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

Patent metadata

Field	Value
Publication number	US-10121974-B2
Application number	US-201514743217-A
Country	US
Kind code	B2
Filing date	Jun 18, 2015
Priority date	Dec 31, 2014
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

A condensed-cyclic compound is represented by Formula 1:

where X, L 1 to L 3 , R 1 to R 3 , Ar 1 to Ar 6 , c1 to c3, a1 to a2, and b1 to b3 are as defined in the specification.

First claim

What is claimed is:

1. A condensed-cyclic compound represented by one of Formula 1, 1B, and 1C:

wherein, in Formula 1, X is selected from O, S, and N(R 11 );
when X is O, A is selected from a naphthalene, an anthracene, a phenanthrene, a chrysene, and a pyrene, and ii) when X is S or N(R 11 ), A is selected from a benzene, a naphthalene, an anthracene, a phenanthrene, a chrysene, and a pyrene;
in Formulae 1B and 1C,
X is selected from O, S, N(R 11 ), Si(R 12 )(R 13 ) and C(R 15 )(R 16 );
in Formula 1, 1B, and 1C
L 1 to L 3 are each independently selected from:
a phenylene group, and
a phenylene group substituted with at least one selected from a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group
a1 to a3 are each independently selected from 0 and 1;
Ar 1 to Ar 6 are each independently selected from a group represented by one of Formulae 6-1 to 6-28:

wherein, in Formulae 6-1 to 6-28, * indicates a binding site to an adjacent atom;
c1 to c3 are each independently selected from 0 and 1, provided that a sum of c1, c2, and c3 is 1 or more;
R 1 to R 3 are each independently selected from a hydrogen, a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a methyl group and a phenyl group
b1 to b3 are each independently an integer selected from 0 to 3;
R 11 , R 12 , R 13 , R 15 , and R 16 are each independently selected from a methyl group and a phenyl group;
and
B is a boron atom.

2. The condensed-cyclic compound as claimed in claim 1 , wherein
L 1 to L 3 are each independently selected from a group represented by one of Formulae 3-1 to 3-3:

wherein, in Formulae 3-1 to 3-3,
Z 1 is selected from a hydrogen, a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group
d1 is an integer selected from 1 to 4;
and
* and *′ each indicate a binding site to an adjacent atom.

3. The condensed-cyclic compound as claimed in claim 1 , wherein
L 1 to L 3 are each independently selected from a group represented by one of Formulae 4-1, 4-3, 4-8, 4-10, 4-17, 4-24, 4-26, and 4-28:

wherein, in Formulae 4-1, 4-3, 4-8, 4-10, 4-17, 4-24, 4-26, and 4-28, *and *′ each indicate a binding site to an adjacent atom.

4. The condensed-cyclic compound as claimed in claim 1 , wherein a sum of c1, c2, and c3 is selected from 1 and 2.

5. The condensed-cyclic compound as claimed in claim 1 , wherein the condensed-cyclic compound is represented by one of Formulae 1A to 1C:

wherein,
in Formulae 1A, X is selected from S and N(R 11 ),
in Formulae 1B and 1C, X is selected from O, S, N(R 11 ), Si(R 12 )(R 13 ), and C(R 15 )(R 16 ), and L 1 to L 3 , a1 to a3, Ar 1 to Ar 6 , c1 to c3, R 1 to R 3 , b1 to b3 and R 11 , R 12 , R 13 , R 15 , and R 16 are the same as defined in claim 1 .

6. The condensed-cyclic compound as claimed in claim 1 , wherein
the condensed-cyclic compound is represented by one of Formulae 1-1 to 1-3 and Formulae 2-1 to 2-3:

wherein,
in Formulae 1-1 and 2-1, X is selected from S and N(R 11 ),
in Formulae 1-2, 1-3, 2-2 and 2-3, X is selected from O, S, N(R 11 ), Si(R 12 )(R 13 ), and C(R 15 )(R 16 ),
and
in Formulae 1-1 to 1-3 and Formulae 2-1 to 2-3, L 1 , L 2 , a1, a2, Ar 1 to Ar 4 , R 1 to R 3 , b1 to b3, R 11 , R 12 , R 13 , R 15 , and R 16 are the same as defined in claim 1 .

7. The condensed-cyclic compound as claimed in claim 1 , wherein
the condensed-cyclic compound is represented by one selected from Formulae 1-1(1) to 1-3(1) and Formulae 2-1(1) to 2-3(1):

wherein,
in Formulae 1-1(1) and 2-1(1), X is selected from S and N(R 11 ),
in Formulae 1-2(1), 1-3(1), 2-2(1) and 2-3(1), X is selected from O, S, N(R 11 ), Si(R 12 )(R 13 ), and C(R 15 )(R 16 ),
in Formulae 1-1(1) to 1-3(1) and Formulae 2-1(1) to 2-3(1), L 1 , L 2 , a1, a2, Ar 1 to Ar 4 and R 11 , R 12 , R 13 , R 15 , and R 16 are the same as defined in claim 1 , and R 1a to R 1f , R 2a to R 2c , and R 3a to R 3c are the same as defined in connection with R 1 as described in claim 1 .

8. The condensed-cyclic compound as claimed in claim 7 , wherein
Ar 1 to Ar 4 are each independently selected from Formulae 6-1 to 6-28, and
R 1a to R 1f , R 2a to R 2c , and R 3a to R 3c are each independently selected from a hydrogen, a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a methyl group, and a group represented by Formula 6-1:

wherein, in Formulae 6-1 to 6-28, * indicates a binding site to an adjacent atom.

9. The condensed-cyclic compound as claimed in claim 1 , wherein the condensed-cyclic compound is represented by one of Compounds 14 to 26, 40 to 169 and 182 to 231:

Assignees

• Samsung Display Co Ltd

Inventors

• Jun Mieun
• Kim Sooyon
• Kim Youngkook
• Hwang Seokhwan
• Yang Seunggak

Classifications

• H01L51/0072

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F7/082

  Chemistry & Metallurgy · mapped topic

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title