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Miazines deviate and application thereof

A technology of pyrimidine derivatives, applied in the field of pyrimidine derivatives and their applications, can solve problems such as low efficiency and poor stability of blue light materials

Active Publication Date: 2018-07-17
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above defects or improvement needs of the prior art, the object of the present invention is to provide a pyrimidine derivative and its application, wherein the key chemical structure of the pyrimidine derivative is improved, and the pyrimidine derivative Used as an electroluminescent layer material in organic electroluminescent devices, compared with the prior art, it can effectively solve the problems of poor stability and low efficiency of blue light materials in organic electroluminescent devices.

Method used

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  • Miazines deviate and application thereof

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preparation example Construction

[0034] The preparation method of pyrimidine derivatives in the present invention comprises the following steps:

[0035] One, the synthesis of various intermediates needed for pyrimidine derivatives in the present invention:

[0036] Intermediates (1), (2) can adopt the following synthetic route:

[0037] (1):

[0038] (2):

[0039] Taking the synthesis of intermediate (1) (5H-benzofuro[3,2-c]carbazole) as an example, the following steps are included:

[0040] ① Preparation of 4-boronic acid dibenzofuran (dibenzo[b,d]furan-4-ylboronic acid):

[0041] 4-Bromodibenzofuran (1eq), add dry tetrahydrofuran solution, cool down to -78°C, replace N 2 Three times, to ensure the oxygen-free environment of the system, after adding n-butyllithium (2.5M, 1.1eq) dropwise, keep it at -78°C for 1.5h, then add triisopropyl borate (ρ=0.815g / ml, 1.1 eq), rise to room temperature after the dropwise addition, drop dilute hydrochloric acid to quench the reaction after 8h, distill off THF un...

Embodiment 1

[0080] Taking the asymmetric pyrimidine derivatives shown in formula 2 as an example, the following synthetic route is adopted:

[0081]

[0082] (E)-1-(2-bromophenyl)-3-phenyl-prop-2-en-1-one ((E)-1-(2-bromophenyl)-3-phenylprop-2-en-1 -one) preparation:

[0083] Add a solution of 7g of NaOH and 50ml of water into a 250ml three-neck flask, add 25g of ethanol, stir vigorously, then dropwise add 18.5g of o-bromobenzaldehyde (2-bromobenzaldehyde, 100mmol), and add dropwise 12g of benzene after 30 minutes. Acetophenone (acetophenone, 100mmol), stir at 15-30°C for 2-3h, until light yellow solid appears, stirring is difficult, filter, wash with water to remove alkali until neutral, then wash with ice ethanol, distill the filter cake to remove ethanol under reduced pressure , to obtain 26 g of yellow sticky solid, yield 90%;

[0084] Preparation of (2-bromophenyl)-2,6-diphenylpyrimidine (4-(2-bromophenyl)-2,6-diphenylpyrimidine):

[0085] (E)-1-(2-bromophenyl)-3-phenyl-prop-2-e...

Embodiment 2

[0090] Taking the asymmetric pyrimidine derivatives shown in formula 5 as an example, the following synthetic route is adopted:

[0091]

[0092] 5-(4-(6-Chloro-2-phenylpyrimidin-4-yl)phenyl)-5H-benzofuro[3,2-c]carbazole (5-(4-(6-chloro- Synthesis of 2-phenylpyrimidin-4-yl)phenyl)-5H-benzofuro[3,2-c]carbazole):

[0093] 3.77g (4-(5H-benzofuro[3,2-c]carbazol-5-yl)phenyl)boronate ((4-(5H-benzofuro[3,2-c]carbazol-5 -yl)phenyl)boronic acid) (10mmol, 1eq) and 9g (22mmol, 4eq) of 4,6-dichloro-2-phenylpyrimidine, replace N 2 three times at N 2 Add 0.16g (0.1mmol, 1%eq) of palladium tetraphenylphosphine under the protection of 2M K 2 CO 3 Aqueous solution, ethanol, toluene (volume ratio = 1:2:1), 100ml in total, react in an oxygen-free environment for 12h, remove ethanol and toluene by distillation under reduced pressure, dissolve in dichloromethane, wash the organic phase with water, extract the aqueous phase, anhydrous Magnesium sulfate was dried, filtered, and the filtrate ...

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Abstract

The invention discloses a miazines derivate and application thereof. The miazines derivate is provided with the structure shown as the formula (I), wherein R1, R2 and R3 are any one of alkyl groups with 1-60 carbon atoms, substituted and unsubstituted aromatic heterocyclic group, and substituted and unsubstituted aromatic ring groups. According to the miazines derivate, the key chemical structureand the like are improved, and the miazines derivate is used as an electroluminescence layer material to be used in an organic electroluminescence device. Compared with the prior art, the miazines derivate is capable of effectively solving the problems of low stability of a blue material in the organic electroluminescence device and low efficiency. The formula sees the description.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of organic photoelectric materials, and more specifically relates to a pyrimidine derivative and its application. The pyrimidine derivative (especially an asymmetric pyrimidine derivative) can be used in organic light-emitting diodes. Background technique [0002] Organic electroluminescence (OLED) has the advantages of thinness, self-luminescence, high contrast, easy to manufacture in large areas, and can be used in the fields of flexible and transparent display and lighting. It is known as "dream display" and the next generation of solid-state lighting technology. Since 1963, Professor Pope applied a bias voltage of hundreds of volts to the crystal of anthracene, and faint blue light will appear, but due to the high voltage and poor luminous efficiency, it has not attracted people's attention. In 1987, Deng Qingyun Ph.D. (C.W.Tang) and Steve VanSlyke made a multi-layer OLED d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D471/04C07D519/00C07D495/04C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/04C07D491/048C07D495/04C07D519/00C09K2211/1088C09K2211/1092C09K2211/1029C09K2211/1007C09K2211/1044H10K85/654H10K85/657H10K85/6572H10K50/00
Inventor 王磊张庆庄少卿
Owner HUAZHONG UNIV OF SCI & TECH
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