Condensed cyclic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12358876-B2
Application number	US-202218045345-A
Country	US
Kind code	B2
Filing date	Oct 10, 2022
Priority date	Oct 5, 2015
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

A condensed cyclic compound represented by Formula 1:

wherein in Formula 1, Ar 1 and R 1 to R 8 are the same as described in the specification.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:

wherein Ar 1 in Formula 1 is selected from groups represented by Formulae 2A-1 to 2A-3

wherein, in Formulae 2A-1 to 2A-3,
X 1 is C(R 31 )(R 32 ), or Si(R 31 )(R 32 ),
X 2 is C(R 33 )(R 34 ), or Si(R 33 )(R 34 ),
X 3 is C(R 35 )(R 36 ), or Si(R 35 )(R 36 ),
wherein
R 1 to R 8 , R 11 to R 17 , R 21 to R 25 , and R 31 to R 36 are each independently selected from hydrogen, deuterium, a cyano group, and groups represented by Formulae 4-1 to 4-29:

wherein at least one of R 1 and R 2 in Formula 1 is a cyano group,
wherein the number of cyano groups in each of Formulae 2A-1 to 2A-3 is 2, 3, or 4, and
* indicates a binding site to an adjacent atom.

2. The condensed cyclic compound of claim 1 , wherein
R 1 to R 8 , R 11 to R 17 , R 21 to R 25 , and R 31 to R 36 are each independently selected from
hydrogen, deuterium, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a dibenzosilolyl group;
a C 1 -C 20 alkyl group substituted with at least one of deuterium and a cyano group; and
a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a dibenzosilolyl group.

3. The condensed cyclic compound of claim 1 , wherein
i) at least one of R 17 and R 25 in Formula 2A-1,
ii) at least one of R 17 and R 25 in Formula 2A-2, and
iii) R 17 in Formula 2A-3 are each independently selected from a cyano group and groups represented by Formulae 4-1 to 4-29:

wherein, in Formula 4-1 to 4-29, * indicates a binding site to an adjacent atom.

4. The condensed cyclic compound of claim 1 , wherein the number of cyano groups in each of Formulae 2A-1 to 2A-3 is 4.

5. The condensed cyclic compound of claim 1 , wherein each of the condensed cyclic compounds has a difference between a triplet (T 1 ) energy level and a singlet (S 1 ) energy level in a range from about 0.1 electron Volts to about 0.6 electron Volts.

6. The condensed cyclic compound of claim 1 , wherein each of the condensed cyclic compounds has a triplet (T 1 ) energy level in a range from about 2.9 electron Volts to about 3.1 electron Volts.

7. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer and at least one condensed cyclic compound represented by Formula 1 of claim 1 .

8. The organic light-emitting device of claim 7 , wherein
the first electrode is an anode,
the second electrode is a cathode, and
the organic layer comprises
a hole transport region disposed between the first electrode and the emission layer, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and
an electron transport region disposed between the emission layer and the second electrode, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

9. The organic light-emitting device of claim 7 , wherein the emission layer comprises the at least one condensed cyclic compound represented by Formula 1.

10. The organic light-emitting device of claim 9 , wherein the emission layer further comprises a phosphorescent dopant comprising an organometallic compound represented by Formula 81:
M(L 81 ) n81 (L 82 ) n82   Formula 81

wherein, in Formula 81,
M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and Rh,
L 81 is a ligand represented by Formula 81A,
n81 is an integer selected from 1 to 3, provided that when n81 is 2 or greater, two or more groups L 81 are identical to or different from each other,
L 82 is an organic ligand,
n82 is an integer selected from 0 to 4, provided that when n82 is 2 or greater, two or more groups L 82 are identical to or different from each other,

wherein, in Formula 81A,
Y 81 to Y 84 are each independently C or N,
Y 81 and Y 82 are linked to each other via a single bond or a double bond, and Y 83 and Y 84 are linked to each other via a single bond or a double bond,
CY 81 and CY 82 are each independently selected from a C 5 -C 30 carbocyclic group and a C 3 -C 30 hetero carbocyclic group,
CY 81 and CY 82 are optionally further linked to each other via an organic linking group,
R 81 to R 85 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, 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, —SF 5 , 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 81 )(Q 82 )(Q 83 ), —N(Q 84 )(Q 85 ), —B(Q 86 )(Q 87 ), and —P(═O)(Q 88 )(Q 89 ),
a81 to a83 are each independently an integer selected from 0 to 5, provided that
when a81 is 2 or greater, two or more groups R 81 are identical to or different from each other,
when a82 is 2 or greater, two or more groups R 82 are identical to or different from each other,
when a81 is 2 or greater, adjacent groups R 81 are optionally linked to each other to form a saturated or unsaturated ring,
when a82 is 2 or greater, adjacent groups R 82 are optionally linked to each other to form a saturated or unsaturated ring,
whe

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kim Hyunjung
• Chae Miyoung
• Kwon Eunsuk
• Kim Sangmo
• Jeon Soonok
• Chung Yeonsook
• Huh Dalho
• Park Youngseok
• Son Youngmok

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title