Organic electroluminescent material, the process for preparing the same and OLED device using the same
The present invention provides an organic electroluminescent material, the process for preparing same and an OLED device using same. The organic electroluminescent material has a general formula (I): wherein, each of R 1 , R 2 , R 3 and R 4 is independently selected from the group consisting of H, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, ether groups and aromatic amino groups; each of Z is carbon atom or each of Z is nitrogen atom; R is carbazolyl, wherein, n is an integer ranging from 1 to 3 when each of Z is carbon atom, and n is an integer ranging from 1 to 2 when each of Z is nitrogen atom. The organic electroluminescent material of the invention can be used as emitting layer material in an OLED device and improve the luminescent efficiency and lifetime of the device. The luminescence spectral peakmay be adjusted by changing the group on the molecular structure.
1. An organic electroluminescent material having general formula (I):
wherein:
each of R 1 , R 2 , R 3 and R 4 is independently selected from the group consisting of H, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, ether groups and aromatic amino groups;
each of Z is carbon atom or each of Z is nitrogen atom; and
R is carbazolyl,
wherein, n is an integer ranging from 2 to 3 when each of Z is carbon atom, and n is an integer ranging from 1 to 2 when each of Z is nitrogen atom.
2. The organic electroluminescent material according to claim 1 , wherein each of R 1 and R 2 is independently selected from the group consisting of H, C 1 -C 20 alkoxy, C 1 -C 20 alkyl and ether groups, and each of R 3 and R 4 is independently selected from the group consisting of H, C 1 -C 20 alkyl, C 1 -C 20 alkoxy and aromatic amino groups.
3. The organic electroluminescent material according to claim 1 , wherein each of Z is carbon atom; n is 3; each of R 1 and R 2 is independently selected from the group consisting of alkoxythienyl, alkoxybithiennyl, alkoxyterphenyl, alkoxyperylenyl, alkoxystyryl, alkoxyphenylethynyl, and 7-alkoxypyrenyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, 4-(N,N-diphenyl)phenyl, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a red luminescent material.
4. The organic electroluminescent material according to claim 1 , wherein each of Z is nitrogen atom; n is 2; each of R 1 and R 2 is independently selected from the group consisting of methoxy-6-pyrenyl, methoxychrysenyl, methoxyphenanthryl, methoxybenzophenanthryl, methoxybenzoanthryl, methoxyquinacridonyl, and 5-methoxynaphthacenyl-p-phenyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a green luminescent material.
5. The organic electroluminescent material according to claim 1 , wherein each of Z is nitrogen atom; n is 1; each of R 1 and R 2 is independently selected from the group consisting of methoxyphenyl, phenoxyphenyl, methoxy-1-naphthyl, methoxy-2-naphthyl, methoxy-1-anthryl, methoxy-2-anthryl, methoxyfluorenyl, methoxyspirobifluorenyl, 6-methoxypyrenyl, and 3,6-dimethoxy-N-carbazolyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a blue luminescent material.
6. A process for preparing the organic electroluminescent material as defined in claim 1 , including the following steps:
a) subjecting the compound indicated by formula (II) to a boration to form The compound indicated by formula (III),
b) reacting the compound indicated by formula (III) with the compound indicated by formula (IV) in the presence of a metal catalyst, to obtain the organic electroluminescent material indicated by formula (I),
wherein:
each of R 1 , R 2 , R 3 and R 4 is independently selected from the group consisting of H, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, ether groups and aromatic amino groups;
B is boron atom;
each of Z is carbon atom or each of Z is nitrogen atom; and
R is carbazolyl, wherein, n is an integer ranging from 2 to 3 when each of Z is carbon atom, and n is an integer ranging from 1 to 2 when each of Z is nitrogen atom.
7. The process according to claim 6 , wherein the metal catalyst is palladium catalyst.
8. The process according to claim 6 , wherein each of R 1 and R 2 is independently selected from the group consisting of H, C 1 -C 20 alkoxy, C 1 -C 20 alkyl and ether groups, and each of R 3 and R 4 is independently selected from the group consisting of H, C 1 -C 20 alkyl, alkoxy and aromatic amino groups.
9. The process according to claim 6 , wherein each of Z is carbon atom; n is 3; each of R 1 and R 2 is independently selected from the group consisting of alkoxythienyl, alkoxybithiennyl, alkoxyterphenyl, alkoxyperylenyl, alkoxystyryl, alkoxyphenylethynyl, and 7-alkoxypyrenyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, 4-(N,N-diphenyl)phenyl, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a red luminescent material.
10. The process according to claim 6 , wherein each of Z is nitrogen atom; n is 2; each of R 1 and R 2 is independently selected from the group consisting of methoxy-6-pyrenyl, methoxychrysenyl, methoxyphenanthryl, methoxybenzophenanthryl, methoxybenzoanthryl, methoxyquinacridonyl, and 5-methoxynaphthacenyl-p-phenyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a green luminescent material.
11. The process according to claim 6 , wherein each of Z is nitrogen atom; n is 1; each of R 1 and R 2 is independently selected from the group consisting of methoxyphenyl, phenoxyphenyl, methoxy-1-naphthyl, methoxy-2-naphthyl, methoxy-1-anthryl, methoxy-2-anthryl, methoxyfluorenyl, methoxyspirobifluorenyl, 6-methoxypyrenyl, and 3,6-dimethoxy-N-carbazolyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a blue luminescent material.
12. An OLED device having a light emitting layer, said light emitting layer is made of an organic electroluminescent material as defined in claim 1 .
13. The OLED device according to claim 12 , wherein each of R 1 and R 2 is independently selected from the group consisting of H, C 1 -C 20 alkoxy, C 1 -C 20 alkyl and ether groups, and each of R 3 and R 4 is independently selected from the group consisting of H, C 1 -C 20 alkyl, C 1 -C 20 alkoxy and aromatic amino groups.
14. The OLED device according to claim 12 , wherein each of Z is carbon atom; n is 3; each of R 1 and R 2 is independently selected from the group consisting of alkoxythienyl, alkoxybithiennyl, alkoxyterphenyl, alkoxyperylenyl, alkoxystyryl, alkoxyphenylethynyl, and 7-alkoxypyrenyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, 4-(N,N-diphenyl)phenyl, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a red luminescent material.
15. The OLED device according to claim 12 , wherein each of Z is nitrogen atom; n is 2; each of R 1 and R 2 is independently selected from the group consisting of methoxy-6-pyrenyl, methoxychrysenyl, methoxyphenanthryl, methoxybenzophenanthryl, methoxybenzoanthryl, methoxyquinacridonyl, and 5-methoxynaphthacenyl-p-phenyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a green luminescent material.
16. The OLED device according to claim 12 , wherein each of Z is nitrogen atom; n is 1; each of R 1 and R 2 is independently selected from the group consisting of methoxyphenyl, phenoxyphenyl, methoxy-1-naphthyl, methoxy-2-naphthyl, methoxy-1-anthryl, methoxy-2-anthryl, methoxyfluorenyl, methoxyspirobifluorenyl, 6-methoxypyrenyl, and 3,6-dimethoxy-N-carbazolyl; and each of R 3 and R 4 is independently selected from the group consisting of H, straight and branched C 1 -C 8 alkyl, straight and branched C 1 -C 8 alkoxy, diphenylamino, N-phenylnaphthyl-2-amino, dinaphthylamino, N-phenylpyridin-2-amino, N-phenylpyrenyl-1-amino, N-phenylpyrenyl-2-amino, N-phenylbiphenyl-4-amino, N-phenylphenanthryl-2-amino, and N-phenylanthryl-2-amino; and the organic electroluminescent material is a blue luminescent material.