IP Library › Granted Patent US 12,532,597

Granted Patent B2

US 12,532,597 · App. 16/859,763 · Granted Jan 20, 2026

Organic light-emitting device

Inventors: Jinwon Sun (Yongin-si, KR); Jaejin Lyu (Yongin-si, KR); Jungsub Lee (Yongin-si, KR); Hyun Shin (Yongin-si, KR); Yoonkyoo Lee (Yongin-si, KR)

Assignee: Samsung Display Co., Ltd.

H10K50/11 H10K50/12 H10K50/15 H10K50/16 H10K50/171 H10K59/131 H10K85/40 H10K85/654 H10K85/6572 H10K2101/40

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Quick Facts

Patent No.: US 12,532,597
App. No.: 16/859,763
Granted: Jan 20, 2026
Kind: B2

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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 layer having a first layer, and the first layer includes a first compound, a second compound, and a third compound. The first compound is a hole transporting host compound, the second compound is an electron transporting host compound, and the third compound is a hole transporting host compound or an electron transporting host compound. The first compound and the second compound form a first exciplex, and the first compound and the third compound, or the second compound and the third compound form a second exciplex, where the first exciplex and the second exciplex are different from each other.

Claims (162)

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 layer comprising a first layer,

the first layer comprises a first compound, a second compound, and a third compound,

the first compound is a hole transporting host compound,

the second compound is an electron transporting host compound,

the third compound is a hole transporting host compound or an electron transporting host compound,

the first compound and the second compound form a first exciplex,

the first compound and the third compound, or the second compound and the third compound, form a second exciplex,

the first exciplex and the second exciplex are different from each other, and

the emission layer further comprises a dopant.

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

the first compound and the second compound satisfy at least one selected from Inequations 1 and 2, and

i) the first compound and the third compound satisfy at least one selected from Inequations 3 and 4, or ii) the second compound and the third compound satisfy at least one selected from Inequations 5 and 6:

|HOMO C1 -HOMO C2 |≥0.1 eV Inequation 1

|LUMO C1 -LUMO C2 |≥0.1 eV Inequation 2

|HOMO C1 -HOMO C3 |≥0.1 eV Inequation 3

|LUMO C1 -LUMO C3 |≥0.1 eV Inequation 4

|HOMO C2 -HOMO C3 |≥0.1 eV Inequation 5

|LUMO C2 -LUMO C3 |≥0.1 eV. Inequation 6

wherein, in Inequations 1 to 6, HOMO C1 , HOMO C2 , and HOMO C3 indicate highest occupied molecular orbital (HOMO) energy levels of the first compound, the second compound, and the third compound, respectively, and LUMO C1 , LUMO C2 , and LUMO C3 indicate lowest unoccupied molecular orbital (LUMO) energy levels of the first compound, the second compound, and the third compound, respectively.

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

the second compound is represented by Formula 2:

wherein, in Formula 2,

L 11 is a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

a11 is an integer from 1 to 3,

R 11 to R 14 are each independently selected from 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 41 )(Q 42 )(Q 43 ), —N(Q 41 )(Q 42 ), —B(Q 41 )(Q 42 ), —C(═O)(Q 41 ), —S(═O) 2 (Q 41 ), and —P(═O)(Q 41 )(Q 42 ),

b11 to b14 are each independently an integer from 0 to 4,

c11 and c12 are each independently 0 or 1, wherein at least one selected from c11 and c12 is 1,

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 monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is 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, and 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, and 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 51 )(Q 52 )(Q 53 ), —N(Q 51 )(Q 52 ), —B(Q 51 )(Q 52 ), —C(═O)(Q 51 ), —S(═O) 2 (Q 51 ), and —P(═O)(Q 51 )(Q 52 );

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, a biphenyl group, and a terphenyl 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, a biphenyl group, a terphenyl group, —Si(Q 61 )(Q 62 )(Q 63 ), —N(Q 61 )(Q 62 ), —B(Q 61 )(Q 62 ), —C(═O)(Q 61 ), —S(═O) 2 (Q 61 ), and —P(═O)(Q 61 )(Q 62 ); and

—Si(Q 71 )(Q 72 )(Q 73 ), —N(Q 71 )(Q 72 ), —B(Q 71 )(Q 72 ), —C(═O)(Q 71 ), —S(═O) 2 (Q 71 ), and —P(═O)(Q 71 )(Q 72 ), and

Q 41 to Q 43 , Q 51 to Q 53 , Q 61 to Q 63 , and Q 71 to Q 73 are each independently selected from 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 6 -C 60 aryl group substituted with a C 1 -C 60 alkyl 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, and a terphenyl group.

4 . The organic light-emitting device of claim 3 , wherein the second compound is represented by one selected from Formulae 2-1 and 2-2:

wherein, in Formulae 2-1 and 2-2,

R 11 to R 16 and b11 to b16 are each independently respectively the same as defined in connection with R 11 to R 14 and b11 to b14 in claim 3 ,

c11 to c14 are each independently 0 or 1, wherein at least one selected from c11 and c12 is 1, and

the sum of c11, c12, c13, and c14 is 2 or more.

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

the third compound is an electron transporting host compound, and

the first compound and the third compound form the second exciplex.

6 . The organic light-emitting device of claim 1 , wherein the third compound is represented by Formula 3:

wherein, in Formula 3,

Ar 21 to Ar 23 are each independently a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

at least one substituent of the substituted C 5 -C 60 carbocyclic group and the substituted C 1 -C 60 heterocyclic group is selected from:

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and 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, —C(Q 81 )(Q 82 )(Q 83 ), —Si(Q 81 )(Q 82 )(Q 83 ), —N(Q 81 )(Q 82 ), —B(Q 81 )(Q 82 ), —C(═O)(Q 81 ), —S(═O) 2 (Q 81 ), and —P(═O)(Q 81 )(Q 82 );

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, a biphenyl group, and a terphenyl 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, a biphenyl group, a terphenyl group, —C(Q 91 )(Q 92 )(Q 93 ), —Si(Q 91 )(Q 92 )(Q 93 ), —N(Q 91 )(Q 92 ), —B(Q 91 )(Q 92 ), —C(═O)(Q 91 ), —S(═O) 2 (Q 91 ), and —P(═O)(Q 91 )(Q 92 ); and

—C(Q 101 )(Q 102 )(Q 103 ), —Si(Q 101 )(Q 102 )(Q 103 ), —N(Q 101 )(Q 102 ), —B(Q 101 )(Q 102 ), —C(═O)(Q 101 ), —S(═O) 2 (Q 101 ), and —P(═O)(Q 101 )(Q 102 ), and

Q 81 to Q 83 , Q 91 to Q 93 , and Q 101 to Q 103 are each independently be selected from 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 6 -C 60 aryl group substituted with a C 1 -C 60 alkyl 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, and a terphenyl group.

7 . The organic light-emitting device of claim 6 , wherein

Ar 21 to Ar 23 are each independently selected from groups represented by Formulae 6-1 to 6-5:

wherein, in Formulae 6-1 to 6-5,

Y 31 may be O, S, C(Z 33 )(Z 34 ), N(Z 35 ), or Si(Z 36 )(Z 37 ),

Z 31 to Z 37 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl 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 fluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, —C(Q 31 )(Q 32 )(Q 33 ), and —Si(Q 31 )(Q 32 )(Q 33 ),

Q 31 to Q 33 may each independently be selected from 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, and a pyridinyl group,

e3 may be an integer from 0 to 3,

e4 may be an integer from 0 to 4,

e5 may be an integer from 0 to 5,

Ph indicates a phenyl group, and

* indicates a binding site to a neighboring atom.

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

the first compound is at least one selected from Compounds HT-01 to HT-09,

the second compound is at least one selected from Compounds ET-1-01 to ET-1-18, and

the third compound is at least one selected from Compounds ET-2-01 to ET-2-18:

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

the dopant is to emit phosphorescence or delayed fluorescence.

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

the dopant comprises a compound represented by Formula 4:

wherein, in Formula 4,

M 41 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),

Y 41 to Y 44 may each independently be N or C,

two bonds selected from a bond between Y 41 and M 41 , a bond between Y 42 and M 41 , a bond between Y 43 and M 41 , and a bond between Y 44 and M 41 are each a coordinate bond, and the other two bonds may each be a covalent bond,

A 41 to A 44 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,

L 41 to L 43 are each independently selected from a single bond, a double bond, *—N(R 45 )—*′, *—B(R 45 )—*′, *—P(R 45 )—*′, *—C(R 45 )(R 46 )—*′, *—Si(R 45 )(R 46 )—*′, *—Ge(R 45 )(R 46 )—*′, *S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 *′, *—C(R 45 )=*′, *═C(R 45 )—*′, *—C(R 45 )═C(R 45 )—*′, *—C(═S)—*′, and *—C≡C—*′,

R 41 to R 46 are each independently selected from 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 111 )(Q 112 )(Q 113 ), —B(Q 111 )(Q 112 ), —N(Q 111 )(Q 112 ), —P(Q 111 )(Q 112 ), —C(═O)(Q 111 ), —S(═O)(Q 112 ), —S(═O) 2 (Q 111 ), —P(═O)(Q 111 )(Q 112 ), and —P(═S)(Q 111 )(Q 112 ),

b41 to b44 are each independently an integer from 0 to 20,

any two neighboring groups selected from R 41 (s) in the number of b41, R 42 (s) in the number of b42, R 43 (s) in the number of b43, R 44 (s) in the number of b44, R 45 , and R 46 are optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,

Q 111 to Q 113 may each independently be selected from 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,

* and *′ each indicate a binding site to a neighboring atom,

at least one substituent of the substituted C 5 -C 30 carbocyclic group, the substituted C 1 -C 30 hetrocyclic group, the substituted C 1 -C 60 alkynyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alknyl group, the substituted C 1 -C 10 alkoxy group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl 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, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and 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 121 )(Q 122 )(Q 123 ), —N(Q 121 )(Q 122 ), —B(Q 121 )(Q 122 ), —C(═O)(Q 121 ), —S(═O) 2 (Q 121 ), and —P(═O)(Q 121 )(Q 122 );

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, and 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 131 )(Q 132 )(Q 133 ), —N(Q 131 )(Q 132 ), —B(Q 131 )(Q 132 ), —C(═O)(Q 131 ), —S(═O) 2 (Q 131 ), and —P(═O)(Q 131 )(Q 132 ); and

—Si(Q 141 )(Q 142 )(Q 143 ), —N(Q 141 )(Q 142 ), —B(Q 141 )(Q 142 ), —C(═O)(Q 141 ), —S(═O) 2 (Q 141 ), and —P(═O)(Q 141 )(Q 142 ), and

Q 111 to Q 113 , Q 121 to Q 123 , Q 131 to Q 133 , and Q 141 to Q 143 are each independently selected from 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 C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group.

11 . The organic light-emitting device of claim 10 , wherein

at least one selected from Y 41 and Y 44 is N, and

at least one selected from Y 42 and Y 43 is C.

12 . The organic light-emitting device of claim 10 , wherein

two or more selected from L 41 to L 43 are each not a single bond.

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

the dopant comprises a compound represented by Formula 5:

wherein, in Formula 5,

M 51 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),

L 51 in Formula 5 is a ligand represented by Formula 5-1, wherein n51 is 1 or 2, and when n51 is 2, two L 51 (s) are identical to or different from each other,

L 52 in Formula 5 is a ligand represented by Formula 5-2, wherein n52 is 1 or 2, and when n52 is 2, two L 52 (s) are identical to or different from each other,

the sum of n51 and n52 in Formula 5 is 2 or 3,

L 51 (s) in the number of n51 and L 52 (s) in the number of n52 in Formula 5 are be linked to each other via a single bond or a first linking group,

the first linking group may be selected from *″—N(R 53 )—*′″, *″—B(R 53 )—*′″, *″—P(R 53 )—*′″, *″—C(R 53 )(R 54 )—*′″, *″—Si(R 53 )(R 54 )—*′″, *″—Ge(R 53 )(R 54 )—*′″, *″—S—*′″ *—Se—*′″, *″—O—*′, *″—C(═O)—*″, *″—S(═O)*′″, *″—S(═O) 2 *′″, *″—C(R 53 )═*′ *″═C(R 53 )—*′, *″, —C(R 53 )═C(R 54 )—*′, *″C(═S)—*′″, and *″—C≡C*′″,

X 51 to X 54 in Formula 5-1 are each independently N or C(R 55 ),

Y 51 to Y 54 in Formula 5-2 are each independently N or C(R 56 ),

Z 51 to Z 54 are each independently N or C(R 57 ),

R 51 to R 57 in Formulae 5, 5-1, and 5-2 are each independently selected from 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 151 )(Q 152 )(Q 153 ), —N(Q 151 )(Q 152 ), —B(Q 151 )(Q 152 ), —P(Q 151 )(Q 152 ), —C(═O)(Q 151 ), —S(═O) 2 (Q 151 ), and —P(═O)(Q 151 )(Q 152 ),

* and *′ in Formulae 5-1 and 5-2 each indicate a binding site to M in Formula 5,

at least one substituent of 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 monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and 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 161 )(Q 162 )(Q 163 ), —N(Q 161 )(Q 162 ), —B(Q 161 )(Q 162 ), —C(═O)(Q 161 ), —S(═O) 2 (Q 161 ), and —P(═O)(Q 161 )(Q 162 );

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, and 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 171 )(Q 172 )(Q 173 ), —N(Q 171 )(Q 172 ), —B(Q 171 )(Q 172 ), —C(═O)(Q 171 ), —S(═O) 2 (Q 171 ), and —P(═O)(Q 171 )(Q 172 ); and

—Si(Q 181 )(Q 182 )(Q 183 ), —N(Q 181 )(Q 182 ), —B(Q 181 )(Q 182 ), —C(═O)(Q 181 ), —S(═O) 2 (Q 181 ), and —P(═O)(Q 181 )(Q 182 ), and

Q 151 to Q 153 , Q 161 to Q 163 , Q 171 to Q 173 , and Q 181 to Q 183 are each independently selected from 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 C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group.

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

the dopant comprises at least one compound selected from Compounds BD1 to BD40 and Compounds 1 to 84:

15 . 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 at least one selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer, and

the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

16 . A display apparatus comprising:

a thin-film transistor comprising a source electrode, a drain electrode, and an active layer; and

the organic light-emitting device of claim 1 ,

wherein the first electrode of the organic light-emitting device is electrically connected to one of the source electrode and the drain electrode of the thin-film transistor.

17 . 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 layer comprising a first layer,

the first layer comprises a first compound, a second compound, and a third compound,

the first compound is a hole transporting host compound and is represented by Formula 1,

the second compound is an electron transporting host compound,

the third compound is a hole transporting host compound or an electron transporting host compound,

the first compound and the second compound form a first exciplex,

the first compound and the third compound, or the second compound and the third compound, form a second exciplex, and

the first exciplex and the second exciplex are different from each other:

wherein, in Formula 1,

X 1 is N or C(R 5 ),

L 1 is a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

a1 is an integer from 1 to 3,

Ar 1 is a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

c1 is an integer from 1 to 3,

R 1 , R 2 , and R 5 are each independently selected from 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 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 ), and —P(═O)(Q 1 )(Q 2 ),

b1 and b2 are each independently an integer from 0 to 4,

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and 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 ), and —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, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl 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, a biphenyl group, a terphenyl 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 ), and —P(═O)(Q 21 )(Q 22 ); and

—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 ), and —P(═O)(Q 31 )(Q 32 ), and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from 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 6 -C 60 aryl group substituted with a C 1 -C 60 alkyl 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, and a terphenyl group.

18 . The organic light-emitting device of claim 17 , wherein

Ar 1 comprises at least one π electron-depleted nitrogen-containing ring.

19 . The organic light-emitting device of claim 17 , wherein

the first compound does not comprise a cyano group.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2020

From: SUN, JINWON; LYU, JAEJIN; LEE, JUNGSUB; SHIN, HYUN; LEE, YOONKYOO

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 052505/0754 →

Priority Claims (1)

KR 10-2019-0050990 · Apr 30, 2019 · national

Continuity (1)

Related Publication 20200350507A1 · Nov 5, 2020

References Cited (252)

US 7381479B2 · Lamansky et al. · 2008 [cited by applicant]

US 7393599B2 · Thompson et al. · 2008 [cited by applicant]

US 7585573B2 · Lee et al. · 2009 [cited by applicant]

US 7652287B2 · Jeong et al. · 2010 [cited by applicant]

US 7776458B2 · Ragini et al. · 2010 [cited by applicant]

US 8106199B2 · Jabbour et al. · 2012 [cited by applicant]

US 8389725B2 · Li et al. · 2013 [cited by applicant]

US 8669364B2 · Li et al. · 2014 [cited by applicant]

US 8680760B2 · Cheng et al. · 2014 [cited by applicant]

US 8816080B2 · Li et al. · 2014 [cited by applicant]

US 8846940B2 · Li et al. · 2014 [cited by applicant]

US 8883322B2 · Wu et al. · 2014 [cited by applicant]

US 8946417B2 · Jian et al. · 2015 [cited by applicant]

US 9051344B2 · Lin et al. · 2015 [cited by applicant]

US 9076974B2 · Li et al. · 2015 [cited by applicant]

US 9093650B2 · Kim et al. · 2015 [cited by applicant]

US 9142710B2 · Seo · 2015 [cited by examiner]

US 9142791B2 · Adamovich et al. · 2015 [cited by applicant]

US 9172046B1 · Kim et al. · 2015 [cited by applicant]

US 9203039B2 · Li et al. · 2015 [cited by applicant]

US 9221857B2 · Li et al. · 2015 [cited by applicant]

US 9224963B2 · Li et al. · 2015 [cited by applicant]

US 9238668B2 · Li et al. · 2016 [cited by applicant]

US 9299944B2 · Seo et al. · 2016 [cited by applicant]

US 9312502B2 · Li et al. · 2016 [cited by applicant]

US 9324957B2 · Li et al. · 2016 [cited by applicant]

US 9340728B2 · Ise et al. · 2016 [cited by applicant]

US 9382273B2 · Li et al. · 2016 [cited by applicant]

US 9391289B2 · Seo · 2016 [cited by examiner]

US 9425415B2 · Li et al. · 2016 [cited by applicant]

US 9478764B2 · Seo · 2016 [cited by applicant]

US 9620722B2 · Martynova et al. · 2017 [cited by applicant]

US 9783564B2 · Kottas et al. · 2017 [cited by applicant]

US 9923155B2 · Li et al. · 2018 [cited by applicant]

US 10256419B2 · Brooks et al. · 2019 [cited by applicant]

US 10326111B2 · Yoo et al. · 2019 [cited by applicant]

US 10361388B2 · Mitsumori et al. · 2019 [cited by applicant]

US 10374186B2 · Ohsawa · 2019 [cited by examiner]

US 10586932B2 · Hosoumi et al. · 2020 [cited by applicant]

US 10833280B2 · Ahn · 2020 [cited by examiner]

US 10847727B2 · Hayer et al. · 2020 [cited by applicant]

US 11289668B2 · Kwak et al. · 2022 [cited by applicant]

US 12035617B2 · Shin et al. · 2024 [cited by applicant]

US 12201017B2 · Lee et al. · 2025 [cited by applicant]

US 12250873B2 · Lee et al. · 2025 [cited by applicant]

US 12250874B2 · Ahn et al. · 2025 [cited by applicant]

US 20030175553A1 · Thompson et al. · 2003 [cited by applicant]

US 20040080267A1 · Cok · 2004 [cited by applicant]

US 20050287394A1 · Yang et al. · 2005 [cited by applicant]

US 20060103298A1 · Lee · 2006 [cited by applicant]

US 20080018221A1 · Egen et al. · 2008 [cited by applicant]

US 20110024735A1 · Sawada et al. · 2011 [cited by applicant]

US 20110114922A1 · Pretot et al. · 2011 [cited by applicant]

US 20110272679A1 · Yokoyama et al. · 2011 [cited by applicant]

US 20120256535A1 · Seo · 2012 [cited by examiner]

US 20130168656A1 · Tsai et al. · 2013 [cited by applicant]

US 20130264561A1 · Dobbs et al. · 2013 [cited by applicant]

US 20130270531A1 · Seo · 2013 [cited by examiner]

US 20140027733A1 · Zeng et al. · 2014 [cited by applicant]

US 20140042370A1 · Martynova et al. · 2014 [cited by applicant]

US 20140246660A1 · Tanaka et al. · 2014 [cited by applicant]

US 20140309428A1 · Egen et al. · 2014 [cited by applicant]

US 20150053958A1 · Ishisone · 2015 [cited by examiner]

US 20150060794A1 · Oh et al. · 2015 [cited by applicant]

US 20150105556A1 · Li et al. · 2015 [cited by applicant]

US 20150137051A1 · Jung et al. · 2015 [cited by applicant]

US 20150155511A1 · Ohsawa · 2015 [cited by examiner]

US 20150194616A1 · Li et al. · 2015 [cited by applicant]

US 20150194622A1 · Yamamoto et al. · 2015 [cited by applicant]

US 20150280140A1 · Matsuki et al. · 2015 [cited by applicant]

US 20150340618A1 · Lee et al. · 2015 [cited by applicant]

US 20150349279A1 · Li et al. · 2015 [cited by applicant]

US 20160013427A1 · Kim · 2016 [cited by examiner]

US 20160028028A1 · Li et al. · 2016 [cited by applicant]

US 20160056401A1 · Lee et al. · 2016 [cited by applicant]

US 20160072078A1 · Lee et al. · 2016 [cited by applicant]

US 20160351829A1 · Hosoumi et al. · 2016 [cited by applicant]

US 20170018600A1 · Ito et al. · 2017 [cited by applicant]

US 20170062752A1 · Ihn et al. · 2017 [cited by applicant]

US 20170077421A1 · Ihn et al. · 2017 [cited by applicant]

US 20170092873A1 · Kang et al. · 2017 [cited by applicant]

US 20170098778A1 · Oh et al. · 2017 [cited by applicant]

US 20170162796A1 · Jeong et al. · 2017 [cited by applicant]

US 20170194570A1 · Kang et al. · 2017 [cited by applicant]

US 20170200899A1 · Kim et al. · 2017 [cited by applicant]

US 20170309687A1 · Watabe et al. · 2017 [cited by applicant]

US 20170309829A1 · Jung et al. · 2017 [cited by applicant]

US 20170338436A1 · Mitsumori · 2017 [cited by examiner]

US 20170346029A1 · Kim · 2017 [cited by examiner]

US 20170352819A1 · Son et al. · 2017 [cited by applicant]

US 20180013073A1 · Duan et al. · 2018 [cited by applicant]

US 20180105741A1 · Ko · 2018 [cited by examiner]

US 20180151630A1 · Yamaoka · 2018 [cited by examiner]

US 20180269410A1 · Shitagaki et al. · 2018 [cited by applicant]

US 20180309080A1 · Seo et al. · 2018 [cited by applicant]

US 20190006608A1 · Koo et al. · 2019 [cited by applicant]

US 20190051834A1 · Liu et al. · 2019 [cited by applicant]

US 20190074468A1 · Kwak et al. · 2019 [cited by applicant]

US 20190140204A1 · Seo · 2019 [cited by examiner]

US 20190157599A1 · Nakamura et al. · 2019 [cited by applicant]

US 20190165286A1 · Li et al. · 2019 [cited by applicant]

US 20190203114A1 · Ihn et al. · 2019 [cited by applicant]

US 20190214584A1 · Chen et al. · 2019 [cited by applicant]

US 20190284137A1 · Baek et al. · 2019 [cited by applicant]

US 20190296254A1 · Ko et al. · 2019 [cited by applicant]

US 20190312210A1 · Akashi et al. · 2019 [cited by applicant]

US 20190375768A1 · Kim et al. · 2019 [cited by applicant]

US 20200020870A1 · Seo · 2020 [cited by examiner]

US 20200136059A1 · Hong · 2020 [cited by examiner]

US 20200140471A1 · Chen et al. · 2020 [cited by applicant]

US 20200168818A1 · Lin et al. · 2020 [cited by applicant]

US 20200203610A1 · Duan et al. · 2020 [cited by applicant]

US 20200295272A1 · Lee · 2020 [cited by examiner]

US 20200308209A1 · Yoon et al. · 2020 [cited by applicant]

US 20200313096A1 · Kim et al. · 2020 [cited by applicant]

US 20200350507A1 · Sun et al. · 2020 [cited by applicant]

US 20210159440A1 · Mitsumori · 2021 [cited by examiner]

US 20210257574A1 · Ishisone · 2021 [cited by examiner]

US 20210343965A1 · Seo · 2021 [cited by examiner]

US 20210359227A1 · Shin et al. · 2021 [cited by applicant]

US 20210376248A1 · Song et al. · 2021 [cited by applicant]

US 20220020939A1 · Lee et al. · 2022 [cited by applicant]

US 20220131095A1 · Ko et al. · 2022 [cited by applicant]

US 20220173339A1 · Lee et al. · 2022 [cited by applicant]

US 20220190246A1 · Ishisone · 2022 [cited by examiner]

US 20220190276A1 · Naijo et al. · 2022 [cited by applicant]

US 20220199918A1 · Ahn et al. · 2022 [cited by applicant]

US 20220340550A1 · Yang · 2022 [cited by examiner]

US 20240138221A1 · Song · 2024 [cited by examiner]

CN 103360303 · 2013 [cited by applicant]

CN 103492383A · 2014 [cited by applicant]

CN 103682108A · 2014 [cited by applicant]

CN 104370974A · 2015 [cited by applicant]

DE 102014008722A1 · 2015 [cited by applicant]

EP 1820801A1 · 2007 [cited by applicant]

EP 2461390A1 · 2012 [cited by applicant]

EP 3275968 · 2018 [cited by applicant]

EP 2461390B1 · 2018 [cited by applicant]

EP 3425690A1 · 2019 [cited by applicant]

EP 3432380A2 · 2019 [cited by applicant]

EP 3428174 · 2019 [cited by applicant]

EP 3439063A1 · 2019 [cited by applicant]

EP 3451403A1 · 2019 [cited by applicant]

EP 3537495A1 · 2019 [cited by applicant]

JP 2004273190A · 2004 [cited by applicant]

JP 2005514754A · 2005 [cited by applicant]

JP 200745742A · 2007 [cited by applicant]

JP 2007335904 · 2007 [cited by applicant]

JP 2008147424A · 2008 [cited by applicant]

JP 2008525366A · 2008 [cited by applicant]

JP 2010184910A · 2010 [cited by applicant]

JP 2011091366A · 2011 [cited by applicant]

JP 2011216656A · 2011 [cited by applicant]

JP 2011256143A · 2011 [cited by applicant]

JP 2013023500A · 2013 [cited by applicant]

JP 2014513679A · 2014 [cited by applicant]

JP 201517231A · 2015 [cited by applicant]

JP 2017123463A · 2017 [cited by applicant]

JP 2017523270A · 2017 [cited by applicant]

JP 2017199903A · 2017 [cited by applicant]

JP 2017212443A · 2017 [cited by applicant]

JP 2019016788A · 2019 [cited by applicant]

JP 2019047124A · 2019 [cited by applicant]

JP 2019062184A · 2019 [cited by applicant]

KR 100730115B1 · 2007 [cited by applicant]

KR 1020120042886A · 2012 [cited by applicant]

KR 1020130116185A · 2013 [cited by applicant]

KR 1020140015298A · 2014 [cited by applicant]

KR 1020140033091A · 2014 [cited by applicant]

KR 1020140092826A · 2014 [cited by applicant]

KR 1020150030660A · 2015 [cited by applicant]

KR 1020160012941A · 2016 [cited by applicant]

KR 1020160045508A · 2016 [cited by applicant]

KR 1020160080090A · 2016 [cited by applicant]

KR 1020160130940A · 2016 [cited by applicant]

KR 1020170026075A · 2017 [cited by applicant]

KR 1020170065733A · 2017 [cited by applicant]

KR 1020170136823A · 2017 [cited by applicant]

KR 1020180013958 · 2018 [cited by applicant]

KR 1020180085007A · 2018 [cited by applicant]

KR 1020190004236A · 2019 [cited by applicant]

KR 1020190011754A · 2019 [cited by applicant]

KR 1020190026618A · 2019 [cited by applicant]

KR 1020190069584A · 2019 [cited by applicant]

KR 1020190112232A · 2019 [cited by applicant]

KR 1020200011059A · 2020 [cited by applicant]

KR 102083434B1 · 2020 [cited by applicant]

KR 1020200115795A · 2020 [cited by applicant]

KR 1020200115890A · 2020 [cited by applicant]

TW 201711243A · 2017 [cited by examiner]

WO 2011013830 · 2011 [cited by examiner]

WO 2011013830A1 · 2011 [cited by examiner]

WO WO2011055912A1 · 2011 [cited by applicant]

WO WO2012121936A2 · 2012 [cited by applicant]

WO WO2012143080A2 · 2012 [cited by applicant]

WO WO2013069338A1 · 2013 [cited by applicant]

WO WO2015171627A1 · 2015 [cited by applicant]

WO 2017111543A1 · 2017 [cited by applicant]

Graves, David et al.; “Photophysical Investigation of the Thermally Activated Delayed Emission from Films of m-MTDATA:PBD Exciplex”; Adv. Funct. Mater. 2014; 24; pp. 2343-2351. [cited by applicant]

Extended European Patent Office Search Report for corresponding European Application No. 19163558.0, dated Jul. 25, 2019, 7 pages. [cited by applicant]

European Patent Office, Search report corresponding to related European Application No. 20188007.7, dated Oct. 22, 2020, 9 pages. [cited by applicant]

Goushi, Kenichi et al., “Organic light-emitting diodes employing efficient reverse intersystem crossing for triplet-to-singlet state conversation”, Nature Photonics, Apr. 2012, pp. 253-258, Macmillan Publishers Limited. [cited by applicant]

Kesti, Tero J. et al., “Exciplex Intermediates in Photoinduced Electron Transfer of Porphyrin-Fullerene Dyads”, J. Am. Chem. Soc., 2002, pp. 8067-8077, vol. 124, No. 27, American Chemical Society, U.S. [cited by applicant]

Kim, Kwon-Hyeon et al., “Phosphorescent dye-based supramolecules for high-efficiency organic light-emitting diodes”, Nature Communications, Sep. 10, 2014, pp. 1-8, Macmillan Publishers Limited. [cited by applicant]

Kim, Sei-Yong et al., “Organic Light-Emitting Diodes with 30% External Quantum Efficiency Based on a Horizontally Oriented Emitter”, Advanced Functional Materials, 2013, pp. 3896-3900, vol. 23, Wiley-VCH Verlag GmbH & C… [cited by applicant]

Kuzmin, Michael G. et al., “Exciplex mechanism of excited state electron transfer reactions in polar media”, Journal of Photochemistry and Photobiology A: Chemistry, 1996, pp. 51-57, vol. 102, Elsevier Science S.A. [cited by applicant]

Lee, Jeong-Hwan et al., “An Exciplex Forming Host for Highly Efficient Blue Organic Light Emitting Diodes with Low Driving Voltage”, Advanced Functional Materials, 2014, 6 pages, Wiley-VCH Verlag GmbH & Co. KGaA, Weinhe… [cited by applicant]

Lee, Jeong-Hwan et al., “Exciplex-Forming Co-Host-Based Red Phosphorescent Organic Light-Emitting Diodes with Long Operational Stability and High Efficiency”, Applied Materials & Interfaces, Jan. 18, 2017, 5 pages, ACS … [cited by applicant]

Liu, Xiao-Ke et al., “Prediction and Design of Efficient Exciplex Emitters for High-Efficiency, Thermally Activated Delayed-Fluorescence Organic Light-Emitting Diodes”, Advanced Materials, 2015, 6 pages, Wiley-VCH Verla… [cited by applicant]

Shin, Hyun et al., “Effect of Triplet Exciplex Confinement in Organic Light-Emitting Diodes according to Donor/Acceptor forming ratio”, Organic Photonics Laboratory, Poster, 2020, 1 page, Industrial Technology Developme… [cited by applicant]

Shin, Hyun et al., “Sky-Blue Phosphorescent OLEDs with 34.1% External Quantum Efficiency Using a Low Refractive Index Electron Transporting Layer”, Advanced Materials, 2016, pp. 4920-4925, vol. 28, Wiley-VCH Verlag GmbH… [cited by applicant]

Shin, Hyun, “Exciplex based Organic Light-Emitting Diodes with Theoretical Efficiency and Long Operational Lifetime”, 2018, 185 pages, Department of Materials Science and Engineering, The Graduate School, Seoul National… [cited by applicant]

Wei, Xiaofang et al., “Design of Efficient Exciplex Emitters by Decreasing the Energy Gap between the local excited triplet(3LE) state of the Acceptor and the charge transfer (CT) states of the Exciplex”, Frontiers in C… [cited by applicant]

Office action issued in U.S. Appl. No. 16/360,938, dated Dec. 13, 2021, 73 pages. [cited by applicant]

Office action issued in U.S. Appl. No. 16/360,938, dated Sep. 23, 2021, 8 pages. [cited by applicant]

Hang et al. “Highly Efficient Blue-Emitting Cyclometalated Platinum(II) Complexes by Judicious Molecular Design”, Angew. Chem. Int. Ed., 2013, vol. 52, p. 6753-6756 (Year: 2013). [cited by applicant]

Fleetham et al. “Efficient “Pure” Blue OLEDs Employing Tetradentate Pt Complexes with a Narrow Spectral Bandwidth”, Adv. Mater. 2014, vol. 26, pp. 7116-7121 (Year: 2014). [cited by applicant]

Definition of “apparatus” in Merriam-Webster online dictionary, https://www.merriam-webster.com/dictionary/apparatus (Year: 2021). [cited by applicant]

Pang et al. “A full-color, low-power, wearable display for mobile applications”, SPIE, Mar. 29, 2012 (Year: 2012). [cited by applicant]

Advisory Action for U.S. Appl. No. 16/360,938 dated Aug. 12, 2022, 3 pages. [cited by applicant]

Final Office Action for U.S. Appl. No. 16/360,938 dated May 31, 2022, 66 pages. [cited by applicant]

Cha, Jae-Ryung, et al. “Effect of increasing electron donor units for high-efficiency blue thermally activated delayed fluorescence”, Dyes and Pigments, 2017, vol. 140, p. 399-406. [cited by applicant]

Im, Yirang, et al. “Molecular Design Strategy of Organic Thermally Activated Delayed Fluorescence Emitters”, Chem. Mater. 2017, vol. 29, p. 1946-1963. [cited by applicant]

US Office Action dated Feb. 16, 2023, issued in U.S. Appl. No. 17/003,743 (33 pages). [cited by applicant]

Action for U.S. Appl. No. 16/360,938 dated Oct. 3, 2022, 63 pages. [cited by applicant]

Action for U.S. Appl. No. 17/813,749 dated Jan. 5, 2023,48 pages. [cited by applicant]

Final Rejection for U.S. Appl. No. 16/360,938 dated Mar. 28, 2023, 43 pages. [cited by applicant]

Final Rejection for U.S. Appl. No. 17/003,743, filed Jun. 9, 2023, 42 pages. [cited by applicant]

Final Rejection for U.S. Appl. No. 17/813,749, filed Jun. 20, 2023, 71 pages. [cited by applicant]

Jae-Wook Kang et al. “A Host Material Containing Tetraphenylsilane for Phosphorescent OLEDs with High Efficiency and Operational Stability,” Org. Electronics 2008, 9, pp. 452-460. [cited by applicant]

Office Action for U.S. Appl. No. 16/360,938 dated Sep. 12, 2023, 60 pages. [cited by applicant]

US Office Action dated Oct. 11, 2023, issued in U.S. Appl. No. 18/157,335 (10 pages). [cited by applicant]

US Office Action dated Nov. 24, 2023, issued in U.S. Appl. No. 17/813,749 (56 pages). [cited by applicant]

Restriction Requirement for U.S. Appl. No. 17/399,013 dated Dec. 20, 2023, 7 pages. [cited by applicant]

US Final Office Action dated Jan. 29, 2024, issued in U.S. Appl. No. 16/360,938 (46 pages). [cited by applicant]

US Notice of Allowance dated Mar. 20, 2024, issued in U.S. Appl. No. 18/157,335 (9 pages). [cited by applicant]

US Office Action dated Mar. 22, 2024, issued in U.S. Appl. No. 17/399,013 (7 pages). [cited by applicant]

English translation of JP 2008147424 A obtained from Global Dossier (Year: 2008). [cited by applicant]

US Office Action dated Apr. 12, 2024, issued in U.S. Appl. No. 17/003,743 (24 pages). [cited by applicant]

US Final Office Action dated Apr. 24, 2024, issued in U.S. Appl. No. 17/813,749 (60 pages). [cited by applicant]

US Notice of Allowance dated Jul. 16, 2024, issued in U.S. Appl. No. 17/399,013 (5 pages). [cited by applicant]

US Office Action dated Jul. 30, 2024, issued in U.S. Appl. No. 16/360,938 (71 pages). [cited by applicant]

US Notice of Allowance dated Aug. 2, 2024, issued in U.S. Appl. No. 18/157,335 (9 pages). [cited by applicant]

US Final Office Action dated Sep. 6, 2024, issued in U.S. Appl. No. 17/003,743 (26 pages). [cited by applicant]

US Office Action dated Oct. 9, 2024, issued in U.S. Appl. No. 17/813,749 (73 pages). [cited by applicant]

US Final Office Action dated Nov. 22, 2024, issued in in U.S. Appl. No. 16/360,938 (49 pages). [cited by applicant]

Final Rejection for U.S. Appl. No. 17/813,749 dated Mar. 5, 2025, 33 pages. [cited by applicant]

Office Acton for U.S. Appl. No. 17/003,743 dated Mar. 12, 2025, 26 pages. [cited by applicant]

US Notice of Allowance dated Jun. 20, 2025, issued in U.S. Appl. No. 17/813,749 (10 pages). [cited by applicant]

US Office Action dated Jul. 2, 2025, issued in U.S. Appl. No. 16/360,938 (38 pages). [cited by applicant]

US Final Office Action dated Aug. 12, 2025, issued in U.S. Appl. No. 17/003,743 (33 pages). [cited by applicant]

US Notice of Allowance dated Oct. 7, 2025, issued in U.S. Appl. No. 16/360,938 (12 pages). [cited by applicant]