Cyclic azine compound, material for organic light emitting diode, electron transport material for organic light emitting diode, and organic light emitting diode
An object of the present invention is to provide a cyclic azine compound exhibiting both excellent driving voltage characteristics and excellent current efficiency characteristics. The desired cyclic azine compound has a specific structure represented by formula (1).
1 . A cyclic azine compound of formula (1):
wherein
Ar 1 is a phenyl group or a 4-biphenylyl group;
Ar 2 has one of formulas (2-1) to (2-3):
Ar 3 has one of formulas (3-2), (3-3), (3-5), (3-6), (3-7) and (3-9);
2 . The cyclic azine compound according to claim 1 , wherein
Ar 2 has one of formulas (2-1), (2-2a), (2-2b), (2-3a), and (2-3b)
3 . The cyclic azine compound according to claim 1 , wherein Ar 2 has formula (2-2b)
4 . The cyclic azine compound according to claim 1 , which has one of formulas (1-6), (1-15), (1-48), (1-51), (1-52), (1-54), (1-65), and (1-66):
5 . An organic light emitting diode, comprising:
an electron transport material comprising the cyclic azine compound of claim 1 .
6 . An organic light emitting diode, comprising:
an electron transport material comprising the cyclic azine compound of claim 2 .
7 . An organic light emitting diode, comprising:
an electron transport material comprising the cyclic azine compound of claim 3 .
8 . A method for producing a cyclic azine compound of formula (1), comprising:
reacting a compound of formula (4) with a compound of formula (3),
wherein
Ar 1 is a phenyl group or a 4-biphenylyl group;
Ar 2 has one of formulas (2-1) to (2-3):
and
Ar 3 has one of formulas (3-2), (3-3), (3-5), (3-6), (3-7), and (3-9):
X 4 is a leaving group; and
Y 4 is a halogen atom, a metal-containing group, or a boron-containing group.
9 . A pyridine compound of formula (5):
wherein
Art has one of formulas (2-1) to (2-3):
Ar 3 has one of formulas (3-2), (3-3), (3-5), (3-6), (3-7) and (3-9):
Y 4 is a halogen atom, a metal-containing group, or a boron-containing group.
10 . The pyridine compound according to claim 9 , which has one of formulas (5-1), (5-2) or (5-3)
wherein
in formula (5-1), Ar 31 is selected from the group consisting of unsubstituted phenyl, unsubstituted 2-biphenylyl, and unsubstituted 4-biphenylyl,
in formula (5-2), Ar 31 is unsubstituted phenyl,
in formula (5-3), Ar 31 is unsubstituted phenyl, and
Y 4 and Ar 2 are as defined in claim 9 .