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Boron-containing organic electroluminescent compound and application to OLED device

A technology of electroluminescent devices and compounds, which is applied in the field of semiconductors, can solve the problems of low external quantum efficiency, large difference, and low internal quantum efficiency, and achieve the effects of improving device efficiency, color purity, and device life.

Active Publication Date: 2017-03-01
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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.
[0008] At present, the research on fluorescent materials has made considerable progress, which can meet the needs of industrialization; traditional organic fluorescent materials can only use 25% singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25 %), resulting in external quantum efficiency generally lower than 5%; especially in the blue light lifetime, there are still huge challenges

Method used

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  • Boron-containing organic electroluminescent compound and application to OLED device
  • Boron-containing organic electroluminescent compound and application to OLED device
  • Boron-containing organic electroluminescent compound and application to OLED device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 (Compound 01)

[0055]

[0056] The concrete synthetic route of this compound is provided now:

[0057]

[0058] 250ml four-necked bottle, under nitrogen protection, add 0.01mol intermediate A, 0.025mol phenylboronic acid, 0.05g pd (pph 3 ) 4 (tetraphenyltriphenylphosphine palladium), 60ml each of toluene, ethanol, and water, heated and refluxed for 20 hours, and the reaction was complete; naturally cooled, filtered, and the filtrate was rotary evaporated, and passed through a silica gel column, with toluene:ethanol=2:1 (volume ratio ) mixed solvent for beating, and a white solid was obtained after recrystallization, the purity (HPLC) was 97.8%, and the yield was 66.6%.

[0059] Elemental analysis structure (molecular formula C 39 h 35 B): theoretical value C, 91.04; H, 6.86; N, 2.10;

[0060] Test values: C, 90.92; H, 6.95; N, 2.13.

Embodiment 2

[0061] Example 2 (Compound 08)

[0062]

[0063] The concrete synthetic route of this compound is provided now:

[0064]

[0065] 250ml four-neck flask, under nitrogen protection, add 0.01mol intermediate A, 0.025mol dibenzofuran-4-boronic acid, 0.05g pd (pph 3 ) 4 (tetraphenyltriphenylphosphine palladium), 60ml each of toluene, ethanol, and water, heated and refluxed for 20 hours, and the reaction was complete; naturally cooled, filtered, and the filtrate was rotary evaporated, and passed through a silica gel column, with toluene:ethanol=2:1 (volume ratio ) mixed solvent for beating, and recrystallized to obtain a white solid with a purity (HPLC) of 98.3% and a yield of 64.6%.

[0066] Elemental analysis structure (molecular formula C 51 h 39 BO 2 ): theoretical value C, 88.18; H, 5.66; B, 1.56; O, 4.61

[0067] Test value: C, 88.25H, 5.53; B, 1.49; O, 4.73

Embodiment 3

[0068] Example 3 (compound 10)

[0069]

[0070] The concrete synthetic route of this compound is provided now:

[0071]

[0072] In a 250ml four-neck flask, under nitrogen protection, add 0.01mol of intermediate A, 0.025mol of bis(3,4-dimethylphenyl)amine, 0.03mol of sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 200ml toluene, heated to reflux for 20 hours, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, passed through a silica gel column, beaten with a mixed solvent of toluene:ethanol=3:1 (volume ratio), and recrystallized A white solid was obtained with a purity (HPLC) of 97.6% and a yield of 64.5%.

[0073] Elemental analysis structure (molecular formula C 59 h 61 BN 2 ): theoretical value C, 87.60; H, 7.60; N, 3.46; B, 1.34

[0074] Test value: C, 87.54; H, 7.54; N, 3.61; B, 1.31

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Abstract

The invention discloses a boron-containing efficient organic electroluminescent compound and application of the compound to an OLED device. The structural formula of the compound is as shown in the general formula (1). Boron atom as the core extends outward three six-membered rings composed of carbon-carbon single bonds, wherein the carbon-carbon single bonds also can be replaced with carbon-oxygen and carbon-nitrogen bonds; a benzene ring is sandwiched between each two six-membered rings; and each phenyl ring is respectively externally connected to hydrogen, aryl group, heteroaryl group, alkyl group, alkyloxy group, or arylamine group. The material has good fluorescence quantum efficiency and electroluminescent efficiency, is easy to form an amorphous film, and has good heat stability. Thus, the material can be used as a luminescent layer material in an organic electroluminescent device.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to the synthesis of a fluorescent compound and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] Currently, 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 the actual product application requirements, the luminous efficiency and service life of OLED devices need to be further improved. [0004] The OLED light-emitting device is like a sandwich structure, including e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F5/02C07F5/027C09K2211/188C09K2211/1096C09K2211/1092C09K2211/1088C09K2211/1044C09K2211/104C09K2211/1037C09K2211/1033C09K2211/1029C09K2211/1022C09K2211/1014C09K2211/1011C09K2211/1007H10K85/636H10K85/626H10K85/633H10K85/615H10K85/631H10K85/322H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 叶中华李崇王立春张兆超徐凯于凯朝
Owner JIANGSU SUNERA TECH CO LTD
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