
【０００５】[0005]
【課題を解決するための手段】本発明によれば、第一
に、下記一般式（Ｉ）で示されるピリドフェノオキサジ
ン金属キレート化合物が提供される。According to the present invention, first, a pyridophenoxazine metal chelate compound represented by the following general formula (I) is provided.
【化１】 （式中、Ｍ、Ｒ1、Ｒ2、Ｘ及びｎはそれぞれ以下のもの
を表す。 Ｍ：Ｆｅ、Ｃｏ、Ｎｉ、Ｃｕ又はＺｎ金属原子、 Ｒ1、Ｒ2：それぞれ独立に、置換若しくは無置換のアル
キル基、又は置換若しくは無置換のアリール基、 Ｘ：陰イオン、 ｎ：２又は３。） 第二に、前記一般式（Ｉ）において、Ｒ1及びＲ2がそれ
ぞれ独立に、置換若しくは無置換のアルキル基である上
記第一に記載したピリドフェノオキサジン金属キレート
化合物が提供される。Embedded image (Wherein, M, R 1 , R 2 , X and n each represent the following: M: Fe, Co, Ni, Cu or Zn metal atom, R 1 , R 2 : each independently substituted or unsubstituted A substituted alkyl group or a substituted or unsubstituted aryl group, X: anion, n: 2 or 3.) Second, in the general formula (I), R 1 and R 2 are each independently substituted or substituted. A pyridophenoxazine metal chelate compound as described in the first item, which is an unsubstituted alkyl group, is provided.
【０００６】本発明の前記一般式（Ｉ）で示される新規
な金属キレート化合物は、有機溶剤に対する溶解性が高
く、生産性の高い溶剤塗工が可能であり、耐光性及び安
定性に優れた、しかも分解点が２５０℃以下と低い色素
である。従って、該色素は光記録媒体用の記録材料とし
て特に有用であり、該色素を含有することにより、生産
性安定性の高い、高耐光、高感度、高速記録が可能な光
記録媒体が提供される。The novel metal chelate compound represented by the general formula (I) of the present invention has high solubility in organic solvents, enables solvent coating with high productivity, and has excellent light resistance and stability. In addition, the pigment has a decomposition point as low as 250 ° C. or less. Therefore, the dye is particularly useful as a recording material for an optical recording medium, and by containing the dye, an optical recording medium with high productivity stability, high light resistance, high sensitivity, and high-speed recording is provided. You.
【０００７】[0007]
【発明の実施の形態】以下、本発明を詳しく説明する。
本発明は、上記したように下記一般式（Ｉ）で示される
ピリドフェノオキサジン金属キレート化合物に関するも
のであるが、このピリドフェノオキサジン金属キレート
化合物は、新規物質である。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
The present invention relates to a pyridophenoxazine metal chelate compound represented by the following general formula (I) as described above, and this pyridophenoxazine metal chelate compound is a novel substance.
【化１】 Embedded image
【０００８】前記一般式（Ｉ）で示されるピリドフェノ
オキサジン金属キレート化合物において、ＭはＦｅ、Ｃ
ｏ、Ｎｉ、Ｃｕ又はＺｎ金属原子を表す。In the pyridophenoxazine metal chelate compound represented by the general formula (I), M is Fe, C
represents a metal atom of o, Ni, Cu or Zn.
【０００９】前記一般式（Ｉ）において、Ｒ1及びＲ
2は、それぞれ独立に、置換若しくは無置換のアルキル
基、又は置換若しくは無置換のアリール基を表すが、Ｒ
1及びＲ2のアルキル基の具体例としては、次のものが挙
げられる。メチル基、エチル基、ｎ−プロピル基、ｎ−
ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプ
チル基、ｎ−オクチル基、ｎ−ノニル基、ｎ−デシル基
等の一級アルキル基；イソプロピル基、イソブチル基、
ｓｅｃ−ブチル基、イソアミル基等の二級アルキル基；
ネオペンチル基、ｔｅｒｔ−ブチル基、ｔｅｒｔ−ヘキ
シル基、ｔｅｒｔ−アミル基、ｔｅｒｔ−オクチル基等
の三級アルキル基；シクロヘキシル基等のシクロアルキ
ル基等。In the general formula (I), R 1 and R
2 independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;
Specific examples of the alkyl group of 1 and R 2 include the following. Methyl group, ethyl group, n-propyl group, n-
Primary alkyl groups such as butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group; isopropyl group, isobutyl group,
secondary alkyl groups such as sec-butyl group and isoamyl group;
Tertiary alkyl groups such as neopentyl group, tert-butyl group, tert-hexyl group, tert-amyl group, tert-octyl group; cycloalkyl groups such as cyclohexyl group;
【００１０】また、アリール基としては、フェニル基、
エチルフェニル基、ブチルフェニル基、ナフチル基等が
挙げられる。アリール基としては、フェニルチオエチル
基、メチルチオエチル基、ブチルチオエチル基等が、窒
素を介して置換されているアリール基としては、ジメチ
ルアミノフェニル基、ジブチルアミノフェニル基等が挙
げられる。The aryl group includes a phenyl group,
Examples include an ethylphenyl group, a butylphenyl group, and a naphthyl group. As the aryl group, a phenylthioethyl group, a methylthioethyl group, a butylthioethyl group and the like are substituted through nitrogen, and as the aryl group, a dimethylaminophenyl group, a dibutylaminophenyl group and the like are mentioned.
【００１１】また、前記一般式（Ｉ）において、Ｘは陰
イオンを表すが、その具体例としては、表１に示すよう
なものが挙げられる。In the general formula (I), X represents an anion. Specific examples thereof include those shown in Table 1.
【表１】 [Table 1]
【００１２】本発明のピリドフェノオキサジン金属キレ
ート化合物は、例えば次の方法によって製造することが
できる。まず、例えば日本化学会第６８秋季年会講演予
稿集５０２頁に記載の方法に従って配位子を得る。すな
わち、下記一般式（ＩＩ）で示される化合物と、下記一
般式（ＩＩＩ）で示される化合物とを反応させ下記一般
式（ＩＶ）で示される配粒子を得る。The pyridophenoxazine metal chelate compound of the present invention can be produced, for example, by the following method. First, a ligand is obtained in accordance with the method described in, for example, page 502 of the proceedings of the 68th Annual Meeting of the Chemical Society of Japan. That is, a compound represented by the following general formula (II) is reacted with a compound represented by the following general formula (III) to obtain distribution particles represented by the following general formula (IV).
【化２】 Embedded image
【化３】 （式中、Ｒ1及びＲ2は前記定義に同じ。）Embedded image (In the formula, R 1 and R 2 are the same as defined above.)
【化４】 （式中、Ｒ1及びＲ2は前記定義に同じ。） 次いで、上記一般式（ＩＶ）で示される配位子と下記一
般式（Ｖ）で示される金属塩とを反応させることによ
り、前記一般式（Ｉ）で示される化合物を得ることがで
きる。 ＭＸ ・・・・・（Ｖ） （式中、Ｍ及びＸは前記定義に同じ。）Embedded image (In the formula, R 1 and R 2 are the same as defined above.) Then, the ligand represented by the general formula (IV) is reacted with a metal salt represented by the following general formula (V) to thereby obtain the above-mentioned compound. The compound represented by the general formula (I) can be obtained. MX (V) (wherein, M and X are the same as defined above)
【００１３】本発明の前記一般式（Ｉ）で示される金属
キレート化合物の具体例としては、例えば表２−（１）
及び表２−（２）で示されるものが挙げられる。Specific examples of the metal chelate compound represented by the general formula (I) of the present invention include, for example, Table 2- (1)
And Table 2- (2).
【００１４】[0014]
【表２−（１）】 [Table 2- (1)]
【００１５】[0015]
【表２−（２）】 [Table 2- (2)]
【００１６】本発明の前記一般式（Ｉ）で示されるピリ
ドフェノオキサジン金属キレート化合物は、有機溶媒に
対する溶解性が高く、塗布によるコーティングが可能
で、しかも耐光性に優れた新規な金属キレート化合物で
あり、光情報記録用材料として極めて有用な化合物であ
る。The pyridophenoxazine metal chelate compound represented by the general formula (I) of the present invention is a novel metal chelate compound which has high solubility in an organic solvent, can be coated by coating, and has excellent light resistance. Which is an extremely useful compound as an optical information recording material.
【００１７】[0017]
【実施例】以下、実施例により本発明を具体的に説明す
る。 実施例１ 下記構造式（Ａ）で示される化合物１０．０ｇ及び下記
構造式（Ｂ）で示される化合物９．５ｇを、Ｃｕ（ＯＣ
ＯＣＨ3）2１０．５ｇを含む酢酸５０ｍｌに加え、５時
間撹拌した。反応液に氷水を加え、沈殿物を濾取した。
沈殿物はクロロホルムにより抽出し、クロロホルム層を
濃縮、カラムクロマトグラム法により下記構造式（Ｃ）
で示される目的配位子１１．９ｇ収率６５％を分離精製
した。次に、構造式（Ｃ）で示される配位子２．０ｇを
テトラヒドロフラン１００ｍｌに溶解させた後、室温に
てＮｉ（ＣｌＯ4）2６Ｈ2Ｏ ２．３ｇを加え、濾過し
た後、濾液を放置し、析出した結晶を濾取し、下記構造
式（Ｄ）で示される金属キレート化合物１．７ｇを得
た。得られた金属キレート化合物の可視部の吸収スペク
トルは、λｍａｘ６１０ｎｍ（トルエン中）、分解開始
温度２４０℃であった。The present invention will be described below in detail with reference to examples. Example 1 10.0 g of a compound represented by the following structural formula (A) and 9.5 g of a compound represented by the following structural formula (B) were added to Cu (OC)
It was added to 50 ml of acetic acid containing 10.5 g of OCH 3 ) 2 and stirred for 5 hours. Ice water was added to the reaction solution, and the precipitate was collected by filtration.
The precipitate was extracted with chloroform, the chloroform layer was concentrated, and the following structural formula (C) was obtained by column chromatography.
11.9 g of the target ligand represented by the above was isolated and purified at a yield of 65%. Next, after dissolving the ligand 2.0g represented by the structural formula (C) in tetrahydrofuran 100 ml, Ni and (ClO 4) 2 6H 2 O 2.3g was added at room temperature, after filtration, the filtrate The mixture was allowed to stand, and the precipitated crystals were collected by filtration to obtain 1.7 g of a metal chelate compound represented by the following structural formula (D). The absorption spectrum of the visible part of the obtained metal chelate compound was λmax 610 nm (in toluene), and the decomposition initiation temperature was 240 ° C.
【００１８】[0018]
【化５】 Embedded image
【化６】 Embedded image
【化７】 Embedded image
【化８】 Embedded image
【００１９】実施例２ 前記構造式（Ａ）で示される化合物５．２ｇ及び下記構
造式（Ｅ）で示される化合物１０．０ｇを、ＦｅＣｌ
3 ４．９ｇを含む酢酸３０ｍｌに加え、１０時間撹拌
した。反応液に氷水を加え、沈殿物を濾取した。沈殿物
はクロロホルムにより抽出し、クロロホルム層を濃縮、
カラムクロマトグラム法により下記構造式（Ｆ）で示さ
れる目的配位子８．５ｇ収率５８％を分離精製した。次
に、構造式（Ｆ）で示される配位子１．０ｇをエタノー
ル３０ｍｌに溶解させた後、室温にてＣｕＳＯ4５Ｈ2Ｏ
０．５ｇを加え、濾過した後、濾液に水を加え、析出
した結晶を濾取、水洗し、下記構造式（Ｇ）で示される
金属キレート化合物１．２ｇを得た。得られた金属キレ
ート化合物の可視部の吸収スペクトルは、λｍａｘ６１
４ｎｍ（トルエン中）、分解開始温度２２０℃であっ
た。得られた金属キレート化合物のクロロホルム溶液中
の可視吸収スペクトルを図１に、また該化合物の吸収ス
ペクトルを図３に示す。Example 2 5.2 g of the compound represented by the above structural formula (A) and 10.0 g of the compound represented by the following structural formula (E) were combined with FeCl
3 The mixture was added to 30 ml of acetic acid containing 4.9 g and stirred for 10 hours. Ice water was added to the reaction solution, and the precipitate was collected by filtration. The precipitate was extracted with chloroform, and the chloroform layer was concentrated.
By column chromatography, 8.5 g of the target ligand represented by the following structural formula (F) was separated and purified at a yield of 58%. Next, after dissolving 1.0 g of the ligand represented by the structural formula (F) in 30 ml of ethanol, CuSO 4 5H 2 O was added at room temperature.
After adding 0.5 g and filtering, water was added to the filtrate, and the precipitated crystals were collected by filtration and washed with water to obtain 1.2 g of a metal chelate compound represented by the following structural formula (G). The absorption spectrum of the visible part of the obtained metal chelate compound is λmax61.
4 nm (in toluene) and the decomposition initiation temperature was 220 ° C. FIG. 1 shows a visible absorption spectrum of the obtained metal chelate compound in a chloroform solution, and FIG. 3 shows an absorption spectrum of the compound.
【００２０】[0020]
【化９】 Embedded image
【化１０】 Embedded image
【化１１】 Embedded image
【００２１】実施例３ 前記構造式（Ｆ）で示される配位子１．０ｇをエタノー
ル３０ｍｌに溶解させた後、室温にてＣｏＳＯ4７Ｈ2Ｏ
０．６ｇを加え、濾過した後、濾液に水を加え、析出
した結晶を濾取、水洗し、下記構造式（Ｈ）で示される
金属キレート化合物１．１ｇを得た。得られた金属キレ
ート化合物の可視部の吸収スペクトルは、λｍａｘ６４
８ｎｍ（アセトニトリル中）であった。得られた金属キ
レート化合物のメタノール溶液中の可視吸収スペクトル
を図２に示す。Example 3 After dissolving 1.0 g of the ligand represented by the structural formula (F) in 30 ml of ethanol, CoSO 4 7H 2 O was added at room temperature.
After adding 0.6 g and filtering, water was added to the filtrate, and the precipitated crystals were collected by filtration and washed with water to obtain 1.1 g of a metal chelate compound represented by the following structural formula (H). The absorption spectrum of the visible part of the obtained metal chelate compound is λmax64
8 nm (in acetonitrile). FIG. 2 shows a visible absorption spectrum of the obtained metal chelate compound in a methanol solution.
【００２２】[0022]
【化１２】 Embedded image
【００２３】[0023]
【発明の効果】本発明のピリドフェノオキサジン金属キ
レート化合物は前記一般式（Ｉ）で示される構造を有す
ることから、有機溶媒に対する溶解性が高く、生産性の
高い溶剤塗工によるコーティング可能であり、しかも耐
光性に優れ、その上分解点が２５０℃以下と低い色素で
ある。従って、特に光記録媒用の記録材料として極めて
有用である。Since the pyridophenoxazine metal chelate compound of the present invention has the structure represented by the general formula (I), it has high solubility in an organic solvent and can be coated by solvent coating with high productivity. A dye having excellent light fastness and a low decomposition point of 250 ° C. or less. Therefore, it is extremely useful especially as a recording material for an optical recording medium.
【図面の簡単な説明】[Brief description of the drawings]
【図１】本発明の実施例２で得られた銅キレート化合物
のクロロホルム溶液中の可視吸収スペクトルを表す図で
ある。FIG. 1 is a view showing a visible absorption spectrum of a copper chelate compound obtained in Example 2 of the present invention in a chloroform solution.
【図２】本発明の実施例３で得られたコバルトキレート
化合物のメタノール溶液中の可視吸収スペクトルを表す
図である。FIG. 2 is a view showing a visible absorption spectrum of a cobalt chelate compound obtained in Example 3 of the present invention in a methanol solution.
【図３】本発明の実施例２で得られた銅キレート化合物
の赤外吸収スペクトルを表す図である。FIG. 3 is a diagram showing an infrared absorption spectrum of a copper chelate compound obtained in Example 2 of the present invention.
Claims (2)
ノオキサジン金属キレート化合物。 【化１】 （式中、Ｍ、Ｒ1、Ｒ2、Ｘ及びｎはそれぞれ以下のもの
を表す。 Ｍ：Ｆｅ、Ｃｏ、Ｎｉ、Ｃｕ又はＺｎ金属原子、 Ｒ1、Ｒ2：それぞれ独立に、置換若しくは無置換のアル
キル基、又は置換若しくは無置換のアリール基、 Ｘ：陰イオン、 ｎ：２又は３。）1. A pyridophenoxazine metal chelate compound represented by the following general formula (I). Embedded image (Wherein, M, R 1 , R 2 , X and n each represent the following: M: Fe, Co, Ni, Cu or Zn metal atom, R 1 , R 2 : each independently substituted or unsubstituted A substituted alkyl group or a substituted or unsubstituted aryl group, X: anion, n: 2 or 3.)
がそれぞれ独立に、置換若しくは無置換のアルキル基で
ある請求項１記載のピリドフェノオキサジン金属キレー
ト化合物。2. In the general formula (I), R 1 and R 2
The pyridophenoxazine metal chelate compound according to claim 1, wherein each is independently a substituted or unsubstituted alkyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35730496A JP3663528B2 (en) | 1996-12-26 | 1996-12-26 | Pyridophenoxazine metal chelate compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35730496A JP3663528B2 (en) | 1996-12-26 | 1996-12-26 | Pyridophenoxazine metal chelate compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10182651A true JPH10182651A (en) | 1998-07-07 |
| JP3663528B2 JP3663528B2 (en) | 2005-06-22 |
Family
ID=18453443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP35730496A Expired - Fee Related JP3663528B2 (en) | 1996-12-26 | 1996-12-26 | Pyridophenoxazine metal chelate compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3663528B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218072B1 (en) * | 1997-11-20 | 2001-04-17 | Taiyo Yuden Co., Ltd. | Optical information recording medium |
| JP2007119481A (en) * | 1999-01-27 | 2007-05-17 | Mitsubishi Chemicals Corp | Compound for forming organic layer of organic electric field light-emitting element, and organic electric field light-emitting element by using the same |
| CN114773361A (en) * | 2022-04-15 | 2022-07-22 | 山东第一医科大学(山东省医学科学院) | N-heteronile erythronium salt compound and preparation method and application thereof |
-
1996
- 1996-12-26 JP JP35730496A patent/JP3663528B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218072B1 (en) * | 1997-11-20 | 2001-04-17 | Taiyo Yuden Co., Ltd. | Optical information recording medium |
| JP2007119481A (en) * | 1999-01-27 | 2007-05-17 | Mitsubishi Chemicals Corp | Compound for forming organic layer of organic electric field light-emitting element, and organic electric field light-emitting element by using the same |
| CN114773361A (en) * | 2022-04-15 | 2022-07-22 | 山东第一医科大学(山东省医学科学院) | N-heteronile erythronium salt compound and preparation method and application thereof |
| CN114773361B (en) * | 2022-04-15 | 2023-04-11 | 山东第一医科大学(山东省医学科学院) | N-heteronile erythronium salt compound and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3663528B2 (en) | 2005-06-22 |
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