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Light take-out layer material and application thereof

A light extraction layer, unsubstituted technology, applied in luminescent materials, electrical components, circuits, etc., can solve problems such as complex manufacturing processes

Active Publication Date: 2019-01-01
湖北尚赛光电材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure has a complex manufacturing process, and the surface of the electrode is covered with a high-refraction and low-absorption light extraction layer. The process is simple, and it can use wide-angle interference and thin-film interference. The interaction between them reduces the total reflection effect in OLED devices and increases the proportion of light coupled to the external space in front of the device, which is of particular concern

Method used

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  • Light take-out layer material and application thereof
  • Light take-out layer material and application thereof
  • Light take-out layer material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: Compound 6 can be synthesized by the following method:

[0043]

[0044] (1) In a 500mL three-necked flask, add anthracen-1-ylboronic acid (13.32g, 60mmol), 4-bromophenylboronic acid (12.05g, 60mmol), potassium carbonate (16.58g, 120mmol), toluene (150mL), water (75mL), ethanol (75mL), under the protection of nitrogen, continue to add tetrakis(triphenylphosphine)palladium (0.14g, 0.12mmol), heat up to 75°C, react for 8h, HPLC monitors the completion of the reaction, and cool down to stop the reaction. Filtrate, concentrate the organic layer, mix with the filter residue and beat once with ethanol:ethyl acetate at a volume ratio of 10:1 to obtain 15.03 g of 3-(anthracen-1-yl)phenylboronic acid with a yield of 84%;

[0045] (2) In a 500mL three-necked flask, add 3-(anthracene-1-yl)phenylboronic acid (8.94g, 30mmol), 2,5-dibromo-1,3,4-thiadiazole (8.78g, 36mmol) , potassium carbonate (8.29g, 60mmol), toluene (100mL), water (50mL), ethanol (50mL), under nit...

Embodiment 2

[0048] Embodiment 2: Compound 19 can be synthesized by the following method:

[0049]

[0050] (1) Replace anthracene-1-ylboronic acid (13.32g, 60mmol) in Example 1(1) with 3-bromo-N, N-diphenylaniline (17.35g, 60mmol), 4-bromophenylboronic acid (12.05g, 60mmol) was replaced by 3-bromophenylboronic acid (12.05g, 60mmol), and the other steps were the same as in Example 1 (1), to obtain (3'-diphenylamino-[1,1'-linked Benzene]-3-yl)boronic acid 17.53g, yield 80%;

[0051] (2) Replace 3-(anthracene-1-yl)phenylboronic acid (8.94g, 30mmol) in Example 1(2) with (3'-diphenylamine-[1,1'-biphenyl]- 3-yl)boronic acid (10.96g, 30mmol), other steps are the same as in Example 1(2), to obtain 3'-(5-bromo-1,3,4-thiadiazol-2-yl)-N, N-diphenyl-[1,1'-biphenyl]-3-amine 10.75g, yield 74%;

[0052] (3) Replace 2-(3-(anthracene-1-yl)phenyl)-5-bromo-1,3,4-thiadiazole (6.26g, 15mmol) in Example 1(3) with 3 '-(5-bromo-1,3,4-thiadiazol-2-yl)-N,N-diphenyl-[1,1'-biphenyl]-3-amine (7.27g, 15mmol), ...

Embodiment 3

[0054] Embodiment 3: Compound 32 can be synthesized by the following method:

[0055]

[0056] (1) Anthracene-1-ylboronic acid (13.32g, 60mmol) in Example 1(1) is replaced by phenanthrene-4-ylboronic acid (13.32g, 60mmol), and other steps are the same as in Example 1(1), namely 14.67 g of (4-(phenanthren-4-yl)phenyl)boronic acid can be obtained with a yield of 82%;

[0057] (2) In a 250mL three-necked flask, add 2,5-dibromo-1,3,4-thiadiazole (3.66g, 15mmol), (4-(phenanthrene-4-yl)phenyl)boronic acid (10.73g , 36mmol), potassium carbonate (4.15g, 30mmol), toluene (50mL), water (25mL), ethanol (25mL), under nitrogen protection, continue to add tetrakis (triphenylphosphine) palladium (0.04g, 0.03mmol), The temperature was raised to 100° C., and the reaction was carried out for 18 hours. The completion of the reaction was monitored by HPLC, and the reaction was stopped when the temperature was lowered to room temperature. Extracted with dichloromethane, separated, concentrate...

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Abstract

The invention takes symmetrical 1,3,4-thia / oxadiazole as a core group, and a rigid group with relatively great electronic cloud density is bridged on sites 2,5, so that a compound with a high refractive index is formed. The compound is taken as the light take-out layer material to cover an apparatus on a cathode to modify, so that loss, caused by total reflection and light wave guide effect and the like, on the inner part of the apparatus, of light is further improved, and therefore, reduction, caused by heat accumulation, of the apparatus service life and stability is avoided, and light take-out efficiency is improved.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and in particular relates to a material based on a light extraction layer and its application. Background technique [0002] Organic light-emitting diode (OLED) is an all-solid-state light-emitting device, which has the advantages of thinness, high efficiency, low power consumption, flexibility, and simple manufacturing process. It has been the first to be commercialized in the field of mobile phones and televisions. At the same time, OLED began to gradually penetrate into fields such as automobiles, virtual reality and health lighting, demonstrating its irreplaceable excellent characteristics. [0003] In the past research, people paid more attention to the improvement of internal quantum efficiency (IQE), that is, the conversion of charge-hole injection to photons, so the development of functional materials and device structure design have always been the focus of re...

Claims

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Application Information

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IPC IPC(8): C07D285/12C07D417/10C07D417/14C07D271/107C07D413/10C07D413/14C07D417/04C07D413/04C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D271/107C07D285/12C07D413/04C07D413/10C07D413/14C07D417/04C07D417/10C07D417/14C09K2211/1014C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1033C09K2211/1037C09K2211/1048C09K2211/1051C09K2211/1044C09K2211/1088C09K2211/1092H10K85/624H10K85/656H10K85/622H10K85/615H10K85/6565H10K85/631H10K85/633H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 穆广园庄少卿任春婷
Owner 湖北尚赛光电材料有限公司
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