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Bipolar thermal delayed fluorescence compound, and applications thereof

A fluorescent compound and thermal delay technology, applied in the fields of photovoltaic power generation, luminescent materials, organic chemistry, etc., can solve the problems of improving or reducing the intensity of the photoradiation transition constant array, unfavorable molecular luminous efficiency, etc., to increase the crossover probability and improve luminescence The effect of efficiency and device stability

Inactive Publication Date: 2019-05-03
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 delayed fluorescence compound, and applications thereof
  • Bipolar thermal delayed fluorescence compound, and applications thereof
  • Bipolar thermal delayed fluorescence compound, and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0070] The specific embodiment of the present invention also provides the above-mentioned preparation method, which is synthesized through the following general synthetic route:

[0071]

[0072] in,

[0073] Pd(PPh 3 ) 4 Is tetrakis (triphenylphosphine) palladium;

[0074] R 1 , R 2 Each is independently a hydrogen atom, a deuterium atom, a C1-C8 straight chain or branched chain alkyl group, an unsubstituted or C6-C36 aryl group substituted by a C1-C8 straight chain alkyl group, an unsubstituted or C1-C8 straight chain alkyl group, Alkanyl substituted C5-C30 heteroaryl;

[0075] Z1 ring is selected from unsubstituted or C6-C36 aryl substituted by C1-C8 linear alkyl;

[0076] R X selected from hydrogen atom, deuterium atom, C1-C8 straight chain or branched chain alkyl, C6-C36 aryl unsubstituted or substituted by C1-C8 straight chain alkyl, unsubstituted or C1-C8 straight chain alkane C5-C30 heteroaryl substituted by base; R X 0-4;

[0077] m 1 -M 5 Each is indep...

Embodiment 1

[0080] The preparation of embodiment 1:L2

[0081]

[0082] After adding a certain amount of D2 and K2 into the three-necked flask, install a mechanical stirring bar, 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 L2 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.

[0083] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0084] 1 H NMR (400MHZ, DMSO-d6):

[0085] 7.00-7.08ppm (4H, m), 7.24-7.30ppm (10H, m), 7.40-7.55ppm (16H, m), 7.70ppm (4H, m).

Embodiment 2

[0086] The preparation of embodiment 2:L4

[0087]

[0088] After adding a certain amount of D4 and K4 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 L4 powder with a purity of more than 99%. In order to further improve the purity of L4, a vacuum sublimation apparatus is used to carry out one or more sublimation, and an L4 product with a purity greater than 99.5% can be obtained.

[0089] Using CDCL 3 Used as a solvent, tetramethylsilane (δ = 0.00ppm) as an internal standard record 1 H NMR spectrum.

[0090] 1 H NMR (400MHZ, DMSO-d6):

[0091] 7.00-7.08ppm(4H,m),7.24-7.30ppm(10H,m),7.40ppm(2H,d),7.50ppm(4H,d),7.55ppm(2H,d),7.70-7.80ppm(10H ,m).

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Abstract

The invention belongs to the technical field of organic electroluminescent material, and discloses a bipolar thermal delayed fluorescence compound, and applications thereof. When the bipolar thermal delayed fluorescence compound is taken as an organic electroluminescent material, the energy level difference of the singlet state and the triplet state is equal to or lower than 300meV, it is beneficial for increasing of reverse intersystem crossing rate from triplet exciton to singlet exciton; and in addition, when the relatively low delta EST of the bipolar thermal delayed fluorescence compoundis maintained, extremely matching cavity-electron transmissibility is achieved, and the property is beneficial for improvement of material luminescence efficiency and device stability.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, in particular to a bipolar thermally 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): C07D487/04C09K11/06H01L51/30H01L51/46H01L51/54
CPCY02E10/549
Inventor 谢再锋
Owner AAC TECH NANJING
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