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Organic light emitting device, carbonyl bridged triarylamine derivative and application of carbonyl bridged triarylamine derivative

A carbonyl bridged, triarylamine technology, applied in the field of organic electroluminescence devices, achieves the effects of low preparation cost, flexible derivatization methods, and simple synthesis

Inactive Publication Date: 2019-03-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In order to take into account the luminous performance and transmission performance, based on sp 3 The aromatic amine of the hybrid nitrogen atom and the electron-deficient carbonyl group are usually used in organic light-emitting materials as donor and acceptor units respectively, but their free-rotating single bonds lead to more vibrational energy levels in the material, plus in The intramolecular charge transfer between the various parts of the excited state leads to a broad emission peak when the material returns to the ground state from the excited state

Method used

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  • Organic light emitting device, carbonyl bridged triarylamine derivative and application of carbonyl bridged triarylamine derivative
  • Organic light emitting device, carbonyl bridged triarylamine derivative and application of carbonyl bridged triarylamine derivative
  • Organic light emitting device, carbonyl bridged triarylamine derivative and application of carbonyl bridged triarylamine derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The synthesis of embodiment 1 compound C-001

[0063]

[0064] The preparation method of formula i1 compound is: add 4.8g (15mmol) methyl 2-iodoisophthalate, 2.71g (16mmol) diphenylamine, 2.49g (18mmol) salt of wormwood, 0.19g ( 3mmol) of activated copper powder and 100mL o-dichlorobenzene, degas the reaction system, then protect it with argon, stir and heat to 180°C and continue the reaction for 48h. After the reaction is complete, cool the system to room temperature, filter under reduced pressure and wash the filter residue with dichloromethane. After the filtrate is spin-dried, use dichloromethane:petroleum ether=1:1 (volume ratio) eluent on a silica gel column Separation and purification were carried out to obtain 4.53 g of light yellow-green oily liquid with a yield of 83.5%. MS(EI):m / z 361.12[M + ].

[0065] The preparation method of the compound of formula i2 is: in a 250mL round-bottomed flask, 3.61g (10mmol) i1, 2.0g (50mmol) sodium hydroxide are dissolve...

Embodiment 2

[0067] The synthesis of embodiment 2 compound C-026a

[0068]

[0069] The synthesis of formula i3 compound: add 4.31g (15mmol) 2-bromo-5-methyl isophthalic acid methyl esters, 2.71g (16mmol) diphenylamine, 2.49g (18mmol) potassium carbonate successively in 250mL round bottom flask, 0.19g (3mmol) activated copper powder and 100mL o-dichlorobenzene, degas the reaction system, then protect it with argon, stir and heat to 180°C and continue the reaction for 48h. After the reaction is complete, cool the system to room temperature, filter under reduced pressure and wash the filter residue with dichloromethane, spin the filtrate to dryness, and use dichloromethane:petroleum ether=3:2 (volume ratio) eluent Separation and purification were carried out to obtain 4.9 g of light yellow-green oily liquid with a yield of 87.1%. MS(EI):m / z 375.11[M + ].

[0070] The synthesis of formula i4 compound: in the round-bottomed flask of 100mL, under the condition of ice bath and light-shield...

Embodiment 3

[0074] The synthesis of embodiment 3 compound C-037a

[0075]

[0076] The preparation method of formula i7 compound is: add 5.98g (15mmol) 5-bromo-2-iodomethyl isophthalate, 2.71g (16mmol) diphenylamine, 2.49g (18mmol) potassium carbonate successively in 250mL round bottom flask , 0.19g (3mmol) of activated copper powder and 100mL of o-dichlorobenzene, degas the reaction system, then protect it with argon, stir and heat to 180°C and continue the reaction for 48h. After the reaction is complete, cool the system to room temperature, filter under reduced pressure and wash the filter residue with dichloromethane. After the filtrate is spin-dried, use dichloromethane:petroleum ether=1:1 (volume ratio) eluent on a silica gel column Separation and purification were carried out to obtain 4.73 g of light yellow solid with a yield of 71.6%. MS(EI):m / z 439.58[M+ ].

[0077] The preparation method of the compound of formula i8 is: in a 250mL round-bottomed flask, 4.39g (10mmol) i7, ...

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Abstract

The present invention relates to an organic light emitting device, a carbonyl bridged triarylamine derivative and application of the carbonyl bridged triarylamine derivative. The carbonyl bridged triarylamine derivative comprises compounds represented in the following formulas I and II shown in the description. In the formulas I and II, Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are each independently selected from one of an aromatic ring or aromatic heterocyclic ring with a carbon number being C6-C60 and substituted or unsubstituted by halogen, a cyano group, an alkyl group of 1-6 carbons, fluorinated alkyl of 1-6 cartons, an aromatic ring with the carbon atom number of C6-C30, an aromatic heterocyclic ring with a carbon atom number of C3-C30, and the like. The carbonyl bridged triarylamine derivative has electron-rich nitrogen atoms and electron-donating carbonyl groups and thus has bipolar transmission property, and meanwhile, since the rigid structure of the compound can effectively suppressvibration relaxation caused by molecular vibration and rotation, the compound has a narrow light emitting peak. The carbonyl bridged triarylamine derivative is applied to the organic light emitting device and is beneficial to balanced transmission of charge carriers, and therefore performance-excellent emitted light with high color purity is obtained.

Description

technical field [0001] The invention relates to an organic electroluminescent device, a carbonyl-bridged triarylamine derivative and an application thereof. Background technique [0002] Human beings have entered the information age in the 21st century, all kinds of information are growing exponentially, and the related information industry has also undergone tremendous changes. The Internet is gradually being replaced by the mobile Internet, and the era of the Internet of Things is coming. Information display is the most important symbol of this era. As the terminal of information transmission and the main medium of interaction between information and people, its development has attracted much attention. With the progress and development of society, the improvement of people's quality of life, and the change of way of thinking, various electronic information technologies have been integrated into every corner of human life. As a result, people's requirements for the perfor...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D471/16C07D471/22C09K11/06H01L51/54
CPCC09K11/06C07D471/04C07D471/16C07D471/22C09K2211/1029C09K2211/1007C09K2211/1059H10K85/654H10K85/6572
Inventor 廖良生袁熠蒋佐权
Owner SUZHOU UNIV
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