# US 2021/0280804 A1 · Organic electroluminescent materials and devices

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- Number: US 2021/0280804 A1
- Document ID: US20210280804A1
- Status: Published application
- Kind: A1
- Application number: 17/179,915
- Filed: 2021-02-19
- Published: 2021-09-09
- Earliest claimed: 2020-03-06
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Jerald FELDMAN; Jui-YI TSAI; Alexey Borisovich DYATKIN; Zhiqiang JI; Pierre-Luc T. BOUDREAULT
- Web page: https://patentgrep.com/patent/US20210280804A1

## CPC

- H10K 85/346: {comprising platinum}
- C07F 15/0033: {Iridium compounds}
- C07F 15/0086: {Platinum compounds}
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1048: with oxygen
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Provided are novel metal complexes comprising tetradentate pyrimidine and pyrazine ligands. The organometallic compounds can have the structure of that are useful as emitters in OLEDs and when used in OLEDs provides improved device performance. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

## Claims

### Claim 1

A compound of
wherein:
each of X1 and X2 is independently C or N, with at least one being N;
each of X3, X4, and X5 is independently C or N;
at least one of X3, X4, and X5 is C and at least one is N;
L1 and L2 are linkers that can be present, with at least one of them being present and each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, BR, BRR′, NR, alkyl, cycloalkyl, aryl, and heteroaryl when present;
RA, RB, RC, and RD each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
each of R, R′, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
M is Pt, Pd, Au, Ag, Cu or Zn; and
any two adjacent R, R′, RA, RB, RC, and RD can be joined or fused together to form a ring,
with the proviso that the compound is not the one shown below:

### Claim 2 (depends on 1)

The compound of claim 1, wherein each of R, R′, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

### Claim 3 (depends on 1)

The compound of claim 1, wherein one of X1 and X2 is N, and the other is C.

### Claim 4 (depends on 1)

The compound of claim 1, wherein one of X3, X4, and X5 is N, and the remaining ones of X3, X4, and X5 are C.

### Claim 5 (depends on 1)

The compound of claim 1, wherein one of L1 and L2 is present, and the other is not present.

### Claim 6 (depends on 1)

The compound of claim 1, wherein L1 and L2 are each independently selected from the group consisting of O, S, CRR′, SiRR′, and NR when present.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof.

### Claim 8 (depends on 1)

The compound of claim 1, wherein at least one pair of two adjacent RA, RB, RC, and RD are joined or fused together to form a 5-membered or 6-membered aromatic ring.

### Claim 9 (depends on 8)

The compound of claim 8, wherein the 5-membered or 6-membered aromatic ring is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, or thiazole.

### Claim 10 (depends on 8)

The compound of claim 8, wherein the 5-membered or 6-membered aromatic ring is further fused to form a multiple fused ring system

### Claim 11 (depends on 1)

The compound of claim 1, wherein at least one of RA, RB, RC, and RD is Selected from the Group Consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

The compound of claim 1, wherein L1 or L2 is independently O, CRR′, SiRR′, or NR.

### Claim 14 (depends on 12)

The compound of claim 12, wherein two adjacent RA, RB, RC, and RD are joined or fused together to form a 5-membered or 6-membered aromatic ring.

### Claim 15 (depends on 1)

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

### Claim 16 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
Compound 1-1, Compound 1-2,
Compound 1-3, and Compound 1-4
having the following structure
wherein,
in Compound 1-1, L2 = NPh,
in Compound 1-2, L2 = O,
in Compound 1-3, L2 = CMe2, and
in Compound 1-4 L2 = SiPh2,
Compound 2-1, Compound 2-2,
Compound 2-3, and Compound 2-4
having the following structure
wherein,
in Compound 2-1, L2 = Ph,
in Compound 2-2, L2 = O,
in Compound 2-3, L2 = CMe2, and
in Compound 2-4, L2 = SiPh2.,
Compound 3-1, Compound 3-2,
Compound 3-3, and Compound 3-4
having the following structure
wherein,
in Compound 3-1, L2 = Ph,
in Compound 3-2, L2 = O,
in Compound 3-3, L2 = CMe2, and
in Compound 3-4, L2 = SiPh2.,
Compound 4-1, Compound 4-2,
Compound 4-3, and Compound 4-4
having the following structure
wherein.
in Compound 4-1, L2 = NPh,
in Compound 4-2, L2 = O,
in Compound 4-3, L2 = CMe2, and
in Compound 4-4, L2 = SiPh2.,
Compound 5-1, Compound 5-2,
Compound 5-3, and Compound 5-4
having the following structure
wherein,
in Compound 5-1, L2 = NPh,
in Compound 5-2, L2 = O,
in Compound 5-3, L2 = CMe2, and
in Compound 5-4 L2 = SiPh2.,
Compound 6-1, Compound 6-2,
Compound 6-3, and Compound 6-4
having the following structure
wherein,
in Compound 6-1, L2 = Ph,
in Compound 6-2, L2 = O,
in Compound 6-3, L2 = CMe2, and
in Compound 6-4, L2 = SiPh2.,
Compound 7-1, Compound 7-2,
Compound 7-3, and Compound 7-4
having the following structure
wherein,
in Compound 7-1, L2 = Ph,
in Compound 7-2, L2 = O,
in Compound 7-3, L2 = CMe2, and
in Compound 7-4, L2 = SiPh2.,
Compound 8-1, Compound 8-2,
Compound 8-3, and Compound 8-4
having the following structure
wherein.
in Compound 8-1, L2 = NPh,
in Compound 8-2, L2 = O,
in Compound 8-3, L2 = CMe2, and
in Compound 8-4, L2 = SiPh2.,
Compound 9-1, Compound 9-2,
Compound 9-3, and Compound 9-4
having the following structure
wherein,
in Compound 9-1, L2 = NPh,
in Compound 9-2, L2 = O,
in Compound 9-3, L2 = CMe2, and
in Compound 9-4, L2 = SiPh2.,
Compound 11-1, Compound 11-2,
Compound 11-3, and Compound 11-4
having the following structure
wherein,
in Compound 11-1, L2 = NPh,
in Compound 11-2, L2 = O,
in Compound 11-3, L2 = CMe2, and
in Compound 11-4, L2 = SiPh2.,
Compound 12-1, Compound 12-2,
Compound 12-3, and Compound 12-4
having the following structure
wherein,
in Compound 12-1, L2 = NPh,
in Compound 12-2, L2 = O,
in Compound 12-3, L2 = CMe2, and
in Compound 12-4, L2 = SiPh2.,
Compound 13-1, Compound 13-2,
Compound 13-3, and Compound 13-4
having the following structure
wherein,
in Compound 13-1, L2 = NPh,
in Compound 13-2, L2 = O,
in Compound 13-3, L2 = CMe2, and
in Compound 13-4, L2 = SiPh2.,
Compound 14-1, Compound 14-2,
Compound 14-3, and Compound 14-4
having the following structure
wherein,
in Compound 14-1, L2 = NPh,
in Compound 14-2, L2 = O,
in Compound 14-3, L2 = CMe2, and
in Compound 14-4, L2 = SiPh2.,
Compound 15-1, Compound 15-2,
Compound 15-3, and Compound 15-4
having the following structure
wherein,
in Compound 15-1, L2 = NPh,
in Compound 15-2, L2 =O,
in Compound 15-3, L2 = CMe2, and
in Compound 15-4 L2 = SiPh2.,
Compound 16-1, Compound 16-2,
Compound 16-3, and Compound 16-4,
having the following structure
wherein,
in Compound 16-1, L2 = NPh,
in Compound 16-2, L2 = O,
in Compound 16-3, L2 = CMe2, and
in Compound 16-4, L2 = SiPh2.,
Compound 17-1, Compound 17-2,
Compound 17-3, and Compound 17-4
having the following structure
wherein,
in Compound 17-1, L2 = NPh,
in Compound 17-2, L2 = O,
in Compound 17-3, L2 = CMe2, and
in Compound 17-4, L2 = SiPhd2.,
Compound 18-1, Compound 18-2,
Compound 18-3, and Compound 18-4
having the following structure
wherein,
in Compound 18-1, L2 = NPh,
in Compound 18-2, L2 = O,
in Compound 18-3, L2 = CMe2, and
in Compound 18-4, L2 = SiPh2.,
Compound 19-1, Compound 19-2,
Compound 19-3, and Compound 19-4
having the following structure
wherein,
in Compound 19-1, L2 = NPh,
in Compound 19-2, L2 = O,
in Compound 19-3, L2 = CMe2, and
in Compound 19-4, L2 = SiPh2.,
Compound 20-1, Compound 20-2,
Compound 20-3, and Compound 20-4
having the following structure
wherein,
in Compound 20-1, L2 = NPh,
in Compound 20-2, L2 = O,
in Compound 20-3, L2 = CMe2, and
in Compound 20-4, L2 = SiPh2.,
Compound 21-1, Compound 21-2,
Compound 21-3, and Compound 21-4
having the following structure
wherein,
in Compound 21-1, L2 = NPh,
in Compound 21-2, L2 = O,
in Compound 21-3, L2 = CMe2, and
in Compound 21-4, L2 = SiPh2.,
Compound 25-1, Compound 25-2,
Compound 25-3, and Compound 25-4
having the following structure
wherein,
in Compound 25-1, L2 = NPh,
in Compound 25-2, L2 = O,
in Compound 25-3, L2 = CMe2, and
in Compound 25-4, L2 = SiPh2.,
Compound 26-1, Compound 26-2,
Compound 26-3, and Compound 26-4
having the following structure
wherein,
in Compound 26-1, L2 = NPh,
in Compound 26-2, L2 = O,
in Compound 26-3, L2 = CMe2, and
in Compound 26-4, L2 = SiPh2.,
Compound 27-1, Compound 27-2,
Compound 27-3, and Compound 27-4
having the following structure
wherein,
in Compound 27-1, L2 = NPh,
in Compound 27-2, L2 = O,
in Compound 27-3, L2 = CMe2, and
in Compound 27-4, L2 = SiPh2.,
Compound 28-1, Compound 28-2,
Compound 28-3, and Compound 28-4
having the following structure
wherein,
in Compound 28-1, L2 = NPh,
in Compound 28-2, L2 = O,
in Compound 28-3, L2 = CMe2, and
in Compound 28-4, L2 = SiPh2.,
Compound 29-1, Compound 29-2,
Compound 29-3, and Compound 29-4
having the following structure
wherein,
in Compound 29-1, L2 = NPh,
in Compound 29-2, L2 = O,
in Compound 29-3, L2 = CMe2, and
in Compound 29-4, L2 = SiPh2.,
Compound 31-1, Compound 31-2,
Compound 31-3, and Compound 31-4
having the following structure
wherein,
in Compound 31-1, L2 = NPh,
in Compound 31-2, L2 = O,
in Compound 31-3, L2 = CMe2, and
in Compound 31-4, L2 = SiPh2.,
Compound 32-1, Compound 32-2,
Compound 32-3, and Compound 32-4
having the following structure
wherein,
in Compound 32-1, L2 = NPh,
in Compound 32-2, L2 = O,
in Compound 32-3, L2 = CMe2, and
in Compound 32-4, L2 = SiPh2.,
Compound 33-1, Compound 33-2,
Compound 33-3, and Compound 33-4
having the following structure
wherein,
in Compound 33-1, L2 = NPh,
in Compound 33-2, L2 = O,
in Compound 33-3, L2 = CMe2, and
in Compound 33-4, L2 = SiPh2.,
Compound 34-1, Compound 34-2,
Compound 34-3, and Compound 34-4
having the following structure
wherein,
in Compound 34-1, L2 = NPh,
in Compound 34-2, L2 = O,
in Compound 34-3, L2 = CMe2, and
Compound 34-4, L2 in = SiPh2.,
Compound 36-1, Compound 36-2,
Compound 36-3, and Compound 36-4
having the following structure
wherein,
in Compound 36-1, L2 = NPh,
in Compound 36-2, L2 = O,
in Compound 36-3, L2 = CMe2, and
in Compound 36-4, L2 = SiPh2.,
Compound 37-1, Compound 37-2,
Compound 37-3, and Compound 37-4
having the following structure
wherein,
in Compound 37-1, L2 = NPh,
in Compound 37-2, L2 = O,
in Compound 37-3, L2 = CMe2, and
in Compound 37-4, L2 = SiPh2.,
Compound 38-1, Compound 38-2,
Compound 38-3, and Compound 38-4
having the following structure
wherein,
in Compound 38-1, L2 = NPh,
in Compound 38-2, L2 = O,
in Compound 38-3, L2 = CMe2, and
in Compound 38-4, L2 = SiPh2.,
Compound 39-1, Compound 39-2,
Compound 39-3, and Compound 39-4
having the following structure
wherein,
in Compound 39-1, L2 = NPh,
in Compound 39-2, L2 = O,
in Compound 39-3, L2 = CMe2, and
in Compound 39-4, L2 = SiPh2.,
Compound 40-1, Compound 40-2,
Compound 40-3, and Compound 40-4
having the following structure
wherein,
in Compound 40-1, L2 = NPh,
in Compound 40-2, L2 = O,
in Compound 40-3, L2 = CMe2, and
in Compound 40-4, L2 = SiPh2.,
Compound 40-1, Compound 40-2,
Compound 40-3, and Compound 40-4
having the following structure
wherein,
in Compound 41-1, L2 = NPh,
in Compound 41-2, L2 = O,
in Compound 41-3, L2 = CMe2, and
in Compound 41-4, L2 = SiPh2.,
Compound 42-1, Compound 42-2,
Compound 42-3, and Compound 42-4
having the following structure
wherein,
in Compound 42-1, L2 = NPh,
in Compound 42-2, L2 = O,
in Compound 42-3, L2 = CMe2, and
in Compound 42-4, L2 = SiPh2.,
Compound 43-1, Compound 43-2,
Compound 43-3, and Compound 43-4
having the following structure
wherein,
in Compound 43-1, L2 = NPh,
in Compound 43-2, L2 = O,
in Comound 43-3, L2 = CMe2, and
in Compound 43-4, L2 = SiPh2., and
Compound 44-1, Compound 44-2
Compound 44-3, and Compound 44-4
having the following structure
wherein,
in Compound 44-1, L2 = NPh,
in Compound 44-2, L2 = O,
in Compound 44-3, L2 = CMe2, and
in Compound 44-4, L2 = SiPh2..

### Claim 17

An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode,
wherein the organic layer comprises a compound of
wherein:
each of X1 and X2 is independently C or N, with at least one being N;
each of X3, X4, and X5 is independently C or N;
at least one of X3, X4, and X5 is C and at least one is N;
L1 and L2 are linkers that can be present, with at least one of them being present and each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, BR, BRR′, NR, alkyl, cycloalkyl, aryl, and heteroaryl when present;
RA, RB, RC, and RD each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
each of R, R′, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
M is Pt, Pd, Au, Ag, Cu or Zn; and
any two adjacent R, R′, RA, RB, RC, and RD can be joined or fused together to form a ring,
with the proviso that the compound is not the one shown below:

### Claim 18 (depends on 17)

The OLED of claim 17, wherein the organic layer further comprises a host, wherein the host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

### Claim 19 (depends on 18)

The OLED of claim 18, wherein the host is selected from the group consisting of:
and combinations thereof.

### Claim 20

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,
wherein the organic layer comprises a compound of
wherein:
each of X1 and X2 is independently C or N, with at least one being N;
each of X3, X4, and X5 is independently C or N;
at least one of X3, X4, and X5 is C and at least one is N;
L1 and L2 are linkers that can be present, with at least one of them being present and each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, BR, BRR′, NR, alkyl, cycloalkyl, aryl, and heteroaryl when present;
RA, RB, RC, and RD each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
each of R, R′, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
M is Pt, Pd, Au, Ag, Cu or Zn; and
any two adjacent R, R′, RA, RB, RC, and RD can be joined or fused together to form a ring,
with the proviso that the compound is not the one shown below: