Light-emitting device including condensed cyclic compound, and electronic apparatus including the light-emitting device

Patent metadata

Field	Value
Publication number	US-12356853-B2
Application number	US-202418610157-A
Country	US
Kind code	B2
Filing date	Mar 19, 2024
Priority date	Jul 15, 2020
Publication date	Jul 8, 2025
Grant date	Jul 8, 2025

Abstract

Provided are a light-emitting device including a condensed cyclic compound represented by Formula 1 and an electronic apparatus including the light-emitting device, where Formula 1 is the same as described in the present specification. The light-emitting device includes a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode, and emission layer including at least one of the condensed cyclic compound represented by Formula 1.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:

wherein, in Formula 1,
ring A 1 to ring A 4 are each independently a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group,
X 1 is O, S, Se, C(R 1a )(R 1b ), Si(R 1a )(R 1b ), or N(R 1a ),
X 2 is O, S, Se, C(R 2a )(R 2b ), Si(R 2a )(R 2b ), or N(R 2a ),
X 3 is O, S, Se, C(R 3a )(R 3b ), Si(R 3a )(R 3b ), or N(R 3a ),
X 4 is O, S, Se, C(R 4a )(R 4b ), Si(R 4a )(R 4b ), or N(R 4a ),
Y 1 and Y 2 are each independently B, P(═O), or P(═S),
R 1 to R 4 , R 1a to R 4a , and R 1b to R 4b 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 , —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 ),
d1 to d4 are each independently an integer in a range from 1 to 20, and
two or more groups selected from R 1 to R 4 , R 1a to R 4a , and R 1b to R 4b are optionally linked together to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a , and
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, —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 any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —C 1 , —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, —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 any 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; 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; or 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 any combination thereof.

2. The condensed cyclic compound of claim 1 , wherein ring A 1 to ring A 4 are each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, 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, 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 isooxazole 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.

3. The condensed cyclic compound of claim 1 , wherein ring A 1 to ring A 4 are each independently a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzothiophene group, or a dibenzofuran group.

4. The condensed cyclic compound of claim 1 , wherein X 3 is N(R 3a ) or O.

5. The condensed cyclic compound of claim 1 , wherein:
(i) X 1 is O, X 2 is O, X 3 is O, and X 4 is O;
(ii) X 1 is O, X 2 is O, X 3 is N(R 3a ), and X 4 is O;
(iii) X 1 is N(R 1a ), X 2 is O, X 3 is O, and X 4 is O;
(iv) X 1 is N(R 1a ), X 2 is O, X 3 is N(R 3a ), and X 4 is O;
(v) X 1 is O, X 2 is N(R 2a ), X 3 is N(R 3a ), and X 4 is O;
(vi) X 1 is O, X 2 is O, X 3 is N(R 3a ), and X 4 is N(R 4a );
(vii) X 1 is S, X 2 is O, X 3 is N(R 3a ), and X 4 is O;
(viii) X 1 is S, X 2 is S, X 3 is N(R 3a ), and X 4 is N(R 4a );
(ix) X 1 is N(R 1a ), X 2 is N(R 2a ), X 3 is N(R 3a ), and X 4 is O;
(x) X 1 is N(R 1a ), X 2 is O, X 3 is N(R 3a ), and X 4 is N(R 4a );
(xi) X 1 is N(R 1a ), X 2 is S, X 3 is N(R 3a ), and X 4 is N(R 4a ); or
(xii) X 1 is N(R 1a ), X 2 is N(R 2a ), X 3 is N(R 3a ), and X 4 is N(R 4a ).

6. The condensed cyclic compound of claim 1 , wherein Y 1 and Y 2 are each independently B.

7. The condensed cyclic compound of claim 1 , wherein R 1 to R 4 , R 1a to R 4a , and R 1b to R 4b 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 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro g

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junha
• Hwang Seokhwan
• Pak Sunyoung
• Baek Jangyeol
• Sim Munki
• Lee Hyoyoung
• Jung Minjung

Classifications

• H10K85/658 Primary

  Organoboranes · CPC title

• H10K85/00

  Organic materials used in the body or electrodes of devices covered by this subclass · CPC title

• H10H20/851

  Wavelength conversion means · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title