US 2020/0052212 A1 · ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE

Abstract

An organic electroluminescence device having a further improved lifetime, which comprising a cathode, an anode and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises a fluorescent emitting layer and the fluorescent emitting layer comprises at least one dopant material selected from the compounds represented by formulae (D1) and (D2), at least one first compound selected from the compounds represented by formulae (19), (21), (22), and (23), and at least one second compound selected from the compounds represented by formulae (2a), (2b), and (2c) and an electronic device comprising the organic electroluminescence device are described.

An organic electroluminescence device comprising a cathode, an anode and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises a fluorescent emitting layer and the fluorescent emitting layer comprises:
at least one dopant material selected from the compounds represented by formulae (D1) and (D2);
at least one first compound selected from the compounds represented by formulae (19), (21), (22), and (23);
and
at least one second compound selected from the compounds represented by formulae (2a), (2b), and (2c):
wherein:
Z is CRA or N;
π1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 ring atoms;
π2 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 ring atoms;
RA, RB, and RC are each independently a hydrogen atom or a substituent, wherein the substituent is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an amino group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a group represented by —Si(R101)(R102)(R103), a group represented by —N(R104)(R105), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
R101 to R105 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
n and m are each independently an integer of 1 to 4;
adjacent two RA's are bonded to each other to form a substituted or unsubstituted ring structure or not bonded to each other, thereby failing to form a ring structure;
adjacent two RB's are bonded to each other to form a substituted or unsubstituted ring structure or not bonded to each other, thereby failing to form a ring structure;
and
adjacent two RC's are bonded to each other to form a substituted or unsubstituted ring structure or not bonded to each other, thereby failing to form a ring structure;
wherein:
a ring α, a ring β, and a ring γ are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 ring atoms;
Ra and Rb are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;
Ra may be bonded to one or both of the ring α and the ring β directly or via a linker;
and
Rb may be bonded to one or both of the ring α and the ring γ directly or via a linker;
wherein:
R101 to R110 are each independently a hydrogen atom or a substituent, wherein the substituent is as described above with respect to the substituent of RA, RB, and RC;
provided that at least one of R101 to R110 is -L-Ar;
each L is independently a single bond or a linker, wherein the linker is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms;
and
each Ar is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a monovalent group wherein two or more selected from the single ring and the fused ring are bonded to each other via a single bond;
wherein:
R201 to R212 are each independently a hydrogen atom or a substituent, wherein the substituent is as described above with respect to the substituent of RA, RB, and RC;
provided that at least one of R201 to R212 is -L2Ar21;
each L2 is independently a single bond or a linker, wherein the linker is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms;
and
each Ar21 is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a monovalent group wherein two or more selected from the single ring and the fused ring are bonded to each other via a single bond;
wherein:
R301 to R310 are each independently a hydrogen atom or a substituent, wherein the substituent is as described above with respect to the substituent of RA, RB, and RC;
provided that at least one of R301 to R310 is-L3-Ar31;
each L3 is independently a single bond or a linker, wherein the linker is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms;
and
each Ar31 is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a monovalent group wherein two or more selected from the single ring and the fused ring are bonded to each other via a single bond;
wherein:
R401 to R410 are each independently a hydrogen atom or a substituent, wherein the substituent is as described above with respect to the substituent of RA, RB, and RC;
provided that at least one of R401 to R410 is -L4-Ar41;
each L4 is each independently a single bond or a linker, wherein the linker is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms;
each Ar41 is independently a substituted or unsubstituted single ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a monovalent group wherein two or more selected from the single ring and the fused ring are bonded to each other via a single bond;
and
adjacent two selected from R401 and R402, R402 and R403, R403 and R404, R405 and R406, R406 and R407, and R407 and R408 may be bonded to each other to form a substituted or unsubstituted ring structure;
wherein:
Ar11, Ar22, and Ar33 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
L11, L22, and L33 are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms;
and
p, q, and r are each independently 0, 1, or 2, when p is 0, L11 is a single bond, when q is 0, L22 is a single bond, and when r is 0, L33 is a single bond;
wherein:
one selected from R71 to R78 is a single bond bonded to *a and one selected from R81 to R88 is a single bond bonded to *b;
R71 to R78 and R81 to R88 not the single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
adjacent two selected from R71 to R74 not the single bond, adjacent two selected from R75 to R78 not the single bond, adjacent two selected from R81 to R84 not the single bond, and adjacent two selected from R85 to R88 not the single bond may be bonded to each other to form a substituted or unsubstituted ring structure;
Ar44 and Ar55 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
L44, L55, and L66 are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms;
and
m4, m5, and m6 are each independently 0, 1, or 2, when m4 is 0, L44 is a single bond, when m5 is 0, L55 is a single bond, and when m6 is 0, L66 is a single bond;
(Ar80)(Ar81)N-(L80)—N(Ar82)(Ar83) (2c)
wherein:
Ar80 to Ar83 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
and
L80 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.

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Organic electroluminescent element and electronic device

Life of this patent

Organic electroluminescent element and electronic device

Life of this patent

Abstract

Claims25