# US 8,785,003 B2 · Material for organic electroluminescence device and organic electroluminescence device using the same

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- Number: US 8,785,003 B2
- Document ID: US8785003B2
- Status: Granted
- Kind: B2
- Application number: 13/041,071
- Filed: 2011-03-04
- Published: 2011-12-01
- Granted: 2014-07-22
- Earliest claimed: 2010-03-05
- Assignees: Idemtisu Kosan Co., Ltd.
- Applicants: Tetsuya Inoue; Kumiko Hibino; Kei Yoshida; Kazuki Nishimura; Toshihiro Iwakuma
- Inventors: Tetsuya Inoue; Kumiko Hibino; Kei Yoshida; Kazuki Nishimura; Toshihiro Iwakuma
- Web page: https://patentgrep.com/patent/US8785003B2

## CPC

- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- C07F 7/0812: {comprising a heterocyclic ring}
- C07F 7/0814: {said ring is substituted at a C ring atom by Si}
- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/14: Carrier transporting layers
- Y10S 428/917: Electroluminescent
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

An organic EL device material includes at least a unit including 3,5-biscarbazolylphenyl group, a unit including 4-carbazolylphenyl group, and a compound including a unit including a nitrogen-containing aromatic heterocyclic ring bonding the unit including 3,5-biscarbazolylphenyl group and the unit including 4-carbazolylphenyl group.

## Claims

### Claim 1

An organic EL device material comprising:
a unit comprising a 3,5-biscarbazolylphenyl group
a unit comprising a 4-carbazolylphenyl group; and
a compound comprising a unit comprising a nitrogen-containing aromatic heterocyclic ring bonding the unit comprising the 3,5-biscarbazolylphenyl group and the unit comprising the 4-carbazolylphenyl group, wherein the organic EL material is represented by a formula (4)
where: A1, A2 and A3 each represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 ring carbon atoms;
Cz1 to Cz3 each independently represent a substituted or unsubstituted carbazolyl group and is allowed to be mutually the same or different;
Y1 and Y2 each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted and linear, branched or cyclic alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 10 ring carbon atoms;
a represents an integer of 0 to 3 and b represents an integer of 0 to 4;
p and q each independently represent an integer of 0 to 3;
when p is 2 or more, A1 is allowed to be the same or different; and
when q is 2 or more, A2 is allowed to be the same or different

### Claim 2 (depends on 1)

An organic EL device comprising:
a cathode;
an anode; and
an organic thin-film layer provided between the cathode and the anode, the organic thin-film layer formed out of one or more layers comprising an emitting layer, wherein
at least one layer of the organic thin-film layer comprises the organic EL device material according to claim 1.

### Claim 3 (depends on 2)

The organic EL device according to claim 2, wherein the emitting layer comprises the organic EL device material as a host material.

### Claim 4 (depends on 2)

The organic EL device according to claim 2, wherein the emitting layer further comprises a phosphorescent material.

### Claim 5 (depends on 4)

The organic EL device according to claim 4, wherein the emitting layer comprises a host material and a phosphorescent material, the phosphorescent material being an ortho metalation of a complex of a metal atom selected from the group consisting of iridium (Ir), osmium (Os) and platinum (Pt).

### Claim 6 (depends on 2)

The organic EL device according to claim 2, wherein the organic thin-film layer comprises an electron injecting layer provided between the cathode and the emitting layer, the electron injecting layer comprising a nitrogen-containing cyclic derivative.

### Claim 7 (depends on 2)

The organic EL device according to claim 2, wherein the organic thin-film layer comprises an electron transporting layer provided between the cathode and the emitting layer, the electron transporting layer comprising the organic EL device material.

### Claim 8 (depends on 2)

The organic EL device according to claim 2, wherein a reduction-causing dopant is present at an interfacial region between the cathode and the organic thin-film layer.

### Claim 9 (depends on 2)

The organic EL device material according to claim 2, wherein each of Cz1 to Cz3 in the formula (4) is independently represented by a formula (5) or a formula (6) shown below
where: Y3 and Y4 each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted and linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 10 ring carbon atoms;
c and d each independently represent an integer of 1 to 4; and
“*” represents a bond position to a benzene ring
where: Y3′, Y4′ and Y5′ each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted and linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 10 ring carbon atoms;
c’ represents an integer of 1 to 4, d’ represents an integer of 1 to 3, and e’ represents an integer of 1 to 5; and
“*” represents a bond position to a benzene ring.

### Claim 10 (depends on 1)

The organic EL device material according to claim 1, wherein q=0 in the formula (4).

### Claim 11

An organic EL device material comprising:
a unit comprising a 3,5-biscarbazolylphenyl group;
a unit comprising a 4-carbazolylphenyl group; and
a compound comprising a unit comprising a nitrogen-containing aromatic heterocyclic ring bonding the unit comprising the 3,5-biscarbazolylphenyl group and the unit comprising the 4-carbazolylphenyl group, wherein the organic EL material is represented by a formula (1)
where: A1 and A2 each represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 ring carbon atoms;
Cz1 to Cz3 each independently represent a substituted or unsubstituted carbazolyl group and is allowed to be mutually the same or different;
X represents a substituted or unsubstituted nitrogen-containing aromatic heterocyclic ring selected from the group consisting of a substituted triazine ring, an unsubstituted triazine ring, a substituted indole ring and an unsubstituted indole ring;
Y1 and Y2 each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted and linear, branched or cyclic alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted and linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 10 ring carbon atoms;
a represents an integer of 0 to 3 and b represents an integer of 0 to 4;
1, m and n each independently represent an integer of 1 to 3;
when 1 is 2 or more, X is allowed to be the same or different;
m represents an integer of 1 to 3 as the number of substituent(s) being directly bonded to X and being represented by a formula (2) shown below;
when m is 2 or more, structures represented by the formula (2) is allowed to be the same or different;
n represents an integer of 1 to 3 as the number of substituent(s) being directly bonded to X and being represented by a formula (3) shown below;
when n is 2 or more, structures represented by the formula (3) is allowed to be the same or different;
p and q each independently represent an integer of 0 to 3;
when p is 2 or more, A1 is allowed to be the same or different; and
when q is 2 or more, A2 is allowed to be the same or different