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A series of PHOLED (phosphorescent organic light-emitting diode) materials

A luminescent material and electroluminescence technology, applied in the field of phosphorescent OLED materials, can solve the problems of small luminous contribution and difficulty in improving luminous efficiency, etc.

Active Publication Date: 2016-04-20
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually, the generation ratio of singlet excitons and triplet excitons is 1:3, and according to the prohibition effect of quantum statistics, triplet excitons mainly undergo non-radiative attenuation, which contributes very little to luminescence, and only singlet excitons Therefore, for organic / polymer electroluminescent devices, the fundamental reason why the luminous efficiency is difficult to improve is that the luminescence process is the luminescence of singlet excitons

Method used

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  • A series of PHOLED (phosphorescent organic light-emitting diode) materials
  • A series of PHOLED (phosphorescent organic light-emitting diode) materials
  • A series of PHOLED (phosphorescent organic light-emitting diode) materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The preparation of embodiment 1 compound GIR-AC-II-001

[0065]

[0066] The first step: preparation of compound G-0

[0067]

[0068] 20g of 1-cyclohexyl-2,3-difluorobenzene was dissolved in 250ml of anhydrous THF, cooled to -80°C with liquid nitrogen, and slowly added dropwise to 49.5ml of 2.5M n-butyllithium-hexane Alkanes solution, after stirring and reacting for 30 minutes, slowly add 16g of trimethyl borate dissolved in THF solution dropwise, after stirring and reacting for 30 minutes, rise to room temperature and stir for 1 hour, add dropwise 150ml of 6M dilute hydrochloric acid aqueous solution, stir and react for 1 hour hours, extracted with ethyl acetate, dried the organic phase with anhydrous sodium sulfate, filtered, concentrated under reduced pressure to dryness, added 150ml of petroleum ether to the residue, stirred and dispersed, and suction filtered to obtain 21g of compound G-0, a white solid, Yield 86%.

[0069] The second step: the preparation...

Embodiment 2

[0083] The preparation of embodiment 2 compound GIR-AC-IV-001

[0084]

[0085] 1.0 g of GIR-AC-II-001 and 652 mg of compound G-1 prepared in Example 1 were dispersed with 50 ml of glycerin, heated to 180°C under nitrogen protection, stirred for 8 hours, cooled to room temperature, The reaction liquid was poured into 200ml of 1N dilute hydrochloric acid, suction filtered, the filter cake was washed with water, and the obtained solid was separated and purified by a silica gel column to obtain 0.86 g of GIR-AC-IV-001, a yellow solid, with a yield of 71.6%.

[0086] Experimental data:

[0087] (1) 1 HNMR (δ, CDCl 3 ): 1.73~1.76(8H,m); 5.76~5.78(1H,t); 6.58~6.65(1H,t); 6.96(1H,s); 7.75~7.81(2H,m); ,m). LC-MS: 1004.2[M+1] confirms that the substance obtained from the reaction is indeed compound GIR-AC-IV-001;

[0088] (2) Glass transition temperature (DSC): \;

[0089] (3) UV maximum absorption wavelength (DCM): 290nm, 295nm, 320nm;

[0090] (4) Phosphorescence emission w...

Embodiment 3

[0091] The preparation of embodiment 3 compound GIR-AC-I-011

[0092]

[0093] The first step: preparation of compound G-0

[0094]

[0095] Referring to the synthesis method in the first step of Example 1, 1-cyclohexyl-2,3-difluorobenzene was replaced by 2-fluoro-6-(4-methylcyclohexyl)biphenyl to prepare boric acid, a white solid, and rate of 64%.

[0096] The second step: the preparation of compound G-1

[0097]

[0098] Referring to the synthesis method in the second step of Example 1, the G-0 obtained in the previous step and 2-bromopyridine were subjected to SUZUKI coupling reaction to obtain G-1, a white solid, with a yield of 82%.

[0099] The third step: preparation of compound G-2

[0100]

[0101] With reference to the synthetic method of the third step of Example 1, the G-1 and IrCl obtained in the previous step 3 ·3H 2 O undergoes a coordination reaction to obtain G-2, a yellow solid, with a yield of 89%.

[0102] The fourth step: preparation of c...

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Abstract

The invention discloses a series of PHOLED (phosphorescent organic light-emitting diode) materials. The general structural formula of the PHOLED materials is represented as a formula I-1 or a formula I-2. A series of iridium complex electrophosphorescent light-emitting materials with cyclohexyl groups and cyclohexene groups are provided on the basis that electrophosphorescent materials require high thermal stability, high quantum efficiency and lower doping ratio. The compounds have the characteristics of excellent film-forming properties, low probability of crystallization, high luminous efficiency and the like, raw materials are easy to obtain, preparation is simple and convenient, the total yield is high, the cost of phosphorescent materials is reduced greatly, and the PHOLED materials have important application values.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence display and relates to a series of phosphorescent OLED materials. Background technique [0002] Organic electroluminescence (referred to as OLED) and related research As early as 1963, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display. And other advantages, can be widely used in flat panel displays and surface light sources, so it has been widely researched, developed and used. [00...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07D213/127C07D213/16C07D213/26C09K11/06H01L51/54
CPCC09K11/06C07D213/127C07D213/16C07D213/26C07F15/0046C09K2211/1007C09K2211/1029C09K2211/185H10K85/342
Inventor 曹建华
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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