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Organic light emission diode device containing 9, 10-anthrone compound and application thereof

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

Active Publication Date: 2017-08-18
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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  • Organic light emission diode device containing 9, 10-anthrone compound and application thereof
  • Organic light emission diode device containing 9, 10-anthrone compound and application thereof
  • Organic light emission diode device containing 9, 10-anthrone compound and application thereof

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 light emission diode device containing a 9, 10-anthrone compound and an application thereof. The device comprises a hole transport layer, a light emission layer and an electron transport layer. The material of the light emission layer of the device comprises a compound containing a 9, 10-anthrone group, and the structural formula is shown in the general formula (1). According to the material containing the 9, 10-anthrone group, due to a small triplet and singlet energy difference, energy transfer between host and guest materials can be realized easily, energy that is originally lost in a heat form is easily available, and the high efficiency of the device can be acquired more easily. Further, when the material containing the 9, 10-anthrone compound is directly used as a doped material or the 9, 10-anthrone compound as a host material selects a fluorescent material as the doped material, light emission radiation of the doped material is acquired more easily, and a long service life of the material can be acquired more easily.

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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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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