ELECTRON TRANSPORT MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

• US 20170207398A1
• Filed: 07/16/2015
• Published: 07/20/2017
• Est. Priority Date: 07/17/2014
• Status: Abandoned Application

• Current Assignee: Rohm and Haas Electronic Materials Korea, Ltd.
• Original Assignee: Rohm and Haas Electronic Materials Korea, Ltd.
• Inventors: Yang, Jeong-Eun, Lee, Su-Hyun, Kim, Chi-Sik, Cho, Young-Jun, Cho, Sang-Hee, Jeon, Jeong-Hwan, Na, Hong-Yeop, Choi, Kyung-Hoon
• Application Number:
  US15/326,628
• Publication Number:
  US 20170207398A1
• Time in Patent Office: Days
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 491/048 the oxygen-containing ring being five-membered
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds
• CPC Class Codes: C07F 7/08 Compounds having one or more C—Si linkages
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: H10K 2101/30 Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
• CPC Class Codes: H10K 2101/40 Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/165 comprising dopants
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Abstract

The present invention relates to an electron transport material comprising a compound of a certain structure, and an organic electroluminescent device comprising the same. The organic electroluminescent device comprising the electron transport material of the present invention has a low driving voltage, high luminous efficiency and good color purity, and thus effectively shows blue emission.

Claims

1. An electron transport material comprising a compound represented by the following formula 1:

2. The electron transport material according to claim 1, wherein the compound of formula 1 is represented by one of the following formulae 2 to 7:

3. The electron transport material according to claim 1, wherein the substituents of the substituted alkyl group, the substituted alkoxy, the substituted cycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group, the substituted trialkylsilyl group, the substituted triarylsilyl group, the substituted dialkylarylsilyl group, the substituted alkyldiarylsilyl group, the substituted mono- or di-arylamino group, the substituted mono- or di-alkylamino group, the substituted alkylarylamino group, the substituted aralkyl group, and the substituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring in A, L, and R₁ to R₃ are each independently at least one selected from the group consisting of deuterium;

a halogen;

a cyano group;

a carboxyl group;

a nitro group;

a hydroxyl group;

a (C1-C30)alkyl group;

a halo(C1-C30)alkyl group;

a (C2-C30)alkenyl group;

a (C2-C30)alkynyl group;

a (C1-C30)alkoxy group;

a (C1-C30)alkylthio group;

a (C3-C30)cycloalkyl group;

a (C3-C30)cycloalkenyl group;

a 3- to 7-membered heterocycloalkyl group;

a (C6-C30)aryloxy group;

a (C6-C30)arylthio group;

a 3- to 30-membered heteroaryl group which is unsubstituted or substituted with a (C1-C30)alkyl group or a (C6-C30)aryl group;

a (C6-C30)aryl group which is unsubstituted or substituted with a (C1-C30)alkyl group or a 3- to 30-membered heteroaryl group;

a (C6-C30)aryl group which is substituted with a tri(C1-C30)alkylsilyl group;

a (C6-C30)aryl group which is substituted with a tri(C6-C30)arylsilyl group;

a tri(C1-C30)alkylsilyl group;

a tri(C6-C30)arylsilyl group;

a di(C1-C30)alkyl(C6-C30)arylsilyl group;

a (C1-C30)alkyldi(C6-C30)arylsilyl group;

an amino group;

a mono- or di-(C1-C30)alkylamino group;

a mono- or di-(C6-C30)arylamino group;

a (C1-C30)alkyl(C6-C30)arylamino group;

a (C1-C30)alkylcarbonyl group;

a (C1-C30)alkoxycarbonyl group;

a (C6-C30)arylcarbonyl group;

a di(C6-C30)arylboronyl group;

a di(C1-C30)alkylboronyl group;

a (C1-C30)alkyl(C6-C30)arylboronyl group;

a (C6-C30)aryl(C1-C30)alkyl group; and

a (C1-C30)alkyl(C6-C30)aryl group.

4. The electron transport material according to claim 1, wherein A represents a substituted or unsubstituted 5- to 20-membered heteroaryl group;

L represents a single bond, a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted 5- to 20-membered heteroarylene group;

X represents O or S;

R₁ and R₂ each independently represent a hydrogen, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 20-membered heteroaryl group;

R₃ represents a hydrogen;

a and b each independently represent an integer of 1 to 2; and

c represents 1.

5. The electron transport material according to claim 1, wherein A represents an unsubstituted 5- to 20-membered heteroaryl group, a 5- to 20-membered heteroaryl group substituted with a 5- to 20-membered heteroaryl group which is unsubstituted or substituted with a (C1-C20)alkyl group or a (C6-C20)aryl group, a 5- to 20-membered heteroaryl group substituted with a (C6-C20)aryl group, a 5- to 20-membered heteroaryl group substituted with a (C6-C20)aryl group substituted with a 5- to 20-membered heteroaryl group, a 5- to 20-membered heteroaryl group substituted with a (C6-C20)aryl group substituted with a tri(C1-C6)alkylsilyl group, a 5- to 20-membered heteroaryl group substituted with a (C6-C20)aryl group substituted with a tri(C6-C20)arylsilyl group, or a 5- to 20-membered heteroaryl group substituted with a (C1-C6)alkyl(C6-C20)aryl group;

L represents a single bond, an unsubstituted (C6-C20)arylene group, or an unsubstituted 5- to 20-membered heteroarylene group;

X represents O or S;

R₁ and R₂ each independently represent a hydrogen, a (C6-C20)aryl group which is unsubstituted or substituted with a (C6-C12)aryl group, or a 5- to 20-membered heteroaryl group which is unsubstituted or substituted with a (C6-C20)aryl group;

R₃ represents a hydrogen;

a and b each independently represent an integer of 1 to 2; and

c represents an integer of 1.

6. The electron transport material according to claim 1, wherein A represents a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted triazine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted quinoline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted naphthyridine, or a substituted or unsubstituted phenanthroline.

7. The electron transport material according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:

8. An organic electroluminescent device comprising the electron transport material as defined in claim 1.

9. The organic electroluminescent device according to claim 8, further comprising a reducing dopant.

10. The organic electroluminescent device according to claim 9, wherein the reducing dopant is one or more selected from the group consisting of an alkaline metal, an alkaline earth metal, a rare-earth metal, an oxide of an alkaline metal, a halide of an alkaline metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare-earth metal, a halide of a rare-earth metal, an organic complex of an alkaline metal, an organic complex of an alkaline earth metal, and an organic complex of a rare-earth metal.