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Electroluminescent compound, and thermal activation delayed fluorescence material and applications thereof

A technology of thermally activated delayed and fluorescent materials, applied in the field of organic electroluminescent materials, can solve the problems of difficult performance to meet the requirements of high-performance OLED devices, less TADF materials, etc., to achieve good compactness, improved fluorescence lifetime and improved device efficiency Effect

Pending Publication Date: 2020-01-14
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] CN109134520A, CN109503508A, CN108530357A, etc. disclose TADF materials and their applications, but there are few TADF materials found so far, and the performance is difficult to meet people's requirements for high-performance OLED devices

Method used

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  • Electroluminescent compound, and thermal activation delayed fluorescence material and applications thereof
  • Electroluminescent compound, and thermal activation delayed fluorescence material and applications thereof
  • Electroluminescent compound, and thermal activation delayed fluorescence material and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] This embodiment provides an electroluminescent compound with the following structure:

[0112]

[0113] The preparation method comprises the following steps:

[0114] (1)

[0115] Add A (0.5mmol) and B (0.5mmol) sequentially into a microwave vial, dissolve with ethanol (6mL), and then add tetrabutyl acetate (Bu 4 NOAc, 1 mmol) and palladium catalyst Pd En Cat (63 mg, 5 mol%); the reaction was irradiated with a microwave device at 120° C. for 10 minutes. After cooling to room temperature in a microwave cavity, the reaction mixture was purified on a SCXII column using dichloromethane (DCM, 10 mL) as eluent and evaporated to dryness to afford Intermediate C.

[0116] 1 H-NMR (400MHz, CDCl 3 ): δ8.91(s,1H),8.12(d,J=4.0Hz,2H),7.84(s,1H),7.66(s,1H),7.53(s,1H),7.44(s,1H) , 7.32 (d, J=20.0Hz, 2H).

[0117] 13 C-NMR (100MHz, CDCl 3 ): δ148.63(s), 148.12(s), 147.36(s), 143.88(s), 134.18(s), 132.82(s), 131.31(s), 130.07(s), 129.65(s), 127.95 (s), 127.51(s), 126.95(s)...

Embodiment 2

[0127] This embodiment provides an electroluminescent compound with the following structure:

[0128]

[0129] The difference between the preparation method and the preparation method in Example 1 is that the compound E in the step (3) is mixed with an equimolar amount of the compound E2 Instead, the other preparation conditions remain unchanged to obtain the target product M2.

[0130] 1 H-NMR (400MHz, CDCl 3 ): δ8.87(s,1H),8.63(s,1H),8.55(s,1H),8.18(d,J=8.0Hz,2H),7.94(s,4H),7.89(s,4H) ,7.75(d,J=16.0Hz,3H),7.59(s,1H),7.51(d,J=8.0Hz,2H),7.41(d,J=8.0Hz,2H),7.16(dd,J= 22.0, 14.0Hz, 4H).

[0131] 13 C-NMR (100MHz, CDCl 3 ): δ154.08(s), 151.67(d, J=7.0Hz), 146.93(s), 145.60(s), 139.35(s), 135.09(s), 134.01(s), 131.99(s), 130.97 (s), 129.86-129.49(m), 129.27(s), 127.82(s), 127.11(s), 126.91(s), 125.32(s), 124.67(s), 122.99(s), 113.74(s) .

Embodiment 3

[0133] This embodiment provides an electroluminescent compound with the following structure:

[0134]

[0135] The difference between the preparation method and the preparation method in Example 1 is that the compound E in step (3) is mixed with an equimolar amount of compound E3 Instead, the other preparation conditions remain unchanged to obtain the target product M3.

[0136] 1 H-NMR (400MHz, CDCl 3 ): δ8.87(s,1H),8.62(s,1H),8.17(s,1H),7.94(s,1H),7.74(d,J=24.0Hz,3H),7.55(d,J= 36.0Hz, 2H), 7.42(s, 1H), 7.18(dd, J=8.0, 4.0Hz, 8H), 6.94(s, 2H), 1.69(s, 6H).

[0137] 13 C-NMR (100MHz, CDCl 3 ): δ154.08(s), 152.78(s), 151.64(s), 145.60(s), 142.44(s), 139.35(s), 135.09(s), 134.24(s), 133.37(s), 131.99 (s), 130.97(s), 29.86-129.49(m), 128.95(s), 127.82(s), 127.11(s), 126.83(d, J=15.7Hz), 125.32(s), 122.86(s) , 120.00(s), 113.74(s), 35.71(s), 29.68(s).

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Abstract

The invention provides an electroluminescent compound, and a thermal activation delayed fluorescence material and applications thereof, wherein the electroluminescent compound has a structure represented by a formula I, is a small molecular compound containing a boron heterocyclic ring, has TADF characteristic, and can be used as a thermal activation delayed fluorescence material in the light emitting layer of an OLED device, the OLED device comprises an anode, a cathode and at least an organic film layer located between the anode and the cathode, and the light emitting layer in the organic film layer comprises the thermal activation delayed fluorescence material. According to the invention, the electroluminescent compound can effectively reduce the overlapping between HOMO and LUMO through the special design of the molecular structure, so that the delta EST is reduced to less than 0.25 eV, the requirement that the triplet state energy reversely passes through singlet state is met, thetransmission capacity of two kinds of carriers is effectively improved, and the carrier balance is improved so as to significantly improve the light emitting efficiency of the OLED device.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an electroluminescent compound, a thermally activated delayed fluorescent material and applications thereof. Background technique [0002] Organic Light Emitting Display (OLED) is a new type of flat panel display technology. Compared with Liquid Crystal Display (LCD), OLED has the advantages of active light emission, fast response, low energy consumption, and low driving voltage. Low, light and thin, wide viewing angle, continuously adjustable luminous color, low cost, simple production process, high luminous efficiency and flexible display, etc., have attracted great attention from the industry and the scientific community, and have been widely used in flexible displays, flat panels, etc. display, solid-state lighting and automotive display industries. At present, OLED has entered the stage of industrialization, and the development of hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02H01L51/50H01L51/54H10K99/00
CPCC09K11/06C07F5/027C09K2211/1007C09K2211/1029C09K2211/104C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1011H10K85/653H10K85/615H10K85/654H10K85/657H10K85/6572H10K50/12H10K50/11H10K85/658H10K85/324C09K2211/1014C09K2211/1018H10K85/322H10K85/631H10K50/15H10K50/16H10K50/17H10K50/18H10K50/171H10K85/656H10K2101/10
Inventor 汪奎
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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