# US 12,120,945 B2 · Display and lighting devices comprising phosphorescent excimers with preferred molecular orientation as monochromatic emitters

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- Number: US 12,120,945 B2
- Document ID: US12120945B2
- Status: Granted
- Kind: B2
- Application number: 18/167,283
- Filed: 2023-02-10
- Published: 2023-08-03
- Granted: 2024-10-15
- Earliest claimed: 2017-10-17
- Assignees: Arizona Board of Regents on behalf of Arizona State University
- Applicants: Arizona Board of Regents on behalf of Arizona State University
- Inventors: Jian Li
- Web page: https://patentgrep.com/patent/US12120945B2

## CPC

- C07F 15/006: {Palladium compounds}
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/06: containing organic luminescent materials
- H10K 85/341: {Transition metal complexes, e.g. Ru(II)polypyridine complexes (H10K85/331 takes precedence)}
- H10K 85/346: {comprising platinum}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- 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 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2101/10: Triplet emission
- 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
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic light emitting diode having a substrate, a first electrode, a hole transporting layer proximate the first electrode, a second electrode, an electron transporting layer proximate the second electrode, and an emissive layer between the hole transporting layer and the electron transporting layer. The emissive layer includes a square planar tetradentate platinum or palladium complex, and excimers formed by two or more of the complexes are aligned such that emitting dipoles of the excimers are substantially parallel to a surface of the substrate.

## Claims

### Claim 1

An organic light emitting diode comprising:
a substrate;
a first electrode;
a hole transporting layer proximate the first electrode;
a second electrode;
an electron transporting layer proximate the second electrode; and
an emissive layer between the hole transporting layer and the electron transporting layer, wherein the emissive layer comprises a square planar tetradentate platinum complex represented by one of Formulas I-IX, and excimers formed by two or more of the complexes are aligned such that emitting dipoles of the excimers are substantially parallel to a surface of the substrate:
wherein, in Formula I:
M represents Pt(II);
R1, R3, R4, and R5 each independently represents hydrogen, halogen, hydroxyl, nitro, cyanide, thiol, or optionally substituted C1-C4 alkyl, alkoxy, amino, or aryl;
each n is independently an integer as limited by valency;
Y1a, Y1b, Y1c, Y1d, Y1e, Y1f, Y2a, Y2b, Y2c, Y2d, Y2e, Y2f, Y4a, Y4b, Y4c, Y4d, Y4e, Y5a, Y5b, Y5c, Y5d, and Y5e each independently represents C, N, Si, O, S;
X2 represents NR, PR, CRR′, SiRR′, CRR′, SiRR′, O, S, S═O, O═S═O, Se, Se═O, or O═Se═O, where R and R′ each independently represents halogen, hydroxyl, nitro, cyanide, thiol, or optionally substituted C1-C4 alkyl, alkoxy, amino, aryl, or heteroaryl;
each of L1 and L3 is independently present or absent, and if present, represents a substituted or unsubstituted linking atom or group, where a substituted linking atom is bonded to an alkyl, alkoxy, alkenyl, alkynyl, hydroxy, amine, amide, thiol, aryl, heteroaryl, cycloalkyl, or heterocyclyl moiety;
Ar3 and Ar4 each independently represents 6-membered aryl group; and
Ar1 and Ar5 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl; and
wherein, in Formulas II-IX:
M represents Pt(II);
each R1, R2, R3, R4, R5, and R6 present independently represents hydrogen, halogen, hydroxyl, nitro, cyanide, thiol, or optionally substituted C1-C4 alkyl, alkoxy, amino, or aryl;
each n is independently an integer, valency permitting;
each Y1a, Y1b, Y1c, Y1d, Y2a, Y2b, Y2c, Y3a, Y3b, Y3c, Y4a, Y4b, Y4c, Y4d, Y5a, Y5b, Y5c, Y5d, Y6a, Y6b, Y6e, and Y6d present independently represents C, N, or Si;
U1 and U2 each independently represents NR, O or S, wherein R represents hydrogen, halogen, hydroxyl, nitro, cyanide, thiol, or optionally substituted C1-C4 alkyl, alkoxy, amino, or aryl;
U3 and U4 each independently represents N or P; and
X represents O, S, NR, CRR′, SiRR′, PR, BR, S═O, O═S═O, Se, Se═O, or O═Se═O, where R and R′ each independently represents hydrogen, halogen, hydroxyl, nitro, cyanide, thiol, or optionally substituted C1-C4 alkyl, alkoxy, amino, aryl, or heteroaryl.

### Claim 2 (depends on 1)

The organic light emitting diode of claim 1, wherein the complex represented by Formula I comprises one of:
and the complex represented by one of Formulas II-IX comprises one of:
wherein R and R′ each independently represents substituted or unsubstituted C1-C4 alkyl, alkoxy, aryl, or heteroaryl; and wherein M represents Pt(II).

### Claim 3 (depends on 1)

The organic light emitting diode of claim 1, wherein a concentration of the complex in the emissive layer is in a range of 5 wt % to 100 wt %.

### Claim 4 (depends on 3)

The organic light emitting diode of claim 3, wherein the emissive layer comprises a neat film of the complex.

### Claim 5 (depends on 3)

The organic light emitting diode of claim 3, wherein the emissive layer comprises a doped film comprising a host material and the complex.

### Claim 6 (depends on 5)

The organic light emitting diode of claim 5, wherein a concentration of the complex in the doped film is in a range of 5 wt % to 25 wt %.

### Claim 7 (depends on 5)

The organic light emitting diode of claim 5, wherein the host material comprises a carbazole-based host having one to three carbazole skeletons.

### Claim 8 (depends on 7)

The organic light emitting diode of claim 7, wherein the carbazole-based host is represented by one of Formulas 1-3:
wherein each occurrence of R1-R9 independently represents halogen, hydroxyl, nitro, cyanide, thiol, or optionally substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene.

### Claim 9 (depends on 8)

The organic light emitting diode of claim 8, wherein the carbazole-based host comprises one or more of tris-PCz (9,9′,9″-triphenyl-9H,9′H,9″H-3,3′:6′3″-tercarbazole), CBP (4,4-di(9H-carbazol-9-yl) biphenyl), mCBP (3,3-di(9H-carbazol-9-yl) biphenyl), and mCP (meta-di(carbazolyl) phenyl).

### Claim 10 (depends on 1)

The organic light emitting diode of claim 1, wherein the emissive layer comprises one or more doped films comprising the complex, each doped film having a different concentration of the complex.

### Claim 11 (depends on 10)

The organic light emitting diode of claim 10, wherein the emissive layer comprises a first doped film comprising the complex and a second doped film comprising the complex.

### Claim 12 (depends on 11)

The organic light emitting diode of claim 11, wherein a concentration of the complex in the first doped film is in a range of 15 wt % to 25 wt % and a concentration of the complex in the second doped film is in a range of 5 wt % to 15 wt %.

### Claim 13 (depends on 12)

The organic light emitting diode of claim 12, wherein the emissive layer further comprises a third doped film comprising the complex.

### Claim 14 (depends on 13)

The organic light emitting diode of claim 13, wherein a concentration of the complex in the third doped film is in a range of 5 wt % to 10 wt %.

### Claim 15 (depends on 1)

The organic light emitting diode of claim 1, wherein the first electrode is formed on the surface of the substrate.

### Claim 16 (depends on 1)

The organic light emitting diode of claim 1, wherein, in Formula I, Ar1 and Ar5 do not represent imidazolium carbene, pyrazine, or triazole.