Compound taking phenanthroline and derivative thereof as core compound, and OLED device manufactured by taking compound as CPL layer

An o-phenanthroline and compound technology, applied in the field of OLED devices, can solve problems such as constraints, and achieve the effects of high glass transition temperature, low absorption and high refractive index

Inactive Publication Date: 2020-03-24
YURUI SHANGHAI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, OLED has been successfully applied in the field of display, such as smart wearable mobile phones and tablets, and will further develop into the field of large-size TVs. However, the process of converting internal quantum efficiency to external quantum efficiency has a great light loss, which is only about 20%-30%. Quantum efficiency can be successfully converted into external quantum efficiency, which seriously restricts OLED. How to improve the light extraction rate of OLED has become a hot research topic in the scientific field in recent years.

Method used

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  • Compound taking phenanthroline and derivative thereof as core compound, and OLED device manufactured by taking compound as CPL layer
  • Compound taking phenanthroline and derivative thereof as core compound, and OLED device manufactured by taking compound as CPL layer
  • Compound taking phenanthroline and derivative thereof as core compound, and OLED device manufactured by taking compound as CPL layer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of compound H7

[0032]

[0033] 3,5 dibromo-1-(4-bromobiphenyl) terphenyl (0.1mol), 4-(9-phenanthroline) phenylboronic acid (0.05mol) joins in the 3L there-necked flask, adds potassium carbonate ( 0.075mol), toluene (1L), ethanol (500mL), deionized water (500mL), fully stirred, nitrogen protection, added tetrakistriphenylphosphine palladium (5mmol), slowly heated to reflux 110 ° C, kept for 24h, TLC detection The raw materials were completely reacted, cooled to room temperature, allowed to stand and separated, the organic phase was washed with saturated brine three times, dried over anhydrous sodium sulfate, concentrated to semi-dryness, added ethanol, a large amount of solids were produced, vacuum filtered, and the solids were dried in vacuum to obtain Compound H7. HPLC 99.2%, yield 78%. MS(EI) m / z: [M]+calcd for C54H34N4, 738.87; found, 738.28. Anal. Calcd for C54H34N4: C 87.78, H 4.64, N 7.58; found: C 87.75, H 4.86, N 7.39.

Embodiment 2

[0035] Synthesis of Compound H12

[0036]

[0037] Add 3,5-dibromo-1-(4-bromobiphenyl)terphenyl (0.1mol), 4-(9-(1,4diaza)phenanthrene)phenylboronic acid (0.05mol) into a 3L three-necked flask , add potassium carbonate (0.075mol), toluene (1L), ethanol (500mL), deionized water (500mL), stir well, nitrogen protection, add tetrakis triphenylphosphine palladium (5mmol), slowly heat up to reflux 110 ° C, Keep warm for 24 hours, TLC detects that the raw materials have reacted completely, cool down to room temperature, let stand to separate layers, wash the organic phase with saturated brine for 3 times, dry over anhydrous sodium sulfate, concentrate to semi-dryness, add ethanol, a large amount of solids are produced, and vacuum filter , the solid was dried in vacuo to obtain compound H12. HPLC 99.5%, yield 64%. MS(EI) m / z: [M]+calcd for C54H34N4, 738.87; found, 738.28. Anal. Calcd for C54H34N4: C 87.78, H 4.64, N 7.58; found: C 87.75, H 4.86, N7.39.

Embodiment 3

[0039] Synthesis of Compound H28

[0040]

[0041] 2,6 dibromo-4-(4-bromobiphenyl)pyridine (0.1mol), 4-(9-phenanthroline)phenylboronic acid (0.05mol) join in 3L there-necked flask, add potassium carbonate (0.075 mol), toluene (1L), ethanol (500mL), deionized water (500mL), fully stirred, under nitrogen protection, added tetrakistriphenylphosphine palladium (5mmol), slowly heated to reflux 110 ° C, kept for 24h, TLC detection of raw materials After the reaction is complete, cool down to room temperature, let stand to separate layers, wash the organic phase with saturated brine three times, dry over anhydrous sodium sulfate, concentrate to semi-dryness, add ethanol, a large amount of solid is produced, vacuum filter, and dry the solid in vacuum to obtain the compound H28. HPLC 99.5%, yield 90%. MS(EI) m / z: [M]+calcd for C53H33N5, 739.86; found, 739.27. Anal. Calcd for C53H33N5: C 86.04, H 4.50, N 9.47; found: C 86.26, H 4.36, N 9.39 。

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PUM

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Abstract

The invention discloses a compound taking phenanthroline and a derivative thereof as a core compound, and an OLED device manufactured by taking the compound as a CPL layer, wherein the structure of the organic compound is represented by the following general formula (1). According to the invention, the compound has high glass transition temperature and high molecular thermal stability, is low in absorption and high in refractive index in the field of visible light, and can effectively improve the light extraction efficiency of an OLED device after being applied to the CPL layer of the OLED device; the material provided by the invention is applied to the CPL layer in an OLED device, does not participate in electron and hole transport of the device, and has high requirements on thermal stability, film crystallinity and refractive index of the material; and the analysis results show that the high Tg temperature ensures that the material is not crystallized in a film state, the low vacuumevaporation temperature is the premise that the material can be applied to mass production, and the high refractive index is the most important factor for the application of the material in the CPL layer.

Description

technical field [0001] The invention relates to the field of OLED devices, in particular to an OLED device made of o-phenanthroline and its derivatives as core compounds and the compound as a CPL layer. Background technique [0002] The luminescence of OLED belongs to electroluminescence (eletro luminescence EL). Due to its importance in application, electroluminescence phenomenon has always been an interesting science. Organic luminescence phenomenon was first discovered by Professor Pope in 1963. At that time, he applied a bias voltage of hundreds of volts to anthracene crystals and observed luminescence, which was the earliest documented report. Due to the high voltage and poor luminous efficiency, this phenomenon has not been paid much attention. Until 1987, Dr. Deng Qingyun (ching W.Tang) and Steve of Kodak Company of the United States announced that a multi-layer OLED device was made by vacuum evaporation, but the holes and electrons were confined to the electron tran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/30C07D213/16C07D221/10C07D471/04C07D237/36C07D239/70C07D401/14C07D241/38C07D519/00C07D403/14C09K11/06H01L51/52H01L51/50H01L51/54
CPCC07C15/30C07D213/16C07D221/10C07D471/04C07D237/36C07D239/70C07D401/14C07D241/38C07D519/00C07D403/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059H10K85/626H10K85/615H10K85/654H10K85/6572H10K50/16H10K50/85H10K50/11
Inventor 赵晓宇申屠晓波华万鸣汪华月林亚飞
Owner YURUI SHANGHAI CHEM
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