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Bipolar thermal activation delayed fluorescence compound and application thereof

A technology of heat-activated delayed and fluorescent compounds, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of improving or reducing the intensity of the photoradiative transition constant array, unfavorable molecular luminous efficiency, etc., and achieves the improvement of cross-crossing probability , Improve the effect of luminous efficiency and device stability

Inactive Publication Date: 2019-04-26
AAC TECH NANJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although such traditional molecular design has obtained the ideal ΔE ST value, but the complete separation of HOMO and LUMO orbitals and the embedding of barrier units cause the integral of electron exchange between HOMO and LUMO in the molecule to approach 0, that is, the radiative transition rate constant Kr@S1->S in the molecule becomes smaller, Not conducive to the improvement of the luminous efficiency of molecules
In addition, the intermediate barrier unit makes the molecular structure more flexible, thereby reducing the light radiation transition constant of the molecule and the moment intensity during the transition (Kr is proportional to the moment intensity f)

Method used

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  • Bipolar thermal activation delayed fluorescence compound and application thereof
  • Bipolar thermal activation delayed fluorescence compound and application thereof
  • Bipolar thermal activation delayed fluorescence compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0060] The specific embodiment of the present invention also provides the above-mentioned preparation method, which is synthesized through the following general synthetic route:

[0061]

[0062] in,

[0063] Pd(PPh 3 ) 4 Is tetrakis (triphenylphosphine) palladium;

[0064] R 1 , R 2 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C30 heteroaryl group;

[0065] R 3 , R 4 Each is independently substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C5-C30 heteroaryl;

[0066] R 5 It is a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C30 heteroaryl group.

[0067] Synthetic example:

[0068] The preparation methods of the compounds disclosed in the present invention are provided below....

Embodiment 1

[0069] The preparation of embodiment 1:L1

[0070]

[0071] After adding a certain amount of D1 and K1 into the three-necked flask, install a mechanical stirring rod, feed nitrogen for 20 minutes, and add catalyst Pd (PPh 3 ) 4 0.25-3mol%, 0.018mol of 2M alkali solution, heated to reflux, reacted for 5-10 hours, suction filtered after reaction, washed with toluene, washed with ethanol, and recrystallized in xylene to obtain a powder with a purity of more than 99%. In order to further improve the purity of L1, a vacuum sublimation apparatus is used to carry out one or more sublimation, and an L1 product with a purity greater than 99.5% can be obtained.

[0072] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0073] 1 H NMR (400MHZ, DMSO-d6):

[0074] 7.00-7.08ppm(5H,m),7.22ppm(2H,m),7.3-7.32ppm(8H,m),7.40ppm(3H,d),7.48ppm(4H,d),7.55ppm(2H,d ).

Embodiment 2

[0075] The preparation of embodiment 2:L2

[0076]

[0077] After adding a certain amount of D2 and K3 in the there-necked flask, install a mechanical stirring rod, feed nitrogen for 20 minutes, and add catalyst Pd (PPh 3 ) 4 0.25-3mol%, 0.018mol of 2M alkali solution, heated to reflux, reacted for 5-10 hours, suction filtered after reaction, washed with toluene, washed with ethanol, and recrystallized in xylene to obtain a powder with a purity of more than 99%. In order to further improve the purity of L2, a vacuum sublimation apparatus is used to carry out one or more sublimation, and an L2 product with a purity greater than 99.5% can be obtained.

[0078] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0079] 1 H NMR (400MHZ, DMSO-d6):

[0080] 7.00-7.08ppm(4H,m),7.22-7.24ppm(6H,t),7.32ppm(6H,t),7.40ppm(2H,d),7.48ppm(8H,d),7.55ppm(2H,d ).

[0081] The preparation of embodiment 2:L7

[0082]

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Abstract

The invention belongs to the field of organic electroluminescence materials and discloses a bipolar thermal activation delayed fluorescence compound and application thereof. The energy gap between a singlet state and a triplet state of the bipolar thermal activation delayed fluorescence compound as an organic electroluminescence material disclosed by the invention is smaller than 300meV, and improvement on the reverse clearance crossing probability of triplet state exciton to singlet state exciton can be facilitated. In addition, while a low delta EST is maintained, the bipolar thermal activation delayed fluorescence compound disclosed by the invention has well matched hole-electron transmissibility, and the property facilitates the improvements of light emission efficiency of materials and device stability.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to a bipolar thermally activated delayed fluorescent compound and its application. Background technique [0002] Organic electroluminescent materials are classified into fluorescent electroluminescent materials and phosphorescent electroluminescent materials. Among them, phosphorescent electroluminescent materials can utilize the energy of all excitons through the heavy metal effect, so they have greater advantages. In 2009, thermally activated delayed fluorescence compounds, namely TADF (Thermally activated delayed fluorescence) materials, were proposed and applied in the technical field of organic electroluminescent devices. Under thermal excitation, this kind of fluorescent compound can use the reverse gap crossing of triplet excitons to obtain 100% singlet excitons, which not only avoids the use of expensive heavy metal complexes, but also has device efficien...

Claims

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Application Information

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IPC IPC(8): C07D487/04C09K11/06H01L51/54
CPCC09K11/06C07D487/04C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1059H10K85/615H10K85/626H10K85/654H10K85/6572
Inventor 谢再锋
Owner AAC TECH NANJING