# US 10,312,450 B2 · Organic electroluminescent materials and devices

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- Number: US 10,312,450 B2
- Document ID: US10312450B2
- Status: Granted
- Kind: B2
- Application number: 15/449,497
- Filed: 2017-03-03
- Published: 2017-06-22
- Granted: 2019-06-04
- Earliest claimed: 2007-08-08
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Jason Brooks; Chuanjun Xia; Raymond Kwong; James Fiordeliso
- Web page: https://patentgrep.com/patent/US10312450B2

## CPC

- H10K 85/622: {containing four rings, e.g. pyrene}
- C07C 15/38: containing four rings
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C09B 57/00: Other synthetic dyes of known constitution
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- 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 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/141: {comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE}
- H10K 85/342: {comprising iridium}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- C07C 2603/42: containing only six-membered rings
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- H10K 50/12: comprising dopants
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 2101/10: Triplet emission
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- 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

A compound having the structure of Formula I is disclosed. In the structure of Formula I, each of R1, R2, and R3 is independently a hydrogen, a non-fused aryl group having one meta-substituent, or a non-fused heteroaryl six-membered ring having one or more meta-substituents; each meta-substituent is a non-fused aryl or non-fused heteroaryl six-membered ring optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups; and at least one of R1, R2, and R3 is a non-fused aryl having one meta-substituent or a heteroaryl six-membered ring having at least one meta-substituent, wherein each meta-substituent is a non-fused aryl or non-fused heteroaryl group further substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups. The compounds may be useful in phosphorescent organic light emitting devices.

## Claims

### Claim 1

A compound comprising a triphenylene core of Formula I:
wherein each of R1, R2, and R3 is independently a hydrogen, a non-fused aryl group or a non-fused heteroaryl six-membered ring having one or more meta-substituents;
wherein each meta-substituent is a non-fused aryl or non-fused heteroaryl six-membered ring optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups; and
wherein at least one of R1, R2, and R3 is a non-fused aryl having one meta-substituent or a non-fused heteroaryl six-membered ring having at least one meta-substituent, wherein each meta-substituent is a non-fused aryl or non-fused heteroaryl group further substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 2 (depends on 1)

The compound of claim 1, wherein at least two of R1, R2, and R3 are a non-fused aryl group having one meta-substituent or a non-fused heteroaryl six-membered ring having at least one meta-substituent, wherein each meta-substituent is a non-fused aryl or non-fused heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups.

### Claim 3 (depends on 1)

The compound of claim 1, wherein each of R1, R2, and R3 includes no more than three para-substituted phenyl rings.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound has the structure:
wherein R′1 is a non-fused aryl group or a non-fused heteroaryl group; and
wherein R′1 is substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound has the structure:
wherein R′1 is a straight or branched chain of two or more non-fused aryl groups substituted with Ra or a straight or branched chain of two or more non-fused heteroaryl groups substituted with Ra; wherein Ra is a non-fused aryl or non-fused heteroaryl, a branched or straight chain of non-fused aryls or non-fused heteroaryls, or an alkyl substituted non-fused aryl or an alkyl substituted non-fused heteroaryl group.

### Claim 6 (depends on 1)

The compound of claim 1, wherein at least one of R1, R2, and R3 is a non-fused aryl or a non-fused heteroaryl six-membered ring having one meta-substituent that is a non-fused aryl or non-fused heteroaryl group further substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound is any one of:

### Claim 8 (depends on 1)

The compound of claim 1, wherein at least one of R1, R2, and R3 is a heteroaryl six-membered ring selected from the group consisting of pyridine, pyrazine and pyrimidine, wherein said heteroaryl six-membered ring has at least one meta-substituent that is a non-fused aryl or non-fused heteroaryl group further substituted with one or more non-fused aryl or non-fused heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 9

An organic light emitting device, comprising:
an anode;
a cathode;
an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a triphenylene core of Formula I:
wherein each of R1, R2, and R3 is independently a hydrogen, a non-fused aryl group or a non-fused heteroaryl six-membered ring having one or more meta-substituents;
wherein each meta-substituent is a non-fused aryl or non-fused heteroaryl six-membered ring optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups; and
wherein at least one of R1, R2, and R3 is a non-fused aryl having one meta-substituent or a non-fused heteroaryl six-membered ring having at least one meta-substituent, wherein each meta-substituent is a non-fused aryl or non-fused heteroaryl group further substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 10 (depends on 9)

The organic light emitting device of claim 9, wherein at least one of R1, R2, and R3 is a heteroaryl six-membered ring selected from the group consisting of pyridine, pyrazine and pyrimidine, wherein said heteroaryl six-membered ring has at least one meta-substituent that is a non-fused aryl or non-fused heteroaryl group further substituted with one or more non-fused aryl or non-fused heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 11 (depends on 9)

The organic light emitting device of claim 9, wherein at least two of R1, R2, and R3 are a non-fused aryl group having one meta-substituent or a non-fused heteroaryl six-membered ring having at least one meta-substituent, wherein each meta-substituent is a non-fused aryl or non-fused heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups.

### Claim 12 (depends on 9)

The organic light emitting device of claim 9, wherein each of R1, R2, and R3 includes no more than three para-substituted phenyl rings.

### Claim 13 (depends on 9)

The organic light emitting device of claim 9, wherein the compound has the structure:
wherein R′1 is a non-fused aryl group or a non-fused heteroaryl group; and
wherein R′1 is substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 14 (depends on 9)

The organic light emitting device of claim 9, wherein the compound has the structure:
wherein R′1 is a straight or branched chain of two or more non-fused aryl groups substituted with Ra or a straight or branched chain of two or more non-fused heteroaryl groups substituted with Ra; wherein Ra is a non-fused aryl or non-fused heteroaryl, a branched or straight chain of non-fused aryls or non-fused heteroaryls, or an alkyl substituted non-fused aryl or an alkyl substituted non-fused heteroaryl group.

### Claim 15 (depends on 9)

The organic light emitting device of claim 9, wherein at least one of R1, R2, and R3 is a non-fused aryl or a non-fused heteroaryl six-membered ring having one meta-substituent that is a non-fused aryl or non-fused heteroaryl group further substituted with a chain of at least two non-fused aryl or non-fused heteroaryl groups.

### Claim 16 (depends on 9)

The organic light emitting device of claim 9, wherein the compound is any one of:

### Claim 17 (depends on 9)

The organic light emitting device of claim 9, wherein the first device is a consumer product selected from the group consisting of flat panel displays, computer monitors, televisions, billboards, heads up displays, fully transparent displays, flexible displays, a wall, theater or stadium screen, and a sign.

### Claim 18 (depends on 9)

The first device of claim 9, wherein the first device is a consumer product selected from the group consisting of laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, and micro-displays.

### Claim 19 (depends on 9)

The organic light emitting device of claim 9, wherein the first device is a consumer product selected from the group consisting of lights for interior or exterior illumination, lights for interior or exterior illumination signaling, and vehicles.