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A high refractive index benzoheterocyclic compound, organic light-emitting device and display device

A high-refractive-index, compound technology, applied in the field of organic electroluminescent materials, can solve the problems of poor coverage tightness, unfavorable light extraction, weak luminous efficiency, etc., to improve external quantum efficiency, alleviate angle dependence, and improve luminous efficiency. Effect

Active Publication Date: 2022-07-22
SHANGHAI TIANMA AM OLED
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its refractive index is generally below 1.9, which cannot meet the requirements of high refractive index; even if the refractive index meets the requirements, it has strong absorption or large extinction coefficient in the visible light region; amine derivatives with specific structures with high refractive index Although the use of materials and materials that meet specific parameters improves the light extraction efficiency, it does not solve the problems of luminous efficiency and chromaticity at the same time (especially in blue light-emitting elements)
In addition, in order to increase the molecular density and achieve high thermal stability of the existing CPL materials, the molecular structure is designed to be large and loose, and the molecules cannot be tightly packed, resulting in too many holes in the molecular gel during evaporation. , the covering tightness is poor; moreover, it is simply designed as an electronic covering layer material to achieve the effect of electron transmission and light extraction at the same time. Although it saves the preparation cost of the device to a certain extent and can achieve multiple effects, it is not conducive to light Taking it out only slightly improved the luminous efficiency, and the chromaticity did not solve the problem.

Method used

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  • A high refractive index benzoheterocyclic compound, organic light-emitting device and display device
  • A high refractive index benzoheterocyclic compound, organic light-emitting device and display device
  • A high refractive index benzoheterocyclic compound, organic light-emitting device and display device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] The synthetic route is as follows:

[0071]

[0072] The specific preparation method specifically includes the following steps:

[0073] (1) P2-1 (3.0 mmol), 2-naphthoic acid (7.0 mmol) and polyphosphate (16 g) were mixed, put into a 100 mL flask, and reacted at 150° C. for 24 hours. Cool to room temperature, then slowly add 1M sodium hydroxide solution to the solution to neutralize, then filter out the solid particles, wash the dark solid with water, ethanol and ethyl acetate, and then air dry to obtain crude product P2-2.

[0074] Test the structure of the target product P2-2: MALDI-TOF MS (m / z): C 28 H 14 Br 2 N 2 O 2 , the calculated value is 567.9, and the test value is 568.0.

[0075] (2) In a 100 mL round-bottomed flask, mix the intermediate product P2-2 (15 mmol) and potassium acetate (30 mmol) with dry 1,4-dioxane (60 mL), Pd (PPh) 3 ) 2 Cl 2 (0.50 mmol) and pinacol diboronate (35 mmol) were mixed and stirred at 90°C for 48 hours under nitrogen atmo...

Embodiment 2

[0081] The synthetic route is as follows:

[0082]

[0083] The specific preparation method specifically includes the following steps:

[0084] (1) P20-1 (3.0 mmol), P20-2 (7.0 mmol) and polyphosphate (16 g) were mixed, put into a 100 mL flask, and reacted at 150° C. for 24 hours. Cool to room temperature, then slowly add 1M sodium hydroxide solution to the solution for neutralization, filter out the solid particles, wash the dark solid with water, ethanol and ethyl acetate, and then air dry to obtain the crude product P20-3.

[0085] Test the structure of the target product P20-3: MALDI-TOF MS (m / z): C by matrix-assisted laser desorption ionization time-of-flight mass spectrometry 26 H 13 BrN 4 O 2 , the calculated value is 492.0, and the test value is 492.1.

[0086] (2) In a 100 mL round-bottomed flask, mix the intermediate product P20-3 (15 mmol) and potassium acetate (20 mmol) with dry 1,4-dioxane (60 mL), Pd (PPh) 3 ) 2 Cl 2 (0.50 mmol) and pinacol diboronate ...

Embodiment 3

[0092] The synthetic route is as follows:

[0093]

[0094] (1) In a 100 mL round-bottomed flask, combine P24-1 (10 mmol), P24-2 (12 mmol) and Pd (PPh 3 ) 4 (0.5 mmol) was added to a mixture of toluene (30 mL) / ethanol (20 mL) and potassium carbonate (25 mmol) aqueous solution (10 mL), and the reaction was refluxed under nitrogen atmosphere for 12 h. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude was purified by silica gel column chromatography. The product gave the final product P24.

[0095] Test the structure of the target product P24: MALDI-TOF MS (m / z): C by matrix-assisted laser desorption ionization time-of-flight mass spectrometry 40 H 22 N 4 O 2 , the calculated value is 590.2, and the test value is 590.1.

[0096] Elemental analysis: t...

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Abstract

The invention discloses a high-refractive-index benzoheterocyclic compound represented by formula (I), wherein X 1 with X 2 Each is independently selected from O or S; R 1 ~R 4 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heterocyclic group; and the R 1 ~R 4 At least one of which is not hydrogen or deuterium. Compared with the prior art, the benzoheterocyclic compound provided by the present invention has a higher refractive index, which can effectively improve the external quantum efficiency of the organic light-emitting device as an organic cover layer material, and alleviate the angular dependence of its light emission; Moreover, the benzoheterocyclic compound has a small extinction coefficient in the blue light region, and hardly absorbs blue light, which is beneficial to improve the luminous efficiency; in addition, the benzoheterocyclic compound has a deep LUMO energy level, which can be used as a Electron transport material, which is beneficial to light extraction of bottom-emitting devices.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a high refractive index benzoheterocyclic compound, an organic light-emitting device and a display device. Background technique [0002] Organic electroluminescent devices (OLEDs) have come a long way after decades of development. Although the internal quantum efficiency of OLED is close to 100%, the external quantum efficiency is only about 20%. Most of the light emitted by OLEDs is confined inside the light-emitting device due to factors such as substrate mode loss, surface plasmon loss, and waveguide effects, resulting in a large amount of energy loss. [0003] In top-emitting devices, a layer of organic capping layer (Capping Layer, CPL) can be evaporated on the semi-transparent metal electrode Al to adjust the optical interference distance, suppress the reflection of external light, and suppress the extinction caused by the movement of surface plasmons, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04C07D513/04C07D519/00H01L51/54H01L51/50H01L51/52
CPCC07D498/04C07D513/04C07D519/00H10K85/622H10K85/615H10K85/624H10K85/626H10K85/653H10K85/654H10K85/655H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/16H10K50/858
Inventor 代文朋高威张磊冉佺翟露
Owner SHANGHAI TIANMA AM OLED
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