# US 2025/0169352 A1 · Organic Light Emitting Diode and Organic Light Emitting Device Having the Diode

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- Number: US 2025/0169352 A1
- Document ID: US20250169352A1
- Status: Published application
- Kind: A1
- Application number: 18/933,870
- Filed: 2024-10-31
- Published: 2025-05-22
- Earliest claimed: 2023-11-22
- Assignees: LG Display Co., Ltd.
- Applicants: LG Display Co., Ltd.
- Inventors: Ji-Ae Lee
- Web page: https://patentgrep.com/patent/US20250169352A1

## CPC

- H10K 85/342: {comprising iridium}
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1033: with oxygen
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/12: comprising dopants
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

At least one emitting material layer in an organic light emitting diode (OLED) includes a first compound of phosphorescent material having the following structure of Chemical Formula 1, Ir(LA)m(LB)n, a second compound of a P-type host, and optionally a third compound of an N-type host. The luminous efficiency, color purity and luminous lifespan of the OLED and the organic light emitting device can be improved.

## Claims

### Claim 1

An organic light emitting diode comprising:
a first electrode;
a second electrode facing the first electrode; and
an emissive layer disposed between the first and second electrodes and comprising at least one emitting material layer,
wherein the at least one emitting material layer comprises a first compound and a second compound,
wherein the first compound comprises an organometallic compound having the structure of Chemical Formula 1:
Ir(LA)m(LB)n, [Chemical Formula 1]
wherein:
LA is a ligand having the structure of Chemical Formula 2:
wherein:
each of X1 to X4 is independently CR3 or N, wherein at least one of X1 to X4 is CR3;
one of Y1 and Y2 is a single bond and another of Y1 and Y2 is CR4R5, NR4, O or S;
each of R1 to R5 is independently chosen from hydrogen, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C2-C20 alkenyl group, an unsubstituted or substituted C2-C20 alkynyl group, an unsubstituted or substituted C1-C20 alkoxy group, an unsubstituted or substituted C1-C20 alkyl amino group, an unsubstituted or substituted C1-C20 alkyl silyl group, an unsubstituted or substituted C4-C30 cycloalkyl group, an unsubstituted or substituted C3-C30 hetero cycloalkyl group, an unsubstituted or substituted C6-C30 aryl group, an unsubstituted or substituted C2-C30 hetero aryl group, an unsubstituted or substituted C7-C30 aralkyl group, an unsubstituted or substituted C3-C30 hetero aralkyl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C2-C30 hetero aryloxy group, an unsubstituted or substituted C6-C30 aryl amino group, an unsubstituted or substituted C2-C30 hetero aryl amino group, an unsubstituted or substituted C6-C30 aryl silyl group, and an unsubstituted or substituted C2-C30 hetero aryl silyl group, wherein each R1 is identical to or different from each other when a1 is 2, 3, or 4, wherein each R2 is identical to or different from each other when a2 is 2, and wherein each R3 is identical to or different from each other when a3 is 2, 3 or 4, or
optionally,
two adjacent R1 are further linked together to form an unsubstituted or substituted C4-C20 alicyclic ring, an unsubstituted or substituted C3-C20 hetero alicyclic ring, an unsubstituted or substituted C6-C20 aromatic ring or an unsubstituted or substituted C2-C20 hetero aromatic ring when a1 is 2, 3, or 4, and/or
two adjacent R2 are further linked together to form an unsubstituted or substituted C4-C20 alicyclic ring, an unsubstituted or substituted C3-C20 hetero alicyclic ring, an unsubstituted or substituted C6-C20 aromatic ring or an unsubstituted or substituted C2-C20 hetero aromatic ring when a2 is 2,
two adjacent R3 are further linked together to form an unsubstituted or substituted C4-C20 alicyclic ring, an unsubstituted or substituted C3-C20 hetero alicyclic ring, an unsubstituted or substituted C6-C20 aromatic ring or an unsubstituted or substituted C2-C20 hetero aromatic ring when a3 is 2, 3 or 4, and/or
R4 and R5 are further linked together to form an unsubstituted or substituted C4-C20 alicyclic ring, an unsubstituted or substituted C3-C20 hetero alicyclic ring, an unsubstituted or substituted C6-C20 aromatic ring or an unsubstituted or substituted C2-C20 hetero aromatic ring;
each of a1 and a3 is independently 0, 1, 2, 3, or 4;
a2 is 0, 1, or 2,
LB is an auxiliary ligand;
m is 1, 2 or 3;
n is 0, 1 or 2; and
m+n is 3; and
wherein the second compound includes an organic compound having the structure of Chemical Formula 8:
wherein:
each of R31 to R33 is independently chosen from hydrogen, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C2-C20 alkenyl group, an unsubstituted or substituted C2-C20 alkynyl group, an unsubstituted or substituted C1-C20 alkoxy group, an unsubstituted or substituted C1-C20 alkyl amino group, an unsubstituted or substituted C1-C20 alkyl silyl group, an unsubstituted or substituted C4-C30 cycloalkyl group, an aryl group, an unsubstituted or substituted C2-C30 hetero aryl group, an unsubstituted or substituted C7-C30 aralkyl group, an unsubstituted or substituted C3-C30 hetero aralkyl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C2-C30 hetero aryloxy group, an unsubstituted or substituted C6-C30 aryl amino group, an unsubstituted or substituted C2-C30 hetero aryl amino group, an unsubstituted or substituted C6-C30 aryl silyl group, and an unsubstituted or substituted C2-C30 hetero aryl silyl group, wherein each R31 is identical to or different from each other when d is 2, 3, 4, 5, 6, 7, 8 or 9;
each of L31 and L32 is independently a single bond, an unsubstituted or substituted C6-C30 arylene group or an unsubstituted or substituted C2-C30 hetero arylene group; and
d is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

### Claim 2 (depends on 1)

The organic light emitting diode of claim 1, wherein the at least one emitting material layer further comprises a third compound, and wherein the third compound comprises an organic compound having the following structure of Chemical Formula 11:
wherein:
each of R41 to R43 is independently chosen from hydrogen, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C2-C20 alkenyl group, an unsubstituted or substituted C2-C20 alkynyl group, an unsubstituted or substituted C1-C20 alkoxy group, an unsubstituted or substituted C1-C20 alkyl amino group, an unsubstituted or substituted C1-C20 alkyl silyl group, an unsubstituted or substituted C4-C30 cycloalkyl group, an aryl group, an unsubstituted or substituted C2-C30 hetero aryl group, an unsubstituted or substituted C7-C30 aralkyl group, an unsubstituted or substituted C3-C30 hetero aralkyl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C2-C30 hetero aryloxy group, an unsubstituted or substituted C6-C30 aryl amino group, an unsubstituted or substituted C2-C30 hetero aryl amino group, an unsubstituted or substituted C6-C30 aryl silyl group, and an unsubstituted or substituted C2-C30 hetero aryl silyl group; and
each of L41 to L43 is independently a single bond, an unsubstituted or substituted C6-C30 arylene group or an unsubstituted or substituted C2-C30 hetero arylene group.

### Claim 3 (depends on 1)

The organic light emitting diode of claim 1, wherein the LA in Chemical Formula 1 has the structure of Chemical Formula 3:
wherein:
Y3 is CR4R5, NR4, O or S; and
each of X1 to X4, R1 to R5, a1, a2 and a3 is as defined in Chemical Formula 2.

### Claim 4 (depends on 1)

The organic light emitting diode of claim 1, wherein the LA in Chemical Formula 1 has the structure of Chemical Formula 4:
wherein:
each of X11 to X14 is independently CR3 or N, wherein at least two of X11 to X14 are CR3, and at least one of X11 to X14 is N;
Y4 is NR4, O or S;
84 is 0, 1, 2, or 3; and
each of R1 to R4, a1 and a2 is as defined in Chemical Formula 2.

### Claim 5 (depends on 1)

The organic light emitting diode of claim 1, wherein the LA in Chemical Formula 1 has the structure of Chemical Formula 5:
wherein:
Y5 is O or S;
a5 is 0, 1, 2 or 3; and
each of R1 to R3, a1 and a2 is as defined in Chemical Formula 2.

### Claim 6 (depends on 1)

The organic light emitting diode of claim 1, wherein each R1 in Chemical Formula 2 is independently hydrogen, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C6-C30 aryl group or an unsubstituted or substituted C7-C30 aralkyl group.

### Claim 7 (depends on 1)

The organic light emitting diode of claim 1, wherein each of R2 and R3 in Chemical Formula 2 is independently hydrogen, or an unsubstituted or substituted C1-C20 alkyl group.

### Claim 8 (depends on 1)

The organic light emitting diode of claim 1, wherein one of X1 to X4 is N and three of X1 to X4 are CR3 in Chemical Formula 2.

### Claim 9 (depends on 1)

The organic light emitting diode of claim 1, wherein Y1 is O or S, and Y2 is the single bond in Chemical Formula 2.

### Claim 10 (depends on 1)

The organic light emitting diode of claim 1, wherein the LB in Chemical Formula 1 has the structure of Chemical Formula 6A or Chemical Formula 6B:
wherein:
each of R11, R12 and R21 to R23 is independently chosen from hydrogen, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C2-C20 alkenyl group, an unsubstituted or substituted C2-C20 alkynyl group, an unsubstituted or substituted C1-C20 alkoxy group, an unsubstituted or substituted C1-C20 alkyl amino group, an unsubstituted or substituted C1-C20 alkyl silyl group, an unsubstituted or substituted C4-C30 cycloalkyl group, an unsubstituted or substituted C3-C30 hetero cycloalkyl group, an unsubstituted or substituted C6-C30 aryl group, an unsubstituted or substituted C2-C30 hetero aryl group, an unsubstituted or substituted C7-C30 aralkyl group, an unsubstituted or substituted C3-C30 hetero aralkyl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C2-C30 hetero aryloxy group, an unsubstituted or substituted C6-C30 aryl amino group, an unsubstituted or substituted C2-C30 hetero aryl amino group, an unsubstituted or substituted C6-C30 aryl silyl group, and an unsubstituted or substituted C2-C30 hetero aryl silyl group, wherein each R11 is identical to or different from each other when b1 is 2, 3 or 4, and wherein each R12 is identical to or different from each other when b2 is 2, 3 or 4, or
optionally,
two adjacent R11 are further linked together to form an unsubstituted or substituted C4-C20 alicyclic ring, an unsubstituted or substituted C3-C20 hetero alicyclic ring, an unsubstituted or substituted C6-C20 aromatic ring or an unsubstituted or substituted C2-C20 hetero aromatic ring when b1 is 2, 3 or 4, and/or
two adjacent R12 are further linked together to form an unsubstituted or substituted C4-C20 alicyclic ring, an unsubstituted or substituted C3-C20 hetero alicyclic ring, an unsubstituted or substituted C6-C20 aromatic ring or an unsubstituted or substituted C2-C20 hetero aromatic ring when b2 is 2, 3 or 4, and/or
two adjacent groups among R21 to R23 are further linked together to form an unsubstituted or substituted C4-C20 alicyclic ring, an unsubstituted or substituted C3-C20 hetero alicyclic ring, an unsubstituted or substituted C6-C20 aromatic ring or an unsubstituted or substituted C2-C20 hetero aromatic ring; and
each of b1 and b2 is independently 0, 1, 2, 3 or 4.

### Claim 11 (depends on 1)

The organometallic compound of claim 1, wherein LA in Chemical Formula 1 is chosen from:

### Claim 12 (depends on 1)

The organometallic compound of claim 1, wherein R1 in Chemical Formula 1 is chosen from:
H, CH3, C2H5,

### Claim 13 (depends on 1)

The organometallic compound of claim 1, wherein R2 in Chemical Formula 1 is hydrogen.

### Claim 14 (depends on 1)

The organometallic compound of claim 1, wherein Ra in Chemical Formula 1 is chosen from:
H, CH3,

### Claim 15 (depends on 1)

The organometallic compound of claim 1, wherein LB in Chemical Formula 1 is chosen from:

### Claim 16 (depends on 11)

The organic light emitting diode of claim 11, wherein the first compound is at least one of:

### Claim 17

The organic light emitting diode, wherein the second compound has the structure of Chemical Formula 9:
wherein each of R31 to R33, L31 to L33 and d as defined in Chemical Formula 8.

### Claim 18 (depends on 1)

The organic light emitting diode of claim 1, wherein R31 is hydrogen or a C1-C10 alkyl group,
each of R32 and R33 is independently selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, dibenzofuranyl and dibenzothiophenyl each of which is independently unsubstituted or substituted with at least one of C1-C10 alkyl and C6-C30 aryl, and
each of L31 to L33 is independently a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group in Chemical Formula 8.

### Claim 19 (depends on 17)

The organic light emitting diode of claim 17, wherein R31 is hydrogen.

### Claim 20 (depends on 17)

The organic light emitting diode of claim 17, wherein R32 is chosen from:
H, CH3,

### Claim 21 (depends on 17)

The organic light emitting diode of claim 17, wherein R33 is chosen from:

### Claim 22 (depends on 17)

The organic light emitting diode of claim 17, wherein each of L31, L32, and L33 is independently chosen from a single bond,

### Claim 23 (depends on 1)

The organic light emitting diode of claim 1, wherein the second compound is at least one of:

### Claim 24 (depends on 2)

The organic light emitting diode of claim 2, wherein R41 is selected from phenyl, naphthyl, dibenzofuranyl and dibenzothiophenyl each of which is independently unsubstituted or substituted with at least one of C1-C10 alkyl and C6-C20 aryl,
each of R42 and R43 is independently selected from phenyl, biphenyl, terphenyl and naphthyl each of which is independently unsubstituted or substituted with at least one of C1-C10 alkyl and C6-C20 aryl, and
each of L41 to L43 is independently a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group in Chemical Formula 11.

### Claim 25 (depends on 2)

The organic light emitting diode of claim 2, wherein the third compound is at least one of:

### Claim 26 (depends on 1)

The organic light emitting diode of claim 1, wherein the emissive layer comprises:
a first emitting part disposed between the first and second electrodes and comprising a first emitting material layer;
a second emitting part disposed between the first emitting part and the second electrode and comprising a second emitting material layer; and
a first charge generation layer disposed between the first emitting part and the second emitting part, and
wherein at least one of the first emitting material layer and the second emitting material layer comprises the first compound and the second compound.

### Claim 27 (depends on 26)

The organic light emitting diode of claim 26, wherein the at least one of the first emitting material layer and the second emitting material layer further comprises a third compound, and wherein the third compound comprises an organic compound having the structure of Chemical Formula 11:
wherein:
each of R41 to R43 is independently chosen from hydrogen, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C2-C20 alkenyl group, an unsubstituted or substituted C2-C20 alkynyl group, an unsubstituted or substituted C1-C20 alkoxy group, an unsubstituted or substituted C1-C20 alkyl amino group, an unsubstituted or substituted C1-C20 alkyl silyl group, an unsubstituted or substituted C4-C30 cycloalkyl group, an aryl group, an unsubstituted or substituted C2-C30 hetero aryl group, an unsubstituted or substituted C7-C30 aralkyl group, an unsubstituted or substituted C3-C30 hetero aralkyl group, an unsubstituted or substituted C6-C30 aryloxy group, an unsubstituted or substituted C2-C30 hetero aryloxy group, an unsubstituted or substituted C6-C30 aryl amino group, an unsubstituted or substituted C2-C30 hetero aryl amino group, an unsubstituted or substituted C6-C30 aryl silyl group, and an unsubstituted or substituted C2-C30 hetero aryl silyl group; and
each of L41 to L43 is independently a single bond, an unsubstituted or substituted C6-C30 arylene group or an unsubstituted or substituted C2-C30 hetero arylene group.

### Claim 28 (depends on 26)

The organic light emitting diode of claim 26, wherein each of L41, L42, and L43 is independently chosen from a single bond,

### Claim 29 (depends on 26)

The organic light emitting diode of claim 26, wherein R41 is chosen from:

### Claim 30 (depends on 26)

The organic light emitting diode of claim 26, wherein each of R42 and R43 is independently chosen from:

### Claim 31 (depends on 27)

The organic light emitting diode of claim 27, wherein the second emitting material layer comprises:
a first layer disposed between the first charge generation layer and the second electrode; and
a second layer disposed between the first layer and the second electrode, and
wherein one of the first layer and the second layer comprises the first compound, the second compound and the third compound.

### Claim 32 (depends on 27)

The organic light emitting diode of claim 27, wherein the emissive layer further comprises:
a third emitting part disposed between the second emitting part and the second electrode and comprising a third emitting material layer; and
a second charge generation layer disposed between the second emitting part and the third emitting part.

### Claim 33 (depends on 32)

The organic light emitting diode of claim 32, wherein the second emitting material layer comprises:
a first layer disposed between the first charge generation layer and the second electrode; and
a second layer disposed between the first layer and the second electrode, and
wherein one of the first layer and the second layer comprises the first compound, the second compound and the third compound.

### Claim 34 (depends on 1)

An organic light emitting device comprising:
a substrate; and
the organic light emitting diode of claim 1 disposed over the substrate.