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Organic photoelectric device containing oxathiocyclic triarylamine compounds and application thereof

A technology of optoelectronic devices and triarylamines, which is applied in the field of organic optoelectronic devices of oxygen-sulfur-containing heterocyclic triarylamine compounds, and can solve the problems of large influence on device yield, complex structure of OLED devices, and complex matching

Active Publication Date: 2018-12-07
YURUI SHANGHAI CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the early OLED devices, the hole injection layer, the hole transport layer and the electron blocking layer were made of different compounds, which made the structure of the OLED device complicated, and at the same time, the matching required for the preparation of such an OLED device also became complicated. Multiple preparation chambers are required, and at the same time, due to the separate production of multiple layers, it has a great impact on the yield of the device

Method used

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  • Organic photoelectric device containing oxathiocyclic triarylamine compounds and application thereof
  • Organic photoelectric device containing oxathiocyclic triarylamine compounds and application thereof
  • Organic photoelectric device containing oxathiocyclic triarylamine compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Synthesis of intermediate oxygen-containing heterocycle-boronic acid intermediate O:

[0085]

[0086] Intermediate O-1 Synthesis

[0087]

[0088] 1) Dissolve dibenzofuran-4-boronic acid (S1) (2g) and 2-nitrobromobenzene (2g) in 60ml tetrahydrofuran completely in a 250ml round bottom flask under nitrogen atmosphere, then add 2M sodium carbonate aqueous solution After adding tetrakis-(triphenylphosphine)palladium (0.2g), the mixture was heated and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed. Add 100 ml of dichloromethane, and wash twice with 30 ml of saturated brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Then petroleum ether: ethyl acetate (20:1~2:1) was used as eluent to purify and separate on a silica gel column to obtain S2 (yield 84%);

[0089]

[0090] 2) S2 (6g) and triethyl phosphite (16g) were completely dissolved in o-dichlorobenzene (120ml) in a 25...

Embodiment 2

[0103] Embodiment 2: the preparation of compound 3-1

[0104]

[0105] Dissolve spirobifluorene-2-boronic acid (6.8g) and MO-1 (10g) in 120ml toluene / tetrahydrofuran (1:1) completely in a 250ml round bottom flask under nitrogen atmosphere, then add 80ml of 2M sodium carbonate aqueous solution , and then tetrakis-(triphenylphosphine)palladium (0.2 g) was added, and the mixture was heated and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed. Add 200 ml of dichloromethane, and wash twice with 30 ml of saturated brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Then use petroleum ether: dichloro (20:1 ~ 1:1) as eluent to purify and separate on a silica gel column to obtain compound 12.3 g (yield 75.8%). Measured MS (ESI): 815.2

Embodiment 3

[0106] Embodiment 3: the preparation of compound 3-11

[0107]

[0108] As shown in Example 1, after replacing MO-1 with MO-2, compound 3-11 was obtained with an isolated yield of 70.2%, and the measured MS (ESI): 891.3.

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Abstract

The invention provides an organic photoelectric device containing oxathiocyclic triarylamine compounds and an application thereof. The organic photoelectric device comprises an organic light-emittingdevice (OLED), an organic field effect transistor (OFET), organic solar cells and the like. Particularly, the hole injection layer, the hole transport layer, the electron blocking layer or the luminous layer in the OLED contain the oxathiocyclic triarylamine compounds. Since the oxathiocyclic triarylamine compound has excellent energy level matching property and high glass-transition temperature,the compound has fairly good thermal and optical stability and triplet state energy level so as to meet the exciton binding requirement. Therefore, the OLED has the advantages of high efficiency, lowoperating voltage and long service life and has excellent application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to an organic optoelectronic device of an oxygen-sulfur heterocyclic triarylamine compound and its application. Background technique [0002] Since mankind entered the information society of the 21st century, display devices, as an essential interface for human-computer interaction, have played a vital role. Information display devices have developed from the simplest light bulb switch to cathode ray tube (CRT) displays, until today's liquid crystal (LCD), plasma (PDP), field emission (FED) displays. However, with the improvement of people's viewing needs and visual enjoyment, the existing display technology cannot meet people's increasingly high requirements for display devices. Newer and more efficient luminescent materials are sought to prepare displays with higher performance and lower cost. Devices have become the pursuit of people. [0003] Among ...

Claims

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Application Information

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IPC IPC(8): C07D491/048C07D495/04C09K11/06H01L51/30H01L51/46H01L51/54
CPCC09K11/06C07D491/048C07D495/04C09K2211/1088C09K2211/1092C09K2211/1014C09K2211/1007C09K2211/1011C09K2211/1029H10K85/624H10K85/615H10K85/636H10K85/657Y02E10/549
Inventor 王子兴吴跃初赵晓宇
Owner YURUI SHANGHAI CHEM
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