Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-2019157569-A1
Application number	US-201716099211-A
Country	US
Kind code	A1
Filing date	Apr 12, 2017
Priority date	May 17, 2016
Publication date	May 23, 2019
Grant date	—

Abstract

The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material, and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device having improved lifespan properties, compared to the organic electroluminescent device comprising a conventional organic electroluminescent compound.

First claim

1 . An organic electroluminescent compound represented by the following formula 1:

wherein
X 1 and X 2 , each independently, represent N or CH, with the proviso, at least one of X 1 and X 2 represents N,
La represents a substituted or unsubstituted divalent (C10-C30) aromatic ring, which is one condensed ring,
A ring and C ring, each independently, represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring, with the proviso, at least one of A ring and C ring represents a substituted or unsubstituted naphthalene ring,
B ring represents a substituted or unsubstituted benzene ring,
Ar 1 , Ar 2 and Ar 3 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, and
the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P.

2 . The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl, the substituted (3- to 30-membered)heteroaryl, the substituted (C3-C30)cycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di-(C1-C30)alkylamino, the substituted mono- or di-(C6-C30)arylamino, the substituted (C1-C30)alkyl(C6-C30)arylamino, the substituted divalent (C10-C30) aromatic ring, the substituted benzene ring, and the substituted naphthalene ring in La, Ar 1 , Ar 2 , Ar 3 , A ring, B ring, and C ring, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.

3 . The organic electroluminescent compound according to claim 1 , wherein formula 1 is represented by any one of the following formulas 2 to 5:

wherein
R 1 and R 2 , each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino,
a represents an integer of 0 to 4, and b represents an integer of 0 to 6; where if a and b, each independently, represent an integer of 2 or more, each of R 1 and R 2 may be the same or different,
the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and
X 1 , X 2 , La, Ar 1 , Ar 2 , and Ar 3 are as defined in claim 1 .

4 . The organic electroluminescent compound according to claim 1 , wherein formula 1 is represented by any one of the following formulas 6 to 17:

wherein
R 1 and R 2 , each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino,
a represents an integer of 0 to 4, and b represents an integer of 0 to 6; where if a and b, each independently, represent an integer of 2 or more, each of R 1 and R 2 may be the same or different,
the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and
X 1 , X 2 , La, Ar 1 , Ar 2 , and Ar 3 are as defined in claim 1 .

5 . The organic electroluminescent compound according to claim 1 , wherein La represents a naphthylene, an anthracenylene, a triphenylenylene, a dimethylbenzofluorenylene, or a phenanthrenylene.

6 . The organic electroluminescent compound according to claim 1 , wherein any one of A ring and C ring represents a substituted or unsubstituted naphthalene ring, and the other represents a substituted or unsubstituted benzene ring; and Ar 1 to Ar 3 , each independently, represent a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.

7 . The organic electroluminescent compound according to claim 3 , wherein R 1 and R 2 , each independently, represent a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl;
and a and b, each independently, represent 0 or 1.

8 . The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of:

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Lee Hyo-Jung
• Lim Young-Mook
• Kim Bitnari

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• H01L51/0067

  Electricity · mapped topic

• H01L51/0072 Primary

  Electricity · mapped topic

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title