Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12593606-B2
Application number	US-202217860399-A
Country	US
Kind code	B2
Filing date	Jul 8, 2022
Priority date	Jul 16, 2021
Publication date	Mar 31, 2026
Grant date	Mar 31, 2026

Abstract

An organic light-emitting device including: a first electrode and a second electrode each having a surface opposite the other; and an intermediate layer disposed between the first electrode and the second electrode, the intermediate layer including a first compound and a second compound, wherein the first compound includes a first silyl group-containing group and at least two carbazole-derived groups, wherein one carbazole-derived group of the at least two carbazole-derived groups is bonded via a N atom to another carbazole-derived group, the second compound includes a second silyl group-containing group, a triazine group, and a carbazole-derived group, and at least one of the first compound or the second compound has a triplet (T 1 ) energy level of 2.81 eV or more.

First claim

What is claimed is:

1 . An organic light-emitting device comprising:
a first electrode and a second electrode each having a surface opposite the other; and an intermediate layer disposed between the first electrode and the second electrode, the intermediate layer comprising a first compound and a second compound, wherein the intermediate layer comprises an emission layer, and the emission layer comprises the first compound, the second compound, and at least one dopant compound, wherein the first compound comprises a silyl group-containing group and at least two carbazole-derived groups, wherein one carbazole-derived group of the at least two carbazole-derived groups is bonded via a N atom to another carbazole-derived group and is represented by Formula 1-2, and the second compound comprises a silyl group-containing group, a triazine group, and a carbazole-derived group, and

wherein, in Formula 1-2,
CY 15 to CY 19 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 15 to T 19 are each independently a group represented by Formula A, and
c15 to c18 are each independently an integer from 0 to 10, and c19 is 0, where the sum of the sum of c15, c16, c17, and c18 is 1 or more, and
in Formula 1-2 and Formula A,

L 11 to L 14 are each independently a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 5 -C 60 carbocyclic group, or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a11 to a14 are each independently an integer from 0 to 5, when a11 is 0, L 11 is not present, and the N atom of one carbazole-derived group is directly bonded to CY 17 , when a12 is 0, L 12 is not present, and the N atom of one carbazole-derived group is directly bonded to CY 19 , when a13 is 0, L 13 is not present, and a Si atom of the first silyl group-containing group of Formula A is directly bonded to CY 10 to CY 19 , or when a14 is 0, L 14 is not present, and a Si atom of the first silyl group-containing group of Formula A is directly bonded to a neighboring Si atom of the first silyl group-containing group of Formula A,
n is an integer from 0 to 3,
R 15 to R 19 and R 51 to R 55 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxy 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 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, —N(Q 1 )(Q 2 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
b15 to b19 are each independently an integer from 0 to 10,
b51 to b55 are each independently an integer from 0 to 5, and
a substituent of each of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 20 alkylene group, the substituted C 2 -C 20 alkenylene 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, or 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 or a salt thereof, 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, —N(Q 1 )(Q 12 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination thereof;
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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or 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 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, 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, —N(Q 21 )(Q 22 ), —Ge(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), —P(Q 28 )(Q 29 ), or any combination thereof;
—N(Q 31 )(Q 32 ), —Ge(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), —P(═O)(Q 38 )(Q 39 ), or —P(Q 38 )(Q 39 ); or
any combination thereof,
wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a

Assignees

• Samsung Electronics Co Ltd
• Samsung Display Co Ltd

Inventors

• Kim Jong Soo
• Kwon Eunsuk
• Kim Hwang Suk
• Chung Yeon Sook
• Jung Yongsik
• Jeon Soonok
• Kim Hyeongmin
• Ahn Heechoon
• Um Hyunah
• Lee Yeseul
• Kang Hosuk
• Kim Joonghyuk
• Kim Jiwhan
• Nam Sungho
• Park Sangho
• Son Youngmok
• Ihn Sooghang
• Choi Hyeonho

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

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K85/346

  comprising platinum · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title