9,10-bis[2-(p-substituted phenyl)pyrimidin-4-yl] anthracene compounds, methods of preparing the same, organic electroluminescent devices and organic electroluminescent display apparatus

Patent metadata

Field	Value
Publication number	US-9716235-B2
Application number	US-201314361699-A
Country	US
Kind code	B2
Filing date	Nov 6, 2013
Priority date	Jul 9, 2013
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

The invention relates to organic electroluminescent materials and provides 9,10-bis[2-(p-substituted phenyl)pyrimidin-4-yl] anthracene compounds and methods of preparing the same, organic electroluminescent devices comprising the compounds, and organic electroluminescent display apparatus comprising the devices. The compounds of the invention are easy to be synthesized and can be used as blue-phosphorescent organic electroluminescent materials. Due to the inherent ability of the materials to block holes, there is no need to arrange a hole-blocking layer between a light-emitting layer and an electron transport layer, which simplifies the manufacturing process of full color display panels of organic electroluminescent display apparatus and reduces the manufacture cost and time. The organic electroluminescent devices made from the materials exhibit high luminous efficiency.

First claim

What is claimed is:

1. A 9,10-bis[2-(p-substituted phenyl)pyrimidin-4-yl] anthracene compound, characterized by having the following formula:

wherein R1 and R2, which is identical or different, are each individually selected from:
hydrogen, carboxyl, cyano, nitro,
paraffinic alkyl having 1 to 20 carbon atoms,
cyclic alkyl having 3 to 20 carbon atoms,
paraffinic alkoxyl having 1 to 20 carbon atoms,
aromatic hydrocarbyl having 6 to 50 ring carbon atoms,
aryloxy having 5 to 50 ring atoms, and
an ester group having 2 to 20 carbon atoms.

2. The compound according to claim 1 , characterized in that R1 and R2 are each individually selected from:
C1-C20 paraffinic alkyl, optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano, nitro, pyrrolyl, naphthyl, and substituted or unsubstituted phenyl, wherein the substituted phenyl refers to a benzene ring substituted by methyl, hydroxyl, halogen, amino, carboxyl, cyano or nitro;
C3-C20 cyclic alkyl, optionally substituted by 1 to 3 substituents selected from C1-C4 alkyl, hydroxyl, halogen, amino, carboxyl, cyano and nitro;
C1-C20 paraffinic alkyl-O—, in which the C1-C20 paraffinic alkyl is optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano, nitro, pyrrolyl, naphthyl, and substituted or unsubstituted phenyl, wherein the substituted phenyl refers to a benzene ring substituted by methyl, hydroxyl, halogen, amino, carboxyl, cyano or nitro;
aromatic hydrocarbyl having 6 to 50 ring carbon atoms, optionally substituted by C1-C4 linear or branched alkyl, or by phenyl substituted with C1-C4 linear or branched alkyl;
aromatic hydrocarbonoxy having 6 to 50 ring carbon atoms, in which the aromatic hydrocarbon carbon ring is optionally substituted by C1-C4 linear or branched alkyl, or by phenyl substituted with C1-C4 linear or branched alkyl;
heteroaromatic hydrocarbonoxy having 5 to 50 ring atoms, in which the heteroaromatic hydrocarbon ring comprises at least one unsaturated double bond and heteroatom selected from O, N and S, and the ring carbon atom of the heteroaromatic hydrocarbon ring is optionally substituted by C1-C4 linear or branched alkyl, or by phenyl substituted with C1-C4 linear or branched alkyl; and
C1-C19 alkyl-OC(O)—, in which the C1-C19 alkyl is linear, branched, or cyclic alkyl optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano and nitro.

3. The compound according to claim 2 , characterized in that
the aromatic hydrocarbyl having 6 to 50 ring carbon atoms is selected from phenyl, a polybenzene ring group in which 2-8 benzene rings are connected by single bond(s), or a fused ring group in which 2-10 benzene rings are fused at two or more positions;
the aromatic hydrocarbyl of the aromatic hydrocarbonoxy having 6 to 50 ring carbon atoms is selected from phenyl, a polybenzene ring group in which 2-8 benzene rings are connected by single bond(s), or a fused ring group in which 2-10 benzene rings are fused at two or more positions; and
the heteroaromatic hydrocarbon ring of the heteroaromatic hydrocarbonoxy having 5 to 50 ring atoms comprises one or two heteroatom(s) selected from O, N and S and at least two unsaturated double bonds.

4. The compound according to claim 2 , characterized in that R1 and R2 are each individually selected from:
C1-C12 linear alkyl or C3-C12 branched alkyl, optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano, nitro, pyrrolyl, naphthyl, and substituted or unsubstituted phenyl, wherein the substituted phenyl refers to a benzene ring substituted by methyl, hydroxyl, halogen, amino, carboxyl, cyano or nitro;
C3-C12 cyclic alkyl, optionally substituted by 1 to 3 substituents selected from C1-C4 alkyl, hydroxyl, halogen, amino, carboxyl, cyano and nitro;
C1-C12 paraffinic alkyl-O—, in which the C1-C12 paraffinic alkyl is optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano, nitro, pyrrolyl, naphthyl, and substituted or unsubstituted phenyl, wherein the substituted phenyl refers to a benzene ring substituted by methyl, hydroxyl, halogen, amino, carboxyl, cyano or nitro;
aromatic hydrocarbyl having 6 to 30 ring carbon atoms selected from phenyl, a polybenzene group in which 2-5 benzene rings are connected by single bond(s), or a fused group in which 2-8 benzene rings are fused at two or more positions, wherein the phenyl, the polybenzene group or the fused group is optionally substituted by C1-C4 linear or branched alkyl;
aromatic hydrocarbonoxy having 6 to 30 ring carbon atoms, in which the aromatic hydrocarbyl is selected from phenyl, a polybenzene group in which 2-5 benzene rings are connected by single bond(s), or a fused group in which 2-8 benzene rings are fused at two or more positions, wherein the phenyl, the polybenzene group or the fused group is optionally substituted by C1-C4 linear or branched alkyl;
heteroaromatic hydrocarbonoxy having 5 to 20 ring atoms, in which the heteroaromatic hydrocarbon ring comprises one or two heteroatom(s) selected from O, N and S and at least two unsaturated double bonds, and the ring carbon atom of the heteroaromatic hydrocarbon ring is optionally substituted by C1-C4 linear or branched alkyl; and
C1-C12 alkyl-OC(O)—, in which the C1-C12 alkyl is linear, branched, or cyclic alkyl optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano and nitro.

5. The compound according to claim 4 , characterized in that R1 and R2 are each individually selected from:
C1-C8 linear alkyl or C3-C8 branched alkyl, optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano, nitro, pyrrolyl, naphthyl, and substituted or unsubstituted phenyl, wherein the substituted phenyl refers to a benzene ring substituted by methyl, hydroxyl, halogen, amino, carboxyl, cyano or nitro;
C3-C8 cyclic alkyl, optionally substituted by 1 to 3 substituents selected from C1-C4 alkyl, hydroxyl, halogen, amino, carboxyl, cyano and nitro;
C1-C8 paraffinic alkyl-O—, in which the C1-C8 paraffinic alkyl is optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carboxyl, cyano, nitro, pyrrolyl, naphthyl, and substituted or unsubstituted phenyl, wherein the substituted phenyl refers to a benzene ring substituted by methyl, hydroxyl, halogen, amino, carboxyl, cyano or nitro;
phenyl, a polybenzene group in which 2-4 benzene rings are connected by single bond(s), or a fused group in which 2-5 benzene rings are fused at two or more positions, wherein the phenyl, the polybenzene group or the fused group is optionally substituted by C1-C4 linear or branched alkyl;
phenyl-O—, a polybenzene group-O—, or a fused group-O—, wherein the polybenzene group is a group in which 2-4 benzene rings are connected by single bond(s), the fused group is a group in which 2-5 benzene rings are fused at two or more positions, and the phenyl, the polybenzene group or the fused group is optionally substituted by C1-C4 linear or branched alkyl;
heteroaromatic hydrocarbonoxy having 5 to 14 ring atoms, in which the heteroaromatic hydrocarbon ring comprises one or two heteroatom(s) selected from O, N and S and at least two unsaturated double bonds, and the ring carbon atom of the heteroaromatic hydrocarbon ring is optionally substituted by C1-C4 linear or branched alkyl; and
C1-C8 alkyl-OC(O)—, in which the C1-C8 alkyl is linear, branched, or cyclic alkyl optionally substituted by 1 to 3 substituents selected from hydroxyl, halogen, amino, carbo

Assignees

• Boe Technology Group Co Ltd

Inventors

• Li Na
• Li Yansong
• Huangfu Lujiang

Classifications

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title

• H01L51/5096

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• C07C249/02

  of compounds containing imino groups · CPC title