Back to results
US 2025/0040433 A1Published application
Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
AssigneeIdemitsu Kosan Co., Ltd.
InventorsSayaka MIZUTANI, Takayasu SADO
Life of this patent
Estimating the term…
Abstract
An organic EL device includes an anode, an emitting layer, an electron transporting zone and a cathode in this sequence, in which the electron transporting zone contains an aromatic heterocyclic derivative represented by a formula (1) below. In the formula (1), X1 to X3 are a nitrogen atom or CR1, and A is represented by a formula (2) below. In the formula (2), L1 is s single bond or a linking group, and HAr is represented by a formula (3) below. In the formula (3), Y1 is an oxygen atom, a sulfur atom or the like, and one of X11 to X18 is a carbon atom bonded to L1 by a single bond and the rest of X11 to X18 are a nitrogen atom or CR13.
Claims28
(canceled)
2:
- An aromatic heterocyclic derivative represented by a formula (1),
- wherein
- X1 to X3 are a nitrogen atom or CR1, with a proviso that two or three of X1 to X3 are each a nitrogen atom,
- R1 independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
- A is represented by a formula (2),
- (HAr)a-L1- (2)
- wherein
- HAr is represented by a formula (3),
- a is an integer of 1 to 5,
- when a is 1, L1 is a single bond or a divalent linking group,
- when a is in a range of 2 to 5, L1 is a trivalent to hexavalent linking group and a plurality of HAr are the same or different,
- the linking group is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a divalent to hexavalent residue induced from any one of a group formed by mutually bonding two or three of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- the mutually bonded groups are the same or different,
- wherein
- one of X14 and X15 is a carbon atom bonded to L1 by a single bond and the other of X14 and X15 is a nitrogen atom or CR13;
- X11, X12, X13, X16, X17 and X18 are each independently a nitrogen atom, or CR13,
- Y1 is an oxygen atom, a sulfur atom, or SiR11R12,
- R11 and R12 represent the same as R1 in the formula (1);
- R11 and R12 are the same or different;
- R13 independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;
- a plurality of R13 are mutually the same or different;
- adjacent R13 optionally bond to each other to form a ring, and
- Ar1 and Ar2 each are independently represented by the formula (2), or represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
20 more elements
3:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), a is an integer of 1 to 3.
4:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), a is 1 or 2.
5:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), a is 1.
6:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), a is 1 and L1 is a linking group which is a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
7:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), L1 is a single bond.
8:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (3), Y1 is an oxygen atom or a sulfur atom.
9:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), a is 2 and L1 is a linking group which is a trivalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a trivalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
10:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (3),
- Y1 is an oxygen atom or a sulfur atom,
- one of X14 and X15 is a carbon atom bonded to L1 by a single bond and the other of X14 and X15 is CR13, and
- X11, X12, X13, X16, X17 and X18 are each CR13.
1 more element
11:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (1), two of X1 to X3 are each a nitrogen atom.
12:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (1), X1, X2, and X3 are each a nitrogen atom.
13:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), L1 is a divalent or trivalent residue induced from any one of benzene, biphenyl, terphenyl, naphthalene and phenanthrene.
14:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (1), Ar1 and Ar2 are each independently represented by the formula (2), or represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
15:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (1), Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
16:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (1), Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.
17:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (1), Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.
18:
- The aromatic heterocyclic derivative according to claim 2, wherein
- in the formula (3), R13 each independently represent a hydrogen atom, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
19:
- The aromatic heterocyclic derivative according to claim 2, wherein
- in the formula (1), R1 each independently represent a hydrogen atom, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
20:
- The aromatic heterocyclic derivative according to claim 2, wherein
- a substituent for the “substituted or unsubstituted” group is an aryl group, heterocyclic group, alkyl group, halogen atom, alkylsilyl group, arylsilyl group, or cyano group.
21:
- The aromatic heterocyclic derivative according to claim 2, wherein in the formula (2), a is 1 or 2,
- when a is 1, L1 is a single bond or a divalent linking group,
- when a is 2, L1 is a trivalent linking group,
- the linking group is a divalent or trivalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent or trivalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- in the formula (3),
- Y1 is an oxygen atom or a sulfur atom,
- one of X14 and X15 is a carbon atom bonded to L1 by a single bond and the other of X14 and X15 is CR13, and
- X13, X12, X13, X16, X17 and X18 are each CR13.
5 more elements
22:
- The aromatic heterocyclic derivative according to claim 2, wherein at least one hydrogen atom is deuterium.
23:
- An organic-EL-device material comprising the aromatic heterocyclic derivative according to claim 2.
24:
- An organic electroluminescence device comprising the aromatic heterocyclic derivative according to claim 2.
25:
- The organic electroluminescence device according to claim 24, wherein the organic electroluminescence device has an emitting layer which contains a host material and a dopant material.
26:
- The organic electroluminescence device according to claim 25, wherein the dopant material is a fluorescent dopant material.
27:
- The organic electroluminescence device according to claim 25, wherein the dopant material is a phosphorescent dopant material.
28:
- The organic electroluminescence device according to claim 24, wherein the organic electroluminescence device has an electron transporting zone which contains the aromatic heterocyclic derivative.
Dependencies are inferred from the claim text.