# US 8,465,851 B2 · Materials and structures for enhancing the performance of organic light emitting devices

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- Number: US 8,465,851 B2
- Document ID: US8465851B2
- Status: Granted
- Kind: B2
- Application number: 13/334,498
- Filed: 2011-12-22
- Published: 2012-05-31
- Granted: 2013-06-18
- Earliest claimed: 2004-02-23
- Assignees: Universal Display Corporation; University of Southern California
- Applicants: Mark E. Thompson; Raymond Kwong; Yeh-Jiun Tung; Jason Brooks
- Inventors: Mark E. Thompson; Raymond Kwong; Yeh-Jiun Tung; Jason Brooks
- Web page: https://patentgrep.com/patent/US8465851B2

## CPC

- H10K 50/11: characterised by the electroluminescent [EL] layers
- C07C 13/567: with a fluorene or hydrogenated fluorene ring system
- C07C 13/66: the condensed ring system contains only four rings
- C07C 15/24: containing two rings
- C07C 15/38: containing four rings
- 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 50/14: Carrier transporting layers
- H10K 85/60: Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence)
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- H10K 85/10: Organic polymers or oligomers
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 2101/10: Triplet emission
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y10S 428/917: Electroluminescent
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A device is provided, having an anode, a cathode, and two adjacent organic layers disposed between the anode and the cathode. One organic layer is a phosphorescent emissive material. The other organic layer may comprise an aromatic hydrocarbon material, comprising an aromatic non-heterocyclic hydrocarbon core optionally substituted, and wherein the substituents are the same or different, and each is selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heteroalkyl, substituted aryl, substituted heteroaryl and heterocyclic groups. The second organic layer may comprise a material having a molecular dipole moment less than about 2.0 debyes, such that the device has an unmodified external quantum efficiency of at least about 3% and a lifetime of at least about 1000 hours at an initial luminance of about 100 to about 1000 cd/m2.

## Claims

### Claim 1

A device, comprising:
an anode;
a cathode;
a first organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a phosphorescent material; and
a second organic layer disposed between the first organic layer and the cathode, wherein the second organic layer comprises the following compound:
wherein each of R14-R25 are one or more of the same or different optional substitutions on the respective ring, and each is selected from the group consisting of alkyl, alkenyl, aryl, heteroalkyl, and heterocyclic groups.

### Claim 2 (depends on 1)

The device of claim 1, wherein the compound has a molecular dipole moment of less than about 2.0 debyes.

### Claim 3 (depends on 2)

The device of claim 2, wherein the compound has a molecular dipole moment of zero.

### Claim 4 (depends on 1)

The device of claim 1, wherein the second organic layer is in direct contact with the cathode.

### Claim 5 (depends on 1)

The device of claim 1, further comprising a third organic layer disposed between the second organic layer and the cathode.

### Claim 6 (depends on 5)

The device of claim 5, wherein the second organic layer and the third organic layer are both electron transport layers, wherein the electron transport layers are different.

### Claim 7 (depends on 1)

The device of claim 1, wherein the first organic layer further comprises a hole transporting material, and wherein the compound has a highest occupied molecular orbital that is not more than 0.81 eV less than the highest occupied molecular orbital of the hole transporting material in the first organic layer.

### Claim 8 (depends on 7)

The device of claim 7, wherein the compound has a molecular dipole moment less than about 2.0 debyes.

### Claim 9 (depends on 1)

The device of claim 1, wherein compound is

### Claim 10 (depends on 1)

The device of claim 1, wherein the second organic layer is in direct contact with the first organic layer.

### Claim 11 (depends on 10)

The device of claim 10, wherein the second organic layer is a hole blocking layer.

### Claim 12 (depends on 11)

The device of claim 11, wherein the compound has no substitutions.

### Claim 13 (depends on 1)

The device of claim 1, wherein the second organic layer is an electron transport layer.