IP Library › Granted Patent US 10,756,277

Granted Patent B2

US 10,756,277 · App. 15/302,301 · Granted Aug 25, 2020

Organic compound and organic electroluminescent device comprising the same

Inventors: Tae Jin Choi (Seoul, KR); Ho-Cheol Park (Yongin-si, KR); Youngmi Beak (Yongin-si, KR); Eunjin Kim (Seoul, KR)

Assignee: DOOSAN SOLUS CO., LTD.

H01L51/0071 C07D319/24 C07D491/04 C07D491/056 C07D493/04 C07D495/04 C09K11/06 H01L51/006 H01L51/0059 H01L51/0061 H01L51/0067 H01L51/0072 H01L51/0074 C09K2211/1007 C09K2211/1011 C09K2211/1014 C09K2211/1033 C09K2211/1037 C09K2211/1044 C09K2211/1059 C09K2211/1088 C09K2211/1092 H01L51/0052 H01L51/0054 H01L51/0058 H01L51/0065 H01L51/0068 H01L51/0069 H01L51/0081 H01L51/0085 H01L51/5012 H01L51/5016 H01L51/5056 H01L51/5072

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Quick Facts

Patent No.: US 10,756,277
App. No.: 15/302,301
Granted: Aug 25, 2020
Kind: B2

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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.

Claims (119)

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 the same as or different from each other, a plurality of R e 's is the same as or different from each other, and a plurality of R f 's is the same as or different from each other, and

the arylene group and the heteroarylene group of L 1 and the alkyl group, the aryl group, and the heteroaryl group of R a and R b 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 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 6 to C 60 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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.

4. The compound of claim 1 , wherein at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 8 , and R 9 is represented by the following Formula 9:

in Formula 9,

* 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 2 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,

Z 1 to Z 5 are the same as or different from each other, and are each independently N or C(R 11 ), and in this case, at least one of the Z 1 to Z 5 is N, and when C(R 11 ) is present in plural numbers, a plurality of C(R 11 )'s is the same as or different from each other,

R 11 is selected from the group consisting of hydrogen, 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, or optionally combines with an adjacent group to form a fused ring, and

the arylene group and the heteroarylene group of L 2 and the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylsilyl group of R 11 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 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 6 to C 60 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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.

5. The compound of claim 1 , wherein at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 8 , and R 9 is selected from the group consisting of substituents represented by the following Formulae A-1 to A-15:

in Formulae A-1 to A-15,

* 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 2 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,

when R 11 is present in plural numbers, a plurality of R 11 's is the same as or different from each other,

n is an integer of 0 to 4, and when the n is an integer of 1 to 4, R 21 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, or optionally combines with an adjacent group to form a fused ring, and

the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylsilyl group of R 11 and R 21 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 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 6 to C 60 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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.

6. 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 10 or 11:

in Formulae 10 and 11,

* 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 3 and L 4 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,

Z 6 to Z 8 are the same as or different from each other, and are each independently a single bond, or O, S, or N(R 16 ),

provided that a case where Z 6 and Z 7 are all a single bond is excluded,

in this case, when N(R 16 ) is present in plural numbers, a plurality of N(R 16 )'s is the same as or different from each other,

R 16 is selected from the group consisting of hydrogen, 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, or optionally combines with an adjacent group to form a fused ring,

e is an integer of 0 to 3, and when the e is 1 to 3, R 12 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,

f, g, and h are an integer of 0 to 4, and when the f, g, and h are each an integer of 1 to 4, R 13 to R 15 are 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, and

in this case, the arylene group and the heteroarylene group of L 3 and the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, and the arylsilyl group of R 12 to R 16 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 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 6 to C 60 arylamine group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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.

7. The compound of claim 1 , wherein the X 1 is N(Ar 1 ), and the Ar 1 is represented by the following Formula 12:

in Formula 12,

* is the location where the Ar 1 is bonded to the N atom of N(Ar 1 ),

L 5 is a single bond, or selected from the group consisting of a C 6 to C 60 aryl group,

m is an integer of 1 and 2,

A is a 6-membered aromatic ring,

x is an integer of 0 to 2, and when the x is an integer of 1 and 2, R 31 are selected from the group consisting of 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 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, and in this case, when R 31 is present in plural numbers, a plurality of R 31 's is the same as or different from each other,

Y 5 to Y 8 are each independently N or C(R 36 ), and in this case, when C(R 36 ) is present in plural numbers, a plurality of C(R 36 )'s is the same as or different from each other,

R 32 to R 36 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 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, 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 R 31 to R 36 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 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, the substituent optionally combines with an adjacent group to form a fused ring, and in this case, when the substituent is present in plural numbers, the substituents are the same as or different from each other.

8. An organic electroluminescent device comprising:

an anode;

a cathode; and

one or more organic material layers interposed between the anode and the cathode,

wherein at least one of the organic material layers comprises the compound described in claim 1 .

9. The organic electroluminescent device of claim 8 , wherein the one or more organic material layers comprise a hole transport layer, a light emitting layer, and an electron transport layer, and the organic material layer comprising the compound is a light emitting layer or an electron transport layer.

10. The organic electroluminescent device of claim 8 , wherein the one or more organic material layers comprise a hole transport layer, a light emitting auxiliary layer, a light emitting layer, and an electron transport layer, and the organic material layer comprising the compound is a light emitting auxiliary layer.

11. The organic electroluminescent device of claim 8 , wherein the one or more organic material layers comprise a hole transport layer, a light emitting layer, an electron transport auxiliary layer, and an electron transport layer, and the organic material layer comprising the compound is an electron transport auxiliary layer.

12. The organic electroluminescent device of claim 8 , 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 8 .

13. The organic electroluminescent device of claim 8 , wherein at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 8 , 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,

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 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 Ra an Rb 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,

14. The organic electroluminescent device of claim 8 , wherein at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 8 , and R 9 is represented by the following Formula 9:

in Formula 9,

* 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 2 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,

15. The organic electroluminescent device of claim 8 , wherein at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 8 , and R 9 is selected from the group consisting of substituents represented by the following Formulae A-1 to A-15:

in Formulae A-1 to A-15,

* 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 2 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,

when R 11 is present in plural numbers, a plurality of R 11 's is the same as or different from each other,

16. The organic electroluminescent device of claim 8 , wherein at least one of the Ar 1 to Ar 5 , R 1 to R 6 , R 8 , and R 9 is represented by the following Formula 10 or 11:

in Formulae 10 and 11,

* 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 3 and L 4 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,

Z 6 to Z 8 are the same as or different from each other, and are each independently a single bond, or O, S, or N(R 16 ),

provided that a case where Z 6 and Z 7 are all a single bond is excluded,

in this case, when N(R 16 ) is present in plural numbers, a plurality of N(R 16 )'s is the same as or different from each other,

17. The organic electroluminescent device of claim 9 , wherein the X 1 is N(Ar 1 ), and the Ar 1 is represented by the following Formula 11:

in Formula 12,

* is the location where the Ar 1 is bonded to the N atom of N(Ar 1 ),

L 5 is a single bond, or selected from the group consisting of a C 6 to C 60 aryl group,

m is an integer of 1 and 2,

A is a 6-membered aromatic ring,

Y 5 to Y 8 are each independently N or C(R 36 ), and in this case, when C(R 36 ) is present in plural numbers, a plurality of C(R 36 )'s is the same as or different from each other,

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 R 31 to R 36 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 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, the substituent optionally combines with an adjacent group to form a fused ring, and in this case, when the substituent is present in plural numbers, the substituents are the same as or different from each other.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2020

From: DOOSAN CORPORATION

To: DOOSAN SOLUS CO., LTD.

Reel/Frame 052128/0274 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2016

From: CHOI, TAE JIN; PARK, HO-CHEOL; BEAK, YOUNGMI; KIM, EUNJIN

To: DOOSAN CORPORATION

Reel/Frame 040533/0869 →

Priority Claims (1)

KR 10-2014-0042512 · Apr 9, 2014 · national

Continuity (1)

Related Publication 20170170406A1 · Jun 15, 2017

Cited By (1)

US 12,187,697