Imidazole ring-containing compound and organic electroluminescence display device
View Patent ↗The present invention is related to an imidazole ring-containing compound and an organic electroluminescence (EL) display device using the same. In particular, the imidazole ring-containing compound may be used alone or in combination with a dopant as a material for organic films such as an electroluminescent layer. The organic EL display device using an organic film made of the imidazole ring-containing compound has improved characteristics such as luminance, efficiency, driving voltage, and color purity.
1. An imidazole ring-containing compound, comprising:
where A is selected from the group consisting of
B is selected from the group consisting of
where X is; X′ is selected from the group consisting of CR and N; where each of R 1 through R 5 , R 11 , and R 12 is independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C4-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroacryl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 condensed polycyclic group, an amino group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a cyano group, a nitro group, a hydroxy group, a halogen atom, a substituted or unsubstituted C6-C30 arylsulfonyl group, and a substituted or unsubstituted C1-C30 alkylsulfonyl group, where adjacent groups among R 1 through R 5 , R 11 , and R 12 can combine together to form a substituted or unsubstituted C 2 -C 30 saturated or unsaturated ring; where each of R′ and R″, which are monosubstituted or multi-substituted groups, is selected from the group consisting of a hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C4-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroacryl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 condensed polycyclic group, an amino group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a cyano group, a nitro group, a hydroxy group, a halogen atom, a substituted or unsubstituted C6-C30 arylsulfonyl group, and a substituted or unsubstituted C1-C30 alkylsulfonyl group, and where R′ and R″ can combine together to form a saturated or unsaturated ring.
2. The imidazole ring-containing compound of claim 1 , further represented by:
where each of R 1 through R 5 are independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C4-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroacryl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 condensed polycyclic group, an amino group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a cyano group, a nitro group, a hydroxy group, a halogen atom, a substituted or unsubstituted C6-C30 arylsulfonyl group, and a substituted or unsubstituted C1-C30 alkylsulfonyl group, where adjacent groups among R 1 through R 5 , R 11 , and R 12 can combine together to form a substituted or unsubstituted C2-C30 saturated or unsaturated ring, both R 11 and R 12 are hydrogen or combine together to form a substituted or unsubstituted C2-C30 saturated or unsaturated ring, and both R′ and R″ are hydrogen.
3. An organic electroluminesence display device comprising an organic film between a pair of electrodes, wherein the organic film is composed of an imidazole ring-containing compound, comprising:
where A is selected from the group consisting of
B is selected from the group consisting of
where X is S; X′ is selected from the group consisting of CR and N; each of R 1 through R 11 , and R 12 is independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C4-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroacryl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 condensed polycyclic group, an amino group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a cyano group, a nitro group, a hydroxy group, a halogen atom, a substituted or unsubstituted C6-C30 arylsulfonyl group, and a substituted or unsubstituted C1-C30 alkylsulfonyl group, wherein adjacent groups among R 1 through R 5 , R 11 , and R 12 can combine together to form a substituted or unsubstituted C 2 -C 30 saturated or unsaturated ring;
where each of R′ and R″, which are monosubstituted or multi-substituted groups, is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C4-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroacryl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 condensed polycyclic group, an amino group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a cyano group, a nitro group, a hydroxy group, a halogen atom, a substituted or unsubstituted C6-C30 arylsulfonyl group, and a substituted or unsubstituted C1-C30 alkylsulfonyl group, wherein R′ and R″ can combine together to form a saturated or unsaturated ring.
4. The organic electroluminescence display device of claim 3 , wherein the organic film is an electroluminescent layer.
5. The organic electroluminescence display device of claim 4 , wherein the electroluminescent layer further comprises a phosphorescent or fluorescent dopant emitting visible range light.
6. The organic electroluminescence display device of claim 3 , wherein the organic film is a hole injecting layer or a hole transporting layer.
7. The organic electroluminescence display device of claim 3 , wherein the compound of Formula (1) is further represented by:
where each of R 1 through R 5 , R 11 , and R 12 is independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted C4-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroacryl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 condensed polycyclic group, an amino group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a cyano group, a nitro group, a hydroxy group, a halogen atom, a substituted or unsubstituted C6-C30 arylsulfonyl group, and a substituted or unsubstituted C1-C30 alkylsulfonyl group, wherein adjacent groups among R 1 through R 5 , R 11 , and R 12 can combine together to form a substituted or unsubstituted C2-C30 saturated or unsaturated ring, both R 11 and R 12 are hydrogen or combine together to form a substituted or unsubstituted C2-C30 saturated or unsaturated ring, and both R′ and R″ are hydrogen.