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A kind of organic electroluminescent device containing 9,10-anthraquinone compound and its application

A technology of electroluminescent devices and compounds, applied in the field of organic electroluminescent devices, can solve the problems of high exciton utilization rate, high fluorescence radiation efficiency, low S1 state radiation transition rate, efficiency roll-off, etc., and achieve high efficiency , good industrialization prospects, and the effect of improving device life

Active Publication Date: 2018-12-28
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (1) The T1 and S1 states of the designed molecule have strong CT features and a very small S1-T1 state energy gap, although high T can be achieved by the TADF process 1 →S 1 State exciton conversion rate, but at the same time lead to low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization rate and high fluorescence radiation efficiency;
[0007] (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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  • A kind of organic electroluminescent device containing 9,10-anthraquinone compound and its application
  • A kind of organic electroluminescent device containing 9,10-anthraquinone compound and its application
  • A kind of organic electroluminescent device containing 9,10-anthraquinone compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1 Compound A1

[0059]

[0060] In a 250ml four-necked flask, add 0.01mol 2,6-dibromo-4a,9a-dihydro-anthraquinone, 0.025mol 6,6-dimethyl-6,11-dihydro -13-Oxa-11-aza-indole[1,2-b]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 97.2% and a yield of 75.00%.

[0061] Elemental analysis structure (molecular formula C 56 h 40 N 2 o 4 ): theoretical value C, 83.56; H, 5.01; N, 3.48; 0, 7.95; test value: C, 83.65;

[0062] HPLC-MS: The molecular weight of the material is 804.30, and the measured molecular weight is 804.96.

Embodiment 2

[0063] Example 2 Compound A5

[0064]

[0065] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 1,5-dibromo-4a,9a-dihydro-anthraquinone, 0.025mol 6,6,13,13-tetramethyl-11, 13-Dihydro-11-aza-indo[1,2-b]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.2% and a yield of 72.00%.

[0066] Elemental analysis structure (molecular formula C 62 h 52 N 2 o 2 ): theoretical value C, 86.88; H, 6.12; N, 3.27; O, 3.73; test value: C, 86.93; H, 6.11; N, 3.20;

[0067] HPLC-MS: The molecular weight of the material is 856.40, and the measured molecular weight is 857.10.

Embodiment 3

[0068] Example 3 Compound A6

[0069]

[0070] In a 250ml four-neck flask, add 0.01mol 2,6-bis-(4'-bromobiphenyl-3-yl)-4a,9a-dihydro-anthraquinone, 0.025mol 11H- 6,13-Dioxa-11-aza-indole[1,2-b]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.5% and a yield of 68.00%.

[0071] Elemental analysis structure (molecular formula C 74 h 44 N 2 o 6 ): theoretical value C, 84.07; H, 4.20; N, 2.65; 0, 9.08; test value: C, 84.21;

[0072] HPLC-MS: The molecular weight of the material is 1056.32, and the measured molecular weight is 1056.80.

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Abstract

The invention discloses an organic electroluminescent device containing 9,10-anthraquinone compounds and its application. The device includes a hole transport layer, a light-emitting layer, and an electron transport layer. The material of the light-emitting layer of the device includes 9,10 -The compound of anthraquinone group, the structural formula is as shown in general formula (1). The 9,10-anthraquinone group materials used in the present invention are easy to realize the energy transfer between the host and guest materials because of the small triplet and singlet energy difference, so that the energy originally dissipated in the form of heat is easy to be utilized, thereby It is easier to obtain high efficiency of the device. Further, when the 9,10-anthraquinone compound material is directly used as a dopant material, or the 9,10-anthraquinone compound is used as the host material, the fluorescent material is selected as the doping material When the material is used, it is easier to obtain the luminescent radiation of the doped material, and thus it is easier to obtain the long life of the material.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic electroluminescence device in which the light-emitting layer material is a 9,10-anthraquinone compound and an application thereof. 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. [0003] 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/50H01L51/54
CPCH10K85/626H10K85/615H10K85/6572H10K85/657H10K50/11
Inventor 李崇张兆超徐凯
Owner VALIANT CO LTD
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