A kind of compound and application thereof with imidazocarbazole as acceptor

A compound, imidazolium technology, applied in the field of organic electroluminescence functional materials and devices, can solve the problems of unsatisfactory device life, inability to meet practical requirements, color purity defects of blue light materials, etc., to improve the orbital energy level and triplet state. energy, improving electron transport properties, and optimizing the effect of orbital energy levels

Active Publication Date: 2021-03-19
XIAN RUILIAN NEW MATERIAL CO LTD
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The structure of TADF materials is generally composed of electron-donating groups-electron-withdrawing groups connected by π bonds, but there are very few types of electron-withdrawing groups that can be used at present, especially there are few high-quality TADF blue light materials, and the current ones The reported blue light materials have defects in color purity, and the device life is not ideal enough to meet the practical requirements. Therefore, it is very important to design and invent new electron-withdrawing groups to develop new blue light TADF materials.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of compound and application thereof with imidazocarbazole as acceptor
  • A kind of compound and application thereof with imidazocarbazole as acceptor
  • A kind of compound and application thereof with imidazocarbazole as acceptor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: the preparation of compound 3

[0060]

[0061] Add 10g of intermediate 1, 9.1g of compound 3-1, 7.9g of potassium carbonate, 0.93g of tetrabutylammonium bromide, 200ml of toluene, 60ml of ethanol, and 40ml of water into a 500ml three-necked flask, and blow nitrogen into the system for 5 minutes to exhaust the oxygen in the system , 1.66 g of tetrakis(triphenylphosphine)palladium was added. The system was heated to 80°C for 6 hours, and then a TCL sample was taken to monitor the reaction. When the raw materials were completely reacted, the heating was stopped and the temperature was lowered to room temperature. The reaction solution was filtered and washed with water until pH = 7. The organic phase was dried over anhydrous sodium sulfate and then purified by silica gel column to remove insoluble impurities. The crude product obtained by concentrating the eluent was recrystallized from toluene to obtain 12.5 g of compound 3 with a yield of 85.3%.

[006...

Embodiment 2

[0063] Embodiment 2: the preparation of compound 13

[0064]

[0065] Add 10g of intermediate 1, 14.3g of compound 13-1, 7.9g of potassium carbonate, 0.93g of tetrabutylammonium bromide, 200ml of toluene, 60ml of ethanol, and 40ml of water into a 500ml three-necked flask, and blow nitrogen into the system for 5 minutes to exhaust the oxygen in the system , 1.66 g of tetrakis(triphenylphosphine)palladium was added. The system was heated to 80°C for 6 hours, and then a TCL sample was taken to monitor the reaction. When the raw materials were completely reacted, the heating was stopped and the temperature was lowered to room temperature. The reaction solution was filtered and washed with water until pH = 7. The organic phase was dried over anhydrous sodium sulfate and then purified by silica gel column to remove insoluble impurities. The crude product obtained by concentrating the eluent was recrystallized from toluene to obtain 14.1 g of compound 13 with a yield of 72.6%.

...

Embodiment 3

[0067] Embodiment 3: the preparation of compound 14

[0068]

[0069] Add 10g of intermediate 1, 10.4g of compound 14-1, 7.9g of potassium carbonate, 0.93g of tetrabutylammonium bromide, 200ml of toluene, 60ml of ethanol, and 40ml of water into a 500ml three-necked flask, and blow nitrogen into the system for 5 minutes to exhaust the oxygen in the system , 1.66 g of tetrakis(triphenylphosphine)palladium was added. The system was heated to 80°C for 6 hours, and then a TCL sample was taken to monitor the reaction. When the raw materials were completely reacted, the heating was stopped and the temperature was lowered to room temperature. The reaction solution was filtered and washed with water to pH = 7. The organic phase was dried over anhydrous sodium sulfate and then purified by silica gel column to remove insoluble impurities. The crude product obtained by concentrating the eluent was recrystallized from toluene to obtain 12.4 g of compound 14 with a yield of 78.2%.

[00...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
thicknessaaaaaaaaaa
thicknessaaaaaaaaaa
thicknessaaaaaaaaaa
Login to View More

Abstract

The invention discloses a compound with imidazocarbazole as an acceptor, belonging to the technical field of organic electroluminescent materials. The general structural formula of this type of compound is shown in formula (I), wherein, Ar 1 is an electron-donating group or an electron-accepting group, when Ar 1 When it is an electron-donating group, it is selected from substituted or unsubstituted carbazolyl, acridinyl, furyl, amine, 9,9-dimethyl-9H-fluorenyl, phenazinyl or phenothiazinyl ; when Ar 1 When it is an electron-accepting group, it is selected from substituted or unsubstituted triazinyl, pyrimidinyl, pyridyl, phenanthroline, sulfone, benzimidazolyl, triphenylborinyl, phenanthrenyl, di Benzophenonyl or spirobifluorenyl. The brand-new compound formed by introducing a specific group modification at a specific position in the present invention has better energy transport ability and charge transport ability, has a suitable HOMO / LUMO value and triplet energy, and can be used in organic electroluminescent devices to achieve high Brightness, low voltage, high efficiency and long service life. General structural formula is as shown in formula (I):

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent functional materials and devices, and specifically relates to a compound with imidazocarbazole as an acceptor and its application. Background technique [0002] Organic light-emitting diodes (OLED: Organic Light Emission Diodes) are self-luminous electronic components. The light-emitting mechanism is a new type of photoelectric information technology that directly converts electrical energy into light energy with the help of organic semiconductor functional materials under the action of a DC electric field. Its luminous color can be a single red, green, blue, yellow light or a combination of white light. The biggest feature of OLED light-emitting display technology is ultra-thin, fast response, ultra-lightweight, surface-emitting and flexible display. It can be used to manufacture monochrome or full-color displays. As a new light source technology, it can also be used to produce...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D487/06C07F7/08C07F5/02H01L51/54C07D519/00C09K11/06
CPCC07D487/06C07F7/0816C07F5/02C07D519/00C09K11/06C09K2211/1044C09K2211/1059C09K2211/1029C09K2211/1088C09K2211/1033H10K85/624H10K85/615H10K85/654H10K85/657H10K85/6574H10K85/40H10K85/6572
Inventor孙军张宏科刘凯鹏田密何海晓高仁孝
OwnerXIAN RUILIAN NEW MATERIAL CO LTD