# US 12,010,859 B2 · Organic electroluminescent materials and devices

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- Number: US 12,010,859 B2
- Document ID: US12010859B2
- Status: Granted
- Kind: B2
- Application number: 16/867,073
- Filed: 2020-05-05
- Published: 2020-11-26
- Granted: 2024-06-11
- Earliest claimed: 2019-05-24
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Chun Lin; Tyler Fleetham; Michael S. Weaver
- Web page: https://patentgrep.com/patent/US12010859B2

## CPC

- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K 2101/27: {Combination of fluorescent and phosphorescent emission}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

Provided is an OLED that includes in its emissive region a first compound, a second compound, and a third compound, where the first compound is capable of functioning as a phosphorescent emitter in an OLED at room temperature, the second compound meets at least one of the following conditions: (1) the second compound is capable of functioning as a TADF emitter in an OLED at room temperature; and (2) the second compound is capable of forming an exciplex with the first compound in an OLED at room temperature, and the third compound is a fluorescent compound that functions as an emitter in the OLED of the present disclosure at room temperature.

## Claims

### Claim 1

An organic light emitting device (OLED) comprising, sequentially:
an anode;
a hole transporting layer;
an emissive region;
an electron transporting layer; and
a cathode; wherein the emissive region comprises:
a first compound;
a second compound; and
a third compound;
wherein the first compound is capable of functioning as a phosphorescent emitter in an OLED at room temperature;
wherein the second compound meets at least one of the following conditions:
(1) the second compound is capable of functioning as a TADF emitter in an OLED at room temperature; and
(2) the second compound is capable of forming an exciplex with the first compound in an OLED at room temperature;
wherein the third compound is a fluorescent compound functioning as an emitter in said OLED at room temperature; and
wherein the OLED emits a luminescent emission comprising an emission component from the S1 energy of the third compound when a voltage is applied across the OLED, wherein at least 65% of the emission from the OLED is produced from the third compound with a luminance of at least 10 cd/m2.

### Claim 2 (depends on 1)

The OLED of claim 1, wherein the second compound is capable of functioning as a TADF emitter in an OLED at room temperature.

### Claim 3 (depends on 2)

The OLED of claim 2, wherein S1-T1 energy gap of the first compound is less than 300 meV.

### Claim 4 (depends on 2)

The OLED of claim 2, wherein S1-T1 energy gap of the second compound is less than 300 meV.

### Claim 5 (depends on 1)

The OLED of claim 1, wherein the second compound is capable of forming an exciplex with the first compound in an OLED at room temperature.

### Claim 6 (depends on 5)

The OLED of claim 5, wherein the exciplex when formed has an emission energy less than 300 meV lower than T1 energy of the first compound.

### Claim 7 (depends on 1)

The OLED of claim 1, wherein at least two of the first, second, and third compounds are in a separate layer within the emissive region.

### Claim 8 (depends on 1)

The OLED of claim 1, wherein the first, second, and third compounds are present as a mixture in the emissive region.

### Claim 9 (depends on 1)

The OLED of claim 1, wherein the first compound has the formula of M(L1)x(L2)y(L3)z;
wherein L1, L2, and L3 can be the same or different;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein L1 is selected from the group consisting of:
wherein L2 and L3 are independently selected from the group consisting of
wherein each Y1 to Y13 are independently selected from the group consisting of carbon and nitrogen;
wherein Y′ is selected from the group consisting of B Re, N Re, P Re, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf;
wherein Re and Rf can be fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd can independently represent from mono to the maximum possible number of substitutions, or no substitution;
wherein each Ra, Rb, Rc, Rd, Re, and Rf is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Rd can be fused or joined to form a ring or form a multidentate ligand.

### Claim 10 (depends on 1)

The OLED of claim 1, wherein the second compound comprises at least one donor group and at least one acceptor group.

### Claim 11 (depends on 1)

The OLED of claim 1, wherein the second compound comprises at least one of the chemical moieties selected from the group consisting of:
wherein X is selected from the group consisting of O, S, Se, and NR;
wherein each R can be the same or different and each R is independently an acceptor group, an organic linker bonded to an acceptor group, or a terminal group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryl, heteroaryl, and combinations thereof; and
wherein each R′ can be the same or different and each R′ is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

### Claim 12 (depends on 1)

The OLED of claim 1, wherein the third compound comprises at least one organic group selected from the group consisting of:
and aza analogues thereof;
wherein A is selected from the group consisting of O, S, Se, NR′ and CR′R″;
wherein each R′ can be the same or different and each R′ is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

### Claim 13 (depends on 1)

The OLED of claim 1, wherein the third compound is selected from the group consisting of:
wherein R1 to R5 each independently represents from mono to maximum possible number of substitutions, or no substitution; and
wherein R1 to R5 are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof.

### Claim 14 (depends on 1)

A consumer product comprising an OLED according to claim 1.

### Claim 15 (depends on 1)

A formulation comprising:
the first compound;
the second compound; and
the third compound of claim 1.

### Claim 16 (depends on 1)

A chemical structure selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule, wherein the chemical structure comprises:
a first compound, a monovalent or polyvalent variant thereof;
a second compound, a monovalent or polyvalent variant thereof; and
a third compound, a monovalent or polyvalent variant thereof; wherein the first compound, the second compound, and the third compound are as defined in claim 1.

### Claim 17

An organic light emitting device (OLED) comprising, sequentially:
an anode;
a hole transporting layer;
an emissive region;
an electron transporting layer; and
a cathode; wherein the emissive region comprises:
a first compound;
a second compound; and
a third compound;
wherein the first compound is capable of functioning as a phosphorescent emitter in an OLED at room temperature;
wherein the second compound meets at least one of the following conditions:
(1) the second compound is capable of functioning as a TADF emitter in an OLED at room temperature; and
(2) the second compound is capable of forming an exciplex with the first compound in an OLED at room temperature;
wherein the third compound is a fluorescent compound functioning as an emitter in said OLED at room temperature;
wherein when a voltage is applied across the OLED, (i) excitons are transferred from the first compound to the second compound, which are further transferred to the third compound, or (ii) excitons are transferred from the second compound to the first compound, which are further transferred to the third compound.

### Claim 18 (depends on 17)

A consumer product comprising an OLED according to claim 17.

### Claim 19 (depends on 17)

A chemical structure selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule, wherein the chemical structure comprises:
a first compound, a monovalent or polyvalent variant thereof;
a second compound, a monovalent or polyvalent variant thereof; and
a third compound, a monovalent or polyvalent variant thereof; wherein the first compound, the second compound, and the third compound are as defined in claim 17.