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TADF polymer containing meta-position electron donors and electron acceptors in alternate connection and preparation method and application thereof

An electron acceptor and electron donor technology, applied in the field of TADF polymers and their preparation, can solve the problems of difficult TADF materials, excessive overlap of frontier orbitals, etc.

Active Publication Date: 2020-07-03
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of this, the present invention makes full use of the effect of the meta-position connection on the overlap of front-line orbitals between electron donors and acceptors, thereby realizing the energy difference between the lowest singlet state and the lowest triplet state of the polymer and the TADF performance determined thereby. Adjustment, finally solved the problem that the current polymers with electron donors and electron acceptors alternately connected have excessive overlap of front orbitals, which is difficult to be used as TADF materials

Method used

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  • TADF polymer containing meta-position electron donors and electron acceptors in alternate connection and preparation method and application thereof
  • TADF polymer containing meta-position electron donors and electron acceptors in alternate connection and preparation method and application thereof
  • TADF polymer containing meta-position electron donors and electron acceptors in alternate connection and preparation method and application thereof

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preparation example Construction

[0082] The present invention provides a method for preparing a TADF polymer containing meta-positioned electron donors and electron acceptors alternately connected in the above technical scheme, comprising the following steps:

[0083] Under an inert atmosphere, mix the bis-boron ester monomer with the structure of formula (II), the dibromo monomer with the structure of formula (III), palladium catalyst, phase transfer catalyst, alkali and reaction solvent, and heat up to carry out Suzuki polymerization reaction, the reaction After the end, add the end-capping agent of bromine and the end-capping agent of boron ester respectively, then add chelating agent to quench the palladium catalyst, obtain the TADF polymer with formula (I) structure:

[0084]

[0085] In the bis-boron ester monomer of the formula (II) structure As described in the above technical solution The range of options is the same and will not be described in detail here. In the dibromine monomer of the for...

Embodiment 1

[0108] A TADF polymer whose structure is poly(TPAp-DCBm) para-meta electron donor and electron acceptor alternately connected, the synthetic route is as follows:

[0109]

[0110] Synthesis conditions: tetrakis (triphenylphosphine) palladium, methyl trioctyl ammonium chloride, potassium carbonate aqueous solution, toluene, 95°C.

[0111] Synthesis of polymers with the chemical structure poly(TPAp-DCBm): under an inert gas atmosphere, M1 (0.6095g, 1.0mmol), 2,6-dibromoterephthalonitrile (0.2860g, 1.0mmol) and formaldehyde Trioctyl ammonium chloride (Aliquat 336, ~100mg), tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 , 10mg) placed in the polymerization bottle. Anhydrous and oxygen-free toluene (toluene, 20 ml) was introduced. After the temperature was raised to 80°C, an aqueous solution of potassium carbonate (K 2 CO 3 / H 2 0, 2mol / L, 10ml), the temperature was raised to 95°C. Observe the viscosity of the system during this period, and when the viscosity of egg ...

Embodiment 2

[0114] A TADF polymer whose structure is poly(TPAm-DCBp) meta-para-position electron donors and electron acceptors alternately connected, the synthetic route is as follows:

[0115]

[0116]Synthesis conditions: i. Sodium tert-butoxide, bis(dibenzylideneacetone)palladium, 1,1'-bis(diphenylphosphino)ferrocene, toluene, 120°C; ii. pinacol diborate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, potassium acetate, dimethylformamide, 120°C; iii. tetrakis(triphenylphosphine)palladium, methyl trioctyl ammonium chloride, potassium carbonate aqueous solution, toluene, 95°C.

[0117] (1) Synthesis of intermediates with chemical structure 2: m-bromoiodobenzene (11.88g, 42mmol), p-octylaniline (4.11g, 20mmol), sodium tert-butoxide (t-BuONa, 4.03g, 42mmol), Bis(dibenzylideneacetone) palladium (Pd 2 (dba) 3 , 0.92g, 1mmol) and 1,1'-bis(diphenylphosphino)ferrocene (DPPF, 2.22g, 4mmol) were added to a round bottom flask with a magnetic stirrer. After three cycles of vacuu...

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Abstract

The invention provides a TADF polymer containing meta-position electron donors and electron acceptors in alternate connection, and a preparation method and application thereof in the field of electroluminescent devices. The TADF polymer has a structure shown as a formula (I). Same electron donor units and same electron acceptor units are alternately connected, and the delay components of a photo-induced transient attenuation curve of a corresponding polymer are gradually increased only by changing the connection mode between electron donors and acceptors from alignment to meta-position, whichindicates that the properties of TADF are gradually enhanced. The polymer of which the donor and the acceptor are in meta-position connection shows a good electroluminescent performance; when the polymer is used as a luminescent layer dye, the maximum external quantum efficiency of the device is 8.8%; as a sensitizer of a light-emitting layer, a red phosphorescent dye is sensitized, and the maximum external quantum efficiency of the device is 8.2%.

Description

technical field [0001] The invention belongs to the field of organic semiconductor optoelectronic materials, in particular to a TADF polymer containing meta-position electron donors and electron acceptors alternately connected and its preparation method and application. Background technique [0002] In 2012, Professor Adachi's research group from Kyushu University in Japan reported a series of compounds based on distorted conformation of carbazole and dicyanobenzene, these molecules have obvious thermally activated delayed fluorescence (TADF) characteristics , of which 4CzIPN exhibits high-efficiency electroluminescent properties, with an external quantum efficiency (EQE) of 19.3% (Nature, 2012, 492, 234-238.). Since then, the research work on the design, synthesis and performance of TADF molecules has emerged in an endless stream, and the electroluminescence EQE in the full visible spectrum range has been reported to be close to or even exceed 30% (Chem.Soc.Rev., 2017, 46, ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/54
CPCC08G61/121C08G61/122C08G61/124C09K11/06C08G2261/124C08G2261/143C08G2261/148C08G2261/1412C08G2261/344C08G2261/411C08G2261/3424C08G2261/5222C08G2261/95H10K85/151
Inventor 丁军桥饶建成王利祥王淑萌赵磊
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI