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Aromatic amine derivative organic electroluminescent material and device

An aryl and compound technology, applied in the field of aromatic amine derivative organic electroluminescent materials and devices thereof, can solve problems such as undisclosed and taught, undisclosed and taught aromatic amine device effects, unaware of device performance effects, etc. , to achieve the effect of high external quantum efficiency, narrow half-peak width, and good device performance

Pending Publication Date: 2021-11-23
BEIJING SUMMER SPROUT TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The specific structure disclosed is and However, the patent application did not recognize the impact of the introduction of benzocyclohydrocarbons in aromatic amines on device performance, nor did it disclose and teach that having benzocyclohydrocarbons and biaryl structures would improve device performance
[0008] A kind of pyrene compound containing acridine structure is disclosed in CN107556239A, the general formula is as follows where Ar 1 and Ar 2 Can be a heterocyclic group, the specific structure is etc., but the patent application is mainly aimed at a series of pyrene compounds with acridine-substituted aromatic amines, and does not pay attention to the improvement of device performance by benzoheterocyclic hydrocarbons, nor does it disclose and teach the introduction of aromatic amines The device effect of benzocyclic hydrocarbon or benzoheterocyclic hydrocarbon and the other aryl group in the arylamine is a biaryl group

Method used

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  • Aromatic amine derivative organic electroluminescent material and device
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  • Aromatic amine derivative organic electroluminescent material and device

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preparation example Construction

[0156] The preparation method of the compound of the present invention is not limited, and the following compounds are typically, but not limited to, exemplified. The synthetic route and preparation method are as follows:

[0157] Synthesis Example 1: Synthesis of Compound BD32

[0158] first step:

[0159]

[0160] Put LDA (100mL, 200mmol) in a 250mL three-neck flask, place it under dry ice-ethanol and stir for half an hour, add methyl isobutyrate (23mL, 200mmol), and continue stirring for half an hour. 1-Bromo-2-(bromomethyl)benzene (25 g, 100 mmol) was added and filtered through celite. After concentration, the crude product intermediate 1 was obtained, which was directly carried out to the next reaction.

[0161] Step two:

[0162]

[0163] Intermediate 1 (27g, 100mmol) and potassium hydroxide (56g, 1mol) were mixed, 100mL of water and 10mL of methanol were added, and the reaction was heated to 100°C until the reaction was detected by TLC. After cooling, after th...

Embodiment 3

[0369] In Example 3, the N-ortho position of the arylamine further introduces a neopentyl group, compared to the introduction of a methyl group in the N-ortho position of the arylamine in Example 1, the addition of the ortho substituent and the increase in the molecular volume of the ortho substituent The EQE increases gradually (9.48vs.9.11), and the half-width also narrows (28.5nm vs.29.7nm). Compared with Comparative Example 1, both EQE and half peak width were improved. The results show that based on the dual structure of arylamine with benzo five-membered ring and biaryl substituent, the introduction of substituents at the N-ortho position can further improve the blue light-emitting performance, and this effect varies with the N-ortho position Substituents increase in molecular volume.

[0370] The device data of table 4 embodiment 5 and embodiment 6

[0371] part number CIE(x,y) λmax(nm) FWHM(nm) EQE(%) Example 5 0.139,0.089 456 31.3 8.99 ...

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Abstract

The invention discloses an aromatic amine derivative organic electroluminescent material and a device. The compound is an aromatic amine substituted pyrene compound, and the pyrene compound has a substituted or unsubstituted (hetero) aryl five-membered (hetero) cyclic hydrocarbon and substituted or unsubstituted (hetero) aryl aromatic amine structure, and can be used as a luminescent material in an organic electroluminescent device. The novel compounds can provide better device performance, such as higher external quantum efficiency and narrower half-peak width.

Description

technical field [0001] The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to an aromatic amine-substituted pyrene compound and an organic electroluminescent device and compound formulation comprising the compound. Background technique [0002] Organic electronic devices include but are not limited to the following categories: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs) , organic optical detectors, organic photoreceptors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasmonic light-emitting devices. [0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device that included an arylamine hole-transport lay...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D307/87C07D209/44C07D333/72C09K11/06H01L51/50H01L51/54
CPCC07C211/61C07D307/87C07D209/44C07D333/72C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/622H10K85/615H10K85/631H10K85/636H10K85/626H10K85/633H10K85/6576H10K85/6574H10K85/6572H10K50/11
Inventor 田学超毕欣张少博王峥赵春亮邝志远夏传军
Owner BEIJING SUMMER SPROUT TECH CO LTD