Compound taking dibenzo heptenone as core and application on organic light-emitting device (OLED) thereof

A technology for dibenzoheptenone and compounds, which is applied in the directions of organic chemistry, chemical instruments and methods, electrical components, etc., can solve the problems of low external quantum efficiency, low internal quantum efficiency, and disparity, etc., so as to improve the luminous efficiency and improve the Device Efficiency, Effect of Avoiding Aggregation

Active Publication Date: 2017-03-29
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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  • Compound taking dibenzo heptenone as core and application on organic light-emitting device (OLED) thereof
  • Compound taking dibenzo heptenone as core and application on organic light-emitting device (OLED) thereof
  • Compound taking dibenzo heptenone as core and application on organic light-emitting device (OLED) thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of Example 1 Compound 02

[0055]

[0056] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 3-bromodibenzoheptenone, 0.011mol intermediate a, 0.03mol sodium carbonate, 1×10 -4 mol tetrakis(triphenylphosphine) palladium, 50ml toluene, 50ml ethanol, 50ml water, heated to reflux for 20 hours, sampling point plate, complete reaction, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product, purity 98.40 %, yield 60.6%. Elemental analysis structure (molecular formula C 45 h 30 N 2 O): theoretical value C, 87.92; H, 4.92; N, 4.56; O, 2.60;

[0057] Test value: C, 87.86; H, 4.89; N, 4.60; O, 2.65

[0058] HPLC-MS: The molecular weight of the material is 614.73, and the measured molecular weight is 614.81.

Embodiment 2

[0059] Synthesis of Example 2 Compound 46

[0060]

[0061] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 2-bromodibenzoheptenone, 0.011mol intermediate b, 0.03mol sodium carbonate, 1×10 -4 mol tetrakis(triphenylphosphine) palladium, 50ml toluene, 50ml ethanol, 50ml water, heated to reflux for 20 hours, sampling point plate, complete reaction, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product, purity 98.60 %, yield 61.5%.

[0062] Elemental analysis structure (molecular formula C 57 h 39 N 3 O): theoretical value C, 87.55; H, 5.03; N, 5.37; O, 2.05;

[0063] Test value: C, 87.56; H, 4.95; N, 5.38; O, 2.11

[0064] HPLC-MS: The molecular weight of the material is 781.94, and the measured molecular weight is 781.87.

Embodiment 3

[0065] Synthesis of Example 3 Compound 48

[0066]

[0067] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 2-bromodibenzoheptenone, 0.011mol intermediate c, 0.03mol sodium carbonate, 1×10 -4 mol tetrakis(triphenylphosphine)palladium, 50ml toluene, 50ml ethanol, 50ml water, heated to reflux for 20 hours, sampling point plate, complete reaction, natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product, purity 99.20 %, yield 63.0%.

[0068] Elemental analysis structure (molecular formula C 67 h 41 N 3 O): theoretical value C, 87.42; H, 5.65; N, 5.01; O, 1.91;

[0069] Test value: C, 87.50; H, 5.61; N, 5.05; O, 1.84

[0070] HPLC-MS: The molecular weight of the material is 835.05, and the measured molecular weight is 835.10.

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Abstract

The invention discloses a compound taking a dibenzo heptenone skeleton as the core and an application on an organic light-emitting device thereof. The compound takes dibenzo heptenone as the core, a material is not liable to crystallization, and the compound has the characteristics of good film-forming property, heat stability and the like. Meanwhile, the material has a smaller energy difference of a triplet state and a singlet state, and triplet state energy can be made full use. When the compound is used as a luminescent layer doping material of the OLED, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved, and meanwhile, the service life of the device is prolonged obviously.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a dibenzoheptenone 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 electrode mat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88C07D209/86C07D405/12C07D409/12C07D405/14C07D409/14C07D413/04C07D417/04C07D403/04C07D401/04C07D413/12C07D401/12C07D417/12C07D413/14C07D417/14C07D401/14C07D491/048C07D495/04C07D487/04C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/86C07D209/88C07D401/04C07D401/12C07D401/14C07D403/04C07D405/12C07D405/14C07D409/12C07D409/14C07D413/04C07D413/12C07D413/14C07D417/04C07D417/12C07D417/14C07D487/04C07D491/048C07D495/04C09K2211/1029C09K2211/1037C09K2211/1033C09K2211/1092C09K2211/1088H10K85/6576H10K85/6572H10K85/6574H10K50/11
Inventor 叶中华李崇徐凯张小庆张兆超
Owner JIANGSU SUNERA TECH CO LTD
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