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Organic compound and organic electroluminescent device

A technology of organic compounds and substituents, applied in the field of organic electroluminescent devices, can solve problems such as carrier imbalance, reduced efficiency of organic electroluminescent devices, energy loss, etc.

Active Publication Date: 2021-07-23
BEIJING GREEN GUARDEE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Electrons and holes transition from the ground state to the excited state to form excitons, and the process of excitons transitioning from the excited state back to the ground state is a luminescent process. The triplet excitons in fluorescent materials are spin-forbidden, and only the singlet excitons transition back to the ground state. Complete luminescence, this process is called electroluminescence, and the internal quantum efficiency is theoretically 25%. Heavy metal phosphorescent materials use the spin-orbit coupling effect to make the radiative transition from the excited triplet state to the ground state, which is originally spin-forbidden, become localized. Allowed, singlet and triplet excitons can be captured at the same time to complete light emission. This process is called electrophosphorescence, and the internal quantum efficiency can theoretically reach 100%, thereby improving the efficiency of organic electroluminescent devices, but the triplet excitons During the transfer process, triplet-triplet annihilation (TTA) will occur, resulting in energy loss, which will reduce the efficiency of organic electroluminescent devices. Therefore, it is necessary to dope heavy metal phosphorescent materials into suitable host materials to make heavy metal phosphorescent Dispersion of material onto the host reduces TTA and improves device efficiency
[0004] Due to the imbalance of carriers, traditional host materials tend to form a narrow charge recombination region at the interface between the light-emitting layer and the hole transport layer or electron transport layer, resulting in severe roll-off at high brightness. Therefore, it is necessary to develop a new type of host Material

Method used

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  • Organic compound and organic electroluminescent device
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  • Organic compound and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0146]

[0147] Synthesis of Intermediate 3-1: In a 500ml three-neck flask, under nitrogen protection, sequentially add Intermediate M1 (50mmol, 14.8g), biborpinacol ester (60mmol, 15.3g), potassium acetate (0.13mol, 12.8 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.5mmol, 0.37g) and 1,4-dioxane solvent (160ml), heating and stirring, heating After 8 hours of reflux reaction, the reaction of the raw materials was detected by HPLC. After the reaction solution was lowered to room temperature, the reaction solution was spin-dried under reduced pressure to obtain a crude product. The crude product was dissolved in chlorobenzene solvent, heated and stirred, heated to reflux, and heated through a silica gel column for For decolorization, the filtrate was spin-dried under reduced pressure until there was a small amount of solvent, then 200 ml of ethanol was added to make a slurry, and recrystallized with toluene / ethanol to obtain a white solid (yield: 88%).

[...

preparation example 2

[0153]

[0154] Synthesis of Intermediate 11-1: The synthesis method was the same as that of Intermediate 3-1 to obtain a white solid (yield: 86%).

[0155] Synthesis of Intermediate 11-2: The synthesis method was the same as that of Intermediate 3-2 to obtain a white solid (yield: 70%).

[0156] Synthesis of Intermediate 11-3: The synthesis method was the same as that of Intermediate 3-3 to obtain a white solid (yield: 93%).

[0157] Synthesis of compound 11: the synthesis method was the same as that of compound 3 to obtain a white solid (yield: 65%).

[0158] Mass spectrum: C50H31N5O, theoretical value: 717.25, measured value: 717.2. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.10~7.17 (2H, m), 7.33~7.38 (1H, m), 7.42~7.49 (10H , m), 7.50~7.52(1H, m), 7.53~7.61(4H, m), 7.63~7.68(2H, m), 7.80~7.85(1H, m), 8.12~8.16(1H, m), 8.22 ~8.26 (3H, m), 8.28 ~ 8.35 (4H, m), 8.38 ~ 8.40 (1H, m), 8.53 ~ 8.55 (1H, m).

preparation example 3

[0160]

[0161] Synthesis of Intermediate 18-1: The synthesis method was the same as that of Intermediate 3-1 to obtain a white solid (yield: 83%).

[0162] Synthesis of Intermediate 18-2: The synthesis method was the same as that of Intermediate 3-2 to obtain a white solid (yield: 72%).

[0163] Synthesis of Intermediate 18-3: The synthesis method was the same as that of Intermediate 3-3 to obtain a white solid (yield: 89%).

[0164] Synthesis of Compound 18: The synthesis method was the same as that of Compound 3 to obtain a white solid (yield: 66%).

[0165]Mass spectrum: C50H31N5O, theoretical value: 717.25, measured value: 717.2. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.16~7.21 (2H, m), 7.38~7.44 (1H, m), 7.48~7.53 (11H , m), 7.55~7.61(5H, m), 7.61~7.63(1H, m), 7.69~7.73(1H, d), 7.85~7.89(1H, m), 8.17~8.21(1H, m), 8.27 ~8.31 (2H, m), 8.34~8.39 (5H, m), 8.44~8.44 (1H, s).

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Abstract

The invention provides an organic compound as shown in a formula I. The invention also provides an application of the organic compound in an electroluminescent device. The organic compound provided by the invention not only can transmit electrons, but also can transmit holes, has a relatively high carrier transmission rate, and can balance the migration rates of the electrons and the holes, so that a relatively wide carrier recombination region is obtained, and the luminous efficiency of the device is improved.

Description

technical field [0001] The invention relates to the field of organic electroluminescent devices, in particular to an organic compound and an organic electroluminescent device. Background technique [0002] The phenomenon of organic electroluminescence was first discovered by Pope et al. in 1963. They found that the single-layer crystal of anthracene can emit weak blue light when driven by a voltage above 100V, but the driving voltage is high and the thickness of the single crystal anthracene is large. widespread attention. Until 1987, Dr. Deng Qingyun of Kodak Company reported two organic semiconductor materials based on 8-hydroxyquinoline aluminum with high fluorescence efficiency and good electron transport properties and aromatic diamine with good hole transport properties. A sandwich-type OLED device was prepared, and the external quantum efficiency reached 1% when the driving voltage was less than 10V, which made organic electroluminescent materials and devices practic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D495/04C09K11/06H01L51/50H01L51/54
CPCC07D491/048C07D495/04C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1059C09K2211/1044H10K85/654H10K85/6572H10K85/657H10K50/18H10K50/16H10K50/11
Inventor 吕瑶冯美娟
Owner BEIJING GREEN GUARDEE TECH
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