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Pyrimidine derivative and organic electroluminescence element

一种嘧啶衍生物、致发光的技术，应用在电固体器件、电气元件、发光材料等方向，能够解决缺乏阻挡、缺乏稳定性空穴阻挡层、缺乏稳定性等问题，达到改善耐电流性、优异空穴阻挡能力、改善最大亮度的效果

Active Publication Date: 2017-11-28
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, in the thin film state, BCP lacks stability and still cannot be considered to function sufficiently as a hole blocking layer
[0013] As described above, either material still lacks stability or lacks the function of blocking holes to a sufficient degree when it is formed into a film

Method used

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  • Pyrimidine derivative and organic electroluminescence element
  • Pyrimidine derivative and organic electroluminescence element
  • Pyrimidine derivative and organic electroluminescence element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0194]

[0195] Synthesis of 2-(biphenyl-4-yl)-4-phenyl-6-{4’-(pyridin-3-yl)biphenyl-4-yl}pyrimidine;

[0196]

[0197] It was added to a reaction vessel purged with nitrogen, heated and stirred at 80°C for 12 hours to prepare a reaction solution. The reaction solution was cooled to room temperature, and the organic layer was collected by a liquid separation operation. Then, the solution was concentrated under reduced pressure to obtain a crude product, followed by purification by column chromatography (carrier: silica gel, eluent: ethyl acetate / heptane), and then, by recrystallization by using a mixed solvent of tetrahydrofuran / acetone. Obtain 3.0g of 2-(biphenyl-4-yl)-4-phenyl-6-{4'-(pyridin-3-yl)biphenyl-4-yl)pyrimidine (compound 1) as a white powder Rate, 30%).

[0198]

[0199] The structure of the obtained white powder was identified by NMR. Figure 24 show 1 The result of H-NMR measurement. by 1 H-NMR(CDCl 3 ) The following 27 hydrogen signals were detected.

[0200] δ(ppm...

Embodiment 2

[0206]

[0207] Synthesis of 2-{4-(naphthalene-1-yl)phenyl}-4-phenyl-6-{4’-(pyridin-3-yl)biphenyl-4-yl}pyrimidine;

[0208] In addition to using

[0209] {4-(Naphthalene-1-yl)phenyl}boronic acid

[0210] Use instead

[0211] Other than 4-biphenylboronic acid,

[0212] The reaction was carried out under the same conditions as in Example 1.

[0213] As a result, 1.6 g of 2-{4-(naphthalen-1-yl)phenyl}-4-phenyl-6-{4'-(pyridin-3-yl)biphenyl-4-yl}pyrimidine (compound 2) White powder (yield, 15%).

[0214]

[0215] The structure of the obtained white powder was identified by NMR. Figure 25 show 1 The result of H-NMR measurement. by 1 H-NMR(CDCl 3 ) The following 29 hydrogen signals were detected.

[0216] δ(ppm)=9.00-8.81(3H)

[0217] 8.65(1H)

[0218] 8.51-8.28(4H)

[0219] 8.11-7.32(21H)

Embodiment 3

[0220]

[0221] Synthesis of 2,4-bis(phenanthrene-9-yl)-6-{4’-(pyridin-3-yl)biphenyl-4-yl}pyrimidine;

[0222] In addition to using

[0223] 2-chloro-4-(phenanthrene-9-yl)-6-{4’-(pyridin-3-yl)biphenyl-4-yl}pyrimidine

[0224] Use instead

[0225] 2-chloro-4-phenyl-6-{4’-(pyridin-3-yl)biphenyl-4-yl}pyrimidine,

[0226] and use

[0227] Phenanthrene-9-boric acid

[0228] Use instead

[0229] Other than 4-biphenylboronic acid,

[0230] The reaction was carried out under the same conditions as in Example 1.

[0231] As a result, 1.2 g of white powder of 2,4-bis(phenanthrene-9-yl)-6-{4'-(pyridin-3-yl)-biphenyl-4-yl}pyrimidine (compound 29) was obtained (yield Rate, 14%).

[0232]

[0233] The structure of the obtained white powder was identified by NMR. Figure 26 show 1 The result of H-NMR measurement. by 1 H-NMR(CDCl 3 ) The following 31 hydrogen signals were detected.

[0234] δ(ppm)=9.05-8.35(14H)

[0235] 8.25-7.52(15H)

[0236] 7.45-7.35(2H)

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Abstract

The present invention provides a pyrimidine derivative represented by formula (1). The pyrimidine derivative is a novel compound that (1) has good electron injection characteristics, (2) has fast electronic movement speed, (3) has excellent hole-blocking ability, (4) is stable in a thin film state, and (5) has excellent heat resistance.

Description

Technical field [0001] The present invention relates to compounds suitable for manufacturing organic electroluminescent devices and organic electroluminescent devices (hereinafter generally referred to as organic EL devices). More specifically, the present invention relates to pyrimidine derivatives and organic EL devices using the pyrimidine derivatives. Background technique [0002] Organic EL devices are self-luminous devices, which have higher brightness and higher visibility than liquid crystal devices, can realize clear display, and therefore have been actively studied. [0003] In 1987, C.W. Tang and others of Eastman Kodak Corporation have developed a device including a laminated structure of various materials that share their respective roles, and have put organic EL devices using organic materials into practical use. The above organic EL device is constructed by laminating a layer of a phosphor capable of transporting electrons and a layer of an organic substance capable...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C09K11/06H01L51/50
CPCC07D401/10C09K11/06C07D471/04C09K2211/1011C09K2211/1007C09K2211/1044C09K2211/1029H10K85/615H10K85/654H10K50/11H10K50/16H10K50/171H10K50/18H10K50/00H10K50/81H10K50/82H10K71/164H10K2101/10
Inventor 横山纪昌林秀一北原秀良崔圣根金是仁金志泳吴贤珠
Owner HODOGOYA CHEMICAL CO LTD
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