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Compound having pyrimidine ring structure and organic electroluminescent element

A technology of pyrimidine ring and compound, which is applied in the field of compounds with pyrimidine ring structure and organic electroluminescence elements, can solve the problems of insufficient film stability, insufficient hole blocking function, and inability to fully exert the function, etc.

Pending Publication Date: 2020-05-01
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, the low electron transport property is a major problem in TAZ, and it is necessary to combine with an electron transport material with higher electron transport property to produce an organic EL device (for example, refer to Non-Patent Document 5).
[0015] In addition, for BCP, although the work function is as high as 6.7eV and the hole blocking ability is high, because the glass transition temperature (Tg) is as low as 83°C, it lacks the stability of the film, and it cannot be used as a hole blocking layer. say fully functional
[0016] All materials have insufficient film stability or insufficient function of blocking holes

Method used

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  • Compound having pyrimidine ring structure and organic electroluminescent element
  • Compound having pyrimidine ring structure and organic electroluminescent element
  • Compound having pyrimidine ring structure and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0119]

[0120] 6-(biphenyl-4-yl)-2-chloro-4-(pyridin-3-yl)-pyrimidine: 7.5 g, 4-(phenanthrene-9-yl)-phenylboronic acid: 7.2g, four (triphenylphosphine) palladium (0): 0.5g, potassium carbonate: 6.0g, in toluene, ethanol, H 2 O mixed solvent under reflux and stirred overnight. After cooling naturally, the organic layer was extracted by a liquid separation operation, and then concentrated under reduced pressure. Purify the obtained crude product by column chromatography (carrier: silica gel, eluent: toluene / ethyl acetate) to obtain 6-(biphenyl-4-yl)-2-{4-(phenanthrene-9 White powder of -yl)-phenyl}-4-(pyridin-3-yl)-pyrimidine (compound-17): 1.5 g (yield 12%).

[0121] [chemical 6]

[0122]

[0123] The structure of the obtained white powder was identified using NMR.

[0124] use 1 H-NMR (CDCl 3 ) detected the following 27 hydrogen signals.

[0125] δ(ppm)=9.55(1H), 8.90(2H), 8.85(1H), 8.82(1H), 8.78(1H), 8.70(1H), 8.46(2H), 8.15(1H), 8.04(1H), 7.97(1H), 7.86(2H), 7...

Embodiment 2

[0127] Synthesis of

[0128] Charge 6-(biphenyl-4-yl)-2-chloro-4-(pyridin-3-yl)-pyrimidine in the reaction vessel: 5.0 g, 2-(9,9-diphenyl[9H]fluorene ) boric acid: 6.8g, tetrakis (triphenylphosphine) palladium (0): 0.3g, potassium carbonate: 2.4g, in toluene, ethanol, H 2 O mixed solvent under reflux and stirred overnight. After cooling naturally, the organic layer was extracted by a liquid separation operation, and then concentrated under reduced pressure. By purifying the obtained crude product by column chromatography (carrier: silica gel, eluent: toluene / ethyl acetate), 6-(biphenyl-4-yl)-2-(9,9-diphenyl Light gray brown powder of [9H]fluoren-2-yl)-4-(pyridin-3-yl)-pyrimidine (compound-26): 6.6 g (yield 73%).

[0129] [chemical 7]

[0130]

[0131] The structure of the obtained light gray-brown powder was identified using NMR.

[0132] use 1 H-NMR (DMSO-d6) detected the following 31 hydrogen signals.

[0133] δ(ppm)=9.63(1H), 8.81(2H), 8.77(1H), 8.69(2H), 8.58(2H...

Embodiment 3

[0135] Synthesis of

[0136] Charge 6-(biphenyl-4-yl)-2-chloro-4-(pyridin-3-yl)-pyrimidine in the reaction vessel: 7.0 g, 2-(9,9'-spirobis[9H]fluorene ) boric acid: 8.1g, tetrakis (triphenylphosphine) palladium (0): 0.5g, potassium carbonate: 3.4g, in toluene, ethanol, H 2 O mixed solvent under reflux and stirred overnight. After natural cooling, the organic layer was extracted by a liquid separation operation, and then concentrated under reduced pressure. Purify the obtained crude product by column chromatography (carrier: silica gel, eluent: dichloromethane / ethyl acetate) to obtain 6-(biphenyl-4-yl)-4-(pyridine-3- White powder of yl)-2-(9,9'-spirobis[9H]fluoren-2-yl)-pyrimidine (compound-27): 5.5 g (yield 43%).

[0137] [chemical 8]

[0138]

[0139] The structure of the obtained white powder was identified using NMR.

[0140] use 1 H-NMR (CDCl 3 ) detected the following 29 hydrogen signals.

[0141] δ(ppm)=9.37(1H), 8.85(1H), 8.75(1H), 8.46(1H), 8.26(2H), 8.06(1H)...

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Abstract

The purpose of the present invention is to provide: an organic compound which serves as a material for organic EL elements having high efficiency and high durability, and which has excellent characteristics such as excellent electron injection / transport performance, hole blocking ability, and high stability in a thin film state; and an organic EL element having high efficiency and high durability,which is obtained using the compound. A compound which is represented by general formula (1) and has a pyrimidine ring structure. (In the formula, A1 represents a substituted or unsubstituted aromatic heterocyclic group; Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensedpolycyclic aromatic group; Ar2 represents a deuterium atom, a trimethylsilyl group, a triphenylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; m represents an integer of 1-3; n represents an integer of 0-2; o represents an integer of 1-2; in cases where m is an integer of 2 or more, a plurality of Ar1 moieties bonded to a same pyrimidine ring may be the same as or different from each other; in cases where n is an integer of 2, a plurality ofAr2 moieties bonded to a same pyrimidine ring may be the same as or different from each other; in cases where o is the integer of 2, a plurality of A1 moieties bonded to a same pyrimidine ring may bethe same as or different from each other; the sum of the integers of m, n and o is 4 or less; and in cases where n is 0, Ar2 represents a hydrogen atom.)

Description

technical field [0001] The present invention relates to compounds and elements suitable for use in organic electroluminescence elements (hereinafter simply referred to as organic EL elements) as self-luminous elements suitable for various display devices. Specifically, it relates to compounds having a pyrimidine ring structure and using Organic EL elements of this compound. Background technique [0002] Since the organic EL element is a self-luminous element, it is brighter than a liquid crystal element, has excellent visibility, and can perform a clear display, so active research has been conducted. [0003] In 1987, C.W.Tang and others from Eastman Kodak developed a layered structure device in which various functions are distributed to each material, thus making the organic EL device using organic materials a practical device. . They layered a phosphor capable of transporting electrons and an organic substance capable of transporting holes, and injected the charges of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14C07D405/14C07D409/14C07D413/14C07D471/04C09K11/06H01L51/50H10K99/00
CPCC07D401/04H10K85/626H10K85/615H10K85/654H10K85/6572H10K50/16H10K50/18C07D401/14C07D405/14C07D409/14C07D413/14C07D471/04C09K11/06H10K50/171H10K50/11C07F7/0814H10K85/40H10K85/622H10K85/6574H10K85/6576
Inventor 加濑幸喜金是仁平山雄太骏河和行
Owner HODOGOYA CHEMICAL CO LTD
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