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Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device

a technology of light-emitting elements and compounds, which is applied in the direction of luminescent compositions, chemistry apparatuses and processes, organic chemistry, etc., can solve the problems of prolonging unable to provide high efficiency and long life of near-infrared-emitting elements, and unable to prolong the life of light-emitting elements, etc., to achieve excellent reliability, long life, and high efficiency

Active Publication Date: 2016-03-15
SEIKO EPSON CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0009]An advantage of some aspects of the invention is that they provide a near-infrared-emitting, high-efficiency, and long-life thiadiazole, a near-infrared-emitting, high-efficiency, and long-life compound for light-emitting elements, a near-infrared-emitting, high-efficiency, and long-life light-emitting element, and a light-emitting apparatus, an authentication apparatus, and an electronic device provided with such a light-emitting element.

Problems solved by technology

However, it has been impossible to provide such near-infrared-emitting elements with high efficiency and long life.
Thus, the use of the tetracene-based host material also extends the life of the light-emitting layer and, accordingly, prolongs the life of the light-emitting element.
Thus, the use of the anthracene-based host material also extends the life of the light-emitting layer and, accordingly, prolongs the life of the light-emitting element.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

embodiment 1

Configuration of the Light-Emitting Element

[0082]FIG. 1 schematically illustrates a cross-section of a light-emitting element according to Embodiment 1 of an aspect of the invention. For convenience of explanation, the top and bottom in FIG. 1 are hereinafter regarded as the top and bottom of the light-emitting element, respectively.

[0083]The light-emitting element (electroluminescence element) 1A illustrated in FIG. 1 has an anode 3, a hole injection layer 4, a hole transport layer 5, a light-emitting layer 6A, an electron transport layer 7, an electron injection layer 8, and a cathode 9 stacked in this order. In other words, the light-emitting element 1A has a laminate 14 disposed between the anode 3 and the cathode 9, and the laminate 14 contains the hole injection layer 4, the hole transport layer 5, the light-emitting layer 6A, the electron transport layer 7, and the electron injection layer 8 stacked in this order from the anode 3 side to the cathode 9 side.

[0084]The entire li...

synthesis example a1

Synthesis of Compound D-1

[0208]

Synthesis Step A1-1

[0209]First, 1500 mL of fuming nitric acid was put into a 5-L flask and then cooled. To this flask, 1500 mL of sulfuric acid was added in several steps so that the temperature was maintained at 10° C. to 50° C. Subsequently, 150 g of compound (a), raw material dibromobenzothiadiazole, was added to the flask in small amounts over 1 hour. The temperature of the solution was maintained at not more than 5° C. during this operation. After all of compound (a) was added, the reaction was allowed to proceed at room temperature (25° C.) for 20 hours. After the completion of the reaction, the reaction solution was poured into 3 kg of ice and stirred overnight. Subsequently, the solution was filtered, and the residue was washed with methanol and heptane.

[0210]The residue was then dissolved in 200 mL of toluene by heating. The solution was allowed to cool to room temperature and then filtered. The residue was washed with a small amount of toluen...

synthesis example a2

Synthesis of Compound D-2

[0219]

[0220]The same synthesis steps as in Synthesis Example A1 were repeated except phenylboronic acid, which was used in Synthesis Step A1-2 in Synthesis Example A1, was replaced with triphenylamine boronic acid. In this way, compound (h), i.e., the compound represented by formula D-2, was obtained.

[0221]The triphenylamine boronic acid used in this example was synthesized by the following procedure. In an Ar atmosphere, 246 g of 4-bromotriphenylamine (a commercially available product) and 1500 mL of anhydrous tetrahydrofuran were put into a 5-L flask, and then 570 mL of a 1.6 mol / L n-BuLi solution in hexane was added dropwise at −60° C. over 3 hours. Thirty minutes later, 429 g of triisopropyl borate was added dropwise over 1 hour. Subsequently, the reaction was allowed to proceed overnight with no temperature control. After the completion of the reaction, 2 L of water was added dropwise, and the obtained solution was subjected to extraction with 2 L of to...

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Abstract

The thiadiazole represented by formula (1), when used as a light-emitting material in a light-emitting element, allows the light-emitting element to emit near-infrared light:wherein, in formula (1), each A independently represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl amino group, or a substituted or unsubstituted triarylamine.

Description

CROSS REFERENCES TO RELATED APPLICATIONS[0001]The present application claims priority to Japanese Patent Application No. 2012-041223 and Japanese Patent Application No. 2012-041224 filed in the Japanese Patent Office on Feb. 28, 2012 and Japanese Patent Application No. 2012-230597 filed in the Japanese Patent Office on Oct. 18, 2012, the entire contents of which are incorporated herein by reference.BACKGROUND[0002]1. Technical Field[0003]The present invention relates to a thiadiazole, a compound for light-emitting elements, a light-emitting element, a light-emitting apparatus, an authentication apparatus, and an electronic device.[0004]2. Related Art[0005]Organic electroluminescent elements (organic EL elements) are light-emitting elements composed of an anode, a cathode, and at least one organic light-emitting layer disposed between them. Upon the application of an electric field between the anode and the cathode, holes in the anode and electrons in the cathode are injected into th...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): H01L51/00C09K11/06C07D513/04H01L51/50
CPCH01L51/0071C07D513/04C09K11/06H01L51/0058H01L51/0061H01L51/5012
Inventor YAMAMOTO, HIDETOSHIFUJITA, TETSUJI
Owner SEIKO EPSON CORP