US 2025/0084047 A1 · COMPOUND, ORGANIC ELECTROLUMINESCENT ELEMENT, AND ELECTRONIC DEVICE

1:

A compound represented by a formula (1A) below,
where, in the formula (1A):
one of R4 to R5 and R10 to R12 is a group represented by a formula (1B) above;
R1 to R3, R9, and R4 to R5 and R10 to R12 not being the group represented by the formula (1B) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
R901, R902, R903, R904, R905, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different;
and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different,
in the formula (1B):
n1 is 0 or an integer of 1 or more;
when n1 is an integer of 1 or more, L1 is an unsubstituted arylene group having 6 to 50 ring carbon atoms, an arylene group having 10 to 50 ring carbon atoms and fused with two or more substituted or unsubstituted rings, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
an unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring;
when two or more L1 are present, the two or more L1 are mutually the same or different;
Ar1 is an aryl group fused with four or more substituted or unsubstituted rings, or a heterocyclic group fused with four or more substituted or unsubstituted rings;
and
* represents a bonding position to a benz[a]anthracene ring in the formula (1A), and
at least one of R1 to R12 in the formula (1A), L1 or Ar1 in the formula (1B) has at least one deuterium atom, and when only L1 has at least one deuterium atom, the at least one deuterium atom is bonded to a ring that is of rings forming L1 and directly bonded to a benz[a]anthracene ring in the formula (1A).

19 more elements

11:

The compound according to claim 1, wherein Ar1 is a group represented by a formula (1B-1), (1B-2), (1B-3) or (1D) below,
where, in the groups represented by the formulae (1B-1), (1B-2), and (1B-3):
n1 is 0, 1, 2, or 3;
when n1 is 1, 2, or 3, L1 is an unsubstituted arylene group having 6 to 50 ring carbon atoms, an arylene group having 10 to 50 ring carbon atoms and fused with two or more substituted or unsubstituted rings, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
an unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring;
and
when two or more L1 are present, the two or more L1 are mutually the same or different,
in the formula (1B-1):
at least one combination of adjacent two or more of R51 to R54, R57, and R61 to R64 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R51 to R54, R57, and R61 to R64 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
and
* represents a bonding position to a benz[a]anthracene ring in the formula (1A),
in the formula (1B-2):
at least one combination of adjacent two or more of R51 to R53, R56, R57, and R71 to R74 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R51 to R53, R56, R57, and R71 to R74 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring each independently represent the same as R51 to R54, R57, and R61 to R64 in the formula (1B-1);
and
* represents a bonding position to a benz[a]anthracene ring in the formula (1A),
in the formula (1B-3):
at least one combination of adjacent two or more of R51 to R55 and R81 to R84 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R51 to R55 and R81 to R84 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring each independently represent the same as R51 to R54, R57 and R61 to R64 in the formula (1B-1);
and
* represents a bonding position to a benz[a]anthracene ring in the formula (1A), and
in the formula (1D), one of R21 to R30 represents a bonding position to a benz[a]anthracene ring in the formula (1A), and at least one combination of adjacent two or more of R21 to R30 not being the bonding position in the formula (1D) are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R21 to R30 not being the bonding position to a benz[a]anthracene ring in the formula (1A) and forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring in the formula (1D) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
R901, R902, R903, R904, R905, R906, and R907 in a group represented by each of the formulae (1B-1), (1B-2), (1B-3), and (1D) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R906 are present, the plurality of R906 are mutually the same or different;
and
when a plurality of R907 are present, the plurality of R907 are mutually the same or different.

30 more elements

16:

An organic electroluminescence device comprising:
an anode;
a cathode;
and
an emitting region provided between the anode and the cathode, wherein
the emitting region comprises a first emitting layer and a second emitting layer,
the first emitting layer comprises a first compound represented by a formula (100A) below, and
the second emitting layer comprises a second compound,
where, in the formula (100A):
one of R101 to R112 is a group represented by a formula (100B) above;
R101 to R112 except the group represented by the formula (100B) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
R901, R902, R903, R904, R905, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different;
and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different,
in the formula (100B):
n101 is 0 or an integer of 1 or more;
when n101 is an integer of 1 or more, L101 is an unsubstituted arylene group having 6 to 50 ring carbon atoms, an arylene group having 10 to 50 ring carbon atoms and fused with two or more substituted or unsubstituted rings, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
and
an unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring;
when two or more L101 are present, the two or more L101 are mutually the same or different;
Ar101 is an aryl group fused with three or more substituted or unsubstituted rings, or a heterocyclic group fused with three or more substituted or unsubstituted rings;
* represents a bonding position to a benz[a]anthracene ring in the formula (100A);
and
at least one of R101 to R112 in the formula (100A), L101 or Ar101 in the formula (100B) has at least one deuterium atom, and when only L101 has at least one deuterium atom, the at least one deuterium atom is bonded to a ring that is of rings forming L101 and directly bonded to a benz[a]anthracene ring in the formula (100A).

27 more elements

28:

The organic electroluminescence device according to claim 16, wherein Ar101 is a group represented by a formula (1B-1), (1B-2), (1B-3) or (1D) below,
where, in the groups represented by the formulae (1B-1), (1B-2), and (1B-3):
n1 is 0, 1, 2, or 3;
when n1 is 1, 2, or 3, L1 is an unsubstituted arylene group having 6 to 50 ring carbon atoms, an arylene group having 10 to 50 ring carbon atoms and fused with two or more substituted or unsubstituted rings, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
an unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring;
and
when two or more L1 are present, the two or more L1 are mutually the same or different,
in the formula (1B-1):
at least one combination of adjacent two or more of R51 to R54, R57, and R61 to R64 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R51 to R54, R57, and R61 to R64 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
and
* represents a bonding position to a benz[a]anthracene ring in the formula (100A),
in the formula (1B-2):
at least one combination of adjacent two or more of R51 to R53, R56, R57, and R71 to R74 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R51 to R53, R56, R57, and R71 to R74 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring each independently represent the same as R51 to R54, R57, and R61 to R64 in the formula (1B-1);
and
* represents a bonding position to a benz[a]anthracene ring in the formula (100A),
in the formula (1B-3):
at least one combination of adjacent two or more of R51 to R55 and R81 to R84 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R51 to R55 and R81 to R84 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring each independently represent the same as R51 to R54, R57 and R61 to R64 in the formula (1B-1);
and
* represents a bonding position to a benz[a]anthracene ring in the formula (100A), and
in the formula (1D), one of R21 to R30 represents a bonding position to a benz[a]anthracene ring in the formula (100A), and at least one combination of adjacent two or more of R21 to R30 not being the bonding position in the formula (1D) are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R21 to R30 not being the bonding position to a benz[a]anthracene ring in the formula (100A) and forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring in the formula (1D) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
R901, R902, R903, R904, R905, R906, and R907 in a group represented by each of the formulae (1B-1), (1B-2), (1B-3), and (1D) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R906 are present, the plurality of R906 are mutually the same or different;
and
when a plurality of R907 are present, the plurality of R907 are mutually the same or different.

30 more elements

Compound, organic electroluminescent element, and electronic device

Life of this patent

Compound, organic electroluminescent element, and electronic device

Life of this patent

Abstract

Claims33