Thiophene oxide derivative and organic light-emitting device thereof

A technology of oxides and derivatives, applied in the field of thiophene oxide derivatives and their organic light-emitting devices, can solve the problems of electron mobility slower than hole mobility, triplet energy quenching, efficiency roll-off, etc., to achieve luminescence Efficiency enhancement, solution to carrier imbalance, effect of high triplet energy level

Inactive Publication Date: 2017-09-29
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In practical applications, since the hole transport performance is better than that of electrons in organic photoelectric materials, the mobility of electrons is slower than that of holes, and the recombination region of holes and electrons in the light-emitting layer will be selectively biased to one side, resulting in its luminous efficiency. The change of light color can even lead to energy quenching between triplet states in severe cases, resulting in serious efficiency roll-off at high brightness. Today, with the development of large-scale OLED panels, more delicate and colorful materials are required. Among them The focus of the solution is the luminous efficiency and the lifetime of the device. This requires the combination of holes and electrons in the light-emitting layer to be efficient, and it is necessary to use effective electron transport materials. From the cathode to the transport materials of each layer of the light-emitting layer, it is necessary to improve its Electron injection and migration, while cutting off part of the hole movement

Method used

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  • Thiophene oxide derivative and organic light-emitting device thereof
  • Thiophene oxide derivative and organic light-emitting device thereof
  • Thiophene oxide derivative and organic light-emitting device thereof

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preparation example Construction

[0033] The preparation method of the thiophene oxide derivatives described in the present invention can obtain compound A by bromination of thiophene, and then obtain compound B through coupling reaction, compound B obtains compound C through a series of bromination and coupling reactions, compound C is oxidized to obtain the target compound.

[0034]

[0035] The present invention also provides an organic light-emitting device, comprising a first electrode, a second electrode, and one or more organic compound layers placed between the two electrodes, at least one of the organic compound layers containing the present Invention of the thiophene oxide derivatives. The organic compound layer includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0036] The thiophene oxide derivative provided by the present invention can e...

Embodiment 1

[0040] [Example 1] Synthesis of compound 2

[0041]

[0042] *Synthesis of intermediate 2-1

[0043] The three-necked flask of the reactor was placed in an ice bath, and thiophene (8.4g, 0.1mol), 20mL of CCl 4 , control the temperature at 0-5°C, stir and add dropwise 4.8mL of bromine (15g, 0.115mol) and 19mL of hydrobromic acid (23.5g, 0.116mol), the dropwise addition is completed within 80min, and then stirred for 60min, then washed with water and dried 1. The solvent was recovered by atmospheric distillation, the product was transferred into a distillation flask, and the fraction at 58-62° C. / 7.33 KPa was collected to obtain a colorless liquid 2-1 (14.3 g, 88%).

[0044] *Synthesis of intermediate 2-2

[0045] The reactor was put into an ice bath, and 20 mL of THF, compound 2-1 (3.26 g, 20 mmol), NiCl 2 (dppp) (0.54g, 1mmol), the temperature was controlled at 0-5°C, and then a solution of 2-thiophene magnesium bromide (4.5g, 24mmol) dissolved in 20mLTHF was added dropw...

Embodiment 2

[0050] Under the protection of argon, 20ml of H 2 o 2 Slowly added dropwise to 2-4 (6.73, 8.4mmol) in a mixed solvent of acetic acid (60ml) and DCM (25ml). After the reaction system was reacted at room temperature for 1 h, it was heated to 90°C and reacted for 36 h. After the initial product of the reactant was extracted with DCM, it was separated by column to obtain compound 2 (3.71 g, 53%). [Example 2] Synthesis of compound 4

[0051] According to the synthetic method of compound 2, compound 4 (2.91 g, 50%) was obtained.

[0052]

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Abstract

The invention discloses a thiophene oxide derivative and an organic light-emitting device thereof and belongs to the technical field of organic photoelectric materials. [2,2'-bithiophene]1,1,1',1'-tetroxide is taken as a main body structure, and the pi conjugacy, electrophilicity and charge transfer ability of the material are adjusted through changing a structure and a link method of a ligand, so that the thiophene oxide derivative has high luminous performance, electronic transmission performance, membrane stability and heat stability and high triplet level, and is capable of effectively solving the problem of charge carrier imbalance of unipolar luminescent materials. The luminous efficiency of the organic light-emitting device prepared from the thiophene oxide derivative is strengthened, and the organic light-emitting device is more stable in light and color, has the characteristics of excellent electron chemistry and heat stability and long service life, and also has high luminous efficiency under the condition of low starting voltage.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a thiophene oxide derivative and an organic light-emitting device thereof. Background technique [0002] Organic electroluminescence refers to the phenomenon that organic materials are excited by electric current and electric field to emit light under the action of electric field. The organic electroluminescent device (OLED) prepared by this light-emitting mechanism has the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, long life, light weight, and thin thickness. It is a new type of flat display. device. Due to the rapid development of optoelectronic communication and multimedia fields in recent years, organic optoelectronic materials occupy more and more market share in the information and electronics industries of modern society. [0003] In the current OLED application, the organic ligh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/48C07D409/14C07D333/76C07D413/14H01L51/54H01L51/46H01L51/50H01L51/42
CPCC07D333/48C07D333/76C07D409/14C07D413/14H10K85/622H10K85/626H10K85/656H10K85/654H10K85/655H10K85/6574H10K85/6576H10K30/00H10K50/00H10K50/16Y02E10/549
Inventor 董秀芹蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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