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

Patent metadata

Field	Value
Publication number	US-11414430-B2
Application number	US-201916514854-A
Country	US
Kind code	B2
Filing date	Jul 17, 2019
Priority date	Dec 17, 2018
Publication date	Aug 16, 2022
Grant date	Aug 16, 2022

Abstract

A condensed cyclic compound is represented by Formula 1. An organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and comprising an emission layer, the organic layer including the condensed cyclic compound represented by Formula 1. A display apparatus includes: a thin-film transistor comprising a source electrode, a drain electrode, and an active layer; and the organic light-emitting device.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:
(A 11 ) n11 -(L 11 ) a11 -(A 12 ) n12 ,  Formula 1

wherein, in Formula 1,
a11 is an integer of 0 to 5,
A 11 and A 12 are each independently selected from a group represented by Formula 1A and a group represented by Formula 1B, and
n11 and n12 are each 1:

wherein, in Formulae 1A and 1B,
X 11 is selected from C(R 14 )(R 15 ), Si(R 14 )(R 15 ), O, and S,
X 12 is selected from C(R 16 )(R 17 ), Si(R 16 )(R 17 ), O, and S,
b11 is selected from 1 and 2,
b12 and b13 are each independently an integer from 1 to 3,
Q 1 to Q 3 are each independently selected from 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, 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 C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* indicates a binding site to a neighboring atom,
wherein, in Formula 1:
L 11 is selected from groups represented by Formulae 4-1 to 4-35;

wherein, in Formulae 4-1 to 4-35,
X 41 is C(R 43 )(R 44 ),
R 41 to R 44 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a perylenyl group,
b41 is selected from 1, 2, 3, and 4,
b42 is selected from 1, 2, 3, 4, 5, and 6,
b43 is selected from 1, 2, 3, 4, 5, 6, 7, and 8,
b44 is selected from 1, 2, 3, 4, and 5,
b45 is selected from 1, 2, and 3,
b46 is selected from 1 and 2, and
* and *′ each indicate a binding site to a neighboring atom,
wherein, in Formula 1:
R 11 to R 13 are each hydrogen,
R 14 to R 17 are each independently selected from:
hydrogen, deuterium, —F, —Cl , —Br, —I, a cyano group, and a C 1 -C 20 alkyl group;
a C 1 -C 20 alkyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, and a cyano group; and
groups represented by Formulae 5-1 to 5-9:

wherein, in Formulae 5-1 to 5-9,
R 51 and R 52 are each independently selected from hydrogen, deuterium, —F, —Cl , —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a perylenyl group,
b51 is selected from 1, 2, 3, 4, and 5,
b52 is selected from 1, 2, 3, 4, 5, 6, and 7,
b53 is selected from 1, 2, 3, 4, 5, 6, 7, 8, and 9,
b54 is selected from 1, 2, 3, and 4, and
* indicates a binding site to a neighboring atom.

2. The condensed cyclic compound of claim 1 , wherein:
L 11 is selected from groups represented by Formulae 4-1 to 4-12.

3. The condensed cyclic compound of claim 1 , wherein:
a11 is selected from 0, 1, and 2.

4. The condensed cyclic compound of claim 1 , wherein:
X 11 is C(R 14 )(R 15 ), and
X 12 is C(R 16 )(R 17 ).

5. The condensed cyclic compound of claim 1 , wherein:
the condensed cyclic compound is represented by one selected from Formulae 1-1 and 1-2:

wherein, in Formulae 1-1 and 1-2,
L 11 and a11 are each independently the same as defined in connection with Formula 1,
X 11a and X 11b are each independently the same as defined in connection with X 11 in Formula 1A,
X 12a and X 12b are each independently the same as defined in connection with X 12 in Formula 1A,
R 11a , R 11b , R 12a , R 12b , R 13a , and R 13b are each independently the same as defined in connection with R 11 in Formula 1A,
b11a and b11b are each independently the same as defined in connection with b11 in Formula 1A, and
b12a, b12b, b13a, and b13b are each independently the same as defined in connection with b12 in Formula 1A.

6. The condensed cyclic compound of claim 1 , wherein:
the condensed cyclic compound is represented by one selected from Formulae 1-11 and 1-12:

wherein, in Formulae 1-11 and 1-12,
L 11 is selected from groups represented by Formulae 4-1 to 4-12:

wherein, in Formulae 4-1 to 4-12,
R 41 is selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a perylenyl group,
b41 is selected from 1, 2, 3, and 4,
b42 is selected from 1, 2, 3, 4, 5, and 6,
* and *′ each indicate a binding site to a neighboring atom,
a11 is selected from 0, 1, and 2,
R 11a , R 11b , R 12a , R 12b , R 13a , R 13b , R 14a , R 14b , R 15a , R 15b , R 16a , R 16b , R 17a , and R 17b are each independently the same as defined in connection with R 11 in Formula 1A,
b11a and b11b are each independently the same as defined in connection with b11 in Formula 1A, and
b12a, b12b, b13a, and b13b are each independently defined the same as b12 in Formula 1A.

7. The condensed cyclic compound of claim 1 , wherein:
the condensed cyclic compound is selected from Compounds 1 to 6:

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Seulong
• Kang Sunwoo
• Kang Pilgu
• Kwon Jiyoung
• Kim Taekyung
• Chang Soonchul
• Cho Dahye

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title