Small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline) and production method and application of small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline)

A technology of luminescent materials and phthalazine, which is applied in the direction of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., and can solve problems such as low efficiency

Inactive Publication Date: 2020-01-24
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with N-hetero six-membered rings, there are very few reports on the use of a series of heterocyclic compounds such as benzodiazetidine as acceptors in TADF materials, especially 1,3-di-N-heterocyclic compounds. Naphthalene (quinazoline), which has important applications in biology and sensing, but it is rarely reported as a light-emitting material applied to OLEDs and the efficiency is less than 5%. As for the application in TADF materials, there is no report yet

Method used

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  • Small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline) and production method and application of small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline)
  • Small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline) and production method and application of small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline)
  • Small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline) and production method and application of small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthesis of small molecule luminescent material P1 based on 1,3-naphthyridine (quinazoline):

[0052]

[0053] (1) Dissolve phenoxazine (1.66g, 5.00mmol), sodium tert-butoxide (0.96g, 10.00mmol) in 80mL1,4-dioxane, stir at room temperature for 30min under a nitrogen atmosphere, then add CuI ( 0.10g, 0.50mmol), 1,10-phenanthroline (0.10g, 0.50mmol), p-bromoiodobenzene (1.69g, 6.00mmol), react at 110°C for 24h. Obtain white solid product and obtain product 1, productive rate 75%, reaction formula is as follows:

[0054]

[0055] (2) Dissolve the product 1 (5.0g, 10.2mmol) in 400mL of anhydrous tetrahydrofuran, and at -78°C, add 4.7mL of n-butyllithium (2.5mol / L, 12.30mmol) dropwise, at -78°C Under reaction 1h. Then 2.30g 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.3g, 12.3mmol) was added dropwise and reacted overnight at room temperature , to obtain white solid product 2 with a yield of 73%, the reaction formula is as follows:

[0056]

[0057] (...

Embodiment 2

[0060] Synthesize small molecule luminescent material P2 based on 1,3-naphthyridine (quinazoline), the reaction formula is as follows:

[0061]

[0062] With embodiment 1, replace 4-phenyl-2-chloro-quinazoline with 2-chloro-quinazoline (0.20g, 1.5mmol), obtain based on 1,3-naphthyridine (quinazoline) The yield of small molecule luminescent material P2 is about 81%.

Embodiment 3

[0064] Synthesis of small molecule luminescent material P3 based on 1,3-naphthyridine (quinazoline), the reaction formula is as follows:

[0065]

[0066] With embodiment 1, replace 4-phenyl-2-chloro-quinazoline with 4-chloro-quinazoline (0.20g, 1.5mmol), obtain based on 1,3-naphthyridine (quinazoline) The small molecule luminescent material P3 has a yield of about 89%.

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Abstract

The invention provides small-molecule luminescent materials based on 1,3-benzodiazine (quinazoline) and a production method and application of the small-molecule luminescent materials based on the 1,3-benzodiazine (quinazoline), and belongs to the technical field of organic photoelectric materials. A structural formula of the luminescent materials is shown in a formula (1)as shown in the description, in theformula (1), each of R1, R2, R3, R4, R5 and R6 is selected from one of a hydrogen atom, an alkoxy group, an alkylthio group, an alkylamine group, an arylamine group, an aryloxy group, an arylthio group, an aryl group and an aromatic heterocyclic group, and at least one of R1, R2, R3, R4, R5 and R6 is an aromatic heterocyclic group. According to the small-molecule luminescent materials based on the 1,3-benzodiazine (quinazoline) and the production method and application of the small-molecule luminescent materials based on the 1,3-benzodiazine (quinazoline), the 1,3-benzodiazine (quinazoline) is introduced into TADF materials for the first time, and high luminescence efficiency is achieved. The materials are simple to synthesize, steps are short, and synthesis cycles are short. Reaction yields are high, and the yields of all the steps are higher than 70%, so that the cost is saved. The OLED luminescent efficiency is high, and the highest efficiency can exceed 20%.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a 1,3-naphthyridine (quinazoline)-based small-molecule light-emitting material and its preparation and application. Background technique [0002] Since the ultrathin multilayer electroluminescent diodes were first reported by C.W.Tang et al. in 1987, organic light-emitting diodes (OLEDs) have received extensive attention in both academia and industry. In the past three decades, researchers have invested a lot of energy to improve the luminous efficiency of OLEDs. These studies mainly include the following two categories: first, the traditional fluorescence emission, that is, the use of singlet exciton radiative transition luminescence, However, since this type of emission can only achieve an internal quantum efficiency (IQE) of 25% at most, it cannot meet the actual needs; second, the spin-orbit coupling using the heavy metal effect makes the t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C07D401/14C07D403/10C07D403/14C07D413/10C07D417/10C07D491/107C07D495/10C09K11/06H01L51/54
CPCC07D413/10C07D417/10C07D401/10C07D491/107C07D495/10C07D401/14C07D403/10C07D403/14C09K11/06C09K2211/1044C09K2211/1088C09K2211/1092H10K85/657H10K85/6572
Inventor 张勇李博文
Owner HARBIN INST OF TECH
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