ELECTROLUMINESCENT MATERIAL

Abstract

An electroluminescent material is provided. 9,9′-bianthracene is used as a homodivalent electron group. The homodivalent electron group in the final compound has mainly functions of absorption and emission and also can control the size of the final molecule. Therefore, a homodivalent system is achieved. Specifically, an electroluminescent material having a wide bandgap, high fluorescence quantum yield, and good thermal stability is prepared by a reaction of 9,9′-bianthryl derivative and 1-bromo-3,5-biphenyl, 9,9′-bianthryl derivative and 1-bromobenzene-3,5-biphenyl, and 9,9′-bianthryl derivative and a mixture of 1-bromo-3,5-biphenyl and 1-bromobenzene-3,5-biphenyl, respectively. Therefore, luminescent efficiency of the electroluminescent material is improved.

Claims

1. An electroluminescent material prepared by a raw material, wherein the raw material comprises: a first compound, wherein a homodivalent electron group of the first compound comprises one of an anthracene group, a pyrene group, a carbazole group, or a fluorene group; and a second compound, wherein the second compound comprises one of phenyl-substituted biphenyl group and a derivative thereof, phenyl-substituted binaphthalene and a derivative thereof, and phenyl-substituted bianthryl and a derivative thereof.

2. The electroluminescent material prepared by and raw material according to claim 1, wherein the anthracene group is 9,9′-bianthracene.

3. The electroluminescent material prepared by and raw material according to claim 2, wherein the 9,9′-bianthracene has a chemical formula as follows: ##STR00017##

4. The electroluminescent material prepared by and raw material according to claim 1, further comprising 10,10′-di-triphenyl-9,9′-bianthryl derivative, wherein the 10,10′-di-triphenyl-9,9′-bianthryl derivative has a chemical formula as follows: ##STR00018##

5. The electroluminescent material prepared by and raw material according to claim 4, wherein the first compound is 9,9′-bianthryl derivative, and the second compound is 1-bromo-3,5-biphenyl, and the 9,9′-bianthryl derivative has a chemical formula as follows: ##STR00019## and the 1-bromo-3,5-biphenyl has a chemical formula as follows: ##STR00020##

6. The electroluminescent material prepared by and raw material according to claim 1, further comprising 10,10′-di-tetraphenyl-9,9′-bianthryl derivative has a chemical formula as follows: ##STR00021##

7. The electroluminescent material prepared by and raw material according to claim 6, wherein the first compound is 9,9′-bianthryl derivative, and the second compound is 1-bromo-3,5-biphenyl, and the 9,9′-bianthryl derivative has a chemical formula as follows: ##STR00022## and the 1-bromobenzene-3,5-biphenyl has a chemical formula as follows: ##STR00023##

8. The electroluminescent material prepared by the raw material according to claim 1, further comprising 10-triphenyl, 10′-tetraphenylenyl-9,9′-bianthryl derivative, and the 10-triphenyl, 10′-tetraphenylenyl-9,9′-bianthryl derivative has a chemical formula as follows: ##STR00024##

9. The electroluminescent material prepared by the raw material according to claim 8, wherein the first compound is 9,9′-bianthryl derivative, and the second compound is a mixture of 1-bromo-3,5-biphenyl and 1-bromobenzene-3,5-biphenyl.

10. The electroluminescent material prepared by the raw material according to claim 9, wherein a ratio of a weight percentage of the 1-bromo-3,5-biphenyl to the 1-bromobenzene-3,5-biphenyl ranges from 0.8 to 1.2.

Description

BRIEF DESCRIPTION OF DRAWINGS

[0018] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly described below. It is obvious that the drawings in the following description are only some embodiments of the present invention. Other drawings can also be obtained from those skilled persons in the art based on these drawings without paying any creative effort.

[0019] FIG. 1 is a luminescence spectrum of electroluminescent materials according to embodiment of the present invention.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

[0020] The preferred embodiments of the present invention are described in detail below with reference to the accompanying drawings. Those skilled persons in the art will easily understand how to implement the invention. The invention can be implemented by the embodiments, so that the technical content of the disclosure will be clear, so that those skilled persons in the art will understand how to implement the invention. The present invention may be accomplished in many different embodiments, and the scope of the invention is not limited to the embodiments described herein.

[0021] Directional terms mentioned in this application, such as “up,” “down,” “forward,” “backward,” “left,” “right,” “inside,” “outside,” “side,” etc., are merely indicated the direction of the drawings. Therefore, the directional terms are used for illustrating and understanding of the application rather than limiting thereof.

[0022] In the drawings, identical components are marked with the same reference numerals, and structural or components having similar functions are marked with similar reference numerals. Moreover, the size and thickness of each component shown in the drawings are arbitrarily shown for understanding and describing, and the invention does not limit the size and thickness of each component.

[0023] When a component is described as “on” another component, the component can be disposed directly on the other component. Also, one component is disposed on an intermediate component, and the intermediate component is disposed on another component. When a component is described as “installed” or “connected” to another component, it can be understood as directly “installed” or “connected” to another component.

[0024] In a first embodiment, an electroluminescent material is prepared by a raw material, and the raw material includes a first compound and a second compound. A homodivalent electron group of the first compound includes one of an anthracene group, a pyrene group, a carbazole group, or a fluorene group. The second compound includes one of phenyl-substituted biphenyl group and a derivative thereof, phenyl-substituted binaphthalene and a derivative thereof, and phenyl-substituted bianthryl and a derivative thereof. Specifically, the anthracene group is 9,9′-bianthracene has a chemical formula as follows:

##STR00009##

[0025] The 10,10′-di-triphenyl-9,9′-bianthryl derivative has a chemical formula as follows:

##STR00010##

[0026] The first compound is 9,9′-bianthryl derivative, and the second compound is 1-bromo-3,5-biphenyl, and the 9,9′-bianthryl derivative has a chemical formula as follows:

##STR00011##

and the 1-bromo-3,5-biphenyl has a chemical formula as follows:

##STR00012##

[0027] The specific preparation steps are described. 4-30 mmol 9,9′-bianthryl derivative, 0.15-0.6 mmol Pd catalyst, and 0.3-1.9 mmol of tricyclohexyl phosphine are added to anhydrous toluene and anhydrous ethanol solution. 1-bromo-3,5-biphenyl is added to a 100 mL beaker, then ethanolamine is slowly added to the beaker by using a pipette and dissolved in the beaker. Next, 15-30 mL ethanolamine including dissolved 1-bromo-3,5-biphenyl is added to the above reaction mixture by using a syringe, and the reaction mixture is refluxed under argon for 4 hours. After the reaction is completed, the reaction mixture is extracted with chloroform and water. The organic layer is dried over anhydrous MgSO.sub.4 and filtered, and then the solution is evaporated. Finally, a product is isolated by silica gel column chromatography to obtain 10,10′-di-triphenyl-9,9′-bianthryl derivative.

[0028] In the first embodiment, 9,9′-bianthracene is used as a homodivalent electron group. The homodivalent electron group in the final compound has mainly functions of absorption and emission and also can control the size of the final molecule. Therefore, a homodivalent system is achieved. Specifically, an electroluminescent material having a wide bandgap, high fluorescence quantum yield, and good thermal stability is prepared by a reaction of 9,9′-bianthryl derivative and 1-bromo-3,5-biphenyl. Therefore, luminescent efficiency of the electroluminescent material is improved.

[0029] In a second embodiment, the difference between the second embodiment and the first embodiment is described below, and the others are not be described herein.

[0030] An electroluminescent material is 10,10′-di-tetraphenyl-9,9′-bianthryl derivative, which has a chemical formula as follows:

##STR00013##

[0031] The first compound is 9,9′-bianthryl derivative, and the second compound is 1-bromo-3,5-biphenyl, and the 9,9′-bianthryl derivative has a chemical formula as follows:

##STR00014##

and the 1-bromobenzene-3,5-biphenyl has a chemical formula as follows:

##STR00015##

[0032] The specific preparation steps are described. 4-30 mmol 9,9′-bianthryl derivative, 0.15-0.6 mmol Pd catalyst, and 0.3-1.9 mmol of tricyclohexyl phosphine are added to anhydrous toluene and anhydrous ethanol solution. 1-bromobenzene-3,5-biphenyl is added to a 100 mL beaker, then ethanolamine is slowly added to the beaker by using a pipette and dissolved in the beaker. Next, 15-30 mL ethanolamine including dissolved 1-bromobenzene-3,5-biphenyl is added to the above reaction mixture by using a syringe, and the reaction mixture is refluxed under argon for 4 hours. After the reaction is completed, the reaction mixture is extracted with chloroform and water. The organic layer is dried over anhydrous MgSO.sub.4 and filtered, and then the solution is evaporated. Finally, a product is isolated by silica gel column chromatography to obtain 10,10′-di-tetraphenyl-9,9′-bianthryl derivative.

[0033] In the second embodiment, 9,9′-bianthracene is used as a homodivalent electron group. The homodivalent electron group in the final compound has mainly functions of absorption and emission and also can control the size of the final molecule. Therefore, a homodivalent system is achieved. Specifically, an electroluminescent material having a wide bandgap, high fluorescence quantum yield, and good thermal stability is prepared by a reaction of 9,9′-bianthryl derivative and 1-bromobenzene-3,5-biphenyl. Therefore, luminescent efficiency of the electroluminescent material is improved.

[0034] In a third embodiment, the difference between the third embodiment and the first embodiment is described below, and the others are not be described herein.

[0035] An electroluminescent material is 10-triphenyl, 10′-tetraphenylenyl-9,9′-bianthryl derivative, which has a chemical formula as follows:

##STR00016##

[0036] The first compound is 9,9′-bianthryl derivative, and the second compound is a mixture of 1-bromo-3,5-biphenyl and 1-bromobenzene-3,5-biphenyl.

[0037] The specific preparation steps are described. 4-30 mmol 9,9′-bianthryl derivative, 0.15-0.6 mmol Pd catalyst, and 0.3-1.9 mmol of tricyclohexyl phosphine are added to anhydrous toluene and anhydrous ethanol solution. 1-bromo-3,5-biphenyl and 1-bromobenzene-3,5-biphenyl are added to a 100 mL beaker, then ethanolamine is slowly added to the beaker by using a pipette and dissolved in the beaker. Next, 15-30 mL ethanolamine including dissolved 1-bromo-3,5-biphenyl and 1-bromobenzene-3,5-biphenyl is added to the above reaction mixture by using a syringe, and the reaction mixture is refluxed under argon for 4 hours. After the reaction is completed, the reaction mixture is extracted with chloroform and water. The organic layer is dried over anhydrous MgSO.sub.4 and filtered, and then the solution is evaporated. Finally, a product is isolated by silica gel column chromatography to obtain 10-triphenyl, 10′-tetraphenylenyl-9,9′-bianthryl derivative.

[0038] A ratio of a weight percentage of the 1-bromo-3,5-biphenyl to the 1-bromobenzene-3,5-biphenyl ranges from 0.8 to 1.2.

[0039] In the first embodiment, 9,9′-bianthracene is used as a homodivalent electron group. The homodivalent electron group in the final compound has mainly functions of absorption and emission and also can control the size of the final molecule. Therefore, a homodivalent system is achieved. Specifically, an electroluminescent material having a wide bandgap, high fluorescence quantum yield, and good thermal stability is prepared by a reaction of 9,9′-bianthryl derivative and a mixture of 1-bromo-3,5-biphenyl and 1-bromobenzene-3,5-biphenyl. Therefore, luminescent efficiency of the electroluminescent material is improved.

[0040] As shown in FIG. 1, three electroluminescent materials according to the three embodiments have a maximum emission peak at 435-480 nm, which are high-efficiency blue luminescent materials. Due to the specific structure of the compound, a blue shift of the electroluminescent material is occurred in the spectrum with an increasing number of benzene rings. However, 9,9′-bianthracene used as a homodivalent electron group limits the size of the molecule, which acts as a core in the molecule. Therefore, molecule size cannot be increased without limit, which only causes the material to fail to emit blue light. At the same time, it will inhibit the π-π accumulation of adjacent molecules, because of its relatively large steric hindrance.

[0041] In the above, the present application has been described in the above preferred embodiments, but the preferred embodiments are not intended to limit the scope of the invention, and a person skilled in the art may make various modifications without departing from the spirit and scope of the application. The scope of the present application is determined by claims.