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Interruption conjugation-based donor/acceptor type intramolecular exciplex light-emitting material and application thereof in preparation of organic light-emitting diode device

A technology of luminescent material and donor-acceptor type, applied in luminescent materials, electro-solid devices, semiconductor devices, etc., can solve the problems of low device efficiency and inability to use triplet state, achieve single structure determination, facilitate injection and transmission, The effect of good thermal stability

Inactive Publication Date: 2018-06-08
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Organic fluorescent materials cannot utilize the triplet state, so the device efficiency is very low

Method used

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  • Interruption conjugation-based donor/acceptor type intramolecular exciplex light-emitting material and application thereof in preparation of organic light-emitting diode device
  • Interruption conjugation-based donor/acceptor type intramolecular exciplex light-emitting material and application thereof in preparation of organic light-emitting diode device
  • Interruption conjugation-based donor/acceptor type intramolecular exciplex light-emitting material and application thereof in preparation of organic light-emitting diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] This embodiment P 1 The preparation comprises the following preparation steps:

[0046] m 1 Synthesis of: M 1 Prepared by Suzuki coupling. In a 100mL round bottom flask, 4,4'-dibromodiphenyl ether (5mmol, 1.63g), 4-cyanophenylboronic acid (5mmol, 735mg), and tetrakistriphenylphosphine palladium (0.1mmol, 115mg) were dissolved in 40mL of toluene and 20mL of potassium carbonate aqueous solution (2.0mol L -1 ), stirred and refluxed at 90°C for 24 hours under nitrogen protection. After the reaction, extract with dichloromethane, concentrate the extract by rotary evaporation, and separate by column chromatography (petroleum ether:dichloromethane=4:1, volume ratio) to obtain a white solid (872 mg, yield: 50%). Mass Spectrum MALDI-TOF(m / z)[M + ]: The test value is 349.16, and the theoretical value is 349.01.

[0047]

[0048] P 1 Synthesis of :P 1 Prepared by Ullmann coupling. In a 100mL round bottom flask, M 1 (5mmol, 1.75g), 9,10-dihydro-9,9-dimethylacridine (5...

Embodiment 2

[0051] This embodiment P 2 The preparation comprises the following preparation steps:

[0052] m 2 Synthesis of: M 2 Prepared by Ullmann coupling. In a 100mL round bottom flask, 4,4'-dibromodiphenyl ether (30mmol, 9.77g), 9,10-dihydro-9,9-dimethylacridine (5mmol, 1.05g), three (di Benzylideneacetonate)dipalladium (0.1mmol, 92mg), 1,1'-bis(diphenylphosphino)ferrocene (0.2mmol, 111mg), potassium tert-butoxide (10mmol, 1.12g) were dissolved in 40mL In toluene, stirred and refluxed at 110°C for 10 hours under the protection of nitrogen. After the reaction, extract with dichloromethane, concentrate the extract by rotary evaporation, and separate by column chromatography (petroleum ether:dichloromethane=50:1, volume ratio) to obtain a white solid (1.03g, yield: 45%). Mass Spectrum MALDI-TOF(m / z)[M + ]: The test value is 455.17, and the theoretical value is 455.09.

[0053]

[0054] m 3 Synthesis of: M 3 Prepared by Suzuki coupling. In a 100mL round bottom flask, M 2 (5...

Embodiment 3

[0059] This embodiment P 3 The preparation comprises the following preparation steps:

[0060] m 4 Synthesis of: M 4 Obtained by nucleophilic substitution reactions. In a 250mL round bottom flask, dissolve 4,4'-dibromodiphenyl ether (30mmol, 9.77g) in freshly distilled tetrahydrofuran, and add n-butyllithium (33mmol, 2.4M, 13.75mL), stirring was continued at -78°C for 4 hours. Bis(mesityl)boron fluoride (30mmol, 8.05g) was dissolved in freshly distilled tetrahydrofuran, and added dropwise to the reaction system, and stirred at room temperature for two days under nitrogen protection. Pour into water to quench the reaction, extract with dichloromethane, concentrate the extract by rotary evaporation, and separate by column chromatography (petroleum ether:dichloromethane=20:1, volume ratio) to obtain a white solid (6.71g, yield: 45% ). Mass Spectrum MALDI-TOF(m / z)[M + ]: The test value is 496.37, and the theoretical value is 496.16.

[0061]

[0062] P 3 Synthesis of :...

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Abstract

The invention discloses preparation of an interruption conjugation-based donor / acceptor type intramolecular exciplex light-emitting material and application thereof in preparation of an Organic Light-Emitting Diode (OLEDs) Device, and belongs to the technical field of organic electroluminescence. Specifically, sp3-hybridized atoms such as C, O, S and Si are used as bridging groups for interruptionconjugation; a donor and an acceptor are connected in an interruption conjugation manner; moreover, a proper donor and a proper acceptor are selected; a charge transfer excited state between the donor and the acceptor is adjusted as a lowest excited state of the whole molecule. Therefore, a hole wave function of a formed exciton is locally defined on the donor, and an electron wave function is locally defined on the acceptor; the hole and electron wave functions are completely separated in space. Therefore, the formed exciton is low in binding energy and favorable for spin flip of excited electrons, and has a reversed intersystem crossing from a triplet state to a singlet state to realize effective utilization of the triplet state by a fluorescent material. Through reasonable donor and acceptor cooperation, the interruption conjugation-based donor / acceptor type intramolecular exciplex light-emitting material also can realize red, green and blue full-color light emission.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to the preparation of a class of donor-type intramolecular exciplex light-emitting materials based on interrupted conjugation and its application in the preparation of OLEDs devices. Background technique [0002] Since Dr. Deng Qingyun of Kodak Company first reported organic ultra-thin film electroluminescent devices with a multilayer device structure in 1987, the OLEDs industry has developed rapidly and moved towards practical applications. However, there are still many unresolved issues in the field of OLEDs. Most of the currently commercialized materials are phosphorescent materials based on heavy metals such as iridium or platinum. Phosphorescent materials can use the strong spin-orbit coupling effect of heavy metal atoms to make the triplet state emit light, so as to achieve 100% internal quantum efficiency. However, the resource reserves of hea...

Claims

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Application Information

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IPC IPC(8): C07D219/02C07D401/12C07D265/38C07D413/12C07F5/02C07F7/08C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D219/02C07D265/38C07D401/12C07D413/12C07F5/027C09K2211/1029C09K2211/1014C09K2211/1007C09K2211/1059C09K2211/1033H10K85/654H10K85/657H10K85/40H10K85/6572H10K50/12H10K50/11
Inventor 路萍唐向阳刘福通刘辉
Owner JILIN UNIV
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