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A light-emitting device based on 1,ω-bis(3,6-diarylcarbazolyl)-alkane

A diarylcarbazolyl, light-emitting device technology, applied in the direction of light-emitting materials, electric solid devices, semiconductor devices, etc., can solve the problem of reducing the external quantum efficiency to only

Inactive Publication Date: 2020-07-07
SHENZHEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the triplet excited state energy of CBP is only 2.56eV. If it is doped with a blue phosphorescent material with a high triplet excited state energy (>2.65eV), the phenomenon of returning energy to the main luminescent material will occur, making the external quantum of the device Efficiency drops to only (5.7±0.3)% [Appl.Phys.Lett., 79, 2082(2001)]

Method used

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  • A light-emitting device based on 1,ω-bis(3,6-diarylcarbazolyl)-alkane
  • A light-emitting device based on 1,ω-bis(3,6-diarylcarbazolyl)-alkane
  • A light-emitting device based on 1,ω-bis(3,6-diarylcarbazolyl)-alkane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Synthetic 3,6-diphenyl-9H-carbazole, the reaction formula is as follows:

[0021]

[0022] Add 3,6-dibromo-9H-carbazole (2.6g, 8mmol) in a 250mL three-necked flask, NaBPh4 (2.736g, 8mmol), tetrabutylammonium bromide (TBAB) (0.12g, 0.5mmol), chloride Palladium (0.05g, 0.25mmol), 30ml of 2M sodium carbonate solution, and 120ml of acetone were refluxed under nitrogen atmosphere for 36h. Acetone was evaporated, the aqueous layer was extracted with dichloromethane, the extract was washed with water and dried with anhydrous magnesium sulfate, and the white floc product 3,6-diphenyl-9H-carbazole (2.3 g, yields: 89%), the eluent is petroleum ether: dichloromethane = 2:1. Melting point: 177.1°C.

[0023] The test results for 3,6-diphenyl-9H-carbazole are as follows:

[0024] Hydrogen spectrum:

[0025] 1 H NMR (CDCl 3 ,400MHz),δ(ppm):8.34(s,2H),7.73(d,J=7.6Hz,4H),7.71-7.68(m,2H),7.49(t,J=7.5Hz,6H),7.36 (t, J=7.4Hz, 2H). Among them, hydrogen No. 9 is unstable and e...

Embodiment 2

[0046] (1) Synthetic 3,6-benzhydryl-9H-carbazole, reaction formula is as follows:

[0047]

[0048] Add 3,6-dibromo-9H-carbazole (2.6g, 8mmol), 4-methylphenylboronic acid (2.72g, 18mmol), tetrabutylammonium bromide (TBAB) (0.12g, 0.5 mmol), palladium chloride (0.05g, 0.25mmol), 2M sodium carbonate solution 30ml, acetone 120ml, refluxed under nitrogen atmosphere for 36h. Acetone was evaporated, the aqueous layer was extracted with dichloromethane, and the extract was washed with water and dried with anhydrous magnesium sulfate, and the white flocculent product 3,6-benzhydryl-9H-carbazole (2.3g , yields: 90%), the eluent is petroleum ether: dichloromethane = 2:1. Melting point: 204.0°C.

[0049] The test results for 3,6-benzhydryl-9H-carbazole are as follows:

[0050] Hydrogen spectrum:

[0051] 1 H NMR (CDCl 3 ,400MHz),δ(ppm):8.46(s,2H),7.82-7.76(m,6H),7.57(s,2H),7.43(d,J=7.9Hz,4H),2.58(s,6H) .

[0052] Carbon spectrum:

[0053] 13 C NMR (CDCl 3 , 400MHz), δ(ppm):...

Embodiment 3

[0072] (I) Synthesis of 3,6-diα-naphthyl-9H-carbazole

[0073]

[0074] Add 3,6-dibromo-9H-carbazole (2.6g, 8mmol), α-naphthyl boronic acid (3.096g, 18mmol), tetrabutylammonium bromide (TBAB) (0.12g, 0.5mmol) in a 250mL three-necked flask ), palladium chloride (0.05g, 0.25mmol), 2M sodium carbonate solution 30ml, acetone 120ml, refluxed under nitrogen atmosphere for 36h. Acetone was evaporated, the aqueous layer was extracted with dichloromethane, and the extract was washed with water and dried with anhydrous magnesium sulfate, and the white floc product 3,6-diα-naphthyl-9H-carbazole (3.0g , yields: 90%), the eluent is petroleum ether: dichloromethane = 2:1. Melting point: 139.4°C.

[0075] The test results for 3,6-diα-naphthyl-9H-carbazole are as follows:

[0076] Hydrogen spectrum:

[0077] 1 H NMR (CDCl 3 ,400MHz),δ(ppm):8.23(s,1H),8.19(s,2H),7.99(d,J=8.5Hz,2H),7.91(d,J=8.0Hz,2H),7.87-7.85 (m, 2H), 7.58 (s, 4H), 7.56-7.48 (m, 4H), 7.48-7.46 (m, 2H), 7.43-7.39 (m, ...

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Abstract

The invention relates to a light-emitting device based on 1,ω-bis(3,6-diarylcarbazolyl)-alkane, which comprises a cathode, an electron injection layer, an electron transport layer, and a hole blocking layer arranged in sequence , a light-emitting layer, and an anode, wherein the material of the light-emitting layer includes 1, ω-bis(3,6-diarylcarbazolyl)-alkane, and the 1,ω-bis(3,6-diarylcarbazolyl) -Alkanes have the following structure: wherein, Ar is phenyl, p-methylphenyl, α-naphthyl, or β-naphthyl; R is ethyl, propyl, butyl, or benzyl.

Description

technical field [0001] The invention relates to a light-emitting device based on 1,ω-bis(3,6-diarylcarbazolyl)-alkane. Background technique [0002] In 1987, Eastern Kodak Company C.W.Tang et al. invented a sandwich structure device in the literature (C.W.Tang, S.A.anslykeAppl.Phys.Lett.1987, 51, 913) and patent US4356429, which has high fluorescence efficiency, electron transport characteristics and energy Use vacuum-coated 8-hydroxyquinoline aluminum (Alq3) and aromatic diamine (diamine) with hole transport properties to make a uniform and dense high-quality film, and make an organic EL device to make organic electroluminescent materials Research work with devices has entered a practical era. In 1990, Friend et al. from the Cavendish Laboratory of the University of Cambridge reported the phenomenon of polymer electroluminescence under low voltage, which opened up a new field of polymer flat panel display research; in 1992, Heeger et al. from Pennsylvania State University ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/54H01L51/56C09K11/06C07D209/86
CPCC09K11/06C07D209/86C09K2211/1007C09K2211/1011C09K2211/1029H10K71/12H10K85/624
Inventor 牛芳芳曾鹏举连加荣李晓聪李佳
Owner SHENZHEN UNIV