# US 2014/0151647 A1 · Material for organic electroluminescence device and organic electroluminescence device

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- Number: US 2014/0151647 A1
- Document ID: US20140151647A1
- Status: Published application
- Kind: A1
- Application number: 13/705,686
- Filed: 2012-12-05
- Published: 2014-06-05
- Earliest claimed: 2011-12-05
- Inventors: Yumiko MIZUKI; Mitsunori Ito; Tetsuya Inoue; Kumiko Hibino; Kazuki Nishimura
- Web page: https://patentgrep.com/patent/US20140151647A1

## CPC

- H10K 50/121: {for assisting energy transfer, e.g. sensitization}
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- H05B 33/20: characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL

## Abstract

An organic electroluminescence device employing a specific biscarbazole derivative having a cyano group as a first host and a compound having both a carbazole structure and a nitrogen-containing aromatic heteroring as a second host. The organic electroluminescence device has a prolonged lifetime.

## Claims

### Claim 1

An organic electroluminescence device which comprises a light emitting layer which is disposed between a cathode and an anode and comprises a first host material, a second host material and a light emitting material,
wherein
the first host material is represented by formula (A):
wherein
each of A1 and A2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms
m represents an integer of 0 to 3;
each of X1 to X8 and Y1 to Y8 independently represents N or CRa;
each of Ra independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon 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 silyl group, a halogen atom, or a cyano group, provided that when two or more Ra groups exist, the Ra groups may be the same or different and one of X5 to X8 and one of Y1 to Y4 are bonded to each other via A3; and
the formula (A) satisfies at least one of the following requirements (i) to (v):
(i) at least one of A1 and A2 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms;
(ii) at least one of X1 to X4 and Y5 to Y8 represents CRa, and at least one of Ra in X1 to X4 and Y5 to Y8 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms;
(iii) m represents an integer of 1 to 3 and at least one of A3 represents a cyano-substituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted divalent heterocyclic group having 5 to 30 ring atoms;
(iv) at least one of X5 to X8 and Y1 to Y4 represents CRa, and at least one of Ra in X5 to X8 and Y1 to Y8 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms; and
(v) at least one of X1 to X8 and Y1 to Y8 represents C—CN; and
the second host material is represented by formula (1):
wherein
Z1 represents a ring structure fused to a side a and represented by formula (1-1) or (1-2), and Z2 represents a ring structure fused to a side b and represented by formula (1-1) or (1-2), provided that at least one of Z1 and Z2 is represented by formula (1-1):
in formula (1-1),
a side c is fused to the side a or b of formula (1);
in formula (1-2),
any one of sides d, e and f is fused to the side a or b of formula (1);
in formulae (1-1) and (1-2),
X11 represents a sulfur atom, an oxygen atom, N—R19, or C(R20)(R21);
each of R11 to R21 independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon 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, provided that adjacent groups of R11 to R21 may be bonded to each other to forma a ring;
M1 represent a substituted or unsubstituted nitrogen-containing aromatic heteroring having 5 to 30 ring atoms;
L1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring atoms, or a group in which the preceding groups are directly linked to each other; and
k represents 1 or 2.

### Claim 2 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the first host material satisfies at least one of the requirements (i) and (ii).

### Claim 3 (depends on 1)

The organic electroluminescence device according to claim 1, wherein A3 of formula (A) represents a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring carbon atoms or a substituted or unsubstituted divalent monocyclic heterocyclic group having 6 or less ring atoms.

### Claim 4 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the second host material is represented by formula (2):
wherein
Z1 represents a ring structure fused to the side a and represented by formula (1-1) or (1-2), and Z2 represents a ring structure fused to the side b and represented by formula (1-1) or (1-2), provided that at least one of Z1 and Z2 is represented by formula (1-1);
L1 is as defined in formula (1);
each of X12 to X14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R31 or L1, provided that at least one of X12 to X14 represents a nitrogen atom;
each of Y11 to Y13 independently represents CH or a carbon atom bonded to R31 or L1;
each of R31 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon 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;
when two or more R31 groups exist, the R31 groups may be the same or different and adjacent R31 groups may be bonded to each other to form a ring;
k represents 1 or 2, and n represents an integer of 0 to 4;
the side c of formula (1-1) is fused to the side a or b of formula (2); and
any one of sides d, e and f of formula (1-2) is fused to the side a or b of formula (2).

### Claim 5 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the second host material is represented by formula (3):
wherein
L1 is as defined in formula (1);
each of X12 to X14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R31 or L1, provided that at least one of X12 to X14 represents a nitrogen atom;
each of Y11 to Y13 independently represents CH or a carbon atom bonded to R31 or L1;
each of R31 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon 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;
when two or more R31 groups exist, the R31 groups may be the same or different and adjacent R31 groups may be bonded to each other to form a ring;
n represents an integer of 0 to 4;
each of R41 to R48 independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon 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; and
adjacent groups of R41 to R48 may be bonded to each other to form a ring.

### Claim 6 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the first host material satisfies only the requirement (i).

### Claim 7 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the second host material is represented by formula (4):
wherein
L1 is as defined in formula (1);
each of X12 to X14 independently represents a nitrogen atom, CH, or a carbon atom bonded to R31 or L1, provided that at least one of X12 to X14 represents a nitrogen atom;
each of Y11 to Y13 independently represents CH or a carbon atom bonded to R31 or L1;
each of R31 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon 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;
when two or more R31 groups exist, the R31 groups may be the same or different and adjacent R31 groups may be bonded to each other to form a ring;
n represents an integer of 0 to 4;
each of L2 and L3 independently represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a cycloalkylene group having 5 to 30 ring atoms, or a group in which the preceding groups are directly linked to each other;
each of R51 to R54 independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon 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;
when two or more R51 groups exist, the R51 groups may be the same or different and adjacent R51 groups may be bonded to each other to form a ring;
when two or more R52 groups exist, the R52 groups may be the same or different and adjacent R52 groups may be bonded to each other to form a ring;
when two or more R53 groups exist, the R53 groups may be the same or different and adjacent R53 groups may be bonded to each other to form a ring;
when two or more R54 groups exist, the R54 groups may be the same or different and adjacent R54 groups may be bonded to each other to form a ring;
M2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and
each of p and s independently represents an integer of 0 to 4, and each of q and r independently represents an integer of 0 to 3.

### Claim 8 (depends on 1)

The organic electroluminescence device according to claim 1, wherein at least one of A1 and A2 represents a cyano-substituted phenyl group, a cyano-substituted naphthyl group, a cyano-substituted phenanthryl group, a cyano-substituted dibenzofuranyl group, a cyano-substituted dibenzothiophenyl group, a cyano-substituted biphenyl group, a cyano-substituted terphenyl group, a cyano-substituted 9,9-diphenylfluorenyl group, a cyano-substituted 9,9′-spirobi[9H-fluorene]-2-yl group, a cyano-substituted 9,9′-dimethylfluorenyl group, or a cyano-substituted triphenylenyl group.

### Claim 9 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the light emitting material comprises a phosphorescent emitting material selected from ortho metallated complexes of a metal selected from iridium (Ir), osmium (Os), and platinum (Pt).

### Claim 10 (depends on 1)

The organic electroluminescence device according to claim 1, wherein a peak of emission wavelength of the phosphorescent emitting material is 490 nm or longer and 700 nm or shorter.