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Organic light-emitting device containing triazine and ketone compound and application of organic light-emitting device

A technology of electroluminescent devices and ketone compounds, applied in the field of organic electroluminescent devices, can solve problems such as efficiency roll-off, low S1 state radiation transition rate, difficult high exciton utilization rate and high fluorescence radiation efficiency

Active Publication Date: 2016-12-07
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-emitting device containing triazine and ketone compound and application of organic light-emitting device
  • Organic light-emitting device containing triazine and ketone compound and application of organic light-emitting device
  • Organic light-emitting device containing triazine and ketone compound and application of organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of Example 1 Compound 1

[0068]

[0069] The concrete synthetic route of this compound is provided now:

[0070]

[0071] In a 500ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4,6-diphenyl-[1,3,5]triazine-2-carbonyl chloride, 0.03mol 9,9-dimethyl- 10-Phenyl-9,10-dihydroacridine 2-boronic acid, dissolved in a mixed solvent (180ml toluene, 90ml ethanol), then added 0.03mol Na 2 CO 3 aqueous solution (2M), then add 0.0001mol Pd (PPh 3 ) 4 , heated to reflux for 10-24 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 HPLC purity of 99.2% and a yield of 58.00%.

[0072] Elemental analysis structure (molecular formula C 37 h 28 N 4 O): theoretical value C, 81.59; H, 5.18; N, 10.29; O, 2.94; tested value: C, 81.66; H, 5.12; N, 10.25;

[0073] HPLC-MS: The molecular weight of the material is 544.2...

Embodiment 2

[0074] Synthesis of Example 2 Compound 5

[0075]

[0076] The concrete synthetic route of this compound is provided now:

[0077]

[0078] In a 500ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 2-chloro-4,6-bis(3,5-dimethylphenyl)-[1,3,5]triazine, 0.03mol2 , 6-anthraquinone diboronic acid, 0.01mol10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine, dissolved in a mixed solvent (180ml toluene, 90ml ethanol), then Add 0.03molNa 2 CO 3 aqueous solution (2M), then add 0.0001mol Pd (PPh 3 ) 4 , heated to reflux for 10-24 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 an HPLC purity of 99.0% and a yield of 35.00%.

[0079] Elemental analysis structure (molecular formula C 54 h 42 N 4 o 2 ): theoretical value C, 83.26; H, 5.43; N, 7.19; O, 4.11; test value: C, 83.35; H, 5.36; N, 7.22;

[0080] HPLC-MS: The mo...

Embodiment 3

[0081] Synthesis of Example 3 Compound 6

[0082]

[0083] The concrete synthetic route of this compound is provided now:

[0084]

[0085] In a 500ml four-neck flask, add 0.01mol 2-chloro-4-naphthalen-2-yl-6-phenyl-[1,3,5]triazine, 0.03mol 2,7-oxa Anthrone diboronic acid, 0.01mol 2-bromo-9,9,10-triphenyl-9,10-dihydroacridine, dissolved in a mixed solvent (180ml toluene, 90ml ethanol), then added 0.03mol Na 2 CO 3 aqueous solution (2M), then add 0.0001mol Pd (PPh 3 ) 4 , heated to reflux for 10-24 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 an HPLC purity of 98.96% and a yield of 46.00%.

[0086] Elemental analysis structure (molecular formula C 63 h 40 N 4 o 2 ): theoretical value C, 85.50; H, 4.56; N, 6.33; O, 3.62; test value: C, 85.56; H, 4.52; N, 6.31;

[0087] HPLC-MS: The molecular weight of the material is 884....

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Abstract

The invention discloses an organic light-emitting device containing a triazine and ketone compound and an application of the organic light-emitting device. The device comprises a hole transport layer, a light-emitting layer and an electron transport layer, wherein a material of the light-emitting layer of the device contains a compound employing triazine and ketone as core groups; and the structural formula of the compound is as shown in a general formula (1). The material employing the triazine and the ketone as the core groups has a relatively small triplet and singlet energy difference, so that energy transfer between a host material and a guest material is easy to implement; the energy which is dissipated in a heat manner in the past is easily obtained; the radiative transition efficiency of the light-emitting layer is improved; and high efficiency of the device is easier to obtain. Furthermore, when a fluorescent material is selected as the doped material, luminous radiation of the doped material is easier to obtain, so that long lifetime of the material is easier to obtain.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic electroluminescent device whose luminescent layer material is a compound with triazine and ketone as the core and its application. 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): H01L51/54H01L51/50
CPCH10K85/615H10K85/654H10K85/6574H10K85/657H10K85/6572H10K50/00H10K2102/00H10K2102/301
Inventor 李崇刘琼文张兆超
Owner VALIANT CO LTD
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