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Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices

An electroluminescence and compound technology, which is applied to boron-containing organic electroluminescence compounds and its application in organic electroluminescence devices, can solve the problem of difficult exciton utilization, high fluorescence radiation efficiency, low state radiation transition rate, problems such as large Stokes shift, to achieve the effect of small FWHM, enhanced thermally activated delayed fluorescence efficiency, and small Stokes shift

Inactive Publication Date: 2020-07-31
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) T of the designed molecule 1 and S 1 states have strong CT features, very small S 1 -T 1 state energy gap, although a high T can be achieved by the TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to low S 1 Therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the quenching effect of T exciton concentration, most devices made of TADF materials The efficiency roll-off is serious at high current density (3) The traditional TADF molecule, due to the space separation structure of D (electron donor group)-A (electron acceptor group), leads to its excited state molecule (S 1 ,T 1 ) has an increased degree of structural relaxation, which leads to its larger Stokes shift, which further leads to its larger FWHM (≥50nm) and lower luminous efficiency

Method used

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  • Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices
  • Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices
  • Boron-containing organic electroluminescent compound and application thereof on organic electroluminescent devices

Examples

Experimental program
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preparation example Construction

[0067] Preparation of Intermediate C

[0068] Preparation of Intermediate C-1:

[0069]

[0070] In a 250mL three-neck flask, under nitrogen protection, 0.02mol raw material A-1, 0.06mol raw material B-1, 0.10mol sodium tert-butoxide, 0.4mmol Pd 2 (dba) 3 Add 0.4mmol tri-tert-butylphosphine into 150mL toluene, stir and mix, heat to 110°C-120°C, reflux for 12h-16h, take a sample point plate, it shows that there is no raw material A-1 remaining, and the reaction is complete; naturally cool to room temperature, Filtration, the filtrate was rotary evaporated under reduced pressure to no fraction, and passed through a neutral silica gel column to obtain intermediate C-1, with an HPLC purity of 99.61% and a yield of 87.1%; elemental analysis structure (molecular formula C 46 h 48 Cl 2 N 2 ): theoretical value C, 78.95; H, 6.91; Cl, ​​10.13; N, 4.00; test value: C, 78.96; H, 6.93; Cl, ​​10.14; N, 4.02. ESI-MS (m / z) (M+): The theoretical value is 698.32, and the measured valu...

preparation Embodiment 1

[0080] Preparation Example 1: Synthesis of Compound 1

[0081]

[0082] Under nitrogen protection, 10 mmol of intermediate C-1 was added to 10 mL of dry, deoxygenated toluene, and 10 ml of n-butyllithium hexane solution (2.5 mol / L) was added at -78 ° C under stirring conditions, and After slowly rising to room temperature, 25ml of boron trichloride in toluene (1mol / L) was added dropwise for reflux reaction for 6h, followed by the addition of 4mmol of AlCl 3 , Continue to reflux for 18h, then add 30mmol raw material D-1 and reflux for 12h. The solvent in the reaction mixture was removed by rotary evaporator, the residue was cooled to room temperature, and dry n-hexane was used as eluent for chromatographic column purification to obtain the target compound 1, HPLC purity: 99.64%, yield 68.7%. Elemental analysis structure (molecular formula C 52 h 51 B 2 N 3 ): theoretical value C, 84.44; H, 6.95; B, 2.92; N, 5.68; test value: C, 84.46; H, 6.97; B, 2.93; N, 5.69. ESI-MS ...

preparation Embodiment 2

[0083] Preparation Example 2: Synthesis of Compound 8

[0084]

[0085] The preparation method of compound 14 is the same as in Example 1, except that intermediate C-1 is replaced by intermediate C-2; elemental analysis structure (molecular formula C 52 h 51 B 2 N 3 ): theoretical value C, 84.44; H, 6.95; B, 2.92; N, 5.68; test value: C, 84.45; H, 6.98; B, 2.91; N, 5.70. ESI-MS (m / z) (M+): theoretical value 739.43, found value 739.47.

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Abstract

The invention discloses a boron-containing organic electroluminescent compound and an application thereof on organic electroluminescent devices, and belongs to the technical field of semiconductors. The boron-containing organic electroluminescent compound has a structure shown in a general formula (1) shown in the specification. The invention also discloses an application of the boron-containing organic electroluminescent compound. The rigidity of groups of the compound is large, and the compound has the characteristics of difficult crystallization and aggregation among molecules, and good film-forming property. When the compound is used as a luminescent layer material of an organic electroluminescent device, the current efficiency, the power efficiency and the external quantum efficiencyof the device are greatly improved; meanwhile, the service life of the device is obviously prolonged; and the compound have a small singlet-triplet state energy level difference ([delta]Est), a smallStokes shift and a narrow FWHM.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a boron-containing organic electroluminescent compound and its application in organic electroluminescent devices. Background technique [0002] The application of organic light-emitting diodes (OLEDs) in large-area flat-panel displays and lighting has attracted extensive attention from both industry and academia. However, traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit coupling at the center of heavy atoms, the singlet and triplet excitons formed by electrical excitation can be effectively used to e...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/02H01L51/50H01L51/54
CPCC09K11/06C07F5/022C09K2211/1007C09K2211/104C09K2211/1029C09K2211/1088H10K85/654H10K85/657H10K85/6572
Inventor 李崇殷梦竹王芳叶中华张兆超
Owner JIANGSU SUNERA TECH CO LTD
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