Granted Patent B2

US 12,598,915 · App. 17/969,989 · Granted Apr 7, 2026

Inventors: Chanseok Oh (Yongin-si, KR); Seran Kim (Yongin-si, KR); Sunyoung Pak (Yongin-si, KR); Kyoung Sunwoo (Yongin-si, KR); Munki Sim (Yongin-si, KR); Moran Ha (Yongin-si, KR)

Assignee: Samsung Display Co., Ltd.

H10K85/658C07F5/027H10K50/11H10K50/121H10K50/15H10K50/16H10K2101/40

Abstract

Claims (141)

1 . A light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

an interlayer between the first electrode and the second electrode, wherein

the interlayer comprises:

an emission layer; and

at least one condensed cyclic compound represented by Formula 1:

wherein in Formulae 1 and 2,

T 1 is B, P(═O), or P(═S),

X 1 is O, S, or N(R 1a ),

X 2 is O, S, or N(R 2a ),

ring A 1 to ring A 3 and ring A 5 to ring A 8 are each independently a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group,

R 1 to R 3 are each independently:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , a C 7 -C 60 arylalkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroarylalkyl group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ); or

a group represented by Formula 2,

a1 to a3 are each independently an integer from 1 to 10,

at least one of R 1 (s) in the number of a1, R 2 (s) in the number of a2, and R 3 (s) in the number of a3 is each independently a group represented by Formula 2,

R 1a , R 2a , and R 4 to R 8 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 6 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , a C 7 -C 60 arylalkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroarylalkyl group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ),

a4 is 0, 1, 2, or 3,

a5 to a8 are each independently an integer from 1 to 10,

* indicates a binding site to a neighboring atom,

R 10a is:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C 1 -C 6 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 unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl 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 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof;

a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, or a C 2 -C 60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl 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 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; 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 ), 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: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or 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 60 carbocyclic group, or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.

2 . The light-emitting device claim 1 , wherein

the first electrode is an anode,

the second electrode is a cathode,

the interlayer further includes:

a hole transport region between the emission layer and the first electrode; and

an electron transport region between the emission layer and the second electrode,

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 buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a combination thereof.

3 . The light-emitting device of claim 2 , wherein the emission layer includes the at least one condensed cyclic compound.

4 . The light-emitting device of claim 3 , wherein the emission layer further includes:

a first compound that is a hole-transporting compound; and

a second compound that is an electron-transporting compound.

5 . The light-emitting device of claim 4 , wherein

the emission layer further includes a third compound, and

the third compound is a phosphorescent sensitizer.

6 . The light-emitting device claim 1 , wherein the emission layer emits light having a maximum emission wavelength in a range of about 400 nm to about 500 nm.

7 . 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.

8 . The electronic apparatus of claim 7 , further comprising a color filter, a quantum dot color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof.

9 . A condensed cyclic compound represented by Formula 1:

wherein in Formulae 1 and 2,

T 1 is B, P(═O), or P(═S),

X 1 is O, S, or N(R 1a ),

X 2 is O, S, or N(R 2a ),

ring A 1 to ring A 3 and ring A 5 to ring A 8 are each independently a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group,

R 1 to R 3 are each independently:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 6 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , a C 7 -C 60 arylalkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroarylalkyl group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ); or

a group represented by Formula 2,

a1 to a3 are each independently an integer from 1 to 10,

at least one of R 1 (s) in the number of a1, R 2 (s) in the number of a2, and R 3 (s) in the number of a3 is each independently a group represented by Formula 2,

R 1a , R 2a , and R 4 to R 8 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 6 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , a C 7 -C 60 arylalkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroarylalkyl group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ),

a4 is 0, 1, 2, or 3,

a5 to a8 are each independently an integer from 1 to 10,

* indicates a binding site to a neighboring atom,

R 10a is:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro 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 unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl 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 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof;

a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, or a C 2 -C 60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl 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 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; 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 ), 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: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or 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 60 carbocyclic group, or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.

10 . The condensed cyclic compound of claim 9 , wherein T 1 is B.

11 . The condensed cyclic compound of claim 9 , wherein ring A 1 to ring A 3 and ring A 5 to ring A 8 are each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

12 . The condensed cyclic compound of claim 9 , wherein ring A 5 to ring A 8 are each independently a benzene group, a pyridine group, or a pyrimidine group.

13 . The condensed cyclic compound of claim 9 , wherein

R 1 to R 3 are each independently:

hydrogen, deuterium, —F, or a cyano group;

a C 1 -C 20 alkyl group or a C 3 -C 20 cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or a combination thereof;

a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, or a combination thereof;

—N(Q 1 )(Q 2 ); or

a group represented by Formula 2, and

Q 1 and Q 2 are each independently:

an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a combination thereof.

14 . The condensed cyclic compound of claim 9 , wherein one of Conditions i to iv is satisfied:

[Condition i]

one of R 1 (s) in the number of a1, R 2 (s) in the number of a2, and R 3 (s) in the number of a3 is a group represented by Formula 2, and the remaining groups are not represented by Formula 2

[Condition ii]

one of R 1 (s) in the number of a1 and one of R 2 (s) in the number of a2 are each independently a group represented by Formula 2, and the remaining groups are not represented by Formula 2

[Condition iii]

one of R 1 (s) in the number of a1 and one of R 3 (s) in the number of a3 are each independently a group represented by Formula 2, and the remaining groups are not represented by Formula 2

[Condition iv]

one of R 2 (s) in the number of a2 and one of R 3 (s) in the number of a3 are each independently a group represented by Formula 2, and the remaining groups are not represented by Formula 2.

15 . The condensed cyclic compound of claim 9 , wherein R 1a and R 2a are each independently a phenyl group unsubstituted or substituted with deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a C 1 -C 20 alkyl group, a phenyl group, or a combination thereof.

16 . The condensed cyclic compound of claim 9 , wherein R 4 to R 8 are each independently:

hydrogen, deuterium, —F, or a cyano group;

a C 1 -C 20 alkyl group or a C 3 -C 10 cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or a combination thereof; or

a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group, each unsubstituted or substituted with deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a C 1 -C 20 alkyl group, a phenyl group, or a combination thereof.

17 . The condensed cyclic compound of claim 9 , wherein Formula 2 is represented by one of Formulae 2-1 to 2-8:

wherein in Formulae 2-1 to 2-8,

ring A 5 to A 8 , R 5 to R 8 , and a5 to a8 are each the same as defined in Formula 2,

R 41 to R 43 are each independently as defined in connection with R 4 in Formula 2, except that each of R 41 to R 43 is not hydrogen, and

* indicates a binding site to a neighboring atom.

18 . The condensed cyclic compound of claim 9 , wherein at least one of Condition a to Condition c is satisfied:

[Condition a]

a group represented by

in Formula 1 is a group represented by Formula A1:

wherein in Formula A1,

R 1 is the same as defined in Formula 1,

R 11 is the same as defined in connection with R 1 in Formula 1, except that R 11 is not a group represented by Formula 2,

d11 is 0, 1, or 2,

* indicates a binding site to X 1 in Formula 1,

*′ indicates a binding site to T 1 in Formula 1, and

*″ indicates a binding site to X 2 in Formula 1;

[Condition b]

a group represented by

 in Formula 1 is a group represented by Formula A2-1 or Formula A2-2:

wherein in Formulae A2-1 and A2-2,

R 2 is the same as defined in Formula 1,

R 21 is the same as defined in connection with R 2 in Formula 1, except that R 21 is not a group represented by Formula 2,

d21 is 0, 1, 2, or 3,

* indicates a binding site to X 1 in Formula 1, and

*′ indicates a binding site to T 1 in Formula 1; and

[Condition c]

a group represented by

 in Formula 1 is a group represented by Formula A3-1 or Formula A3-2:

wherein in Formulae A3-1 and A3-2,

R 3 is the same as defined in Formula 1,

R 31 is the same as defined in connection with R 3 in Formula 1, except that R 31 is not a group represented by Formula 2,

d31 is 0, 1, 2, or 3,

* indicates a binding site to X 2 in Formula 1, and

*′ indicates a binding site to T 1 in Formula 1.

19 . The condensed cyclic compound of claim 9 , wherein the condensed cyclic compound is represented by one of Formulae 1(1) to 1(13):

wherein in Formulae 1(1) to 1(13),

T 1 , X 1 , X 2 , R 1 , R 2 , and R 3 are each the same as defined in Formula 1,

CZ is a group represented by Formula 2,

d1 is an integer from 0 to 3, and

d2 and d3 are each independently an integer from 0 to 4.

20 . The condensed cyclic compound of claim 9 , wherein Equation 1 is satisfied:

Δ E ST =S 1 −T 1≤0.44 eV  [Equation 1]

wherein in Equation 1,

S1 is a lowest excitation singlet energy level (eV) of the condensed cyclic compound, and

T1 is a lowest excitation triplet energy level (eV) of the condensed cyclic compound.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (10)