Organic electroluminescent device
The organic EL device of the present invention has an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, and the hole transport layer contains an arylamine compound represented by the following general formula (1): where Ar 1 to Ar 4 each represent a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group.
1. An organic electroluminescent device having an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, wherein the hole transport layer contains an arylamine compound represented by the following formula (1):
where
Ar 1 represents an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted terphenylyl group, or a phenyl group having a naphthyl group as a substituent;
Ar 2 represents an unsubstituted phenyl group an unsubstituted biphenylyl group; and
Ar 3 and Ar 4 each represents an unsubstituted biphenylyl group, an unsubstituted terphenylyl group, a phenyl group having a naphthyl group or a fluorenyl group as a substituent, or a fluorenyl group having a methyl group or a phenyl group as a substituent.
2. The organic electroluminescent device according to claim 1 , wherein the electron transport layer contains an anthracene derivative represented by the following formula (2):
where
A represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a single bond,
B represents a monovalent aromatic heterocyclic group,
C represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group,
D represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms, and
p and q are such that p denotes an integer of 7 or 8, and q denotes an integer of 1 or 2, provided that p and q total 9.
3. The organic electroluminescent device according to claim 2 , wherein the anthracene derivative is represented by the following formula (2a):
where
A is as defined in the formula (2),
Ar 9 , Ar 10 , and Ar 11 each represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group,
R 1 to R 7 each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, or an aryloxy group, and these groups may bind to each other via a single bond, a methylene group optionally having a substituent, an oxygen atom, or a sulfur atom to form a ring, and
X 1 , X 2 , X 3 , and X 4 each represents a carbon atom or a nitrogen atom, provided that only one of X 1 , X 2 , X 3 , and X 4 represents a nitrogen atom, and any of R 1 to R 4 , including a hydrogen atom, does not bind to the nitrogen atom.
4. The organic electroluminescent device according to claim 2 , wherein the anthracene derivative is represented by the following formula (2b):
where
A is as defined in the formula (2), and
Ar 12 , Ar 13 , and Ar 14 each represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group.
5. The organic electroluminescent device according to claim 2 , wherein the anthracene derivative is represented by the following formula (2c):
where
A is as defined in the formula (2),
Ar 15 , Ar 16 , and Ar 17 each represents a monovalent aromatic hydrocarbon group or a monovalent aromatic heterocyclic group, and
R 8 represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, or an aryloxy group.
6. The organic electroluminescent device according to claim 1 , wherein
the hole transport layer has a two-layer structure having a first hole transport layer and a second hole transport layer, and
the second hole transport layer is located beside the luminous layer, and contains the arylamine compound.
7. The organic electroluminescent device according to claim 6 , wherein
the first hole transport layer contains a triarylamine derivative different from the arylamine compound contained in the second hole transport layer, and
the triarylamine derivative has a molecular structure comprising two triarylamine skeletons coupled together by a single bond or a divalent hydrocarbon group, and has 2 to 6 triarylamine skeletons in the entire molecule.
8. The organic electroluminescent device according to claim 7 , wherein the triarylamine derivative contained in the first hole transport layer is represented by the following formula (3):
where
r 9 , r 10 , r 13 , and r 14 each denotes an integer of 0 to 5,
r 11 and r 12 each denotes an integer of 0 to 4,
R 9 to R 14 each represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, or an aryloxy group and, if a plurality of these groups are present on an identical benzene ring, these groups may bind to each other via a single bond, a methylene group optionally having a substituent, an oxygen atom, or a sulfur atom to form a ring, and
L 1 represents a single bond, or a divalent group represented by the following structural formula (B), (C), (D), (E), (F), or (G):
where n1 denotes an integer of 1 to 4,
9. The organic electroluminescent device according to claim 7 , wherein the triarylamine derivative contained in the first hole transport layer is represented by the following formula (4):
where
r 15 , r 16 , r 19 , r 22 , and r 26 each denotes an integer of 0 to 5,
r 17 , r 18 , r 20 , r 21 , r 23 , and r 24 each denotes an integer of 0 to 4,
R 15 to R 26 each represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, or an aryloxy group and, if a plurality of these groups are present on an identical benzene ring, these groups may bind to each other via a single bond, a methylene group optionally having a substituent, an oxygen atom, or a sulfur atom to form a ring, and
L 2 , L 3 and L 4 each represent a single bond, or a divalent group represented by the following structural formula (B′), (C), (D), (E), (F) or (G):
where n2 denotes an integer of 1 to 3,
10. An arylamine compound represented by the following formula (1):
where
Ar 1 represents an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted terphenylyl group, or a phenyl group having a naphthyl group as a substituent;
Ar 2 represents an unsubstituted phenyl group an unsubstituted biphenylyl group; and
Ar 3 and Ar 4 each represents an unsubstituted biphenylyl group, an unsubstituted terphenylyl group, a phenyl group having a naphthyl group or a fluorenyl group as a substituent, or a fluorenyl group having a methyl group or a phenyl group as a substituent.
11. An organic electroluminescent device having an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, wherein the hole transport layer contains an arylamine compound represented by the following formula (1):
where
Ar 1 represents a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthrenyl group, or a fluorenyl group;
Ar 2 represents an unsubstituted phenyl group an unsubstituted biphenylyl group; and
Ar 3 and Ar 1 each represents an unsubstituted biphenylyl group, an unsubstituted terphenylyl group, a phenyl group having a naphthyl group or a fluorenyl group as a substituent, or a fluorenyl group having a methyl group or a phenyl group as a substituent,
wherein
the hole transport layer has a two-layer structure having a first hole transport layer and a second hole transport layer, and
the second hole transport layer is located beside the luminous layer, and contains the arylamine compound, wherein
the first hole transport layer contains a triarylamine derivative different from the arylamine compound contained in the second hole transport layer, and
the triarylamine derivative has a molecular structure comprising two triarylamine skeletons coupled together by a single bond or a divalent hydrocarbon group, and has 2 to 6 triarylamine skeletons in the entire molecule.
12. The organic electroluminescent device according to claim 11 , wherein the triarylamine derivative contained in the first hole transport layer is represented by the following formula (3):
where
r 9 , r 10 , r 13 , and r 14 each denotes an integer of 0 to 5,
r 11 and r 12 , each denotes an integer of 0 to 4,
R 9 to R 14 each represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, or an aryloxy group and, if a plurality of these groups are present on an identical benzene ring, these groups may bind to each other via a single bond, a methylene group optionally having a substituent, an oxygen atom, or a sulfur atom to form a ring, and
L 1 represents a single bond, or a divalent group represented by the following structural formula (B), (C), (D), (E), (F), or (G):
where n1 denotes an integer of 1 to 4,
13. The organic electroluminescent device according to claim 11 , wherein the triarylamine derivative contained in the first hole transport layer is represented by the following formula (4):
where
r 15 , r 16 , r 19 , r 22 , r 25 , and r 26 each denotes an integer of 0 to 5,
r 17 , r 18 , r 20 , r 21 , r 23 , and r 24 each denote an integer of 0 to 4,
R 15 to R 26 each represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, a monovalent aromatic hydrocarbon group, a monovalent aromatic heterocyclic group, or an aryloxy group and, if a plurality of these groups are present on an identical benzene ring, these groups may bind to each other via a single bond, a methylene group optionally having a substituent, an oxygen atom, or a sulfur atom to form a ring, and
L 2 , L 3 , and L 4 each represents a single bond, or a divalent group represented by the following structural formula (B′), (C), (D), (E), (F), or (G):
where n2 denotes an integer of 1 to 3,