Granted Patent B2

US 12,624,061 · App. 16/829,818 · Granted May 12, 2026

Inventors: Seokgyu Yoon (Yongin-si, KR); Jinwon Sun (Yongin-si, KR); Hyosup Shin (Yongin-si, KR); Hyeongu Cho (Yongin-si, KR)

Assignee: Samsung Display Co., Ltd.

C07F15/0086C07F15/0033H10K50/12H10K85/342H10K85/346H10K50/11H10K85/658H10K2101/40

Abstract

Claims (88)

1 . An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, the emission layer comprises a first host, a first dopant, and a second dopant,

wherein the first dopant is an organometallic compound selected from among Compounds 50-11 to 50-15, 50-21 to 50-28, 50-39 to 50-43, 50-49 to 50-56, 50-67 to 50-71, and 50-77 to 50-84,

wherein the second dopant comprises a heterocyclic compound represented by one of Formula 11(4) or Formula 501:

wherein, in Compounds 50-11 to 50-15, 50-21 to 50-28, 50-39 to 50-43, 50-49 to 50-56, 50-67 to 50-71, and 50-77 to 50-84, “Me” represents a methyl group, “iso-Pr” represents an iso-propyl group, and “tert-Bu” represents a t-butyl group, and

wherein, in Formula 11(4),

CY 11 to CY 13 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

Y 11 and Y 12 are each independently at least one of a single bond, —O—, —S—, —C(R 14 )(R 15 )—, —N(R 14 )—, Si(R 14 )(R 15 )—, —C(═O)—, —S(═O) 2 —, —B(R 14 )—, or —P(═O)(R 14 )—,

at least one selected from among Y 11 or Y 12 is each independently at least one of —C(R 14 )(R 15 )—, —N(R 14 )—, Si(R 14 )(R 15 )—, —C(═O)—, —S(═O) 2 —, —B(R 14 )—, or —P(═O)(R 14 )—,

Y 15 is N, B, or P,

R 11 to R 15 are each independently at least one of 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 substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),

at least two substituents selected from R 11 to R 15 are optionally bound to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

R 14 is bound to at least one of R 11 or R 13 to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, or Formula 11(4) is represented by Compound 12-1 or Compound 12-2:

a11 to a13 are each independently an integer from 1 to 6, and

at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic condensed heteropolycyclic group is at least one of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), or —P(═O)(Q 11 )(Q 12 );

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), or —P(═O)(Q 21 )(Q 22 ); or

—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ),

wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently at least one of 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group,

wherein, in Formula 501,

Ar 501 is selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group,

L 501 to L 503 are each independently at least one of a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xd1 to xd3 are each independently an integer from 0 to 3,

R 501 and R 502 are each independently at least one of a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

xd4 is an integer from 1 to 6.

2 . The organic light-emitting device of claim 1 , wherein the first dopant and the second dopant each satisfy Equations 1-1 and 1-2:

S 1( D 1) onset ≥S 1( D 2) onset   Equation 1-1

S 1( D 1) max ≥S 1( D 2) max ,  Equation 1-2

wherein, in Equations 1-1 and 1-2,

S1(D1) onset indicates a singlet energy at an onset wavelength (λ onset ) in a photoluminescence (PL) spectrum of the first dopant,

S1(D2) onset indicates a singlet energy at an onset wavelength in a PL spectrum of the second dopant,

S1(D1) max indicates a singlet energy at a maximum emission wavelength (λ max ) in a PL spectrum of the first dopant, and

S1(D2) max indicates a singlet energy at a maximum emission wavelength in a PL spectrum of the second dopant.

3 . The organic light-emitting device of claim 1 , wherein the first dopant and the second dopant satisfy Equation 2-1:

S 1( D 1) onset −S 1( D 2) onset ≤0.2 eV,  Equation 2-1

wherein, in Equation 2-1,

S1(D1) onset indicates a singlet energy level at an onset wavelength (λ onset ) in a photoluminescence (PL) spectrum of the first dopant, and

S1(D2) onset indicates a singlet energy level at an onset wavelength in a PL spectrum of the second dopant.

4 . The organic light-emitting device of claim 1 , wherein the first dopant and the second dopant satisfy Equation 2-2:

T 1( D 1) onset −T 1( D 2) onset ≤0.2 eV,  Equation 2-2

wherein, in Equation 2-2,

T1(D1) onset indicates a triplet energy at an onset wavelength in a photoluminescence (PL) spectrum of the first dopant, and

T1(D2) onset indicates a triplet energy at an onset wavelength in a PL spectrum of the second dopant.

5 . The organic light-emitting device of claim 1 , wherein the emission layer is configured to emit blue light having a maximum emission wavelength of about 420 nanometers (nm) or greater to about 470 nm or less.

6 . The organic light-emitting device of claim 1 , wherein a ratio of an emission component emitted from the second dopant to total emission components from the emission layer is 50 percent (%) or greater.

7 . The organic light-emitting device of claim 1 , wherein the emission layer consists of the first host, the first dopant, and the second dopant.

8 . The organic light-emitting device of claim 1 , wherein the second dopant is a delayed fluorescence dopant that satisfies Equation 3-2:

S 1( D 2)− T 1( D 2)≤0.3 eV,  Equation 3-2

wherein, in Equation 3-2,

S1(D2) indicates a singlet energy of the second dopant, and

T1(D2) indicates a triplet energy of the second dopant.

9 . The organic light-emitting device of claim 1 , wherein

CY 11 to CY 13 are each independently at least one of a benzene group, a naphthalene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, and

R 11 to R 15 are each independently at least one of hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, iso-butyl group, a tert-butyl group, an ethenyl group, a propenyl group, a butenyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, a tert-butoxy group, a phenyl group, a biphenyl group, or a group represented by one of Formulae 4-1 to 4-34, Formulae 5-1 to 5-26, and Formulae 6-1 to 6-55:

wherein, in Formulae 4-1 to 4-34, Formulae 5-1 to 5-26, and Formulae 6-1 to 6-55,

Y 21 and Y 22 are each independently O, S, C(Z 26 )(Z 27 ), N(Z 26 ), or Si(Z 26 )(Z 27 ),

Y 23 to Y 26 are each independently a single bond, O, S, C(Z 28 )(Z 29 ), N(Z 28 ), or Si(Z 28 )(Z 29 ),

Y 27 is N, B, or P,

Y 31 and Y 32 are each independently O, S, C(Z 33 )(Z 34 ), N(Z 33 ), or Si(Z 33 )(Z 34 ),

Z 21 to Z 29 and Z 31 to Z 34 are each independently at least one of 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, a phenanthrolinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ), wherein Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

g2 is 1 or 2,

g3 is an integer from 1 to 3,

g4 is an integer from 1 to 4,

g5 is an integer from 1 to 5,

g7 is an integer from 1 to 7,

g8 is an integer from 1 to 8,

e2 is 1 or 2,

e3 is an integer from 1 to 3,

e4 is an integer from 1 to 4,

e5 is an integer from 1 to 5,

e6 is an integer from 1 to 6,

e7 is an integer from 1 to 7,

e9 is an integer from 1 to 9, and

* indicates a binding site to an adjacent atom.

10 . The organic light-emitting device of claim 1 , wherein the second dopant is selected from Compounds FD1 to FD23:

11 . The organic light-emitting device of claim 1 , wherein

the first electrode is an anode,

the second electrode is a cathode,

the organic layer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

the hole transport region comprises 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 comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

12 . The organic light-emitting device of claim 11 , wherein the hole transport region comprises a p-dopant, wherein a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant is −3.5 electron volts (eV) or less.

13 . The organic light-emitting device of claim 11 , wherein the electron transport region comprises a metal-containing material.

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

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (77)