Triarylamine compound and organic light-emitting device thereof

A technology of triarylamines and compounds, applied in the field of organic photoelectric materials, can solve the problems of reduced luminous efficiency of devices, failure to meet high refractive index, and decreased light extraction efficiency, and achieve the effects of improving light extraction efficiency, increasing luminous efficiency, and reducing total reflection

Active Publication Date: 2020-11-17
CHANGCHUN HYPERIONS TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, in order to improve the external quantum efficiency of the device, the main way is to form structures such as wrinkles, photonic crystals, microlens arrays, and add surface covering layers on the light-emitting surface of the substrate. The first two structures will affect the radiation spectral resolution distribution of OLEDs. The manufacturing process of the three structures is relatively complicated, but a covering layer with a high refractive index is provided on the outside of the translucent electrode with a low refractive index, which can adjust the optical interference distance, suppress the extinction caused by the movement of surface plasmons, and increase the luminous efficiency by more than 30%. especially attracted people's attention
[0004] As a covering layer for adjusting the refractive index, tris(8-hydroxyquinoline)aluminum(III)(Alq 3 ), but this material has weak absorption near the wavelength of 450nm emitted by the blue light-emitting device, so Alq 3 When applied to blue light-emitting devices, there will be problems of lower color purity and lower light extraction efficiency
The existing cladding materials can improve the light extraction efficiency to a certain extent, but the refractive index of these materials is generally low, which cannot meet the requirements of high refractive index, so that the luminous efficiency of the device is also reduced.

Method used

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  • Triarylamine compound and organic light-emitting device thereof
  • Triarylamine compound and organic light-emitting device thereof
  • Triarylamine compound and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] [Example 1] Synthesis of Compound 1

[0106]

[0107] Synthesis of intermediate 1-c: Under nitrogen protection, in a 1L three-necked flask, add raw material 1-a (0.05mol, 12.55g), toluene 600ml, add raw material 1-b (0.1mol, 23.90g), potassium carbonate ( 0.12mol, 16.59g), tetrakistriphenylphosphine palladium (0.001mol, 1.16g). Nitrogen replacement was carried out three times, and the reaction was carried out at reflux temperature for 4 h. After the reaction is completed, through CH 2 Cl 2 Extraction, MgSO 4Dry and concentrate in vacuo. The residue was subjected to silica gel column chromatography (eluent: cyclohexane: ethyl acetate = 10:1) and recrystallization (solvent: toluene) to obtain intermediate 1-c (solid purity ≧99.6% by HPLC, 17.26g, Yield 72%).

[0108] Synthesis of compound 1: Under nitrogen protection, intermediate 1-c (0.03mol, 14.39g), raw material 1-f (0.06mol, 9.42g), toluene 300ml, Pd 2 (dba) 3 (0.0006mol, 0.55g), P(t-Bu) 3 (0.005mol, 1.01...

Embodiment 2

[0110] [Example 2] Synthesis of compound 29

[0111]

[0112] Synthesis of Compound 29: The raw material 1-f in Example 1 was replaced with an equimolar raw material 29-f, and compound 29 was obtained according to the synthetic method of compound 1 (solid purity > 99.6% detected by HPLC, 19.48g, yield 75% ).

[0113] Mass Spectrum m / z: 866.2756 (Theoretical: 865.2689). Theoretical element content (%)C 58 h 35 N 5 o 4 : C, 80.45; H, 4.07; N, 8.09; O, 7.39. Measured element content (%): C, 80.48; H, 4.06; N, 8.07, O, 7.39. 1 H NMR (600MHz, CDCl 3 )(δ,ppm):8.15-8.09(m,8H),7.76(t,1H),7.73-7.70(m,4H),7.69-7.66(m,4H),7.63-7.59(m,4H), 7.38-7.32 (m, 8H), 7.31 (d, 2H), 7.29-7.26 (m, 4H). The above results confirmed that the obtained product was the target product.

Embodiment 3

[0114] [Example 3] Synthesis of compound 32

[0115]

[0116] Synthesis of Compound 32: The raw material 1-f in Example 1 was replaced by equimolar raw material 32-f, and compound 32 was obtained according to the synthetic method of compound 1 (solid purity > 99.8% detected by HPLC, 19.18g, yield 74% ).

[0117] Mass Spectrum m / z: 865.3579 (Theoretical: 863.3512). Theoretical element content (%)C 62 h 45 N 3 o 2 : C, 86.18; H, 5.25; N, 4.86; O, 3.70. Measured element content (%): C, 86.11; H, 5.27; N, 4.88, O, 3.73. 1 H NMR (600MHz, CDCl 3 )(δ,ppm):8.14-8.08(m,4H),7.83(td,2H),7.80-7.74(m,7H),7.66-7.59(m,6H),7.54-7.52(m,3H), 7.50 (d, 1H), 7.46-7.40 (m, 5H), 7.38 (tt, 5H), 1.77-1.68 (m, 12H). The above results confirmed that the obtained product was the target product.

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Abstract

The invention provides a triarylamine compound and an organic light-emitting device thereof, and belongs to the technical field of organic photoelectric materials. The triarylamine compound is a compound formed by bonding triarylamine, benzoxazole and / or benzothiazole and / or benzimidazole and / or benzotriazole on a benzene ring serving as a mother nucleus, has a high refractive index, can reduce total reflection of light in a device, greatly improves the light extraction efficiency of the device, and has a wide application prospect. The triarylamine compound has strong rigidity, good thermal stability and good film-forming property, can effectively isolate water and oxygen outside the device and effectively prolong the service life of the device, and is a covering layer material with excellent performance. The triarylamine compound provided by the invention is used as a covering layer to be applied to an organic light-emitting device, and the organic light-emitting device has good light-emitting efficiency and long service life.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a triarylamine compound and an organic light-emitting device thereof. Background technique [0002] Organic Light Emitting Display (OLED) is a new type of flat-panel display. Compared with Liquid Crystal Display (LCD), it has the advantages of thinness, lightness, wide viewing angle, active light emission, fast response speed, and low energy consumption. , low driving voltage, wide operating temperature range, high luminous efficiency and flexible display. After decades of development, OLED has made great progress. Although the internal quantum efficiency of the current device is close to 100%, the external quantum efficiency is only about 20%. Most of the light is confined inside the light-emitting device due to factors such as substrate mode loss, surface plasmon loss, and waveguide effect, resulting in a large amount of energy loss. According to the l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57C07D413/14C07D277/66C07D417/14C07D235/18C07D403/14C07D405/14C07D409/14C07D401/14C07D249/20C07D263/56C07D277/62C09K11/06H01L51/50H01L51/54
CPCC07D263/57C07D413/14C07D277/66C07D417/14C07D235/18C07D403/14C07D405/14C07D409/14C07D401/14C07D249/20C07D263/56C07D277/62C09K11/06C09K2211/1029C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1059C09K2211/1092C09K2211/1088H10K85/636H10K85/633H10K85/631H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/171H10K50/18H10K50/16H10K50/15H10K50/17H10K50/11
Inventor 孙月周雯庭韩春雪王小会
Owner CHANGCHUN HYPERIONS TECH CO LTD
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