# US 12,604,661 B2 · Light-emitting device including fluorescent compound, electronic apparatus including light-emitting device, and fluorescent compound

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- Number: US 12,604,661 B2
- Document ID: US12604661B2
- Status: Granted
- Kind: B2
- Application number: 17/682,249
- Filed: 2022-02-28
- Published: 2023-03-16
- Granted: 2026-04-14
- Earliest claimed: 2021-07-22
- Assignees: Ewha University-Industry Collaboration Foundation; Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.; Ewha University—Industry Collaboration Foundation
- Inventors: Yongsik Jung; Youngmin You; Juhyun Kim; Yusung Chun; Joonghyuk Kim; Dayoon Song; Dongyeun Jeong; Seunghee Choi; Sooghang Ihn; Hyeonho Choi
- Web page: https://patentgrep.com/patent/US12604661B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 235/02: condensed with carbocyclic rings or ring systems
- C09K 11/06: containing organic luminescent materials
- H10K 85/623: {containing five rings, e.g. pentacene}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A light-emitting device including an organic layer disposed between a first electrode and a second electrode, the organic layer comprising a fluorescent compound, wherein upon excitation, excitons in a 3n-π* excited state of the fluorescent compound migrate to a 1π-π* excited state of the fluorescent compound by reverse intersystem crossing with a Rate (rISC), and then undergo radiative transition to a ground state to emit light via fluorescence. The fluorescent compound is defined by a ratio of Rate (rISC) to Rate (IC) is 0.5 or greater. An electronic apparatus including the light-emitting device, and the fluorescent compound.

## Claims

### Claim 1

A light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; and
an organic layer disposed between the first electrode and the second electrode, the organic layer comprising an emission layer and a fluorescent compound,
wherein, upon excitation, excitons in a 3n-π* excited state of the fluorescent compound migrate to a 1π-π* excited state of the fluorescent compound by reverse intersystem crossing with a Rate (rISC), and the excitons in the 1π-π* excited state undergo radiative transition to a ground state to emit light via fluorescence, and
excitons in the 3n-π* excited state of the fluorescent compound migrate to a 3π-π* excited state of the fluorescent compound through reverse internal conversion with a Rate (IC),
wherein a ratio of Rate (rISC) to Rate (IC) is 0.5 or greater,
the index “3” in “3n-π*” and “3π-π*” represents a triplet state, and the index“1” in “1π-π*” represents a singlet state,
Rate (rISC) is evaluated by Equation 1, and Rate (IC) is evaluated by Equation 2:
Rate (rISC)=SOC2/(E(3n-π*)−E(1π-π*))2 Equation 1
Rate (IC)=SOC2/(E(3n-π*)−E(3π-π*))2 Equation 2
wherein, in Equations 1 and 2,
SOC represents a spin-orbit coupling value,
E(3n-π*) represents an energy level of the 3n-π* excited state,
E(1π-π*) represents an energy level of the 1π-π* excited state,
E(π-π*) represents an energy level of the 3π-π* excited state, and
SOC, E(3π-π*), E(1π-π*), and E(3π-π*) are each evaluated according to density functional theory,
wherein an absolute value of a difference between an energy level of the 3n-π* excited state in the fluorescent compound and an energy level of the 3π-π* excited state in the fluorescent compound is in a range of about 0 electron volts to about 0.1 electron volts.

### Claim 2 (depends on 1)

The light-emitting device of claim 1, wherein the ratio of Rate (rISC) to Rate (IC) is in a range of about 0.8 to about 1.5.

### Claim 3 (depends on 1)

The light-emitting device of claim 1, wherein the ratio of Rate (rISC) to Rate (IC) is in a range of about 1.0 to about 1.3.

### Claim 4 (depends on 1)

The light-emitting device of claim 1, wherein an energy level of the 3n-π* excited state is greater than the lowest energy level among energy levels of the 1π-π* excited state in the fluorescent compound.

### Claim 5 (depends on 1)

The light-emitting device of claim 1, wherein an absolute value of a difference between an energy level of the 3n-π* excited state in the fluorescent compound and the lowest energy level among energy levels of the 1π-π* excited state in the fluorescent compound is in a range of about 0 electron volts to about 0.15 electron volts.

### Claim 6 (depends on 1)

The light-emitting device of claim 1, wherein an energy level of the 3π-π* excited state is greater than an energy level of the 3π-π* excited state in the fluorescent compound.

### Claim 7 (depends on 1)

The light-emitting device of claim 1, wherein an additional excited state is not present between the 3n-π* excited state and the 3π-π* excited state in the fluorescent compound.

### Claim 8 (depends on 1)

The light-emitting device of claim 1, wherein the fluorescent compound has a non-bonding orbital.

### Claim 9 (depends on 1)

The light-emitting device of claim 1, wherein the fluorescent compound has at least one carbonyl group.

### Claim 10 (depends on 1)

The light-emitting device of claim 1, wherein the fluorescent compound is represented by Formula 1-1:
wherein, in Formula 1-1, ring A1 is a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
Z1 in Formula 1-1 is a group represented by Formula 2-1 or a group represented by Formula 2-2, and n1 is an integer from 0 to 20,
Z2 in Formula 1-1 is a group represented by Formula 2-2, and n2 is an integer from 1 to 40,
L1 and L2 in Formulae 2-1 and 2-2 are each independently a single bond, a C5-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,
a1 and a2 in Formulae 2-1 and 2-2 are each independently an integer from 1 to 20,
wherein R1 and each R10a in Formulae 2-1 and 2-2, are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9),
b1 in Formulae 2-1 and 2-2 is an integer from 1 to 20,
* in Formulae 2-1 and 2-2 indicates a binding site to an adjacent atom, and
at least one substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), or any combination thereof; or
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), or —P(═O)(Q38)(Q39),
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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, a C1-C60 alkyl group substituted with at least one selected from deuterium, a C1-C60 alkyl group, and a C6-C60 aryl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one selected from deuterium, a C1-C60 alkyl group, and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

### Claim 11 (depends on 10)

The light-emitting device of claim 10, wherein ring A1 in Formula 1-1 is a nitrogen-containing C1-C60 heteropolycyclic group.

### Claim 12 (depends on 10)

The light-emitting device of claim 10, wherein ring A1 in Formula 1-1 is a group represented by one of Formulae A1-1 to A1-6:
wherein, in Formula A1-5, X1 is O, S, N(Z1), N(Z2), or C(Z11)(Z12), wherein Z11 and Z12 are independently a group defined by Z1.

### Claim 13 (depends on 10)

The light-emitting device of claim 10, wherein n2 in Formula 1-1 is 1 or 2.

### Claim 14 (depends on 10)

The light-emitting device of claim 10, wherein the fluorescent compound is represented by Formula A (1) or Formula A(2):
wherein, in Formulae A(1) and A(2), wherein Z11 and Z12 are independently a group defined by Z1, and Z21 and Z22 are independently a group defined by Z2.

### Claim 15 (depends on 1)

The light-emitting device of claim 1, wherein the fluorescent compound is one of Compounds 1, 2, 3, or 4

### Claim 16

A light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; and
an organic layer disposed between the first electrode and the second electrode, the organic layer comprising an emission layer and a fluorescent compound,
wherein, upon excitation, excitons in a 3n-π* excited state of the fluorescent compound migrate to a 1π-π* excited state of the fluorescent compound by reverse intersystem crossing with a Rate (rISC), and the excitons in the 1π-π* excited state undergo radiative transition to a ground state to emit light via fluorescence, and
excitons in the 3n-π* excited state of the fluorescent compound migrate to a 3π-π* excited state of the fluorescent compound through reverse internal conversion with a Rate (IC),
wherein a ratio of Rate (rISC) to Rate (IC) is 0.5 to 1.5,
the index “3” in “3n-π*” and “3π-π*” represents a triplet state, and the index “1” in “1π-π*” represents a singlet state,
Rate (rISC) is evaluated by Equation 1, and Rate (IC) is evaluated by Equation 2:
Rate (rISC)=SOC2/(E(3n-π*)−E(1π-π*))2 Equation 1
Rate (IC)=SOC2/(E(3n-π*)−E(3π-π*))2 Equation 2
wherein, in Equations 1 and 2,
SOC represents a spin-orbit coupling value,
E(3n-π*) represents an energy level of the 3n-π* excited state,
E(1π-π*) represents an energy level of the 1π-π* excited state,
E(3π-π*) represents an energy level of the 3π-π* excited state, and
SOC, E(3n-π*), E(1π-π*), and E(3π-π*) are each evaluated according to density functional theory,
wherein the fluorescent compound is represented by Formula 1-1:
wherein, in Formula 1-1, ring A1 is a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
Z1 in Formula 1-1 is a group represented by Formula 2-1 or a group represented by Formula 2-2, and n1 is an integer from 0 to 20,
Z2 in Formula 1-1 is a group represented by Formula 2-2, and n2 is an integer from 1 to 40,
Land L2 in Formulae 2-1 and 2-2 are each independently a single bond, a C5-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,
a1 and a2 in Formulae 2-1 and 2-2 are each independently an integer from 1 to 20, and
ring A1 in Formula 1-1 is a group represented by one of Formulae A1-1 to A1-4 and A1-6:
wherein R1 and each R10a in Formulae 2-1 and 2-2, are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2),
—Si(Q3)(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9),
b1 in Formulae 2-1 and 2-2 is an integer from 1 to 20,
* in Formulae 2-1 and 2-2 indicates a binding site to an adjacent atom.

### Claim 17

A light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; and
an organic layer disposed between the first electrode and the second electrode, the organic layer comprising an emission layer and a fluorescent compound,
wherein, upon excitation, excitons in a 3n-π* excited state of the fluorescent compound migrate to a 1π-π* excited state of the fluorescent compound by reverse intersystem crossing with a Rate (rISC), and the excitons in the 1π-π* excited state undergo radiative transition to a ground state to emit light via fluorescence, and
excitons in the 3n-π* excited state of the fluorescent compound migrate to a 3π-π* excited state of the fluorescent compound through reverse internal conversion with a Rate (IC),
wherein a ratio of Rate (rISC) to Rate (IC) is 0.5 to 1.5,
the “3” in “3n-π*” and “3π-π*” represents a triplet state, and the “1” in “1π-π*” represents a singlet state,
Rate (rISC) is evaluated by Equation 1, and Rate (IC) is evaluated by Equation 2:
Rate (rISC)=SOC2/(E(3n-π*)−E(1π-π*))2 Equation 1
Rate (IC)=SOC2/(E(3n-π*)−E(3π-π*))2 Equation 2
wherein, in Equations 1 and 2,
SOC represents a spin-orbit coupling value,
E(3n-π*) represents an energy level of the 3n-π* excited state,
E(1π-π*) represents an energy level of the 1π-π* excited state,
E(3π-π*) represents an energy level of the 3π-π* excited state, and
SOC, E(3n-π*), E(1π-π*), and E(3π-π*) are each evaluated according to density functional theory,
wherein an absolute value of a difference between an energy level of the 3n-π* excited state in the fluorescent compound and the lowest energy level among energy levels of the 1π-π* excited state in the fluorescent compound is in a range of about 0 electron volts to about 0.15 electron volts.

### Claim 18 (depends on 16)

The light-emitting device of claim 16, wherein at least two of the following conditions are satisfied:
an additional excited state is not present between the 3n-π* excited state and the 3π-π* excited state in the fluorescent compound;
the fluorescent compound has a non-bonding orbital; and
the fluorescent compound has at least one carbonyl group.

### Claim 19 (depends on 17)

The light-emitting device of claim 17, wherein at least two of the following conditions are satisfied:
an additional excited state is not present between the 3n-π* excited state and the 3π-π* excited state in the fluorescent compound;
the fluorescent compound has a non-bonding orbital; and
the fluorescent compound has at least one carbonyl group.