# US 2014/0151670 A1 · Polycyclic compound and organic electronic device comprising the same

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- Number: US 2014/0151670 A1
- Document ID: US20140151670A1
- Status: Published application
- Kind: A1
- Application number: 14/126,760
- Filed: 2013-07-19
- Published: 2014-06-05
- Earliest claimed: 2012-07-19
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Dong Hoon Lee; Minyoung Kang; Jungi Jang; Boonjae Jang; Minseung Chun; Kidong Koo
- Web page: https://patentgrep.com/patent/US20140151670A1

## CPC

- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C07C 255/52: to carbon atoms of six-membered aromatic rings being part of condensed ring systems
- C07D 213/57: Nitriles
- C07D 217/14: other than aralkyl radicals
- C07D 221/12: Phenanthridines
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- C09K 11/06: containing organic luminescent materials
- H05B 33/10: Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/624: {containing six or more rings}
- 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}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C07C 2603/18: Fluorenes; Hydrogenated fluorenes
- C07C 2603/24: Anthracenes; Hydrogenated anthracenes
- C07C 2603/26: Phenanthrenes; Hydrogenated phenanthrenes
- C07C 2603/97: containing five-membered rings
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 50/165: comprising dopants
- H10K 50/171: {Electron injection layers}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

An exemplary embodiment of the present application provides a new compound and an organic electronic device using the same. The organic electronic device according to an exemplary embodiment of the present application shows excellent characteristics in terms of efficiency, driving voltage, and service life.

## Claims

### Claim 1

A compound represented by the following Formula 1:
in Formula 1,
R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms,
R3 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms,
at least one of R1 to R3 is a group of the following Formula 2,
X is O, S, or CRaRb,
Ra, Rb, R11, and R12 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms, and two or more adjacent groups among Ra, Rb, R11, and R12 are optionally bonded to each other to form a monocyclic or polycyclic ring,
L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted fluorenylene group; or a substituted or unsubstituted heteroarylene group including one or more of N, O, and S atoms, and
n and m are each independently an integer from 0 to 3.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulae 3 to 8:
in Formulae 3 to 8,
X1 to X3 are each independently O, S, or CRaRb,
R1 to R12, Ra, Rb, n, and m are the same as those defined in claim 1,
R13 to R16 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N, O, and S atoms, and two or more adjacent groups among R1 to R16, Ra and Rb are optionally bonded to each other to form a monocyclic or polycyclic ring,
L1 to L3 are each independently a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted fluorenylene group; or a substituted or unsubstituted heteroarylene group including one or more of N, O, and S atoms, and
o, p, q, and r are each independently an integer from 0 to 3.

### Claim 3 (depends on 1)

The compound of claim 1, wherein L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted pyridylene group; or a substituted or unsubstituted biphenylene group.

### Claim 4 (depends on 1)

The compound of claim 1, wherein at least one of R1 and R2 are each independently selected from the group consisting of the following substituted or unsubstituted structural formulae:

### Claim 5 (depends on 1)

The compound of claim 1, wherein Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted pyridyl group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted naphthyl group, and
Ra and Rb are optionally bonded to each other to form a monocyclic or polycyclic ring.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound represented by Formula 1 is any one of the following formulae in Table 1:
TABLE 1
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
[Formula 1-6]
[Formula 1-7]
[Formula 1-8]
[Formula 1-9]
[Formula 1-10]
[Formula 1-11]
[Formula 1-12]
[Formula 1-13]
[Formula 1-14]
[Formula 1-15]
[Formula 1-16]
[Formula 1-17]
[Formula 1-18]
[Formula 1-19]
[Formula 1-20]
[Formula 1-21]
[Formula 1-22]
[Formula 1-23]
[Formula 1-24]
[Formula 1-25]
[Formula 1-26]
[Formula 1-27]
[Formula 1-28]
[Formula 1-29]
[Formula 1-30]
[Formula 1-31]
[Formula 1-32]
[Formula 1-33]
[Formula 1-34]
[Formula 1-35]
[Formula 1-36]
[Formula 1-37]
[Formula 1-38]
[Formula 1-39]
[Formula 1-40]
[Formula 2-1]
[Formula 2-2]
[Formula 2-3]
[Formula 2-4]
[Formula 2-5]
[Formula 2-6]
[Formula 2-7]
[Formula 2-8]
[Formula 3-1]
[Formula 3-2]
[Formula 3-3]
[Formula 3-4]
[Formula 4-1]
[Formula 4-2]
[Formula 4-3]
[Formula 4-4]

### Claim 7 (depends on 1)

An organic electronic device comprising:
a first electrode;
a second electrode; and
an organic material layer having one or more layers disposed between the first electrode and the second electrode,
wherein one or more layers of the organic material layer comprise the compound of any one of claim 1.

### Claim 8 (depends on 7)

The organic electronic device of claim 7, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor.

### Claim 9 (depends on 7)

The organic electronic device of claim 7, wherein the organic electronic device is an organic light emitting device, and has a forward direction structure or a reverse direction structure.

### Claim 10 (depends on 7)

The organic electronic device of claim 7, wherein the organic electronic device is an organic light emitting device, the organic material layer comprises one or more layers of a hole injection layer, a hole transporting layer, and a layer which transports and injects holes simultaneously, and one or more layers of the layers comprise the compound.

### Claim 11 (depends on 7)

The organic electronic device of claim 7, wherein the organic electronic device is an organic light emitting device, the organic material layer comprises one or more layers of a light emitting layer, an electron transporting layer, an electron injection layer, and a layer which transports and injects electrons simultaneously, and one or more layers of the layers comprise the compound.

### Claim 12 (depends on 11)

The organic electronic device of claim 11, wherein the organic material layer comprising the compound further includes an n-type dopant selected from the group consisting of an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, and a combination thereof.

### Claim 13 (depends on 12)

The organic electronic device of claim 12, wherein the n-type dopant is included in an amount from 1% by weight to 70% by weight based on a total weight of the composition of the organic material layer comprising the compound.
