Compounds taking dibenzo nitrogen-containing six-membered heterocycle as core and application of compounds to organic light-emitting device

A technology of six-membered heterocycles and compounds, applied in the application field of organic electroluminescent devices, can solve problems such as disparity

Pending Publication Date: 2020-10-09
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Compounds taking dibenzo nitrogen-containing six-membered heterocycle as core and application of compounds to organic light-emitting device
  • Compounds taking dibenzo nitrogen-containing six-membered heterocycle as core and application of compounds to organic light-emitting device
  • Compounds taking dibenzo nitrogen-containing six-membered heterocycle as core and application of compounds to organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Embodiment 1: the synthesis of compound 2:

[0089]

[0090] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol intermediate B1, 1×10 -4 molPd(PPh 3 ) 4 , 100mL of toluene and 50mL of ethanol were stirred and mixed, 0.03mol of sodium carbonate was dissolved in 50mL of water, and then the aqueous solution of sodium carbonate was added to the reaction system, heated to 110°C, and refluxed for 24 hours. Sampling and pointing plates showed that there was no raw material A1 remaining. The reaction was complete; naturally cooled to room temperature, filtered, the filtrate was separated, the organic phase was taken, and subjected to vacuum rotary evaporation (-0.09MPa, 85° C.), and purified by a neutral silica gel column to obtain the target compound 2 with a HPLC purity of 99.1%. Yield 72.8%;

[0091] Elemental analysis structure (molecular formula C 49 h 31 NO 2 ): theoretical value C, 88.40; H, 4.69; N, 2.10; 0, 4.8...

Embodiment 2

[0092] Embodiment 2: the synthesis of compound 16:

[0093]

[0094] The preparation method of compound 16 is the same as that in Example 1, except that raw material A1 is replaced by raw material A2, and intermediate B1 is replaced by intermediate B2.

[0095] Elemental analysis structure (molecular formula C 59 h 41 NO 3 ): theoretical value C, 87.27; H, 5.09; N, 1.73; 0, 5.91; test value: C, 87.26; H, 5.08; N, 1.72; ESI-MS(m / z)(M + ): The theoretical value is 811.31, and the measured value is 811.62.

Embodiment 3

[0096] Embodiment 3: the synthesis of compound 26:

[0097]

[0098] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A3, 0.012mol intermediate B3, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 1×10 -4 molPd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, heated to 110°C, refluxed for 24 hours, sampled and spotted on the plate, it showed that no raw material A3 remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C ), purified through a neutral silica gel column to obtain the target product compound 26, with an HPLC purity of 98.5% and a yield of 65.1%;

[0099] Elemental analysis structure (molecular formula C 62 h 39 NO 2 ): theoretical value C, 89.72; H, 4.74; N, 1.69; 0, 3.86; test value: C, 89.74; H, 4.73; N, 1.68; ESI-MS(m / z)(M + ): The theoretical value is 829.30, and the measured valu...

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Abstract

The invention discloses compounds taking a dibenzo nitrogen-containing six-membered heterocycle as a core and application of the compounds to an organic light-emitting device. The compounds contain adibenzo nitrogen-containing six-membered heterocyclic structure, have very strong rigidity, and have the characteristics of difficult crystallization among molecules, difficult aggregation and good film-forming property after being connected with a five-membered heterocyclic derivative structure. The compounds disclosed by the invention have double polarities, branched chains are electron-donatinggroups, and the HOMO energy levels of the material are different due to different electron-donating capacities of the groups, so that the compounds can be used as different functional layer materials. In addition, the compounds provided by the invention have a high triplet state energy level, can effectively block energy loss, and are beneficial to energy transfer. Therefore, after the compoundsdisclosed by the invention are applied to OLED devices as organic electroluminescent functional layer materials, the current efficiency, the power efficiency and the external quantum efficiency of thedevices are greatly improved; and meanwhile, the service lifetime of the devices is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with a dibenzonitrogen-containing six-membered heterocycle as the core and its application in organic electroluminescent devices. Background technique [0002] At present, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, compared with actual product application requirements, the luminous efficiency and service life of OLED devices Further improvement is needed. Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to realize the continuous improvement of the performance of OLED devices, not only the innovation of OLED device structure and manufacturing process is required, bu...

Claims

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Application Information

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IPC IPC(8): C07D221/18C07D401/04C07D401/10C07D405/04C07D405/10C07D405/14C07D413/04C07D471/04C07D471/10C07D487/04C07D491/048C07D491/052C07D491/056C07D491/107C07D493/04C07D498/04C07D498/10C07D519/00H01L51/54
CPCC07D491/048C07D519/00C07D405/14C07D405/04C07D405/10C07D493/04C07D498/04C07D401/04C07D487/04C07D401/10C07D221/18C07D413/04C07D471/04C07D491/056C07D491/052C07D491/107C07D471/10C07D498/10H10K85/623H10K85/624H10K85/622H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 李崇张宇阳谢丹丹吴秀芹
Owner JIANGSU SUNERA TECH CO LTD
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