# US 2023/0057590 A1 · Organic electroluminescent materials and devices

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- Number: US 2023/0057590 A1
- Document ID: US20230057590A1
- Status: Published application
- Kind: A1
- Application number: 17/932,755
- Filed: 2022-09-16
- Published: 2023-02-23
- Earliest claimed: 2017-08-10
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Alexey Borisovich Dyatkin; Bin Ma
- Web page: https://patentgrep.com/patent/US20230057590A1

## CPC

- C09K 11/06: containing organic luminescent materials
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/14: containing three or more hetero rings
- C07D 471/14: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 487/14: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/18: Carrier blocking layers
- H10K 50/84: Passivation; Containers; Encapsulations
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention includes a novel series of host materials for OLEDs based on substituted fused 1,2,4-triazines. The compounds of the invention may improve the device EQE and lifetime.

## Claims

### Claim 1

A compound of Formula I:
wherein ring A, ring B, and ring C are independently a 5-membered aromatic ring or a 6-membered aromatic ring;
R1, R2, and R3 represent mono to the maximum allowable substitution, or no substitution;
Y is selected from O, S, Se, NRN, or a direct bond;
R1, R2, and R3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; or any two adjacent R1, R2, and R3 can join together to form a ring; or if Y is a direct bond, then a proximate R2 and R3 can join to form a ring; and
RN is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkenyl, aryl, heteroaryl, and combinations thereof,
provided that when Y is a direct bond, and R2 and R3 represent no substitution, then at least one of B and C is a heteroaromatic ring.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1, R2, and R3 are each independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1, R2, and R3 are each independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Y is a direct bond.

### Claim 5 (depends on 1)

The compound of claim 1, wherein Y is selected from the group consisting of O and S.

### Claim 6 (depends on 1)

The compound of claim 1, wherein at least one of ring A, ring B, and ring C are fused to a 5-membered or 6-membered aromatic ring.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the ring A and the ring B are benzene rings.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the ring B and the ring C are 5-membered aromatic or 6-membered aromatic rings.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
wherein X1, X2, X3, X4, X5, X6, X7, and X8 are each independently selected from the group consisting of C or N; and
Z1 and Z2 are each independently selected from the group consisting of O, C, N and S.

### Claim 11 (depends on 1)

The compound of claim 1, wherein the rings B and C are a structure of Formula A, Formula B, Formula C, or Formula D,
wherein Y is a single bond and is represented by the hash line, and * indicates point attachment to the 1, 2, 4 triazine ring; and
each W is independently selected from the group consisting of O, S. NRN, and CR′R″, wherein R′ and R″ are independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, myloxy, amino, silyl, aryl, heteromyl, and combinations thereof, or R′ and R″ can join to form a ring.

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:

### Claim 13

An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of Formula I:
wherein ring A, ring B, and ring C are independently a 5-membered aromatic ring or a 6-membered aromatic ring;
R1, R2, and R3 represent mono to the maximum allowable substitution, or no substitution;
Y is selected from O, S, Se, NRN, or a direct bond;
R1, R2, and R3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; or any two adjacent R1, R2, and R3 can join together to form a ring; or if Y is a direct bond, then a proximate R2 and R3 can join to form a ring; and
RN is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkenyl, aryl, heteroaryl, and combinations thereof,
provided that when Y is a direct bond, and R2 and R3 represent no substitution, then at least one of B and C is a heteroaromatic ring.

### Claim 14 (depends on 13)

The OLED of claim 13, wherein the organic layer is an emissive layer and the compound of Formula I is a host.

### Claim 15 (depends on 13)

The OLED of claim 13, wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:
wherein each Y1 to Y13 are independently selected from the group consisting of carbon and nitrogen;
Y′ is selected from the group consisting of BRe, NRe, PRe, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf;
Re and Rf are optionally fused or joined to form a ring;
Ra, Rb, R, and Rd may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
wherein each Ra, Rb, Rc, Rd, Re, and Rf is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
or optionally any two adjacent substituents of Ra, Rb, Rc, and Rd can join to form a ring or together form a multidentate ligand.

### Claim 16 (depends on 13)

The OLED of claim 13, wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer, or the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.

### Claim 17

A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of Formula I:
wherein ring A, ring B, and ring C are independently a 5-membered aromatic ring or a 6-membered aromatic ring;
R1, R2, and R3 represent mono to the maximum allowable substitution, or no substitution;
Y is selected from O, S, Se, NRN, or a direct bond;
R1, R2, and R3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; or any two adjacent R1, R2, and R3 can join together to form a ring; or if Y is a direct bond, then a proximate R2 and R3 can join to form a ring; and
RN is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkenyl, aryl, heteroaryl, and combinations thereof,
provided that when Y is a direct bond, and R2 and R3 represent no substitution, then at least one of B and C is a heteroaromatic ring.

### Claim 18 (depends on 17)

The consumer product of claim 17, wherein the consumer product is selected from the group consisting of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display (display that is less than 2 inches diagonal), a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, and a sign.

### Claim 19 (depends on 1)

A formulation comprising a compound according to claim 1.