Boron-containing compound and application thereof to organic light-emitting device

A boron compound, the technology of the compound, applied to the compound and its application in the organic electroluminescence device, can solve the problems of disparity and the like

Pending 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

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Boron-containing compound and application thereof to organic light-emitting device
  • Boron-containing compound and application thereof to organic light-emitting device
  • Boron-containing compound and application thereof to organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the synthesis of intermediate G:

[0061] Take the synthesis of intermediate G1 as an example:

[0062]

[0063] (1) In a 250mL three-necked flask, under a nitrogen atmosphere, add 0.01mol of raw material A-1, 0.015mol of raw material B-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 , 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 J-1 with a purity of 96.4% and a yield of 83.7%. Elemental analysis structure (molecular formula C 18 h 14 BBrClN): theoretical value C, 58.36; H, 3.81; B, 2.92; Br, 21.57; Cl, ​​9.57; N, 3.78; test value C, 58.35; ; N, 3.79. ESI-MS (m / z) (M+): The theoretical value is 369.01, and the measured value is 369.59.

[0064]...

Embodiment 2

[0069] Embodiment 2: the synthesis of compound H2:

[0070]

[0071] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate G-1, 0.012mol raw material C1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , the target product was obtained, the HPLC purity was 99.76%, and the yield was 76.1%. Elemental analysis structure (molecular formula C 52 h 34 B 2 N 4 ): theoretical value: C, 84.80; H, 4.65; B, 2.94; N, 7.61; test value C, 84.84; H, 4.63; B, 2.93; HPLC-MS: The molecular weight of the material is 736.30, and the measured molecular weight is 736.48.

Embodiment 3

[0072] Embodiment 3: the synthesis of compound H43:

[0073]

[0074] Dissolve 0.01 mol of intermediate G-2 and 0.012 mol of raw material C2 in 150 mL of toluene and ethanol (V toluene: V ethanol = 5: 1) mixed solution, add 0.0002 mol of Pd (PPh 3 ) 4 and 0.02mol Na 2 CO 3 , reacted at 110°C for 24 hours under an atmosphere of nitrogen gas, took a sample and spotted the plate, after the raw materials were completely reacted, cooled and filtered, the filtrate was rotary evaporated to remove the solvent, and the crude product was passed through a silica gel column to obtain compound H43; the elemental analysis structure ( Molecular formula C 51 h 37 B 2 N): theoretical value: C, 89.36; H, 5.44; B, 3.15; N, 2.04; test value C, 89.28; H, 3.18; B, 3.15; HPLC-MS: The molecular weight of the material is 685.31, and the measured molecular weight is 685.47.

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Abstract

The invention discloses a boron-containing compound and application thereof to an organic light-emitting device. The compound is of a boron atom-containing structure and has strong rigidity, moleculesare not easy to crystallize and aggregate, and the compound has good film-forming property; the compound disclosed by the invention has the characteristics of TADF, and the HOMO energy levels of thematerial are different due to different electron donating capacities of groups, so that the compound can be used as different functional layer materials; in addition, the compound provided by the invention has high fluorescence quantum efficiency and can effectively generate radiative transition. Therefore, after the compound disclosed by the invention is applied to an OLED device as an organic electroluminescent functional layer material, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; and meanwhile, the service life of thedevice is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a boron-containing compound and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. 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 negativ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07F5/027C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/104C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096H10K85/623H10K85/622H10K85/615H10K85/626H10K85/657H10K85/6576H10K85/6574H10K85/6572H10K50/12H10K50/11
Inventor 李崇陆颖叶中华王芳
Owner JIANGSU SUNERA TECH CO LTD
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