# US 12,765,257 B2 · Organic light-emitting device and an apparatus including the same

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- Number: US 12,765,257 B2
- Document ID: US12765257B2
- Status: Granted
- Kind: B2
- Application number: 17/560,206
- Filed: 2021-12-22
- Published: 2022-06-30
- Granted: 2026-10-13
- Earliest claimed: 2020-12-23
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Sungsoo Bae; Soungwook Kim; Seulong Kim; Hyein Jeong; Hyewon Choi; Jaeweon Hur
- Web page: https://patentgrep.com/patent/US12765257B2

## CPC

- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 50/12: comprising dopants
- H10K 50/13: comprising stacked EL layers within one EL unit
- H10K 50/85: Arrangements for extracting light from the devices
- H10K 59/12: Active-matrix OLED [AMOLED] displays
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes: an emission region; a hole transport region between the first electrode and the emission region; and an electron transport region between the emission region and the second electrode, the emission region includes a first emission layer proximate to the hole transport region and a second emission layer proximate to the electron transport region, the first emission layer and the second emission layer are different from each other, and Equation 1 is satisfied, as described herein.

## Claims

### Claim 1

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, wherein
the organic layer comprises: an emission region; a hole transport region between the first electrode and the emission region; and an electron transport region between the emission region and the second electrode,
the emission region comprises a first emission layer proximate to the hole transport region and a second emission layer proximate to the electron transport region,
the first emission layer and the second emission layer are different from each other, and Equation 1 is satisfied:
VHOD_EML1 (at 10 mA/cm2)+0.5≤VHOD_EML2 (at 10 mA/cm2) Equation 1
wherein, in Equation 1,
VHOD_EML1 (at 10 mA/cm2) is a driving voltage value when a current density of a first hole-only device having a structure comprising the first electrode, the hole transport region, the first emission layer, and the second electrode is 10 mA/cm2,
VHOD_EML2 (at 10 mA/cm2) is a driving voltage value when a current density of a second hole-only device having a structure comprising the first electrode, the hole transport region, the second emission layer, and the second electrode is 10 mA/cm2, and
the first hole-only device and the second hole-only device have substantially the same structure, except that the first emission layer and the second emission layer are respectively used in the first hole-only device and the second hole-only device,
wherein the first emission layer and the second emission layer each, independently from one another, comprise both a first compound comprising a hole transporting host, and a second compound comprising an electron transporting host; or a third compound comprising a bipolar host,
wherein the first compound is of Formula 1:
wherein, in Formula 1,
X11 is O, S, N(R19), or C(R19)(R20),
R11 to R20 are each, independently from one another: *-(L11)a11-A11, hydrogen, deuterium, a C1-C60 alkyl group, a π electron-deficient nitrogen-free cyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), or —N(Q1)(Q2), wherein * indicates a binding site to a neighboring atom;
a π electron-deficient nitrogen-free cyclic group substituted with at least one of deuterium, a C1-C60 alkyl group, a π electron-deficient nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32); or
a π electron-deficient nitrogen-free cyclic group substituted with a π electron-deficient nitrogen-free cyclic group substituted with at least one of deuterium, a C1-C60 alkyl group, a π electron-deficient nitrogen-free cyclic group, —C(Q21)(Q22)(Q23), —Si(Q21)(Q22)(Q23), —B(Q21)(Q22), and —N(Q21)(Q22),
L11 is: a π electron-deficient nitrogen-free cyclic group, —C(Q1)(Q2)—, —Si(Q1)(Q2)—, —B(Q1)—, or —N(Q1)—; or
a π electron-deficient nitrogen-free cyclic group substituted with at least one of deuterium, a C1-C60 alkyl group, a π electron-deficient nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32),
a11 is 1, 2, or 3,
A11 is
a π electron-deficient nitrogen-free cyclic group;
a π electron-deficient nitrogen-free cyclic group substituted with at least one of deuterium, a C1-C60 alkyl group, a π electron-deficient nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32); or
a π electron-deficient nitrogen-free cyclic group substituted with a π electron-deficient nitrogen-free cyclic group substituted with at least one deuterium, a C1-C60 alkyl group, a π electron-deficient nitrogen-free cyclic group, —C(Q21)(Q22)(Q23), —Si(Q21)(Q22)(Q23), —B(Q21)(Q22), and —N(Q21)(Q22), and
any two or more substituents among R11 to R20 are optionally linked to each other to form one: a π electron-deficient nitrogen-free cyclic group; and a π electron-deficient nitrogen-free cyclic group substituted with at least one of deuterium, a C1-C60 alkyl group, a π electron-deficient nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32),
wherein Q1 to Q3, Q21 to Q23, and Q31 to Q33 are each, independently from one another: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group; or a C1-C60 heterocyclic group each, independently from one another unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
wherein the second compound is of Formula 2:
wherein, in Formula 2,
X24 is C(R24) or N, X25 is C(R25) or N, and X26 is C(R26) or N,
at least one of X24 to X26 is N,
R24 to R26, are independently from one another, *-(L27)a27-(Ar27)b27, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
L24 to L27 are each, independently from one another, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
Ar24 to Ar27 are each, independently from one another, a further group represented Formula 2, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
a24 to a27 are each, independently from one another, an integer from 0 to 3,
b24 to b27 are each, independently from one another, an integer from 1 to 8,
two or more neighboring groups of Ar24 to Ar27 and R24 to R26 are, independently from one another, optionally linked to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
* indicates a binding site to a neighboring atom, and
R10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof,
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group,
—Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof, or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 are, independently from one another: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; C1-C60 alkyl group; C2-C60 alkenyl group; C2-C60 alkynyl group; C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof, and
wherein the third compound is of Formula 3:
wherein, in Formula 3,
Y1 is a single bond, —O—, —S—, —C(R27)(R28)—, —N(R27)—, Si(R27)(R28)—, —C(═O)—, —S(═O)2—, —B(R27)—, —P(R27)—, or —P(═O)(R27)(R28)—,
k1 is 0 or 1,
CY21 and CY22 are each, independently from one another, a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
L21 to L23 and L28 are each, independently from one another, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
Ar21 to Ar23 and Ar28 are each, independently from one another, a group represented by Formula 3A, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
at least one of Ar21 to Ar23 is a group represented by Formula 3A,
a21 to a23 and a28 are each, independently from one another, an integer from 0 to 3,
b21 to b23 and b28 are each, independently from one another, an integer from 1 to 8,
c21 to c22 are each, independently from one another, an integer from 1 to 20,
c23 is an integer from 0 to 5,
n21 and n22 are each, independently from one another, an integer from 1 to 8,
X21 to X23 are each, independently from one another, C or N,
when each of X21 to X23 is C, at least one of R21 to R23 is, independently from one another, —F; a cyano group; or a C1-C60 alkyl group substituted with at least one of —F and a cyano group,
R21 to R23, R27 and R28 are each, independently from one another, *-(L28)a28-(Ar28)b28, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
two or more neighboring groups of Ar21 to Ar23, Ar28, R21 to R23, and R28 are, independently from one another, optionally linked to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
* indicates a binding site to a neighboring atom, and
R10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13),
—N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof,
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21),
—S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof, or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or
—P(═O)(Q31)(Q32),
Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 are, independently from one another: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; C1-C60 alkyl group; C2-C60 alkenyl group; C2-C60 alkynyl group; C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

### Claim 2 (depends on 1)

The organic light-emitting device of claim 1, wherein the first electrode comprises an anode,
the second electrode comprises a cathode, and
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region comprises a hole blocking layer, a buffer layer, an electron transport layer, an electron injection layer, or any combination thereof.

### Claim 3 (depends on 1)

The organic light-emitting device of claim 1, wherein the first emission layer directly contacts the second emission layer.

### Claim 4 (depends on 1)

The organic light-emitting device of claim 1, wherein the first emission layer and the second emission layer have different thicknesses from each other.

### Claim 5 (depends on 1)

The organic light-emitting device of claim 1, wherein the first emission layer has a thickness less than or equal to a thickness of the second emission layer.

### Claim 6 (depends on 1)

The organic light-emitting device of claim 1, wherein holes and electrons are recombined at an interface between the first emission layer and the second emission layer.

### Claim 7 (depends on 1)

The organic light-emitting device of claim 1, wherein the first emission layer comprises a first dopant, and the second emission layer comprises a second dopant, and the first dopant and the second dopant are different from each other.

### Claim 8 (depends on 7)

The organic light-emitting device of claim 7, wherein the first dopant and the second dopant are each of Formula 4:
wherein, in Formulae 4 and 4A to 4D,
M31 is selected from a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, and a third-row transition metal of the Periodic Table of Elements;
L31 is a ligand of one of Formulae 4A to 4D;
L32 is a monodentate ligand, a bidentate ligand, or a tridentate ligand;
n31 is 1 or 2;
n32 is 0, 1, 2, 3, or 4;
A31 to A34 are each, independently from one another, a C5-C30 carbocyclic group or a C1-C30 heterocyclic group;
T31 to T34 are each, independently from one another, a single bond, a double bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R35)(R36)—*′, *—C(R35)═C(R36)—*′, *—C(R35)═*′, *—Si(R35)(R36)—*′, *—B(R35)—*′, *—N(R35)—*′, or *—P(R35)—*′;
k31 to k34 are each, independently from one another, of 1, 2, or 3;
Y31 to Y34 are each, independently from one another, a single bond, *—O—*′, *—S—*′, *—C(R37)(R38)—*′, *—Si(R37)(R38)—*′, *—B(R37)—*′, *—N(R37)—*′, or *—P(R37)—*′;
* and *′ each indicate a binding site to a neighboring atom; *1, *2, *3, and *4 each indicate a binding site to M31;
R31 to R38 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2),
—C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), and R31 to R38, independently from one another, are optionally linked to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
b31 to b34 are each, independently from one another, an integer from 0 to 10, and
R10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof,
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group,
—Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof, or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or
—P(═O)(Q31)(Q32),
Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 are, independently from one another: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; C1-C60 alkyl group; C2-C60 alkenyl group; C2-C60 alkynyl group; C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

### Claim 9 (depends on 8)

The organic light-emitting device of claim 8, wherein the first dopant and the second dopant are each, independently from one another, one of Formulae 4-1 and 4-2:
wherein, in Formulae 4-1 and 4-2,
X31 to X40 are each, independently from one another, N or C, and
M31, L32, n31, n32, A31 to A34, T31 to T33, k31 to k33, Y31 to Y34, R31 to R38, and b31 to b34 have, independently from one another, the same meanings as in claim 8.

### Claim 10 (depends on 9)

The organic light-emitting device of claim 9, wherein the first dopant is of Formula 4-2, M31 is Pt, and n32 is 0, and the second dopant is of Formula 4-1, M31 is Ir, and the sum of n31 and n32 is 3.

### Claim 11 (depends on 8)

The organic light-emitting device of claim 8, wherein at least one of A31 to A34 in the first dopant, independently from one another, is a pyridine group.

### Claim 12 (depends on 1)

An electronic apparatus comprising the organic light-emitting device of claim 1.

### Claim 13 (depends on 12)

The electronic apparatus of claim 12, further comprising a thin-film transistor having a source electrode and a drain electrode, and
the first electrode of the organic light-emitting device is electrically connected to at least one of the source electrode and the drain electrode of the thin-film transistor.

### Claim 14 (depends on 12)

The electronic apparatus of claim 12, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.