Compound having pyrimidine ring structure and organic electroluminescent element

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...

Examples

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)...

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...

Examples

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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