# US 2022/0045293 A1 · Light-emitting device and electronic apparatus including the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2022/0045293 A1
- Document ID: US20220045293A1
- Status: Published application
- Kind: A1
- Application number: 17/331,241
- Filed: 2021-05-26
- Published: 2022-02-10
- Earliest claimed: 2020-08-07
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Minkyung KIM; Namsu KANG; Minho PARK; Huiju PARK; Dongkyu LEE; Jongwon LEE; Hyunshik LEE
- Web page: https://patentgrep.com/patent/US20220045293A1

## CPC

- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 50/13: comprising stacked EL layers within one EL unit
- H10K 50/19: Tandem OLEDs
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/658: {Organoboranes}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 59/12: Active-matrix OLED [AMOLED] displays
- H10K 2101/20: Delayed fluorescence emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A light-emitting device includes a first electrode, a second electrode facing the first electrode, a first emission layer between the first electrode and the second electrode, and a second emission layer between the first emission layer and the second electrode. The first emission layer includes a first compound and a second compound, the second emission layer includes a third compound and a fourth compound, the first compound and the second compound are different from each other, and the third compound and the fourth compound are different from each other. The fourth compound includes at least one of an electron transport compound and a bipolar compound. An electronic apparatus including the light-emitting device is also provided.

## Claims

### Claim 1

A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an interlayer disposed between the first electrode and the second electrode, wherein
the interlayer includes a first emission layer, and a second emission layer disposed between the first emission layer and the second electrode,
the first emission layer includes a first compound and a second compound,
the second emission layer includes a third compound and a fourth compound,
the first compound and the second compound are different from each other,
the third compound and the fourth compound are different from each other,
the fourth compound includes at least one selected from an electron transport compound and a bipolar compound, and
the first compound includes a first fluorescent compound, and the third compound includes a second fluorescent compound satisfying Equation 1, or
the first compound includes the second fluorescent compound satisfying Equation 1, and the third compound includes the first fluorescent compound:
ΔEST=S1−T1≤0.5 eV [Equation 1]
wherein in Equation 1,
S1 is the lowest excitation singlet energy level (eV) of the second fluorescent compound, and
T1 is the lowest excitation triplet energy level (eV) of the second fluorescent compound.

### Claim 2 (depends on 1)

The light-emitting device of claim 1, wherein
the first electrode is an anode,
the second electrode is a cathode, and
the interlayer further includes:
a hole transport region disposed between the first electrode and the first emission layer; and
an electron transport region disposed between the second emission layer and the second electrode.

### Claim 3 (depends on 2)

The light-emitting device of claim 2, wherein
the hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and
the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

### Claim 4 (depends on 1)

The light-emitting device of claim 1, wherein the second compound includes a hole transport compound.

### Claim 5 (depends on 1)

The light-emitting device of claim 1, wherein
the second compound and the third compound are different from each other, or
the first compound and the fourth compound are different from each other.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

The light-emitting device of claim 1, wherein each of the first compound and the third compound emits light having a maximum luminescence wavelength in a range of about 400 nm to about 600 nm.

### Claim 8 (depends on 4)

The light-emitting device of claim 4, wherein
the electron transport compound contains at least one electron withdrawing group,
the bipolar compound includes:
at least one electron withdrawing group and at least one electron donating group,
an anthracene group and a furan group, or
at least one electron withdrawing group, at least one electron donating group, an anthracene group, and a furan group, and
the hole transport compound includes at least one electron donating group.

### Claim 9 (depends on 8)

The light-emitting device of claim 8, wherein
the electron withdrawing group is selected from:
—F, —CFH2, —CF2H, —CF3, —CN, and —NO2;
a C1-C60 alkyl group substituted with at least one selected from —F, —CFH2, —CF2H, —CF3, —CN, and —NO2; and
a π electron deficient nitrogen-containing C1-C60 cyclic group, unsubstituted or substituted with at least one R10a, and
the electron donating group is selected from a π electron-rich C3-C60 cyclic group unsubstituted or substituted with at least one R10a, and —N(Q1)(Q2),
R10a is:
deuterium (-D), —F, —C, —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 unsubstituted or substituted with deuterium, —F, —C, —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 a combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each 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 a 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),
wherein Q1, Q2, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: 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; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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 a combination thereof.

### Claim 10 (depends on 1)

The light-emitting device of claim 1, wherein the second compound comprises at least one compound represented by Formula 1:
wherein in Formula 1,
A11 is 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,
L11 to L13 are each independently a single bond, 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,
a11 to a13 are each independently an integer from 1 to 3,
Ar11 and Ar12 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 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, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
m11 is an integer from 1 to 8, and
R10a is:
deuterium (-D), —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 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 a combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each 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 a 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),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: 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; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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 a combination thereof.

### Claim 11 (depends on 1)

The light-emitting device of claim 1, wherein the fourth compound comprises a compound represented by Formula 2:
wherein in Formula 2,
X21 is N or C(R21),
X22 is N or C(R22),
X23 is N or C(R23),
at least one of X21 to X23 is N,
L21 to L23 are each independently selected from a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, and a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
a21 to a23 are each independently an integer from 1 to 3,
Ar21 to Ar23 and R21 to R23 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 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, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
b21 to b23 are each independently an integer from 1 to 10, and
R10a is:
deuterium (-D), —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 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 a combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each 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 a 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),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: 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; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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 a combination thereof.

### Claim 12 (depends on 1)

The light-emitting device of claim 1, wherein the fourth compound comprises a compound represented by Formula 3:
wherein in Formula 3,
Ar31 is represented by one of Formulae A to D, and
k31 is an integer from 0 to 10,
wherein in Formulae 3 and A to D,
A31 and A32 are each independently selected from a C3-C30 carbocyclic group and a C1-C30 heterocyclic group,
R30 to R34 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 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, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
c30 is an integer from 1 to 10,
d31 is an integer from 1 to 10,
d32 is an integer from 1 to 10,
d33 is an integer from 1 to 3,
d34 is 1 or 2,
the sum of k31 and c30 is 10,
* indicates a binding site to a neighboring atom, and
R10a is:
deuterium (-D), —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 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 a combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each 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 a 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),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: 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; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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 a combination thereof.

### Claim 13 (depends on 1)

The light-emitting device of claim 1, wherein the second fluorescent compound does not contain a carbazole group.

### Claim 14 (depends on 1)

The light-emitting device of claim 1, wherein the second fluorescent compound is selected from Compounds 4-1 to 4-12:

### Claim 15

A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
m light-emitting units stacked between the first electrode and the second electrode and including emission layers; and
m-1 charge generation layers disposed between two neighboring light-emitting units from among the m light-emitting units, wherein
m is an integer of 2 or more,
the emission layers include a first emission layer, and a second emission layer disposed between the first emission layer and the second electrode,
the first emission layer includes a first compound and a second compound,
the second emission layer includes a third compound and a fourth compound,
the first compound and the second compound are different from each other,
the third compound and the fourth compound are different from each other,
the fourth compound includes at least one selected from an electron transport compound and a bipolar compound, and
the first compound includes a first fluorescent compound, and the third compound includes a second fluorescent compound satisfying Equation 1, or
the first compound includes the second fluorescent compound satisfying Equation 1, and the third compound includes the first fluorescent compound:
ΔEST=S1−T1≤0.5 eV [Equation 1]
wherein in Equation 1,
S1 is the lowest excitation singlet energy level (eV) of the second fluorescent compound, and
T1 is the lowest excitation triplet energy level (eV) of the second fluorescent compound.

### Claim 16 (depends on 15)

The light-emitting device of claim 15, wherein the maximum luminescence wavelength of light emitted from at least one light-emitting unit is different from the maximum luminescence wavelength of light emitted from at least one light-emitting unit of the remaining light-emitting units.

### Claim 17 (depends on 15)

The light-emitting device of claim 15, wherein light emitted from each of the m light-emitting units has the same maximum luminescence wavelength.

### Claim 18 (depends on 15)

The light-emitting device of claim 15, wherein each of the first compound and the third compound emits light having a maximum luminescence wavelength in a range of about 400 nm to about 600 nm.

### Claim 19 (depends on 1)

An electronic apparatus comprising:
the light-emitting device of claim 1; and
a thin-film transistor, wherein
the thin-film transistor includes a source electrode and a drain electrode, and
the first electrode of the light-emitting device is electrically connected to the source electrode or the drain electrode.

### Claim 20 (depends on 19)

The electronic apparatus of claim 19, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof.