Heterocyclic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12167677-B2
Application number	US-202117469974-A
Country	US
Kind code	B2
Filing date	Sep 9, 2021
Priority date	Mar 19, 2021
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

Provided are a heterocyclic compound represented by Formula 1 and an organic light-emitting device including the heterocyclic compound:wherein, in Formula 1, X1 is Si or Ge, A4 is a group represented by Formula 2, and other substituents are the same as described in the detailed description:

First claim

What is claimed is:

1. A heterocyclic compound represented by any one of Formulae 11-1 to 11-12:

wherein, in Formulae 11-1 to 11-12,
X 1 is Si or Ge,
A 1 and A 3 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
Y 1 and Y 2 are each independently a single bond, O, S, N(R′), C(R′)(R″), or Si(R 4 )(R 5 ),
Ar 1 to Ar 4 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, and X 24 is C(R 24 ) or N,
X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and X 44 is C(R 44 ) or N,
X 45 is C(R 45 ) or N, X 46 is C(R 46 ) or N, X 47 is C(R 47 ) or N, and X 48 is C(R 48 ) or N,
R′, R″, R 1 to R 4 , R 10 , R 21 to R 24 , R 30 , and R 41 to R 48 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted 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, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), or —P(═O)(Q 8 )(Q 9 ),
two or more neighboring groups of R′, R″, R 1 to R 4 , R 10 , R 21 to R 24 , R 30 , and R 41 to R 48 are optionally 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,
b1 to b4, b10, b20, b30, and b40 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12,
when b1 is 2 or more, two or more of R 1 (s) are identical to or different from each other, when b2 is 2 or more, two or more of R 2 (s) are identical to or different from each other, when b3 is 2 or more, two or more of R 3 (s) are identical to or different from each other, and when b4 is 2 or more, two or more of R 4 (s) are identical to or different from each other,
when b10 is 2 or more, two or more of R 10 (s) are identical to or different from each other, when b20 is 2 or more, two or more of R 20 (s) are identical to or different from each other, when b30 is 2 or more, two or more of R 30 (s) are identical to or different from each other, and when b40 is 2 or more, two or more of R 40 (s) are identical to or different from each other,
in Formulae 11-1 to 11-8, provided that when X 1 is Si, then
i) at least one of Ar 1 to Ar 3 comprises a substituted or unsubstituted C 1 -C 30 heterocyclic group,
ii) the heterocyclic compound is represented by any one of Formulae 12-1 to 12-36, or
iii) a combination of i) and ii):

wherein, in Formulae 12-1 to 12-36,
X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, and X 14 is C(R 14 ) or N,
X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, and X 24 is C(R 24 ) or N,
X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, and X 34 is C(R 34 ) or N,
X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and X 44 is C(R 44 ) or N,
X 45 is C(R 45 ) or N, X 46 is C(R 46 ) or N, X 47 is C(R 47 ) or N, and X 48 is C(R 48 ) or N,
R 11 to R 14 are each independently as described in connection with R 10 ,
R 31 to R 34 are each independently as described in connection with R 30 , and
at least one of X 11 to X 14 , X 21 to X 24 , X 31 to X 34 , and X 41 to X 48 in Formulae 12-1 to 12-36 is N, and
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:
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 group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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 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 group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group o

Assignees

• Samsung Electronics Co Ltd

Inventors

• Chung Yeonsook
• Kwon Eunsuk
• Kim Hwangsuk
• Jung Yongsik
• Kang Hosuk
• Kim Joonghyuk
• Nam Sungho
• Son Youngmok
• Hwang Sangyeon
• Sung Youngmo

Classifications

• H10K85/40 Primary

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• C07F7/0812 Primary

  comprising a heterocyclic ring · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title