IP Library Granted Patent US 10,529,933
Granted Patent B2
US 10,529,933 · App. 15/757,725 · Granted Jan 7, 2020

Organic electroluminescent compounds and organic electroluminescent device comprising the same

Inventor: Hee-Choon Ahn (Seoul, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H01L51/0074C07D409/10C07D409/14C09K11/025H01L51/0067H01L51/0072H01L51/5008H01L51/5016H01L51/5072H01L2251/5384
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Quick Facts
Patent No.
US 10,529,933
App. No.
15/757,725
Granted
Jan 7, 2020
Kind
B2
Abstract

The present disclosure relates to organic electroluminescent compounds, and a host material, an electron buffer material, an electron transport material and an organic electroluminescent device comprising the same. By using the organic electroluminescent compounds of the present disclosure, the organic electroluminescent device secures fast electron current properties by intermolecular stacking and interaction, and thus, it is possible to provide the organic electroluminescent device having low driving voltage and/or excellent luminous efficiency and/or efficient lifespan properties.

Claims (26)

1. An organic electroluminescent compound represented by any one of the following formulas 2 to 4:

wherein

X represents O, S, or CR 11 R 12 ;

R 1 to R 4 , 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; wherein, at least one of R 1 to R 4 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino, with the proviso that at least one of R 1 to R 4 does not represent a triphenylenyl;

a represents an integer from 1 to 4;

b and c each independently represent an integer of 1 or 2;

L 1 to L 3 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

X 1 to X 3 , each independently, represent N or CH; with the proviso that at least one of them represents N;

Ar 1 and Ar 2 , each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

W, Y, and Z, each independently, represent a single bond, O, S, NR 13 , or CR 14 R 15 ;

n and m, each independently, represent an integer of 0 or 1;

e represents an integer of 1 to 3; f, g, and h, each independently represent an integer of 1 to 4;

R 5 to R 7 , 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; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; and

R 13 to R 15 , each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 14 and R 15 may be linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, and the substituted mono- or polycyclic, alicyclic or aromatic ring in R 1 to R 7 , R 11 to R 15 , Ar 1 , Ar 2 , and L, to L 3 , 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 (C1-C30)alkyl or a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (C6-C30)aryl, a (5- to 30-membered)heteroaryl, or mono- or di-(C6-C30)arylamino; 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 the compound represented by formula 1 is selected from the group consisting of:

4. A host material comprising the organic electroluminescent compound according to claim 1 .

5. An electron buffer material comprising the organic electroluminescent compound according to claim 1 .

6. An electron transport material comprising the organic electroluminescent compound according to claim 1 .

7. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

8. The organic electroluminescent device according to claim 7 , comprising the organic electroluminescent compound as an electron transport material, and further comprising an electron buffer material.

9. The organic electroluminescent device according to claim 7 , wherein the organic electroluminescent device comprises at least one light-emitting layer disposed between a first electrode and a second electrode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host comprises a plurality of host compounds, and wherein at least a first host compound of the plurality of host compounds is the organic electroluminescent compound, and at least a second host compound of the plurality of host compounds is represented by the following formula 5:

wherein

A 1 and A 2 , each independently, represent a substituted or unsubstituted (C6-C30)aryl; with the proviso that a substituent for neither A 1 nor A 2 is a nitrogen-containing heteroaryl;

L represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; and

Y 1 to Y 16 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2020
From: AHN, HEE-CHOON
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 051613/0038 →
Priority Claims (2)
KR 10-2015-0143015 · Oct 13, 2015 · national
KR 10-2016-0104280 · Aug 17, 2016 · national
Continuity (1)
Related Publication 20180351113A1 · Dec 6, 2018