WO2003106391A1 - Blue-emitting compounds, blue-emitting fluoroalkylated stilbenes, and light emitting devices - Google Patents

Abstract

The invention provides blue-emitting compounds which emit blue light at high color purity and high brightness and exhibit high fastness, and light emitting devices capable of emitting light at high brightness, namely, blue-emitting compounds represented by the general formula (1) or (31) and light-emitting devices containing the compounds in the light-emitting layer: (1) (wherein Ar is an aromatic group; Ar1 is hydrogen or an aromatic substituent; and when Ar1 is hydrogen, Ar2 is an aromatic substituent, while when Ar1 is an aromatic substituent, Ar2 is hydrogen or an aromatic substituent) (31) (wherein Ar is an aromatic group; Y is fluoroalkyl having 1 to 3 carbon atoms; and n is a positive number of 1 to 3; Y is attached to the position ortho or papa to -CZ; Ys on one benzene ring may be the same or different and Ys on the two benzene rings may be the same or different; and Z is hydrogen or a specific fluoroalkylated aromatic group).

Description

 Description Blue light-emitting compound, fluorinated alkyl group-containing stilbene-based blue light-emitting compound, and light-emitting element

 The present invention relates to a blue light-emitting compound, a stilbene-based blue light-emitting compound containing a fluorinated alkyl group, and a light-emitting element. More specifically, the present invention relates to a blue light-emitting compound having high color purity and high luminance, high robustness, and high luminance. The present invention relates to a light-emitting element capable of emitting light. Background art

 Conventionally, there is no organic compound that emits high-purity blue light with high luminance when energy is applied. In addition, there was no organic organoid compound that emits blue light with high luminance and high purity and that is robust. An object of the present invention is to provide a durable organic compound which emits high-purity blue light with high luminance. Another object of the present invention is to provide a durable light-emitting element that emits light of high purity and high luminance. Disclosure of the invention

 (1) A means for solving the above problem is a blue light-emitting compound characterized by having a structure represented by the following formula (1):

(1)

 A r — G H; A r-G H. A

(However, in the formula, one Ar— is an aromatic group, and A r 1_ is a hydrogen atom or an aromatic group. Is a substituent. Ar 2— is an aromatic substituent when Ar 1 is a hydrogen atom, and is a hydrogen atom or an aromatic substituent when Ar 1 is an aromatic substituent. In a preferred embodiment of the blue light-emitting compound, in the formula (1), one Ar— is a 1,4-phenylene group represented by the following formula (la ′), and is represented by the following formula (1b1). A 1,4-naphthylene group, a 2,6-naphthylene group represented by the following formula (lb 2), or a 9,10-anthrylene group represented by the following formula (1c), wherein Ar 1 is a hydrogen atom, Or the following formula

(I d) to an aromatic substituent represented by any of the following formulas (If), and Ar 2 is a hydrogen atom or the following formula (Id) when Ar 1 is the aromatic substituent: To an aromatic substituent represented by any of the following formulas (1f), and when Ar 1 is a hydrogen atom, any one of the following formulas (1d) to (If) Is an aromatic substituent represented by

(Wherein, R ¹ is a hydrogen atom, an alkyl group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, an alkoxy group which may be substituted by a fluorine atom having 1 to 5 carbon atoms or 1 carbon atom Represents an alkenyl group of 5 to 5. m represents 0, and represents an integer of 1 to 5. A plurality of R ¹ may be the same or different, and R ² is a hydrogen atom and a fluorine atom having 1 to 5 carbon atoms. An alkyl group which may be substituted with an atom, an alkoxy group which may be substituted with a fluorine atom having 1 to 5 carbon atoms, or an alkenyl group having 1 to 5 carbon atoms, wherein n is an integer of 0 or 1 to 3; A plurality of R ² may be the same or different R ³ is a hydrogen atom, an alkyl group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, a fluorine atom having 1 to 5 carbon atoms Represents an optionally substituted alkoxy group or an alkenyl group having 1 to 5 carbon atoms, p represents an integer of 0 or 1 to 4. A plurality of R ³ are the same. R ² and R ³ may be the same or different R ⁴ is a hydrogen atom or a fluorine atom having 1 to 5 carbon atoms An alkyl group, an alkoxy group which may be substituted by a fluorine atom having 1 to 5 carbon atoms And a alkenyl group having 1 to 5 carbon atoms. R ⁵ is a hydrogen atom, an alkyl group which may be substituted by a C ^1-5 fluorine atom, an alkoxy group which may be substituted by a C 1-5 fluorine atom, or an alkyl group having 1-5 carbon atoms Represents a group. q represents 0, an integer of 1 to 4. A plurality of R ⁵ may be the same or different. Further, R ⁴ and R ⁵ may be the same or different. )

 (2) Another means for solving the above-mentioned problem is a light-emitting element characterized in that a light-emitting layer containing a blue light-emitting compound represented by the general formula (1) is provided between a pair of electrodes. is there.

(3) Further, the present invention for solving the above problem is a stilbene-based blue light-emitting compound containing an alkyl fluoride group, which has a structure represented by the following formula (31):

(31)

(However, in the formula, Ar— is an aromatic group represented by the following formula (32) or (33). Y represents a fluorinated alkyl group having 1 to 3 carbon atoms. The bond position of Y is ortho-position or para-position with respect to one CZ.A plurality of Ys bonded to one benzene ring may be the same or different. A plurality of Ys bonded to two benzene rings may be the same or different, and Z is a hydrogen atom or represented by the following formula (34).

(In the formulas (32) and (33), X is a hydrogen atom or an alkoxy group having 1 to 5 carbon atoms, and the two Xs may be the same or different.)

(However, in the formula (34), Y represents a fluorinated alkyl group having 1 to 3 carbon atoms. N represents a positive number of 1 to 3. The bonding position of Y is at the ortho or para position. A plurality of Ys bonded to the benzene ring may be the same or different.) (4) Another means for solving the above problem is to provide a light-emitting layer containing a stilbene-based blue light-emitting compound containing a fluorinated alkyl group represented by the general formula (31) between a pair of electrodes. This is a light-emitting element characterized by being formed. BRIEF DESCRIPTION OF THE FIGURES

FIG. 1 is an explanatory diagram showing a light-emitting element as an example according to the present invention. FIG. 2 is an explanatory diagram showing a light emitting element as another example according to the present invention. FIG. 3 is an explanatory view showing a light emitting element as another example according to the present invention. FIG. 4 is an explanatory view showing a light emitting element as still another example according to the present invention. FIG. 5 is a chart showing an IR chart of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 1. FIG. 6 is a chart showing an NMR chart of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 1. FIG. 7 is a spectrum diagram showing a fluorescence spectrum of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 1. FIG. 8 is a chart showing an IR chart of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 2. FIG. 9 is a chart showing an NMR chart of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 2. FIG. 10 is a spectrum diagram showing a fluorescence spectrum of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 2. FIG. 11 is a chart showing an IR chart of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 3. FIG. 12 is a chart showing an NMR chart of a blue light-emitting compound which is an example of the present invention and synthesized in Example 3. FIG. 13 is a spectrum diagram showing a fluorescence spectrum of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 3. FIG. 14 is an IR chart of a blue light-emitting compound synthesized in Example 5, which is an example of the present invention. FIG. 15 is an NMR chart of a blue light-emitting compound synthesized in Example 5, which is an example of the present invention. FIG. 16 is a spectrum diagram showing a fluorescence spectrum of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 5. FIG. 17 is an IR chart showing 1-chloromethyl-4- (2-bromoethyl) benzene synthesized in Example 6. FIG. 18 is an NMR chart showing 1-chloromethyl-41- (2-bromoethyl) benzene synthesized in Example 6 of the present invention. FIG. 19 shows a blue light-emitting compound as an example of the present invention synthesized in Example 6. It is an IR chart. FIG. 20 is an NMR chart of a blue light-emitting compound synthesized in Example 6 and which is an example of the present invention. FIG. 21 is a spectrum diagram showing a fluorescence spectrum of a blue light-emitting compound as an example of the present invention, which was synthesized in Example 6. FIG. 22 is an IR chart of a blue light-emitting compound as an example of the present invention, synthesized in Example 7. FIG. 23 is an NMR chart of the blue light-emitting compound synthesized in Example 7 and which is an example of the present invention. FIG. 24 is an NMR chart of the blue light-emitting compound synthesized in Example 8, which is an example of the present invention. FIG. 25 is a diagram showing an IR chart of a blue light-emitting compound which is an example of the present invention and synthesized in Example 31. FIG. 26 is a diagram showing an NMR chart of a blue light-emitting compound as one example of the present invention, which was synthesized in Example 31. FIG. 27 is a diagram showing an IR chart of a blue light-emitting compound which is an example of the present invention and synthesized in Example 32. FIG. 28 is a diagram showing an NMR chart of a blue light-emitting compound which is an example of the present invention and synthesized in Example 32. FIG. 29 is a fluorescent spectrum chart of a blue light-emitting compound which is an example of the present invention and synthesized in Example 32. BEST MODE FOR CARRYING OUT THE INVENTION

 A novel blue light-emitting compound according to the present invention has a structure represented by Formula (1).

(1)

A r 2 GH _S A r -GH _? —— A r 1

式 （1 a) で示される基は 1， 4ーフヱニル基であり、 式 （1 b 1) で示される 基は、 1, 4一ナフチレン基であり、 式 （l b 2) で示される基は、 2, 6—ナフ チレン基であり、 式 （l c) で示される基は 9, 10—アントリレン基である。 前記式 （l a) 〜 （1 c) で示される四種の芳香族基の中でも、 式 （l a) 及び (1 c) で示される芳香族基が好ましい。 式 （1 a) で示される芳香族基を有する 青色発光化合物は人体に接触しても人体の皮膚に 「かぶれ」 を生じさせない。 また、 好適な A r 1一及び Ar 2—は、 式 （1 d) 〜 （： L f ) で示される。

ただし、 式中、 R ¹ は水素原子、 炭素数 1〜 5のフッ素原子が置換してもよいァ ルキル基、 炭素数 1〜 5のフッ素原子が置換してもよいアルコキシ基又は炭素数 1 〜 5のアルケニル基を示す。 mは 0、 1〜5の整数を示す。 複数の R ¹ は同一であ つても相違していてもよい。 R ² は水素原子、 炭素数 1〜 5のフッ素原子が置換し てもよいアルキル基、 炭素数 1〜 5のフッ素原子が置換してもよレ、アルコキシ基又 は炭素数 1〜 5のァルケ-ル基を示す。 nは、 0、 1〜 3の整数を示す。 複数の R ² は同一であっても相違していてもよい。 R ³ は水素原子、 炭素数 1〜5のフッ素 原子が置換してもよいアルキル基、 炭素数 1〜 5のフッ素原子が置換してもよぃァ ルコキシ基又は炭素数 1〜 5のァルケ-ル基を示す。 pは、 0、 1〜4の整数を示 す。 複数の R ³ は同一であっても相違していてもよい。 また、 R ² と R ³ とは同一 であっても相違していてもよい。 R ⁴ は水素原子、 炭素数 1〜 5のフッ素原子が置 換してもよいアルキル基、 炭素数 1〜 5のフッ素原子が置換してもよいアルコキシ 基又は炭素数 1〜 5のアルケュル基を示す。 R ⁵ は水素原子、 炭素数 1〜 5のフッ 素原子が置換してもよいアルキル基、 炭素数 1〜 5のフッ素原子が置換してもよい アルコキシ基又は炭素数 1〜 5のアルケニル基を示す。 qは、 0、 1〜4の整数を 示す。 複数の R⁵ は同一であっても相違していてもよい。 また、 R⁴ と R⁵ とは同 一であっても相違していてもよい。 前記 R¹ 、 R² 、 R³ 、 R⁴ 及ぴ R⁵ がアルキル基を示す場合、 そのアルキル基 としては、 メチル基、 ェチル基、 プロピル基、 ブチル基及ぴペンチル基等をあげる ことができる。 好適なアルキル基は、 メチル基、 ェチル基及びプロピル基等の炭素 数 1〜 3の低級アルキル基である。 前記 R¹ 、 R² 、 R³ 、 R⁴ 及び R⁵ がフッ素原子を含有するアルキル基 （以下 において、 フッ素原子含有アルキル基と略称することがある。 ） を示す場合、 その フッ素原子含有アルキル基としては、 モノフルォロメチル基、 ジフルォロメチル基 、 トリフルォロメチル基、 1一モノフルォロェチル基、 1， 1ージフルォロェチル 基、 1, 1, 2—トリフルォロェチル基、 1, 1, 2, 2—テトラフルォロェチル 基、 1, 1， 2， 2, 2—ペンタフルォロェチル基、 1〜 7個のフッ素原子を置換 するフッ化プロピル基、 1〜 9個のフッ素原子を置換するフッ化プチル基及び 1〜 1 1個のフッ素原子を置換するペンチル基等をあげることができる。 前記 R¹ 、 R² 、 R³ 、 R 及び R⁵ がアルコキシ基を示す場合、 そのァノレコキ シ基としては、 メ トキシ基、 エトキシ基、 プロポキシ基、 ブトキシ基及びペントキ シ基等を挙げることができる。 好適なアルコキシ基は、 メ トキシ基、 エトキシ基等 の炭素数 1〜 3の低級アルコキシ基である。 前記 R¹ 、 R² 、 R³ 、 R⁴ 及び R⁵ がアルケニル基を示す場合、 そのアルケニ ル基としては、 ビニル基、 プロぺニル基、 ブテュル基、 ペンテ二ル基等をあげるこ とができる。 好適なアルケニル基は、 ビエル基である。 式 （1) で示される青色発光化合物の中でも好適な化合物は、 式 （2) 、 式 （3 ) 及び式 （4) で示すことができる。 However, in the formula (1), one Ar— is an aromatic group, which is a group having a single ring or a condensed ring and having π electrons conjugated together. Ar 1— is a hydrogen atom or an aromatic substituent. Ar 2— is an aromatic substituent when Ar 1 is a hydrogen atom, and is a hydrogen atom or an aromatic substituent when Ar 1 is an aromatic substituent. The aromatic substituent is a substituent having a single ring or a condensed ring, having conjugated π electrons, and bonding to an adjacent methylene group. Examples of the aromatic group include a divalent group having π electrons and having aromaticity (that is, an aromatic group having two bonds), and a phenylene group, a phenanthrylene group, Preferable examples include an anthrylene group, a triphenylene group, a pyrenylene group, and a naphthasenylene group. More preferred examples of Ar— include aromatic groups represented by formulas (la) to (lc).

The group represented by the formula (1a) is a 1,4-phenyl group, the group represented by the formula (1b1) is a 1,4-naphthylene group, and the group represented by the formula (lb 2) is It is a 2,6-naphthylene group, and the group represented by the formula (lc) is a 9,10-anthrylene group. Among the four types of aromatic groups represented by the formulas (la) to (1c), the aromatic groups represented by the formulas (la) and (1c) are preferable. The blue light-emitting compound having an aromatic group represented by the formula (1a) does not cause "rash" on the skin of a human body even when it comes into contact with the human body. Further, preferred Ar 1 and Ar 2 — are represented by the following formulas (1 d) to (: L f).

However, in the formula, R ¹ is a hydrogen atom, an alkyl group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, an alkoxy group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, or 1 to 5 carbon atoms. 5 represents an alkenyl group. m represents 0, an integer of 1 to 5; A plurality of R ¹ may be the same or different. R ² is a hydrogen atom, an alkyl group which may be substituted by a C 1-5 fluorine atom, an alkyl group which may be substituted by a C 1-5 fluorine atom, an alkoxy group or an alkoxy group having 1-5 carbon atoms. -Represents a hydroxyl group. n represents 0, an integer of 1 to 3. A plurality of R ² may be the same or different. R ³ is a hydrogen atom, an alkyl group which may be substituted by a C 1-5 fluorine atom, an alkoxy group which may be substituted by a C 1-5 fluorine atom, or an alkyl group having 1-5 carbon atoms. Represents a hydroxyl group. p represents 0 or an integer of 1 to 4. A plurality of R ³ may be the same or different. Or it may be different from be the same and R ² and R ^3. R ⁴ represents a hydrogen atom, an alkyl group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, an alkoxy group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms. Show. R ⁵ is a hydrogen atom, an alkyl group which may be substituted by a C 1 to C ⁵ fluorine atom, or a C 1 to C ⁵ fluorine atom which may be substituted It represents an alkoxy group or an alkenyl group having 1 to 5 carbon atoms. q represents 0, an integer of 1 to 4. A plurality of R ⁵ may be the same or different. Further, R ⁴ and R ⁵ may be the same or different. When R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent an alkyl group, examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group. . Preferred alkyl groups are lower alkyl groups having 1 to 3 carbon atoms, such as methyl, ethyl and propyl. When R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent an alkyl group containing a fluorine atom (hereinafter sometimes abbreviated as a fluorine-containing alkyl group), the fluorine-containing alkyl group As monofluoromethyl group, difluoromethyl group, trifluoromethyl group, 1-monofluoroethyl group, 1,1-difluoroethyl group, 1,1,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, propyl fluoride group substituting 1 to 7 fluorine atoms, 1 to 9 And a pentyl group which substitutes 1 to 11 fluorine atoms. When R ¹ , R ² , R ³ , R and R ⁵ represent an alkoxy group, examples of the anoreoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group. . Preferred alkoxy groups are lower alkoxy groups having 1 to 3 carbon atoms, such as methoxy and ethoxy. When R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent an alkenyl group, examples of the alkenyl group include a vinyl group, a propenyl group, a butyr group, a pentenyl group and the like. it can. A preferred alkenyl group is a Bier group. Among the blue light-emitting compounds represented by the formula (1), preferred compounds include the formulas (2) and (3) ) And equation (4).

R ² and n in the above formula (2) have the same meaning as described above. A plurality of R ² may be the same or different. Among the blue light-emitting compounds represented by the above formula (2), R ² is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms which may be substituted by a fluorine atom, or a C 1 to 3 carbon atom having a fluorine atom. A blue light-emitting compound in which n is 1 such as an alkoxy group which may be substituted is preferable. When n is 1, the substitution position of R ² is preferably para-position, preferably _π

R ² and n in the above formula (3) have the same meaning as described above. n pieces of R ² may may be the same or may be different. Among the blue light emitting compounds represented by the above formula (3), R ² is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms which may be substituted by a fluorine atom, or a C 1 to 3 carbon atom having a fluorine atom. A blue light-emitting compound in which an alkoxy group which may be substituted, an alkenyl group having 2 to 4 carbon atoms, and n is 1 is preferable. when n is 1 The substitution position of R ² is preferably para-position, preferably _c

上記式 （4 ) において、 R ⁴ は前記と同様の意味を示す。 上記式 （4 ) で示され る青色発光化合物の中でも、 R ⁴ が水素原子、 炭素数が 1〜 3でフッ素原子が置換 してもよいアルキル基、 炭素数が 1〜 3でフッ素原子が置換してもよいアルコキシ 基を有する青色発光化合物が好ましい。 式 （1 ) で示される青色発光化合物は、 芳香族基一 A r—を中心にし、 この芳香 族基一 A r—とメチレン基を介して他の芳香族基一 A r 1ー及ぴ Z又は一A r 2— とが結合した構造を有することが特異的である。 特に芳香族基一 A r—と芳香族基 一 A r 1—及び/又は一 A r 2—との何れかがアントリル基である場合には、 この 発明の目的をよく達成することができる。 すなわち、 アントラセン自体はエレクトロ/レミ不ッセンス（Electroluminescence 、 蛍光発光）可能な物質として最初に発見された化合物である （W. Helfrich, W. G. Sch neider, Phys. Rev. Lett. 14, 229 (1965) ) 。 しかしながら、 アントラセンによる蛍光は 輝度が小さく、 また青色発光化合物としては不十分であった。 これに対して、 この 発明に係る青色発光化合物は、 アントラセン骨格を代表とする芳香族骨格と他の芳 香族骨格とがメチレン結合を介して結合されているので、 この青色発光化合物を励 起した場合に、 メチレン基の両側に位置する芳香族基における励起された π電子が 膨らみ、 芳香環同士が空間的に相互作用を及ぼし合う。 それ故に、 π電子系はメチ レン基で切断された状態ではなくなり、 励起した π電子の励起状態と基底状態との エネルギー差が小さくなり、 高輝度で青色発光可能となるように調整される。 更に いうと、 この発明の青色発光化合物におけるメチレン結合が結合する両側の芳香環 は π電子共役することがなく、 発光する光が長波長側にシフトする。 而してメチレ ン結合における超共役効果によりメチレン基を挟む二種の芳香環における π電子が 相互作用することになる。 その結果、 この青色発光化合物は、 発光強度が大きく、 高輝度で青色発光を呈するようになり、 しかも芳香骨格を有するので耐久性のある 発光化合物である。 反面、 芳香環と芳香環とが単結合で結合していると、 π電子系 平面がツイストすることがあっても、 青色発光より大きく長波長側にシフトし、 つ まり鮮やかな青色発光を呈しなくなり、 また発光輝度も低下して、 この発明の目的 を達成することができなくなる。 前記式 （1) で示される青色発光化合物は、 Η— Ar— Ηと CH₂ X— Ar 1及 ぴ Z又は CH₂ X— Ar 2とを反応させることにより製造され,る。 ここで一Ar— 、 一 Ar 1、 及ぴー A r 2は前記と同様の意味を示す。 また、 Xはハロゲン原子、 特に塩素原子を示す。 また、 一 A r 1及び一 A r 2の何れかが水素原子である青色 発光化合物は、 H— Ar— CH₃ と CH₂ X— Ar 1又は CH₂ X— Ar 2とを反 応させることにより製造される。 前記式 （1) で示される青色発光化合物の合成においても、 反応は、 適宜の溶媒 中で加熱することにより進行する。 加熱温度は、 通常 60〜90°Cである。 反応を 促進するために金属等の触媒を使用することもできる。 反応は、 通常 10分〜数時 間で終了する。 この発明に係る青色発光化合物は、 電磁波エネルギーを与えることにより、 全体 として 400〜470 nmの镇域にわたる可視部発光が見られ、 例えば図 7及ぴ図 10に示されるような蛍光スぺクトルを有し、 青色発光可能な発光素子例えば有機 EL素子に利用することができる。 さらに、 赤色発光化合物、 緑色発光化合物及ぴ この発明の青色発光化合物を含有させた発光層を備えた発光素子は、 白色に発光さ せることができる _t また、 この発明の青色発光化合物は、 式 （31) で示す構造を有する。 (

In the above formula (4), R ⁴ has the same meaning as described above. Among the blue light-emitting compounds represented by the above formula (4), R ⁴ is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms which may be substituted by a fluorine atom, or a C 1 to 3 carbon atom which may be substituted by a fluorine atom. A blue light-emitting compound having an optionally substituted alkoxy group is preferred. The blue light-emitting compound represented by the formula (1) has an aromatic group A r— as a center, and the aromatic group A r— and another aromatic group A r1 —Z through a methylene group. Alternatively, it is specific to have a structure in which one Ar 2— is bonded. In particular, when one of the aromatic group 1 A r— and the aromatic group 1 A r 1— and / or 1 A r 2— is an anthryl group, the object of the present invention can be achieved well. That is, anthracene itself is the first compound discovered as a substance capable of electroluminescence (fluorescence) (W. Helfrich, WG Schneider, Phys. Rev. Lett. 14, 229 (1965)) . However, the fluorescence by anthracene was low in luminance and insufficient as a blue light emitting compound. In contrast, the blue light-emitting compound according to the present invention excites the blue light-emitting compound because the aromatic skeleton represented by the anthracene skeleton and another aromatic skeleton are bonded via a methylene bond. In this case, the excited π electrons in the aromatic groups located on both sides of the methylene group swell, and the aromatic rings interact spatially. Therefore, the π-electron system is no longer in a state cut by the methylene group, and the excited state of the excited π electrons and the ground state It is adjusted so that the energy difference is small and blue light can be emitted with high brightness. More specifically, the aromatic rings on both sides of the blue light emitting compound of the present invention to which the methylene bond is bonded do not have π-electron conjugation, and the emitted light shifts to the longer wavelength side. Thus, the π electrons in the two types of aromatic rings sandwiching the methylene group interact due to the hyperconjugation effect in the methylene bond. As a result, the blue light-emitting compound has high emission intensity, emits blue light with high luminance, and has an aromatic skeleton, and thus is a durable light-emitting compound. On the other hand, if the aromatic ring is bonded by a single bond, even if the π-electron system plane is twisted, it shifts to a longer wavelength side than blue light emission, resulting in vivid blue light emission. In addition, the light emission luminance is reduced, and the object of the present invention cannot be achieved. The blue light-emitting compound represented by the above formula (1) is produced by reacting Η—Ar—Η with CH ₂ X—Ar 1 and ぴ Z or CH ₂ X—Ar 2. Here, 1 Ar—, 1 Ar 1 and Ar 2 have the same meanings as described above. X represents a halogen atom, particularly a chlorine atom. In addition, a blue light-emitting compound in which one of Ar 1 and Ar 2 is a hydrogen atom reacts H—Ar—CH ₃ with CH ₂ X—Ar 1 or CH ₂ X—Ar 2 It is manufactured by In the synthesis of the blue light emitting compound represented by the formula (1), the reaction proceeds by heating in an appropriate solvent. The heating temperature is usually 60-90 ° C. A catalyst such as a metal can be used to promote the reaction. The reaction is usually completed in 10 minutes to several hours. The blue light-emitting compound according to the present invention emits visible light over a range of 400 to 470 nm as a whole by applying electromagnetic wave energy, and emits a fluorescent spectrum as shown in FIGS. 7 and 10, for example. It can be used for a light emitting element capable of emitting blue light, for example, an organic EL element. Further, a red light-emitting compound, a green light-emitting compound, and a light-emitting element including a light-emitting layer containing the blue light-emitting compound of the present invention emit white light. _T also can be a blue light-emitting compound of this invention has a structure represented by formula (31).

In the formula (31), one Ar— is an aromatic group and has one of the following formulas (32) and (33).

X

X is a hydrogen atom or an alkoxy group having 1 to 5 carbon atoms, and two Xs are the same.

'But it can be different.

As X which is an alkoxy group of 5, a methoxy group, an ethoxy group, Examples include a oxy group, a butoxy group and a pentoxy group. X which is preferable as the alkoxy group is an alkoxy group having 1 to 3 carbon atoms. In the formula (31), Y represents a fluorinated alkyl group having 1 to 3 carbon atoms. Examples of the alkyl group include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1,1,1-trifluoroethyl group, a pentafluoroethyl group, a 1,1,1-trifluoromethyl group. Propyl group, 1,1,1,2,2,1-pentafluoropropyl group and the like. Preferred as the fluorinated alkyl group having 1 to 3 carbon atoms is a trifluoromethyl group. Z in the formula (31) represents a hydrogen atom or a group having a structure represented by the following formula (34).

(Y in equation (34) is the same as above.)

Preferred blue light emitting compounds among the blue light emitting compounds represented by the formula (31) are a stilbene blue light emitting compound represented by the formula (35) and a stilbene blue light emitting compound represented by the formula (36) ′. (35)

Here, R ³¹ represents a hydrogen atom or an alkoxy group having 1 to 3 carbon atoms. Two R ³¹ may be the same or different. n shows the integer of 1-3. The bond position of CF ₃₁ is ortho or para to CH =.

(36)

Here, R ³¹ represents a hydrogen atom or an alkoxy group having 1 to 3 carbon atoms. Two R ³¹ may be the same or different. n shows the integer of 1-3. The bonding position of CF ₃ — is at the ortho position or the para position with respect to = CH—. In the blue light-emitting compound according to the present invention, since the fluorinated alkyl groups bonded to both terminals in the skeleton of the blue light-emitting compound are electron-withdrawing, the excited state in which π electrons in one Ar— at the center are excited by electromagnetic wave energy is obtained. The energy difference from the ground state is reduced, and therefore adjustment is made so that blue light can be emitted with high luminance. The blue light-emitting compound according to the present invention provides an And visible light emission over the region of 400 to 600 nm. The blue light emitting compound according to the present invention can be produced as follows.

An aromatic compound represented by H—Ar—H (Ar has the same meaning as described above) is reacted with formaldehyde (formalin or paraformaldehyde) in the presence of hydrogen chloride and zinc chloride. performing chloromethylated Te (see the following reaction formula (37)) ₀

HA r -H + 2 HCHO + 2HC 1 ^ C 1 CH ₂ — A r — CH ₂ C 1

 (37)

Next, the chloromethylated product is reacted with triphenylphosphine to produce a Wittig reagent (ttig reagent) (see the following reaction formula (38)).

C 1C i A r-CH ₂ C 1 + P (CgHg) 3..., 8) P (C ₆ H ₅ ) 3 'C 1CH ₂ — A r— CH ₂ C 1Ρ (C g H ₅ ) ₃

The resulting triphenylphosphine complex and a carbonyl compound represented by the formula (39) (in the formula (39), when Z is a hydrogen atom, a benzaldehyde compound; and when Z is a group represented by the formula (34), The blue light-emitting compound according to the present invention can be obtained by reacting with the following (see the following reaction formula (40)). The reaction represented by the following reaction formula (40) is a general reaction in which a carboxy group (C = 0) is changed to C = C. P (C ₆ H ₅ ) 3 «C 1CH ₂ -A r 1 CH ₂ C 1-P (C ₆ H ₅ ) ₃ + CZ

_C Figure 1 illustrates a light-emitting device according to the invention (40) hereinafter is an explanatory view showing a sectional structure of a light emitting element is a one-layer type organic EL element. As shown in FIG. 1, the light emitting element A is formed by laminating a light emitting layer 3 containing a light emitting material and an electrode layer 4 on a substrate 1 on which a transparent electrode 2 is formed in this order. In the light-emitting device shown in FIG. 1, the light-emitting layer 3 includes a blue light-emitting compound according to the present invention or a stilbene-based blue light-emitting compound containing an alkyl fluoride group. If a red light-emitting compound and a green light-emitting compound are contained in a well-balanced manner, white light is emitted when a current is applied to the transparent electrode 2 and the electrode layer 4. In addition, when the light emitting layer 3 contains the blue light emitting compound, the red light emitting compound, and the green light emitting compound according to the present invention at an appropriate ratio, light can be emitted in a desired color. In light emission, when an electric field is applied between the transparent electrode 2 and the electrode layer 4, electrons are injected from the electrode layer 4 side, holes are injected from the transparent electrode 2, and further electrons are emitted in the light emitting layer 3. This is a phenomenon in which energy is emitted as light when the energy level returns to the valence band from the conduction band by recombination with holes. The light-emitting element A shown in FIG. 1 can be mounted on a wall or a ceiling, for example, mounted on a wall or a ceiling to form a large-area white light-emitting element, a large-area white ceiling light-emitting element, etc. The planar light-emitting lighting device of the above. In other words, this light emitting element It can be used as a surface light source instead of a point light source such as a conventional linear light source such as a fluorescent lamp or a bulb. In particular, the light emitting element can emit or illuminate a wall surface, a ceiling surface, or a floor surface of a living room, an office room, a vehicle room, or the like as a surface light source. Further, the light emitting element A can be used as a backlight for a display screen of a computer, a display screen of a mobile phone, a numeral display screen of a cash register, and the like. In addition, the light emitting element A can be used as various light sources such as direct lighting and indirect lighting, and can be made to emit light at night and has good visibility, an advertisement device, a road sign device, and the like. It can be used as a light-emitting bulletin board, and also as a light source such as a brake lamp in a vehicle such as an automobile. Moreover, since the light emitting element A has a blue light emitting compound having a specific chemical structure in the light emitting layer, the light emitting element A has a long light emitting life. Therefore, the light emitting element A can be used as a light source that emits light for a long time. Further, when the light emitting layer of the light emitting element A contains the blue light emitting compound according to the present invention and does not contain the red light emitting compound and the green light emitting compound, the light emitting element A emits bright blue light. The light-emitting element A is a tubular light-emitting body in which a cylindrical substrate 1 and a transparent electrode 2, a light-emitting layer 3, and an electrode layer 4 are laminated in this order on the inner surface of the substrate 1. Can be done. Since this light emitting element A does not use mercury, it can be used as an environmentally friendly light source instead of a conventional fluorescent lamp using mercury. As the substrate 1, a known substrate can be used as long as the transparent electrode 2 can be formed on the surface thereof. Examples of the substrate 1 include a glass substrate, a plastic sheet, ceramic, and a metal plate whose surface is processed to be insulative, such as forming an insulating paint layer on the surface. When the substrate 1 is opaque, the light emitting element containing the red light emitting compound, the green light emitting compound, and the blue light emitting compound according to the present invention in the light emitting layer has white light on the opposite side to the substrate 1. This is a single-sided illumination device that can emit colored light. Further, when the substrate 1 is transparent, the double-sided illumination device can irradiate white light from the surface of the light emitting element on the substrate 1 side and the opposite side. As the transparent electrode 2, various materials can be adopted as long as they have a large work function and are transparent and can act as an anode by applying a voltage to inject holes into the light emitting layer 3. Specifically, the transparent electrode _{2, ITO, I n 2 0 3} , S N_〇 _{2, Z n O, C d} O , etc., and inorganic transparent conductive material such as those compounds, conductive such及Pi poly Anirin It can be formed of a conductive polymer material or the like. The transparent electrode 2 is formed on the substrate 1 by chemical vapor deposition, spray pyrolysis, vacuum evaporation, electron beam evaporation, sputtering, ion beam sputtering, ion plating, ion assist evaporation, It can be formed by a method. When the substrate is formed of an opaque member, the electrode formed on the substrate does not need to be a transparent electrode. The light emitting layer 3 is a layer containing the blue light emitting compound according to the present invention when emitting blue light, and containing the red light emitting compound, the green light emitting compound and the blue light emitting compound according to the present invention when emitting white light. The light emitting layer 3 can be formed as a polymer film in which the blue light emitting compound according to the present invention, or the red light emitting compound, the green light emitting compound, and the blue light emitting compound according to the present invention are dispersed in a polymer. Further, the blue light-emitting compound according to the present invention, or the red light-emitting compound, the green light-emitting compound, and the blue light-emitting compound according to the present invention can be formed on the transparent electrode 2 as a vapor-deposited film. As the polymer in the polymer film, polyvinyl carbazole, poly (3-A) Ruquinentofen), polyamide containing arylamine, polyfluorene

, Polyphenylenevinylene, poly-CK-methylstyrene, vinylcarbazol-methylstyrene copolymer, and the like. Of these, preferred is polybutyral rubazole. The content of the blue light-emitting compound according to the present invention, the red light-emitting compound, the green light-emitting compound and the blue light-emitting compound according to the present invention in the polymer film is usually 0.01 to 2% by weight. / ₀ , preferably 0.05-0.5 weight. / ₀ . The thickness of the polymer film is usually from 30 to 500 nm, preferably from 100 to 300 nm. If the thickness of the polymer film is too small, the amount of emitted light may be insufficient.If the thickness of the polymer film is too large, the driving voltage may be too high, which is not preferable. In some cases, flexibility may be lacked when making a curved or annular body. The polymer film is formed by dissolving the polymer and the blue light emitting compound according to the present invention, or the red light emitting compound, the green light emitting compound, and the blue light emitting compound according to the present invention in an appropriate solvent. It can be formed by a coating method such as a spin casting method, a coating method, and a dipping method. When the light-emitting layer 3 is a vapor-deposited film, the thickness of the vapor-deposited film varies depending on the layer configuration of the light-emitting layer and the like, but is generally 0.1 to 100 nm. If the thickness of the deposited film is too small or too large, the same problem as described above may occur. The electrode layer 4 is made of a material having a small work function, and can be formed of, for example, a single metal or a metal alloy such as MgAg, an aluminum alloy, or a metal canolesum. A preferred electrode layer 4 is an alloy electrode of aluminum and a small amount of lithium. The electrode layer 4 is formed, for example, on a surface including the light emitting layer 3 formed on the substrate 1 by a vapor deposition technique. Thereby, it can be easily formed. Regardless of which of the coating method and the vapor deposition method is used to form the light emitting layer, it is preferable to interpose a buffer layer between the electrode layer and the light emitting layer. Examples of the material that can form the buffer layer include an alkaline metal compound such as lithium fluoride, an alkaline earth metal compound such as magnesium fluoride, an oxide such as aluminum oxide, 4, 4, and 4. One example is rubazolubiphenylinole (C z -TPD). Also, as a material for forming a buffer layer formed between an anode such as ITO and an organic layer, for example, m-MTDATA (4, 4 ', 4''tris (3-methylphenylphenyl) Mino) triphenylamine), phthalocyanine, polyaniline, polythiophene derivatives, inorganic oxides such as molybdenum oxide, ruthenium oxide, vanadium oxide, and lithium fluoride. By appropriately selecting the material of these buffer layers, the driving voltage of the organic EL element, which is a light emitting element, can be reduced, the quantum efficiency of light emission can be improved, and the light emission luminance can be improved. Can be achieved. Next, a second example of the light emitting device according to the present invention is shown in the drawings. FIG. 2 is an explanatory diagram showing a cross section of a light emitting device which is a multilayer organic EL device. As shown in FIG. 2, the light emitting element B has a transparent electrode 2, a hole transport layer 5, light emitting layers 3a and 3b, an electron transport layer 6, and an electrode layer 4 laminated in this order on the surface of a substrate 1. It becomes. The substrate 1, the transparent electrode 2, and the electrode layer 4 are the same as those in the light emitting element A shown in FIG. The light emitting layer in the light emitting element B shown in FIG. 2 includes a light emitting layer 3a and a light emitting layer 3b. Emitting layer 3b is DPVB i-layer. The DPVB i layer has a function as a host material. Examples of the hole transporting substance contained in the hole transporting layer 5 include trifluoramine-based compounds such as N, N'-diphenyl-N, N'-di (m-tolyl) -benzidine (TPD), and α- Examples include hydrazone-based compounds, stilbene-based compounds, heterocyclic-based compounds, and π-electron-based starburst hole transporting substances such as NPD. Examples of the electron transporting substance contained in the electron transporting layer 6 include, for example, 2- (4-tert-butylphenyl) -15- (4-biphenyl) -11,3,4-o Oxaziazolone derivatives such as oxaziazole and 2,5-bis (1-naphthyl) -1,1,3,4-oxaziazole, and 2,5-bis (5,1-tert-butyl-2, 1-benzoxazolyl) thiophene and the like. Further, as the electron transporting substance, for example, a metal complex-based material such as a quinolino-norrealuminum complex (A1q3) or a benzoquinolinol-beryliridium complex (Bebq2) can be preferably used. In the light emitting device B in FIG. 2, the electron transport layer 6 contains A 1 q 3. The thickness of each layer is the same as in a conventionally known multilayer organic EL device. The light emitting element B shown in FIG. 2 operates in the same manner as the light emitting element A shown in FIG. 1 and emits light. Therefore, the light-emitting element B shown in FIG. 2 has the same use as the light-emitting element A shown in FIG. FIG. 3 shows a third example of the light emitting device according to the present invention. FIG. 3 is an explanatory diagram showing a cross section of a light emitting device that is a multilayer organic EL device. Light emitting device C shown in FIG. 3 has a transparent electrode 2, a hole transport layer 5, The light emitting layer 3, the electron transport layer 8, and the electrode layer 4 are laminated in this order. The light emitting element C shown in FIG. 3 is the same as the light emitting element B. FIG. 4 shows another example of the light emitting device. The light-emitting device D shown in FIG. 4 is formed by laminating a substrate 1, an electrode 2, a hole transport layer 5, a light-emitting layer 3, and an electrode layer 4 in this order. In addition to the light emitting device shown in FIGS. 1 to 4, a hole transport layer containing a hole transport material is provided between a positive electrode, which is a transparent electrode, and a cathode, which is an electrode layer, formed on a substrate. Two-layer organic low-molecular-weight light-emitting device comprising a blue light-emitting compound-containing electron-transporting light-emitting layer according to the present invention (for example, a hole-transporting layer between an anode and a cathode; A two-layer dye-doped light-emitting device formed by laminating a blue light-emitting compound and a light-emitting layer containing a host dye according to (1), a hole-transporting layer containing a hole-transporting substance between an anode and a cathode, A two-layer organic light-emitting device having a blue light-emitting compound and an electron-transporting light-emitting layer formed by co-evaporation of an electron-transporting substance according to the present invention (for example, a hole-transporting layer between an anode and a cathode) And according to the present invention as a guest dye A two-layered dye-doped organic light-emitting device comprising an electron-transporting layer containing a color-emitting compound and a host dye, and a hole-transporting layer between the anode and the cathode. A three-layer organic light-emitting device in which such a light-emitting layer containing a blue light-emitting compound and an electron transport layer are laminated can be given. The electron-transporting light-emitting layer in this light-emitting element usually comprises 50 to 80% of polyvinyl carbazole (PVK), 5 to 40% of an electron-transporting light-emitting agent, and a blue light-emitting compound according to the present invention. When formed at 0.01 to 20% (by weight), blue light emission occurs with high luminance. Further, the light emitting layer preferably contains rubrene as a photosensitive agent, and particularly preferably contains rubrene and A1q3. [0307247] A blue light emitting device using the blue light emitting compound according to the present invention, or a white light emitting device using the red light emitting compound, the green light emitting compound and the blue light emitting compound according to the present invention are generally, for example, a DC-driven organic EL device. It can be used as a pulse-driven organic EL device and an AC-driven organic EL device.

(Example)

 (Example 1)

混合キシレンに 9, 10-ビス [ (4一ナフチル) メチル] アントラセンを 10 mg/Lの濃度になるように溶解して試料液を調製した。 この試料液を、 島津製作 所製の F— 4500型分光蛍光光度計に装填して、 以下の条件にて蛍光スぺク トル を測定した。 得られた蛍光スペク トルを図 7に示した。 測定条件 Premixed anthracene (molecular weight = 17.8.23) 5. Charge Og and 55 g of zinc zinc powder to a 20 Om 1-necked flask equipped with a cooling tube equipped with a calcium chloride tube. Then, 12.4 g of 1-chloromethylnaphthalene (molecular weight = 176.64) was added, and the mixture was heated at 75 ° C. for 1 hour with stirring on an oil bath. After cooling, the reaction product was dissolved in black-mouthed form, and the resulting black-mouthed form solution was poured into ice water. The mixture was transferred to a separatory port, and extracted with black form. After repeating the water washing twice, dehydration was performed with anhydrous sodium sulfate. It was concentrated and dried with an evaporator to obtain 14 g of a white-yellow powder. To this, 4 Oml of benzene was added, and the mixture was stirred, and the insoluble matter was filtered off with a glass filter. Add hot benzene 2 O Oml until this is dissolved, add activated carbon, heat and filter. After the filtrate was allowed to stand for one day, white yellow crystals precipitated. This was recrystallized twice with xylene to obtain 2 g of white crystals. The melting point was measured after sublimation purification of this white crystal, and it was melted at 330 ° C or higher. The IR chart of this white crystal is shown in FIG. 5, and the NMR chart is shown in FIG. From these results, this white crystal was identified as 9,0-bis [41- (naphthyl) methyl] anthracene represented by the formula (5).

A sample solution was prepared by dissolving 9, 10-bis [(4-naphthyl) methyl] anthracene in mixed xylene to a concentration of 10 mg / L. This sample solution was loaded on an F-4500 type spectrofluorometer manufactured by Shimadzu Corporation and the fluorescence spectrum was measured under the following conditions. Fig. 7 shows the obtained fluorescence spectrum. Measurement condition

 Measurement mode

 Excitation wavelength 3 D on m

 Fluorescence start wavelength 365 nm

 Fluorescence end wavelength 720 nm

 Scan speed 2400ηm / min

 Excitation side slit 5.0 nm

 Fluorescent side slit 5.0 nm

 Photo Manore voltage 700V

As can be seen from FIG. 7, the blue light-emitting compound obtained in this example, fluorescence emission is viewed in 400 500 nm _t

(Example 2)

7.02 g of anthracene (molecular weight = 178.23), which was previously mixed, was mixed with 30 _{§ of} 1-methyl-41-chloromethylnaphthalene (molecular weight = 19.0.5) 30 _§ and 1.39 g of zinc metal powder. In a 500 ml three-necked flask equipped with a cooling tube with a calcium tube It was charged and heated at 70 ° C for 30 minutes while stirring on an oil bath, then heated to 75 ° C and heated at that temperature for 30 minutes. After allowing to cool, the reaction product was dissolved in black-mouthed form and poured into ice water. It was transferred to a separating funnel and extracted with black-mouthed form. After washing was repeated twice, dehydration was performed with anhydrous sodium sulfate. A light brown paste was obtained by concentrating to dryness with an evaporator. This paste was dissolved in xylene, activated carbon was added to the obtained solution, filtered, and recrystallized twice. 1.6 g of white crystals were obtained. FIG. 8 shows an IR chart of this crystal, and FIG. 9 shows an NMR chart thereof. The crystals melted above 300 ° C. From these results, this crystal was identified as 9,10-bis [4-((1-methylnaphthyl) methyl] anthracene represented by the formula (6).

The fluorescence spectrum was measured in the same manner as in Example 1 except that this crystal having the structure represented by the formula (6) was used instead of the blue light-emitting compound represented by the formula (5). FIG. 10 shows the obtained fluorescent spectrum.

(Example 3)

Premixed 9,10-bis (chloromethyl) anthracene (molecular weight = 275) 1.0 g and 1-methoxynaphthalene (molecular weight = 158.2) 2.8 g and metallic zinc powder 0.12 The mixture was added to a 300-ml three-necked flask equipped with a condenser tube equipped with a calcium chloride tube, and heated at 75 ° C for 1 hour 30 minutes while stirring on an oil bath. Was. After allowing to cool, the reaction product was dissolved in black-mouthed form, and the obtained black-mouthed form solution was poured into ice water. The solution was made viscous with a 10% NaOH aqueous solution, transferred to a separatory funnel, and extracted into chloroform. After water washing was repeated twice, dehydration was performed with anhydrous sodium sulfate. It was concentrated to dryness by an evaporator to obtain 1.6 g of a dark purple powder. The dark purple powder was melted in xylene, activated carbon was charged, filtered, and recrystallized twice to obtain 0.4 g of pale yellow crystals. The melting point of the pale yellow crystal after sublimation purification was measured. As a result, the crystal was melted at 330 ° C. or higher. The IR chart of this pale yellow crystal is shown in FIG. 11, and the NMR chart is shown in FIG. From these results, the pale yellow crystals were identified as 9,10-bis [4- (1-methoxynaphthyl) methyl] anthracene represented by the formula (7).

G

The fluorescence spectrum was measured in the same manner as in Example 1 except that this crystal having the structure represented by the formula (7) was used instead of the blue light-emitting compound represented by the formula (5). FIG. 13 shows the obtained fluorescent spectrum.

(Example 4)

 Fabrication of light emitting device

 <Emission characteristics 1>

Ultrasonic cleaning of ITO substrate (50 X 50 mm, manufactured by Sanyo Vacuum Industry Co., Ltd.) for 10 minutes with acetone, ultrasonic cleaning with 2-propanol for 10 minutes, and blowing with nitrogen And dried. After that, the ITO substrate was cleaned by irradiating with UV for 5 minutes with Photo 'Surface' Processor 1 (Sen Special Light Source Co., Ltd., wavelength 254 nm). The washed I TO substrate vacuum deposition apparatus (Daya vacuum Giken (Ltd.), UDS-M2-4 6 type) is set to, under a reduced pressure of 4X 10- ⁶ torr or less, a- NPD layer 45 nm, the above described A light-emitting layer obtained by laminating a layer 40 nm of the blue light-emitting compound (formula (5)) obtained in Example 1 and three layers of A 1 q 15 nm in this order, and finally an aluminum alloy electrode (A 1: L i = 99: l weight ratio (manufactured by Kojundo Chemical Laboratory Co., Ltd.) was deposited to a thickness of 150 nm to produce a blue light emitting device having a laminated structure shown in FIG. The luminance and chromaticity of the blue light-emitting device were measured while gradually increasing the voltage using BM-7 Fast manufactured by Topcon Corporation. As a result, a result was obtained at a voltage of 20 V and a current of 32.26 mA, a luminance of 836.3 Cd / m ² , a chromaticity X of 0.163, and a chromaticity Y of 0.1492.

<Emission characteristics 2>

In a 5 ml volumetric flask, 70 mg of polyvinyl carbazole, 30 mg of 2,5-bis (1-naphthyl) -1,3,4-oxadiazole (BND), and the formula (5) obtained in Example 1 described above were used. 0.3 mg of the powder to be obtained was weighed, and dichloroethane was added thereto to prepare a solution containing a blue light-emitting compound so as to have a volume of 5 ml. The solution containing the blue light emitting compound was sufficiently homogenized by irradiating ultrasonic waves for 20 minutes with an ultrasonic cleaner (US-2, manufactured by Sennedy Co., Ltd.). The ITO substrate (50 × 50 mm, ITO transparent electrode thickness 200 μm, manufactured by Sanyo Vacuum Industry Co., Ltd.) is ultrasonically cleaned with acetone for 10 minutes, then ultrasonically cleaned with 2-propanol for 10 minutes, and then nitrogen. Blow and dry. Thereafter, the substrate was washed by irradiating UV for 5 minutes with the above-mentioned photo-face processor (wavelength: 254 nm). Using a spin coater (Mikasa Corporation, 1H-D7), the prepared blue light-emitting compound-containing solution was dropped onto the washed and dried ITO substrate, and the rotation speed was 1,500 rpm and the rotation time was Spy in 3 seconds Then, the film was formed so that the dry thickness was Ι Ο Ομπι. After the formed substrate is dried in a 50 ° C constant temperature bath for 30 minutes, it is subjected to an aluminum alloy (A 1: Li) using a vacuum deposition apparatus (VDS-M2-46, manufactured by Daia Vacuum Engineering Co., Ltd.). = 99: 1 weight ratio, Co., Ltd. high-purity chemical Laboratory Ltd.) electrodes, was deposited to a thickness of about 0.99 nm in 4X 10- ⁶ Torr, it was fabricated blue light emitting device having a structure shown in FIG. The luminance and chromaticity of this blue light-emitting device were measured while gradually increasing the voltage using BM-7 Fast manufactured by Topcon Corporation. As a result, at a voltage of 20 V and a current of 28.72 mA, a luminance of 283.0 Cd / m ² , a chromaticity X of 0.1693, and a chromaticity of 0.107 were obtained.

(Example 5)

A premixed mixture of 2.5 g of 9-methylanthracene and 0.26 g of zinc metal powder is poured into a 50-Om 1 three-necked flask equipped with a condenser tube with a calcium chloride tube. Add 2.53 g of chloromethylnaphthalene and stir in an oil bath 70. (: 30 minutes, then heated at 75. C for 30 minutes. Generation of hydrochloric acid gas was confirmed with pH test paper. After slowly cooling, the reaction product was dissolved in The mixture was neutralized with a 10% aqueous sodium hydroxide solution, transferred to a liquid separating port, extracted with a chloroform port, washed with water twice, dried over anhydrous sodium sulfate, dried to dryness, and concentrated to dryness using an evaporator. A yellow powder was obtained, toluene 20 Om 1 and activated carbon were added thereto, and the mixture was stirred while heating, filtered off with a filter paper, and the filtrate was concentrated and recrystallized to obtain 0.92 g of pale yellow fine crystals. The IR chart of this crystal is shown in Fig. 14 and the NMR chart is shown in Fig. 15. The fluorescence spectrum of this crystal was measured in the same manner as in Example 1 above. The vector is shown in Figure 16. From these data, the crystalline compound was of the formula And those having the structure shown in 8) Identified.

(Example 6)

Concentrated sulfuric acid was added dropwise to a 1-liter tri-frass flask containing 200 g of sodium chloride and an amount of hydrochloric acid to soak it, and the generated hydrogen chloride gas was placed in a 500-ml three-neck flask equipped with a calcium chloride tube-cooled space. 34.6 g of charged 2-bromobenzene (molecular weight: 185), 1.4 g of paraformaldehyde and 2.1 g of zinc chloride (molecular weight: 136) were blown under stirring on an oil bath while blowing. At 70 ° C for 40 minutes. After allowing to cool, the reaction was poured into ice water. It was transferred to a separating funnel and extracted with benzene. This was washed with 2% aqueous sodium hydrogen carbonate until no turbidity was observed. It was concentrated to dryness by an evaporator to obtain 30.4 g of a light brown liquid as a reaction product. This was distilled under reduced pressure at 200 ° C. and 3 mmHg, and the IR spectrum and NMR spectrum of the residue were measured. The resulting material from these data 1 one-chloromethyl -4 i (2 Puromoechiru) benzene (CH ₂ C 1 one _{C 6 H 4 - CH 2 CH} 2 B r) and were identified. 3.7 g of 4- (2-bromoethynole) benzene and 2.5 g of 9-methylanthracene (molecular weight: 192) and 0.43 g of zinc metal powder (atomic weight: 65.39) were combined with The mixture was charged into a 200 ml three-necked flask equipped with a condenser tube with a calcium tube, and heated at 170 ° C. for 1 hour with stirring on an oil bath. Generation of acid gas was confirmed with pH test paper. After slow cooling, the reaction product was dissolved in black-mouthed form and poured into ice water. It was transferred to a separating funnel and extracted with black-mouthed form. Repeat the washing twice After drying over anhydrous sodium sulfate and concentrating to dryness using an evaporator, 4.5 g of a black-brown solid was obtained. It was dissolved in a small amount of black-mouthed form and poured into 50 Om1 of methanol. The generated brown precipitate was filtered through a glass filter and dried. 3.6 g of a brown reaction product powder was obtained. The IR chart of this brown powder is shown in FIG. 17, and the NMR chart is shown in FIG. From these data, this brown powder was identified as a compound having a structure represented by the formula (9). 3.6 g of the brown powder having the structure represented by the formula (9) was taken in a 20-ml beaker, dissolved in 60 ml of THF, and dissolved in 20 ml of ethanol and 3 g of potassium hydroxide. Further, anhydrous sodium sulfate was added to carry out a dehydrobromination reaction.

(9)

Thereafter, the anhydrous sodium sulfate was filtered off, and the filtrate was transferred to a 200 ml eggplant flask equipped with a cooling tube equipped with a calcium chloride tube, to which zeolite was added and heated at 100 ° C for 3 hours on an oil bath. After cooling, the reaction product was poured into ice water. The mixture was transferred to a separating funnel and extracted into chloroform. Washing with water was repeated twice, and then water was removed with anhydrous sodium sulfate. It was concentrated to dryness by an evaporator to obtain a brown carmella-like solid. The benzene was eluted and separated on a column to give 1.4 g of a light brown product. The IR chart of this light brown product is shown in FIG. 19, and the NMR chart is shown in FIG. 20, respectively. The fluorescence spectrum of this crystal was measured in the same manner as in Example 1 above. FIG. 21 shows the obtained fluorescent spectrum. W 03 From these data, the compound of the crystal was identified to have a structure represented by Formula (10).

(Example 7)

A premixed mixture of 2.5 g of 9-methylanthracene and 0.26 g of zinc metal powder is poured into a 50-Om 1 three-necked flask equipped with a cooling tube equipped with a Shiridani calcium tube. 4-Trifluoromethylbenzyl bromide 4.05 § 3 カ, stirred on an oil bath at 70 ° C for 30 minutes, then Ί5. For 30 minutes. The generation of acid gas was confirmed with pH test paper. After cooling slowly, the reaction product was dissolved in a black hole form and poured into ice water. It was transferred to a separatory funnel and extracted into black-mouthed form. After washing was repeated twice, dehydration and drying were performed with anhydrous sodium sulfate. It was concentrated to dryness by an evaporator to obtain a yellow paste. To this, 10 Om1 of toluene and activated carbon were added, and the mixture was heated and stirred, and filtered with filter paper. The filtrate was concentrated and allowed to stand for 24 hours. The resulting crystals were collected and washed with petroleum ether to obtain 0.9 g of pale yellow fine crystals. The fine crystals were purified by sublimation to obtain 0.4 g of purified crystals. FIG. 22 shows an IR chart of the purified crystal. The fluorescence spectrum of this crystal was measured in the same manner as in Example 1 above. FIG. 23 shows the obtained fluorescent spectrum. From these data, the compound of the crystal has a structure represented by the formula (11). Was identified.

Production of light-emitting element>

 <Emission characteristics 1>

The ITO substrate (50 X.5 Omm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was ultrasonically cleaned with acetone for 10 minutes, then ultrasonically cleaned with 2-propanol for 10 minutes, blown with nitrogen and dried. Was. After that, the ITO substrate was washed by irradiating UV for 5 minutes with a photo 'Surface' processor (Sen Special Light Source Co., Ltd., wavelength 254 nm). The washed I TO substrate vacuum deposition apparatus (Daya vacuum Giken (Ltd.), UDS-M2-4 6 type) is set to, under a reduced pressure of less than 4X 10- ⁶ torr, N, N, Jifueniru one N, N′-di (m-tolyl) monobenzidine (TPD) layer 45 nm, the blue light-emitting compound (formula (11)) obtained in Example 7 was converted to a yellow light-emitting compound (Y- 3 20) a 3% -doped layer 40 nm and an Alq 3 layer 2 O nm in this order, a light-emitting layer, and finally an aluminum alloy electrode (A1: Li = 99: 1 weight ratio) And Kojundo Chemical Laboratory Co., Ltd.) were deposited to a thickness of 15 Onm to produce a light emitting device having a laminated structure shown in FIG.

The luminance and chromaticity of this light-emitting device were measured by gradually increasing the voltage using BM-7 Fast manufactured by Topcon Corporation. As a result, at a voltage of 12 V and a current of 23.7 mA, a luminance of 1285 C d / m ² , a chromaticity X of 0.412 and a chromaticity Y of 0.557 were obtained.

This example shows that a light-emitting element including a light-emitting layer containing a blue light-emitting compound and a yellow light-emitting compound emitted yellow-green light.

<Emission characteristics 2>

 In a 5 ml volumetric flask, polyvinylinole force 70 mg 25-bis (1-naphthyl) —1,34-oxadiazole (BND) 30 mg, and the amount obtained in Example 7 above Img of the blue light-emitting compound represented by the formula (11) was weighed, and dichloroethane was added to prepare a solution containing a brown light-emitting compound so as to be 5 ml. The blue luminescent compound-containing solution was sufficiently homogenized by irradiating ultrasonic waves for 20 minutes with an ultrasonic cleaner (US-2, manufactured by Sennedy Co., Ltd.). I TO board

(50 x 50 mm, ITO transparent electrode thickness 200 μm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was ultrasonically washed with acetone for 10 minutes, then with 2-propanol for 10 minutes, and blown with nitrogen. And dried. Thereafter, the substrate was washed by irradiating UV for 5 minutes with the above-mentioned photo 'face' processor (wavelength: 254 nm). Spin coater (Mikasa

Prepare 1H-D 7) on an ITO substrate that has been washed and dried. The solution containing the blue light-emitting compound was dropped, and subjected to spin coating at a rotation speed of 1,500 rpm and a rotation time of 3 seconds to form a film having a dry thickness of 100 / m. After the formed substrate was dried in a 50 ° C constant temperature bath for 30 minutes, the aluminum alloy (A 1: Li) was deposited using a vacuum evaporation apparatus (VDS-M2-46, manufactured by Daia Vacuum Engineering Co., Ltd.). = 9 9: 1 weight ratio, the Corporation of Kojundo Chemical Laboratory, Ltd.) electrode, is deposited about 1 50 nm in thickness at 4 X 1 0- ⁶ Torr, blue light emitting device having a structure shown in FIG. 1 Made. The luminance and chromaticity of this blue light-emitting device were measured while gradually increasing the voltage using BM-7 Fast manufactured by Topcon Corporation. As a result, at a voltage of 16 V and a current of 5.89 mA, the luminance is 11.630 C dZm ² , and the chromaticity: X is 0.18559 and the chromaticity is 0.1368 The result was obtained.

(Example 8)

9-methylanthracene (MW 192.26) 10 g and 1,4-di (chloromethyl) benzene (MW 177.5.02) 2.27 §, zinc 0.5 g and o-dichloro mouth 20 ml of benzene was placed in a 500 ml three-necked flask. While stirring the inside of the three-necked flask, 10 minutes at 85 ° C. in an oil bath, 25 minutes at 90 ° C. in the next step, and 100 times in the next step. Heated at C for 20 minutes. Generation of acid gas was confirmed with pH test paper. After cooling slowly, the reaction product was poured into ice water. It was transferred to a separatory funnel and extracted into black-mouthed form. After repeating the water washing twice, dehydration drying with anhydrous sodium sulfate was performed. It was concentrated to dryness by an evaporator to obtain a yellow paste. To this, xylene (1 ° Om1) and activated carbon were added, and the mixture was heated and stirred, and filtered with filter paper. The filtrate was concentrated and allowed to stand for 24 hours. The crystals generated were collected and washed with petroleum ether to obtain 0.203 g of pale yellow fine crystals. FIG. 24 shows an NMR chart of this microcrystal. This microcrystal was identified as having the structure shown in formula (13).

Light emission characteristics>

The ITO substrate (50 X 5 Omm, manufactured by Sanyo Vacuum Industry Co., Ltd.) was ultrasonically cleaned with acetone for 10 minutes, then ultrasonically cleaned with 2-propanol for 10 minutes, blown with nitrogen and dried. . Thereafter, the ITO substrate was washed by irradiating UV for 5 minutes with a photo surface processor (wavelength: 254 nm, manufactured by Sen Special Light Source Co., Ltd.). The washed ITO substrate is set in a vacuum deposition apparatus (Daia Vacuum Giken Co., Ltd., UDS-M2-46 type), and N, N'-diphenyl is placed under reduced pressure of 4 X 10-6 torr or less. N, N'-di (m-tolyl) benzidine (TPD) layer 45 nm, a blue light-emitting compound having the structure represented by the above formula (13), which is prepared by doping 1.3% of methyl benzyl white on methylbenzyl white. Layer consisting of 35 nm layers and 15 nm layers of A 1 q 3 layers in this order, and finally an aluminum alloy electrode (A 1: L i = 99: 1 weight ratio, High Purity Chemical Laboratory Co., Ltd.) Was deposited to a thickness of 150 ηπι to produce a light emitting device having a laminated structure shown in FIG. The luminance and chromaticity of this light-emitting device were measured by gradually increasing the voltage using BM-7 Fast manufactured by Topcon Corporation. As a result, at a voltage of 12 V and a current of 27.74 mA, a result of luminance of 488.00 CdZm ² , chromaticity X of 0.3777, and chromaticity Y of 0.4777 was obtained. This example also shows that a light-emitting element including a light-emitting layer containing a blue light-emitting compound and a yellow light-emitting compound emits yellow-green light.

(Example 31)

230 ml of formaldehyde solution and 600 ml of hydrochloric acid were added to the three-necked flask, cooled to 0 ° C., 35 g of 1,4-methoxybenzene (molecular weight: 138.22) was added, and the mixture was reacted at 35 for 5 hours. The resulting reaction product was filtered, washed sequentially with water and methanol, and the residue was dried. Carbon tetrachloride was added thereto, and the mixture was heated, dried over sodium sulfate, and filtered. The resulting liquid was recrystallized and filtered, and the residue was dried to obtain 1,4-dimethoxy-2,5-di (chloromethyl) benzene. In a three-neck flask, 16.8 g of 1,4-dimethoxy-2,5-di (chloromethyl) benzene, 75.0 g of triphenylphosphine and 45 Om1 of xylene were mixed, and heated at 130 ° C. The reaction was carried out for 10 minutes, washed with benzene, and the residue was dried to obtain 40 g of 1,4-dimethoxy-1,2,5-di (trifeninolelin'chloromethinole) benzene. 1> 42 g of the obtained 1> 4 dimethoxy 2,5-di (triphenylphosphine. Chloromethyl) benzene was dissolved in 6 Om 1 of distilled ethanol, and 12.0 g of 4-trifluoromethylbenzaldehyde was added to 25 ml of distilled tetrahydrofuran. The reaction solution was mixed overnight with the distilled ethanol solution and the distilled tetrahydrofuran solution, and reacted overnight. After the reaction product was extracted with chloroform, dried, and cyclohexane and activated carbon were added. The mixture was heated, filtered, and the liquid was recrystallized, and the formed crystals were dissolved in cyclohexane. Recrystallization was performed from the obtained cyclohexane solution, and this operation was repeated three times, and the residue and the liquid were dried. These are further washed with cyclohexane, heated by adding iodine and activated carbon, filtered, and then the liquid is recrystallized, washed with hexane, and the residue is dried and sublimated to obtain crystals. Was. The IR chart and the NMR chart of this crystal are shown in FIG. 25 and FIG. 26, respectively. The crystals melted above 150 ° C. From these results, this crystal was identified as a substance represented by the formula (41).

(41)

<Creation of light emitting element>

In a 5 ml volumetric flask, polybulcanolevazo 1 / re 7 Omg, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole (BND) 30 mg, and a crystal represented by the above formula (41) 2 mg was weighed, and dichloroethane was added thereto to prepare a blue light-emitting compound-containing solution to a volume of 5 ml. The solution containing the blue luminescent compound was sufficiently homogenized by irradiating ultrasonic waves for 20 minutes with an ultrasonic cleaner (US-2, manufactured by S.N. Ltd.). The ITO substrate (50 X 50 mm, ITO transparent electrode thickness 200 111, manufactured by Sanyo Vacuum Industry Co., Ltd.) is ultrasonically cleaned with acetone for 10 minutes, then ultrasonically cleaned with 2-propanol for 10 minutes, and then nitrogen. Blow and dry. After that, the substrate was washed by irradiating it with UV for 5 minutes using the above-mentioned Photo Face 'processor (wavelength: 254 nm). Using a spin coater (1H-D7, manufactured by Mikasa Co., Ltd.), the prepared solution containing the blue light-emitting compound was dropped onto the ITO substrate that had been washed and dried. Spin coating was performed for 3 seconds to form a film having a dry thickness of 100 μm. After the formed substrate was dried in a constant temperature bath at 50 ° C for 30 minutes, the aluminum alloy (A) was deposited using a vacuum evaporation system (Dia Vacuum Giken Co., Ltd., 03-] \ [2-46 type). 1: L i = 99: 1 weight ratio, Inc. of Kojundo Chemical Laboratory, Ltd.) electrode was deposited to a thickness of about 0.99 nm at 4 X 10- ⁶ Torr, the blue light emitting device having the structure shown in FIG. 1 Produce did. The luminance and chromaticity of this blue light-emitting device were measured while gradually increasing the voltage with BM-7 Fast manufactured by Topcon Corporation. As a result, at a voltage of 2 IV and a current of 15.28 mA, a result with a luminance of 758.0 Cd / m ² , a chromaticity X of 0.1752, and a chromaticity 0 of 0.26 S 4 was obtained.

(Example 32)

 A three-necked flask was charged with 273 ml of formaldehyde solution and 713 ml of hydrochloric acid, cooled to 0 ° C, and then added with 50 g of 1,4-diethoxybenzene (molecular weight 166.22), and added at 35 ° C. For 5 hours. The reaction product was filtered, washed sequentially with water and methanol, and the residue was dried. Tetrachlorocarbon was added to the residue, and the mixture was dried over sodium sulfate while heating at a high temperature and filtered. The resulting liquid was recrystallized, filtered and the residue was dried to give 1,4-diethoxy-2,5-di (chloromethyl) benzene. A mixture of 13.9 g of the obtained 1,4-diethoxy-1,2,5-di (chloromethyl) benzene, 34.6 g of triphenylenolephosphine and 350 m of toluene was heated at 130 ° C. The resulting reaction product was filtered, the resulting filtrate was washed with benzene, and after washing, the solid was dried to give 1,4-diethoxy-2,5-diene.

(Tripheninolephosphine chloromethinole) Benzene was obtained. A mixture of 6.38 g of the obtained 1,4-jetoxy 2,5-di (triphenylphosphine chloromethyl) benzene, 4.23 g of 4-trifluoromethylbenzaldehyde, 20 g of tetrahydrofuran and 30 g of ethanol Then, 0.3 g of lithium and 50 g of ethanol were added, and the whole was reacted.The mixture was extracted with chloroform, dried, heated by adding cyclohexane and activated carbon, and then filtered. The obtained liquid was recrystallized, and the recrystallized product was dissolved in cyclohexane. Recrystallization from the obtained liquid This operation was repeated three times, and the residue and the liquid were dried. These are combined and further washed with cyclohexane, heated after adding iodine and activated carbon, and after filtration, the liquid is recrystallized, washed with cyclohexane, and the residue is dried and purified by sublimation. Crystals were obtained. FIG. 27 shows an IR chart of this crystal, and FIG. 28 shows an NMR chart thereof. The crystal is 205. Melted above C. From these results, this crystal was identified as a substance represented by the formula (36).

F ₃ (42)

A blue light-emitting compound represented by the formula (42) was dissolved in benzene to a concentration of 1 OmgZL to prepare a sample solution. The sample solution was loaded on a Shimadzu F-4500 spectrofluorometer, and the fluorescence spectrum was measured under the following conditions. Fig. 29 shows the obtained fluorescent spectrum. Measurement condition

 Measurement mode

 Excitation wavelength3 o o n m

 Fluorescence start wavelength 365 nm

 Fluorescence end wavelength 700 nm

 Scan speed 1200 η mZ min

 Excitation side slit 5.0 nm

Fluorescence side slit 5.0 nm Photomal voltage 700V

 As can be seen from FIG. 39, the blue light-emitting compound obtained in this example shows fluorescence emission at 400 to 600 nm.

(Example 33)

 In a three-necked flask, 70 g of diphenyl (molecular weight 154.21), 68.1 g of paraformaldehyde, 630 cc of glacial acetic acid, 650 cc of hydrochloric acid, and 526 g of polyphosphoric acid were sequentially charged, and then placed on an oil path. The mixture was heated at 115 ° C for 7 hours with stirring. After cooling, the reaction product was extracted and dissolved in chloroform, and the obtained chloroform solution was poured into ice water. The mixture was transferred to a separating funnel and extracted with black-mouthed form. After repeating the water washing twice, it was dehydrated with anhydrous sodium sulfate. After filtration with a paper filter, the mixture was concentrated and dried with an evaporator, washed with petroleum ether, further recrystallized with benzene, and dried to obtain 3,3,1-chloromethyldiphenyl. Next, a three-necked flask was charged with 10.3 g (molecular weight 251.21) of 3,3,1-chloromethyldiphenyl, 28.2 g of triphenylphosphine, and 320 ml of xylene, and the resulting mixture was added. The mixture was heated at 120 ° C for 19 hours with stirring on an oil bath. The obtained reaction product was filtered through a 40-mesh glass filter, washed twice with benzene, and dried to obtain a reagent reagent represented by the following formula (43).

In a three-necked flask, 6.4 g (1 mol) of the obtained reagent reagent, 3.60 g (2.5 mol) of 4-trifluoromethylbenzaldehyde, and tetrahydride A mixture of 10 g of furan and 15 g of ethanol was added, and 0.35 g of lithium and 80 g of ethanol were added thereto, and the mixture was allowed to react for 1 hour. The reaction product was extracted with chloroform, dried, and washed with methanol. Later, benzene, iodine and activated carbon were added, heated, filtered and the liquid was recrystallized, and the generated crystals were dissolved in cyclohexane. The obtained benzene solution was recrystallized, filtered, washed with benzene, and the residue was dried and sublimated to obtain a crystal having a structure represented by the formula (44).

<Creation of light emitting element>

In a 5 ml volumetric flask, 70 mg of polyvinylinolecanolebazonole, 30 mg of 2,5-bis (1-naphthyl) -1,3,4-oxadiazole (BND), and a crystal represented by the above formula (44) 2 mg was weighed, and dichloroethane was added to prepare a blue light-emitting compound-containing solution so as to have a volume of 5 ml. The solution containing the blue light-emitting compound was sufficiently homogenized by irradiating ultrasonic waves for 20 minutes with an ultrasonic cleaner (US-2, manufactured by Sennedy Co., Ltd.). The ITO substrate (50 X 50 mm, ITO transparent electrode thickness 200 μπι, manufactured by Sanyo Vacuum Industry Co., Ltd.) is ultrasonically cleaned with acetone for 10 minutes, then ultrasonically cleaned with 2-propanol for 10 minutes, and then nitrogen. Blow and dry. Thereafter, the substrate was washed by irradiating UV for 5 minutes with the above-mentioned photo 'face' processor (wavelength: 254 nm). Using a spin coater (1H-D7, manufactured by Mikasa Corporation), the prepared blue light-emitting compound-containing solution was dropped onto the washed and dried ITO substrate, and the rotation speed was 1,500 rpm and the rotation time was The film was formed by spin coating in 3 seconds to a dry thickness of 100 m. After the formed substrate is dried in a constant temperature bath at 50 ° C for 30 minutes, the aluminum alloy (A) is produced using a vacuum evaporation system (Dia Vacuum Engineering Co., Ltd., ¥ 03-^! 2-46 type). 1: L i = 99 _: 1 weight ratio, manufactured by Kojundo Chemical Laboratory) Electrode, 4 X 1 CT Evaporated to a thickness of about 150 nm at ⁶ Torr to produce a blue light emitting device with the structure shown in Figure 1.

The luminance and chromaticity of this blue light-emitting device were measured while gradually increasing the voltage using BM-7 Fast manufactured by Topcon Corporation. As a result, at a voltage of 18 V and a current of 12.06 mA, the luminance is 151.0 Cd Zm ² , the chromaticity X is 0.1857, and the chromaticity Y is 0.17994. The result was obtained. Industrial applicability

 According to the present invention, it is possible to provide a novel compound which emits blue light with high luminance and high color purity by applying energy and has high durability. According to the present invention, it is possible to emit blue light with high luminance and high color purity by including the novel blue light-emitting compound in the light-emitting layer. A light-emitting element capable of emitting white light with high luminance by including a blue light-emitting compound in a light-emitting layer. A light-emitting element that emits light can be provided. Further, according to the present invention, there is provided a novel blue light-emitting compound capable of emitting blue light with high luminance and high color purity for a long time by applying energy, and a light-emitting element using the blue light-emitting compound. can do.

Claims

The scope of the claims  1. A blue light-emitting compound having a structure represented by the following formula (1). .. (1) A r 2— GH _S A r -GH _H — A r 1 (However, in the formula, one Ar— is an aromatic group, Ar 1— is a hydrogen atom or an aromatic substituent. Ar 2— is an aromatic substituent when A r 1 is a hydrogen atom. And when Ar 1 is an aromatic substituent, it is a hydrogen atom or an aromatic substituent.) 2. The one Ar— is a 1,4-phenylene group represented by the following formula (la), a 1,4-naphthylene group represented by the following formula (lbl), and a following formula (1 b 2) A 2,6-naphthylene group, or a 9,10-anthrylene group represented by the following formula (1c), wherein Ar 1 is a hydrogen atom, or any of the following formulas (Id) to (If) Ar 2 represents a hydrogen atom or any one of the following formulas (1d) to (If) when Ar 1 is the aromatic substituent described above. And wherein when Ar 1 is a hydrogen atom, it is an aromatic substituent represented by any of the following formulas (1d) to (I f). Blue light-emitting compound.

(Wherein, R ¹ is a hydrogen atom, an alkyl group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, an alkoxy group which may be substituted by a fluorine atom having 1 to 5 carbon atoms or 1 carbon atom Represents an alkenyl group of 5 to 5. m represents 0, and represents an integer of 1 to 5. A plurality of R ^{1 s} may be the same or different R ² is a hydrogen atom, a fluorine atom having 1 to 5 carbon atoms An alkyl group which may be substituted with an atom, an alkoxy group which may be substituted with a fluorine atom having 1 to 5 carbon atoms, or an alkenyl group having 1 to 5 carbon atoms, wherein n is an integer of 0 or 1 to 3; A plurality of R ² may be the same or different R ³ is a hydrogen atom, an alkyl group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, a fluorine atom having 1 to 5 carbon atoms There an alkenyl group of 1 to 5 good § alkoxy group carbon atoms or be substituted. p is 0, to indicate an integer of 1 to 4. multiple R ³ are the same May differ even I. Also, R ² and R ³ may be different from be the same. R ⁴ is a hydrogen atom, a fluorine atom of 1 to 5 carbon by replacement An alkyl group, an alkoxy group which may be substituted by a fluorine atom having 1 to 5 carbon atoms or an alkenyl group having 1 to 5 carbon atoms, wherein R ⁵ is a hydrogen atom, a fluorine atom having 1 to 5 carbon atoms. An alkyl group which may be substituted by a hydrogen atom, an alkoxy group which may be substituted by a fluorine atom having 1 to 5 carbon atoms, or an alkenyl group having 1 to 5 carbon atoms. q represents 0, an integer of 1 to 4. A plurality of R ⁵ may be the same or different. Further, R ⁴ and R ⁵ may be the same or different. ) 3. A light-emitting element comprising a light-emitting layer containing a blue light-emitting compound represented by the general formula (1) provided between a pair of electrodes. 4. A stilbene-based blue light-emitting compound having an alkyl fluoride group, having a structure represented by the following formula (31). (31)

(However, in the formula, Ar— is an aromatic group represented by the following formula (32) or (33). Y represents a fluorinated alkyl group having 1 to 3 carbon atoms. The bond position of Y is ortho-position or para-position with respect to one CZ.A plurality of Ys bonded to one benzene ring may be the same or different. A plurality of Y bonded to two benzene rings may be the same or different, and Z is a hydrogen atom or a group represented by the following formula (34).

(In the formulas (32) and (33), X is a hydrogen atom or an alkoxy group having 1 to 5 carbon atoms, and the two Xs may be the same or different.)

(However, in the formula (34), it represents a fluorinated alkyl group having 1 to 3 carbon atoms. N represents a positive number of 1 to 3. The bonding position of Y is ortho-position or para-position. One benzene A plurality of Y bonded to the ring may be the same or different.) 5. A light-emitting element comprising a light-emitting layer containing a stilbene-based blue light-emitting compound containing an alkyl fluoride group represented by the general formula (31) between a pair of electrodes.