Electroluminescent materials with bipolar carrier transport properties and their applications as host materials for organic electroluminescent devices

An electroluminescent material, electroluminescent device technology, applied in the direction of luminescent materials, electro-solid devices, electrical components, etc., to achieve the effect of saving preparation cost, facilitating mass production, and high-efficiency electroluminescent performance

Inactive Publication Date: 2017-07-11
陕西芊华环境科技工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the triplet energy levels of DCzDCN and SF34 are 2.71eV and 2.76eV, respectively, which are not suitable for deep blue phosphorescence and thermoluminescence.

Method used

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  • Electroluminescent materials with bipolar carrier transport properties and their applications as host materials for organic electroluminescent devices
  • Electroluminescent materials with bipolar carrier transport properties and their applications as host materials for organic electroluminescent devices
  • Electroluminescent materials with bipolar carrier transport properties and their applications as host materials for organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]Preparation of electroluminescent materials with the following structural formula

[0033]

[0034] Add 0.30g of 4-bromophenyl-N-benzimidazole, 0.65g of 3,5-dicarbazolyl-1-boronic acid and 0.03g of tetrakis(triphenylphosphine)palladium(0) into a 100mL flask, followed by Inject 40mL of 1,4-dioxane and 2.7mL of 1mol / L sodium carbonate aqueous solution, reflux for 48 hours under the protection of nitrogen, after cooling to room temperature, add distilled water, sequentially extract with chloroform, dry over anhydrous magnesium sulfate, filter, Spin-dried, the obtained crude product was subjected to column chromatography (a mixture of ethyl acetate and petroleum ether with a volume ratio of 2:1 was used as the eluent) and spin-dried to obtain a white powdery electroluminescent material. Its chemical name is It is 4'-N-benzimidazolyl-3,5-(9H)dicarbazolylbiphenyl (abbreviated as Host1), the yield rate is 63%, the triplet state energy level is 2.71eV, and the structural char...

Embodiment 2

[0036] Preparation of electroluminescent materials with the following structural formula

[0037]

[0038] In Example 1, the 4-bromophenyl-N-benzimidazole used will be replaced with an equal mass of 2-bromophenyl-N-benzimidazole, and the other steps are the same as in Example 1 to obtain a white powdery electrode Luminescent material, its chemical name is 2'-N-benzimidazolyl-3,5-(9H) dicarbazolyl biphenyl (referred to as Host2), the yield is 60%, and the triplet energy level is 3.00eV , the structural representation data is: 1 H NMR (600MHz, CDCl 3 )δ (ppm): 8.14 (s, 1H), 8.08 (d, J = 7.7Hz, 4H), 8.01 (d, J = 8.1Hz, 1H), 7.76 (dd, J = 7.7, 1.4Hz, 1H) , 7.68-7.60(m, 4H), 7.55(d, J=7.6Hz, 1H), 7.47(d, J=1.9Hz, 2H), 7.41-7.36(m, 5H), 7.30-7.27(m, 5H ), 7.10 (d, J=8.2Hz, 4H); MS (ESI) m / z: 601 [M+H] + .

Embodiment 3

[0040] Preparation of electroluminescent materials with the following structural formula

[0041]

[0042] In Example 1, the 4-bromophenyl-N-benzimidazole used will be replaced by an equal mass of 3-bromophenyl-N-benzimidazole, and the other steps are the same as in Example 1 to obtain a white powdery electrode Luminescent material, its chemical name is 3'-N-benzimidazolyl-3,5-(9H) dicarbazolylbiphenyl (referred to as Host3), the yield is 62%, and the triplet energy level is 2.80eV , the structural representation data is: 1 H NMR (600MHz, CDCl 3 )δ(ppm): 8.35(s, 1H), 8.17(d, J=7.7Hz, 4H), 7.97-7.83(m, 6H), 7.74(t, J=7.8Hz, 1H), 7.60(d, J=8.2Hz, 6H), 7.46(t, J=7.6Hz, 4H), 7.36(dt, J=31.1, 7.4Hz, 6H); MS(ESI) m / z: 601[M+H] + .

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Abstract

The invention discloses an electroluminescent material with bipolar carrier transport performance and its application as a main body material of an organic electroluminescent device. The luminescent material is 3,5-dicarbazole-1 with hole transport performance The compound of the benzene unit and the benzimidazole derivative unit with electron transport performance is simple, and the present invention uses it as the main material of the light-emitting layer to make an electroluminescent device, blue light, red light, yellow light, green light and White light emitting devices have high current efficiency, power efficiency, external quantum efficiency, and spectral color rendering index, and have good stability in a large voltage range, and have broad application prospects in the fields of full-color display and solid-state lighting. It can be widely used in the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, in particular to a compound containing 3,5-N,N'-dicarbazole-benzene units and benzimidazole derivative units and its use as the main material of the light-emitting layer of an organic electroluminescent device application. Background technique [0002] Since C.W.Tang et al first reported in 1987 that 8-hydroxyquinoline aluminum (Alq 3 ) as the double-layer device structure of the light-emitting material, people have generated strong interest in organic electroluminescence and paid great attention to it. Organic electroluminescence can be divided into fluorescence and phosphorescence. According to the spin quantum statistical theory, the formation probability ratio of singlet excitons and triplet excitons is 1:3, so the radiative transition from singlet excitons The fluorescence only accounts for a quarter of the total input energy, while the electroluminescence of phosphorescent m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D403/14H01L51/54
CPCC09K11/06C07D403/14C09K2211/1044C09K2211/1011C09K2211/1029H10K85/6572H10K50/11Y02B20/00
Inventor 王强赵亚丽武超仇盼龙马武军王彬艳
Owner 陕西芊华环境科技工程有限公司
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