Compound taking triazine derivative as core and application thereof

A technology of triazine derivatives and compounds, which is applied in the field of compounds with triazine derivatives as the core, can solve the problems of hole and electron imbalance, shortened lifespan, device efficiency roll-off, etc., achieve high Tg and reduce crystallinity , the effect of improving efficiency

Active Publication Date: 2022-07-01
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For phosphorescent OLEDs, the use of a single host in the light-emitting layer usually leads to an imbalance of holes and electrons, severe device efficiency roll-off and shortened lifetime at high current densities

Method used

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  • Compound taking triazine derivative as core and application thereof
  • Compound taking triazine derivative as core and application thereof
  • Compound taking triazine derivative as core and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Example 1: Preparation of Compound 4:

[0082]

[0083] (1) In a three-necked flask, under the protection of nitrogen, add 0.01mol of raw material A1, 0.012mol of raw material B1, and 150ml of toluene, stir and mix, and then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105 ° C, refluxed for 24 hours, sampling point plate to confirm the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column to obtain intermediate a1 . LC-MS: found: 612.43 ([M+H] + ), exact mass: 611.15.

[0084] (2) In a three-necked flask, under the protection of nitrogen, add 0.01mol of intermediate a1, 0.012mol of raw material C1, 150ml of toluene, stir and mix, and then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol of sodium tert-butoxide, heated to 105°C, refluxed for 15 hours, and sampled to confirm that the rea...

Embodiment 2

[0085] Example 2: Preparation of Compound 35:

[0086]

[0087] (1) In a three-necked flask, under the protection of nitrogen, add 0.01mol of raw material A1, 0.012mol of raw material B2, and 150ml of toluene, stir and mix, and then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105 ℃, refluxed for 20 hours, sampling point plate to confirm the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column to obtain intermediate a2 ; LC-MS: found: 537.22 ([M+H] + ), exact mass: 536.10.

[0088] (2) In a three-necked flask, under the protection of nitrogen, add 0.01mol of intermediate a2, 0.012mol of raw material C2, dissolve with mixed solvent (90ml toluene, 45ml ethanol), then add 1×10 -4 mol Pd (PPh 3 ) 4 , 3mol / L K 2 CO 3 The aqueous solution was heated to reflux for 15 hours and reacted for 15 hours. The sampling p...

Embodiment 6

[0089] Example 6: Preparation of Compound 65:

[0090] Synthesis of Intermediate b-1:

[0091]

[0092]

[0093] (1) Add 0.01mol raw material M1, 0.011mol raw material M2, 0.02mol potassium carbonate, 5×10- 5 mol Pd (PPh 3 ) 4 , then add 250 ml of toluene and 50 ml of ethanol to dissolve it, stir and reflux at 60° C. for 8 hours, and observe the reaction by TLC until the reaction is complete. Cool to room temperature naturally, filter, and spin the filtrate until there is no fraction. The resulting material was purified by silica gel column (hexane:DCM=4:1 as eluent) to give Intermediate I-1. LC-MS: found: 267.12 ([M+H] + ), exact mass: 266.05.

[0094] (2) 0.14 mol of Intermediate I-1, 0.145 mol of pyridine hydrochloride were added to the round-bottomed flask, followed by reflux and stirring at 200° C. for 24 hours. When the reaction was completed, the resultant was cooled to room temperature, and then slowly poured into distilled water, followed by stirring for ...

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Abstract

The invention discloses a compound taking a triazine derivative as a core and application of the compound, and belongs to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (1); the compound disclosed by the invention contains a triazine parent nucleus structure, and has appropriate HOMO and LUMO energy levels and relatively high triplet state energy level (T1). After the compound is applied to an OLED device, the driving voltage of the device can be effectively reduced, the current efficiency of the device is improved, and the service life of the device is prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with a triazine derivative as the core and its application. Background technique [0002] The organic electroluminescent device includes an anode, a cathode, and an organic functional layer disposed between the anode and the cathode, wherein the organic functional layer is a general term for each layer between the cathode and the anode. The organic functional layer includes a light-emitting layer, a hole-transporting region may exist between the anode and the light-emitting layer, and an electron-transporting region may exist between the light-emitting layer and the cathode. Holes from the anode can migrate to the light-emitting layer through the hole transport region, and electrons from the cathode can migrate to the light-emitting layer through the electron transport region. Carriers (holes and electrons) recombine in the light-emitting layer to generate exci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D491/048C09K11/06H01L51/54H01L51/50
CPCC07D487/04C07D491/048C09K11/06C09K2211/1088C09K2211/1059C09K2211/1033C09K2211/1007C09K2211/1044H10K85/654H10K85/6574H10K85/6572H10K85/657H10K50/11
Inventor 徐浩杰殷梦轩陈海峰张兆超李崇
Owner JIANGSU SUNERA TECH CO LTD
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