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Boron-containing organic compound and application thereof in organic electroluminescent device

A technology of organic compounds and boron compounds, applied in the field of semiconductors, can solve problems such as efficiency roll-off, low S1 state radiation transition rate, difficult exciton utilization rate and high fluorescence radiation efficiency

Inactive Publication Date: 2020-07-07
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) The T1 and S1 states of the designed molecule have strong CT characteristics and a very small S1-T1 state energy gap, although a high T1→S1 state exciton conversion rate can be achieved through the TADF process, but at the same time lead to low S1 state radiation Transition rate, therefore, it is difficult to combine (or achieve simultaneously) high exciton utilization efficiency and high fluorescence radiation efficiency;
[0006] (2) Even if doped devices have been used to alleviate the T-exciton concentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • Boron-containing organic compound and application thereof in organic electroluminescent device
  • Boron-containing organic compound and application thereof in organic electroluminescent device
  • Boron-containing organic compound and application thereof in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1: the synthesis of intermediate G:

[0075] Take the synthesis of intermediate G1 as an example:

[0076]

[0077] In a 250mL three-neck flask, under an atmosphere of nitrogen gas, add 0.012mol of raw material A-1, 0.012mol of raw material B-1, and 0.01mol of raw material C-1, dissolve with a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03 mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate G-1 with a purity of 95.9% and a yield of 87.3%. Elemental analysis structure (molecular formula C 56 h 37 B 2 ClN 2 ): theoretical value C, 84.61; H, 4.69; B, 2.72; Cl, ​​4.46; N, 3.52; test value C, 84.61; ESI-MS (m / z) (M+): theoretical value 794.28, found value 794.13.

[0078] ...

Embodiment 2

[0082] Embodiment 2: the synthesis of compound H2:

[0083]

[0084] (1) Weigh 0.04mol raw material D-1 and 0.025mol raw material E-1, cool down to -78°C; under inert atmosphere, add 0.02mol BCl 3 , heated to 100° C. and refluxed for 48 hours, the reaction was complete, and passed through a silica gel column to obtain intermediate J-1; the HPLC purity was 98.6%, and the yield was 87.2%.

[0085] Elemental analysis structure (molecular formula C 20 h 26 BBr): theoretical value C, 67.26; H, 7.34; B, 3.03; Br, 22.37; found value C, 67.25; H, 7.34; B, 3.03; Br, 22.38. ESI-MS(m / z)(M + ): The theoretical value is 356.13, and the measured value is 356.23.

[0086] (2) In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol of intermediate J-1, 0.015mol of raw material F-1, dissolve in a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03mol of Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4...

Embodiment 3

[0089] Embodiment 3: the synthesis of compound H11:

[0090]

[0091] Take 0.1mol of intermediate G-1, add 0.12mol of tert-butyllithium, 120ml of tert-butylbenzene, keep warm at 60°C for 2 hours, cool down to room temperature, add dropwise 0.12mol of BBr 3 After fully reacting for half an hour, water was added to precipitate a solid, which was washed with n-hexane in sequence and recrystallized with ethanol to obtain compound H11. HPLC purity 97.3%, yield 82.1%.

[0092] Elemental analysis structure (molecular formula C 56 h 35 B 3 N 2 ): theoretical value C, 87.54; H, 4.59; B, 4.22; N, 3.65; test value C, 87.54; H, 4.58; B, 4.22; N, 3.66. ESI-MS(m / z)(M + ): The theoretical value is 768.31, and the measured value is 768.28.

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Abstract

The invention relates to a boron-containing organic compound and application of the boron-containing organic compound to an OLED device. The structure of the compound is shown as a general formula (1), in which the molecules of the boron-containing organic compound are of a large rigid structure as a whole, wherein the planarity of the material is reduced through introduction of substituent groups, so that the steric hindrance of the material is increased, the material is not prone to rotation, the three-dimensional space structure is more stable, and therefore the boron-containing organic compound has the high glass transition temperature and the high molecular thermal stability; in addition, HOMO and LUMO distribution positions of the boron-containing organic compound are separated fromeach other, so that the boron-containing organic compound has appropriate HOMO and LUMO energy levels; therefore, after the compound is applied to the OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a boron-containing organic compound and its application in organic electroluminescent devices. Background technique [0002] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, and the positive and negative charges in the organic layer functional material film are acted on by the electric field, the positive and negative charges are further recombined in the light-emitting layer, that is, OLED electroluminescence is generated. [0003] The application of organic light-emitting diodes (OLEDs) in large-ar...

Claims

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Application Information

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IPC IPC(8): C07F5/02H01L51/54
CPCC07F5/027H10K85/623H10K85/622H10K85/636H10K85/657H10K85/6574H10K85/6572
Inventor 李崇庞羽佳唐丹丹王芳谢丹丹
Owner JIANGSU SUNERA TECH CO LTD
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