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An organic electroluminescent device comprising fluorene derivatives

An electroluminescence device and luminescence technology, which is applied in the direction of electric solid-state devices, organic chemistry, electrical components, etc., can solve the problems of low glass transition temperature, poor device stability, and low triplet energy level, so as to improve the glass transition temperature , charge dispersion, life-enhancing effects

Active Publication Date: 2021-06-22
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the problems of poor device stability and short life due to the low glass transition temperature and low triplet energy level of hole transport materials at the present stage, the present invention provides an organic electroluminescence device, the device hole transport layer The compound of the present invention contained has better hole transport ability, high glass transition temperature and higher triplet energy level. When it is used as a hole transport material, it can effectively improve the crystallization problem and effectively block excitons from the anode side Dissipation, which can improve the stability of the device, improve the luminous efficiency of the device, and prolong the service life of the device

Method used

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  • An organic electroluminescent device comprising fluorene derivatives
  • An organic electroluminescent device comprising fluorene derivatives
  • An organic electroluminescent device comprising fluorene derivatives

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preparation example Construction

[0095] The preparation method of the organic compound of the present invention can be prepared through the following synthetic route, but the present invention is not limited thereto:

[0096] 1, the synthesis of compound of the present invention

[0097]

[0098]2. Synthesis of intermediate S5 / S5'

[0099]

[0100] R 1 ~R 3 、Ar 1 ~ Ar 3 , L 1 , E, and a definition are the same as those defined above; Xa, Xb, Xc, and Xd are respectively any one of Br, Cl, and I.

[0101] Further, the organic layer further includes a hole injection layer, and the hole injection layer includes an axene compound represented by formula IV,

[0102]

[0103] Among them, R 2 , R 3 , R 4 Any one independently selected from substituted C6-C30 aryl groups and substituted C3-C30 heteroaryl groups;

[0104] The substituted group is selected from any one of fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl or nitro.

[0105] Preferably, the axene compound represented by the f...

Embodiment 1

[0141] [Example 1] Synthesis of Compound 1

[0142]

[0143] Synthesis of Intermediate S3-1

[0144] Intermediate S2-1 (6.0g, 21mmol) was dissolved in 500mL of N,N-dimethylformamide (DMF), and N-bromosuccinyl was added to the mixture within 30min at room temperature in the dark. Imine (NBS) (3.7g, 21mmol), the resulting mixture was stirred for 8 hours, after the reaction was completed, the reactant was poured into Na 2 CO 3 solution (3M, 1L), the resulting product was then washed with dichloromethane, the organic phase was separated and the solvent was removed using a rotary evaporator. Subsequently, the solid was recrystallized to obtain intermediate S3-1 (7.0 g, 92%), and the purity of the solid was ≥99.8% as determined by HPLC.

[0145] Mass Spectrum m / z: 361.0645 (Theoretical: 361.0466). Theoretical element content (%)C 21 h 16 BrN: C, 69.63; H, 4.45; Br, 22.06; N, 3.87. Measured element content (%): C, 69.60; H, 4.47; Br, 22.03; N, 3.90. The above results confi...

Embodiment 2

[0152] [Example 2] Synthesis of Compound 7

[0153]

[0154] Synthesis of Intermediate S4-2

[0155] The phenylboronic acid in Example 1 was replaced by an equimolar amount of phenyl-D5-boronic acid, and the intermediate S4-2 (4.4g, 68%) was prepared according to the synthesis method of Example 1, and the solid purity was detected by HPLC≥99.1 %.

[0156] Mass Spectrum m / z: 364.2133 (Theoretical: 364.1988). Theoretical element content (%)C 27 h 16 D. 5 N: C, 88.97; H, 7.19; N, 3.84. Measured element content (%): C, 88.94; H, 7.20; N, 3.86. The above results confirmed that the obtained product was the target product.

[0157] Synthesis of compound 7

[0158] Intermediate S4-1 in Example 1 was replaced by an equimolar amount of Intermediate S4-2, and compound 7 (5.1 g, 75%) was prepared according to the synthesis method of Example 1, and the solid purity was ≥99.4% as determined by HPLC.

[0159] Mass Spectrum m / z: 678.3235 (Theoretical: 678.3083). Theoretical eleme...

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Abstract

The invention provides an organic electroluminescent device containing fluorene derivatives, and relates to the field of organic photoelectric technology. The organic electroluminescent device of the present invention comprises a fluorene derivative, and carbazole / indenocarbazole and its derivative groups are introduced into the fluorene derivative, thereby obtaining a series of compounds with higher glass transition temperature, so it has good thermal stability, and the organic electroluminescent device containing this type of compound also has good stability, so it has the advantage of long service life; at the same time, the compound provided by the invention has better hole mobility , a suitable HOMO energy level, and a higher triplet state energy level are conducive to hole transport and can effectively block the dissipation of excitons, which can significantly improve the luminous efficiency of the device.

Description

technical field [0001] The invention relates to the field of organic photoelectric technology, in particular to an organic electroluminescent device containing fluorene derivatives. Background technique [0002] The era of digital communication continues to advance, and a new generation of flat-panel displays with better performance is required to meet the needs of life. The future trend of flat display is to be able to transmit more information and clearer images on a lightweight carrier. Among them, organic light emitting diode (OLED), as a new generation of flat-panel displays, has attracted widespread attention at home and abroad, because OLED displays have self-illumination, wide viewing angle, short response time, high luminous efficiency, wide color gamut, and work It has the characteristics of low voltage, thin panel, flexible size design, flexible shape design and simple preparation method. [0003] A general organic light-emitting device is composed of a cathode,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/50H01L51/54C07D209/94C07D209/86
CPCC07D209/94C07D209/86H10K85/624H10K85/626H10K85/6572H10K50/15
Inventor 杜明珠朱鸫达王英雪
Owner CHANGCHUN HYPERIONS TECH CO LTD
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