Organic compound and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-10756277-B2
Application number	US-201515302301-A
Country	US
Kind code	B2
Filing date	Apr 7, 2015
Priority date	Apr 9, 2014
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

The present disclosure relates to a novel organic compound and an organic electroluminescent device comprising the same, and the organic compound of the present disclosure may be used for an organic material layer of the organic electroluminescent device, thereby improving the light emitting efficiency, driving voltage, lifetime, and the like of the organic electroluminescent device.

First claim

The invention claimed is:

1. A compound for an organic electroluminescence represented by any one selected from the following Formulae 3 to 5:

in Formulae 3 to 5,
X 1 is selected from the group consisting of N(Ar 1 ), O, S, C(Ar 2 )(Ar 3 ), and Si(Ar 4 )(Ar 5 ), with the proviso that, in Formula 3, C(Ar 2 )(Ar 3 ) is excluded from X 1 ,
Y 1 to Y 4 are each independently N or C(R 9 ),
Ar 1 to Ar 5 are the same as or different from each other, and are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, or optionally combine with an adjacent group to form a fused ring,
R 1 to R 6 , R 8 , and R 9 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, or R 1 to R 4 , and R 9 optionally combine with an adjacent group to form a fused ring, and
the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylamine group of Ar 1 to Ar 5 and R 1 to R 6 , R 8 , and R 9 are each independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, and in this case, the substituent optionally combines with an adjacent group to form a fused ring, and when the substituent is present in plural numbers, the substituents are the same as or different from each other,
with the proviso that where X 1 in the Formula 3 is N(Ar 1 ), said Ar 1 is selected from the group consisting of a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, or optionally combines with an adjacent group to form a fused ring,
with the proviso that where X 1 in the Formula 5 is O, the case where all of R 1 to R 5 , R 8 and R 9 are hydrogen is excluded.

2. The compound of claim 1 , wherein the Y 1 to Y 4 are all C(R 9 ), and a plurality of C(R 9 )'s is the same as or different from each other, and R 9 is the same as that defined in claim 1 .

3. The compound of claim 1 , wherein at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 5 , and R 9 is represented by the following Formula 6:

in Formula 6,
* is the location where the at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 8 , and R 9 is bonded to the structure of Formula 3, 4, or 5,
L 1 is a single bond or selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms, or optionally combines with an adjacent substituent to form a fused ring, and
R a and R b are the same as or different from each other, and are each independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or a substitution product represented by the following Formula 7 or 8, or optionally combine with an adjacent substituent to form a fused ring,

in Formulae 7 and 8,
* is the location where the R a and R b are bonded to the N atom of Formula 6,
X and Y are each a 6-membered aromatic ring,
L 11 and L 12 are each a single bond, or selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Ar 6 is selected from the group consisting of a C 6 to C 18 aryl group and a heteroaryl group having 5 to 18 nuclear atoms,
a, b, and d are each an integer of 0 to 4, and the case where the a, b, and d are 0 means that hydrogen is not substituted with the substituent R c , R d , or R f and when the a, b, and d are each an integer of 1 to 3, R c , R d , or R f are each selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkyloxy group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 arylamine group, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylsilyl group,
c is an integer of 0 to 3, and the case where the c is 0 means that hydrogen is not substituted with the substituent R c , and when the c is 1 to 3, R c is selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkyloxy group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 arylamine group, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylsilyl group,
in this case, a plurality of R c 's is the same as or different from each other, a plurality of R d 's is th

Assignees

• Doosan Corp
• Doosan Solus Co Ltd

Inventors

• Choi Tae Jin
• Park Ho-Cheol
• Beak Youngmi
• Kim Eunjin

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07D491/04

  Ortho-condensed systems · CPC title

• C07D319/24 Primary

  [b,e]-condensed with two six-membered rings · CPC title

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title