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Solution-processable exciplex host material, preparation method and application

A technology of exciplexes and host materials, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of many side reaction products, slow research progress, long synthesis route, etc., and achieve enhanced dissolution and film-forming effects

Pending Publication Date: 2022-05-06
SOUTHEAST UNIV CHENGXIAN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polymer host materials have disadvantages such as long synthetic routes, many side reaction products, difficult purification of polymers, and structural uncertainty, which have always affected the efficiency of electroluminescent devices, so the current research progress is relatively slow.

Method used

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  • Solution-processable exciplex host material, preparation method and application
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  • Solution-processable exciplex host material, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: as figure 1 As shown, compound C1 was synthesized by the following method

[0042]Step 1: Synthesis of AC-Br: Add 9,10-dihydro-9,9-dimethylacridine (4.0 g, 23.92 mmol), 1,6-dibromohexane to toluene solution (80 mL) (33mL, 143.5mmol), KOH (15g, 267.85mmol, first dissolved in 10mL of water), tetrabutylammonium bromide (1g, 1.8mmol). Under the protection of nitrogen, the reaction was stirred at 80° C. for 3 h, and directly spin-dried after the reaction. Purified by column chromatography to obtain the AC-Br product with a yield of 71%.

[0043] Step 2: Synthesis of CZ-ACO: under nitrogen protection, add AC-Br (2.67g, 8.13mmol), 3-hydroxycarbazole (1.59g, 8.13mmol), cesium carbonate (6.7g, 21.12 mmol), DMF (30mL), react at 80°C for 3h. Cool after the reaction, add water to precipitate, and extract with dichloromethane to obtain the product CZ-ACO with a yield of 68%.

[0044] Step 3: Synthesis of C1: Add CZ-ACO (1.42g, 3.15mmol), 4,4',4″-triiodotriphenylam...

Embodiment 2

[0045] Embodiment 2: the synthesis of compound C2

[0046] In the above example, the 3-hydroxycarbazole reacted with AC-Br was replaced with 3,6-dihydroxy-9-hydrogen-carbazole, and the product C2 was obtained through the same synthesis method as in Example 1. Yield 61%. Mass spectrum: 2720.85. Elemental analysis, the results are as follows: C: 83.47, H: 7.76, N: 5.12.

Embodiment 3

[0047] Embodiment 3: as figure 2 As shown, compound C3 was synthesized by the following method

[0048] Step 1: Synthesis of branched CZ-Br: Add carbazole (6.7 g, 23.92 mmol), 1,6-dibromohexane (33 mL, 143.5 mmol), KOH (15 g, 267.85 mmol, first dissolved in 10mL water), tetrabutylammonium bromide (1g, 1.8mmol). Under the protection of nitrogen, the reaction was stirred at 80° C. for 3 h, and directly spin-dried after the reaction. Purified by column chromatography to obtain the CZ-Br product with a yield of 71%.

[0049] Step 2: Synthesis of CZ-CZO: Under nitrogen protection environment, add CZ-Br (3.62g, 8.13mmol), 3-hydroxycarbazole (1.59g, 8.13mmol), cesium carbonate (6.7g, 21.12 mmol), DMF (30 mL). The reaction conditions and post-reaction treatment are the same as the synthesis of CZ-ACO in Example 1. The product CZ-CZO was obtained with a yield of 60%.

[0050] Step 3: Synthesis of C3: Add CZ-CZO (2.63g, 6.08mmol), 4,4',4″-triiodotriphenylamine (3I-TPA) (1.18g, 1....

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Abstract

The invention discloses a solution-processable exciplex host material, a preparation method and an application. The molecule is a donor molecule required for forming an exciplex, structurally comprises two parts, one part is a core formed by 4, 4 ', 4' '-tri (carbazole-9-yl) triphenylamine (TCTA), and the other part is an electron-donating group connected through an alkyl chain, and has a structure as shown in a formula I. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and in particular relates to a solution-processable exciplex host material, a preparation method and an application. Background technique [0002] Organic light-emitting diodes (OLEDs) are known as the most promising new generation of displays due to their advantages such as low driving voltage, fast response, high luminous efficiency, simple manufacturing process, and easy realization of full-color display. In the preparation of organic electroluminescent devices, it is crucial to select a suitable host material for the guest molecules in the light-emitting layer, which plays a decisive role in a series of properties such as the luminous efficiency of the device. At present, due to its simple preparation process, high material utilization rate and easy realization of large-area preparation, the host materials that can be prepared by wet method have attracted extensive attentio...

Claims

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Application Information

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IPC IPC(8): C07D209/88C07D401/14C09K11/06H01L51/54H01L51/50
CPCC07D401/14C07D209/88C09K11/06C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1014H10K85/626H10K85/631H10K85/6572H10K50/11
Inventor 唐霁楠林保平
Owner SOUTHEAST UNIV CHENGXIAN COLLEGE
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