Compound and organic light emitting device comprising same

Patent metadata

Field	Value
Publication number	US-11737358-B2
Application number	US-201916761902-A
Country	US
Kind code	B2
Filing date	Mar 22, 2019
Priority date	Mar 22, 2018
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

Provided is a compound of Chemical Formula 1:HAr-L1-L2-Ar1wherein:HAr is one of Chemical Formula A-1 or A-2:one of L1 and L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group, or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group, and the other one is a direct bond; andAr1 is a cyano group, a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted pyridinyl group; a substituted or unsubstituted triazinyl group; a substituted or unsubstituted polycyclic aryl group; or a substituted or unsubstituted polycyclic heteroaryl group, and an organic light emitting device comprising the same.

First claim

The invention claimed is:

1. A compound of Chemical Formula 1:
Chemical Formula 1
HAr-L1-L2-Ar1

wherein, in Chemical Formula 1:
HAr represents Chemical Formula A-1 or A-2;
L1 and L2 are selected from among a phenylene group that is unsubstituted or substituted with an aryl group substituted with a cyano group, an aryl group substituted with a fluoroalkoxy group, a heteroaryl group substituted with an alkyl group, an aryl group, or a heteroaryl group; a biphenylene group; a divalent naphthyl group that is unsubstituted or substituted with a cyano group; a divalent fluorenyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a divalent dibenzofuranyl group; a divalent dibenzothiophenyl group; a divalent carbazolyl group that is unsubstituted or substituted with an aryl group, a heteroaryl group, or an arylheteroaryl group; and a divalent spirofluorenexanthenyl group; or one of L1 and L2 is a phenylene group that is unsubstituted or substituted with an aryl group substituted with a cyano group, an aryl group substituted with a fluoroalkoxy group, a heteroaryl group substituted with an alkyl group, an aryl group, or a heteroaryl group; a biphenylene group; a divalent naphthyl group that is unsubstituted or substituted with a cyano group; a divalent fluorenyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a divalent dibenzofuranyl group; a divalent dibenzothiophenyl group; a divalent carbazolyl group that is unsubstituted or substituted with an aryl group, a heteroaryl group, or an arylheteroaryl group; or a divalent spirofluorenexanthenyl group, and the other one is a direct bond;
Ar1 is a cyano group; a phenyl group that is unsubstituted or substituted with a cyano group, an arylphosphine oxide group, an aryl group substituted with a fluoroalkoxy group, an aryl group, or a heteroaryl group; a biphenyl group that is unsubstituted or substituted with a cyano group; a naphthyl group that is unsubstituted or substituted with a cyano group; a fluoranthenyl group; a fluorenyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a triphenylenyl group; a spiro[fluorene-9,9′-xanthen]yl group that is unsubstituted or substituted with a cyano group; a pyridinyl group that is unsubstituted or substituted with an alkyl group; a triazinyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a quinolinyl group; an indenocarbazolyl group that is unsubstituted or substituted with an alkyl group; a beta-carbolinyl group; a pyridoindolyl group; a benzothienopyrimidinyl group that is unsubstituted or substituted with an aryl group; a benzimidazolyl group that is unsubstituted or substituted with an aryl group; a benzoxazolyl group; a benzothiazolyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a carbazolyl group that is unsubstituted or substituted with a cyano group or an aryl group; or a phenanthrolinyl group;
with the proviso that at least one of L1 and L2 is a biphenylene group; a divalent naphthyl group that is unsubstituted or substituted with a cyano group; a divalent fluorenyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a divalent dibenzofuranyl group; a divalent dibenzothiophenyl group; a divalent carbazolyl group that is unsubstituted or substituted with an aryl group, a heteroaryl group, or an arylheteroaryl group; or a divalent spirofluorenexanthenyl group; or Ar1 is a cyano group; a biphenyl group that is unsubstituted or substituted with a cyano group; a naphthyl group that is unsubstituted or substituted with a cyano group; a fluoranthenyl group; a fluorenyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a triphenylenyl group; a spiro[fluorene-9,9′-xanthen]yl group that is unsubstituted or substituted with a cyano group; a pyridinyl group that is unsubstituted or substituted with an alkyl group; a triazinyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a quinolinyl group; an indenocarbazolyl group that is unsubstituted or substituted with an alkyl group; a beta-carbolinyl group; a pyridoindolyl group; a benzothienopyrimidinyl group that is unsubstituted or substituted with an aryl group; a benzimidazolyl group that is unsubstituted or substituted with an aryl group; a benzoxazolyl group; a benzothiazolyl group; a dibenzofuranyl group; a dibenzothiophenyl group; or a phenanthrolinyl group;

wherein in Chemical Formula A-1:
one of R1 to R3 is a phenyl group, and the remaining two are the same as or different from each other and each independently is a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted branched alkyl group, a methyl group, or a substituted or unsubstituted monocyclic heteroaryl group; or
two of R1 to R3 are the same as or different from each other and each independently is a phenyl group that is unsubstituted or substituted with an alkyl group, and the remaining one is a substituted or unsubstituted linear or branched alkyl group; a monocyclic or polycyclic aryl group that is unsubstituted or substituted with an alkyl group, an aryl group or an aryloxy group; a pyridinyl group; a dibenzothiophenyl group; a dibenzofuranyl group; or a carbazolyl group;

wherein in Chemical Formula A-2:
one of R1 to R3 is a phenyl group, and the remaining two are the same as or different from each other and each independently is a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted branched alkyl group, a methyl group, or a substituted or unsubstituted monocyclic heteroaryl group; or
two of R1 to R3 are the same as or different from each other and each independently is a phenyl group that is unsubstituted or substituted with an alkyl group, and the remaining one is a substituted or unsubstituted linear or branched alkyl group; a monocyclic aryl group that is substituted with an alkyl group, an aryl group or an aryloxy group; a polycyclic aryl group that is unsubstituted or substituted with an alkyl group, an aryl group or an aryloxy group; a pyridinyl group; a dibenzothiophenyl group; a dibenzofuranyl group; or a carbazolyl group; or
R1 to R3 are each a phenyl group, and the phenyl groups bond to each other so the Chemical Formula A-2 is a tribenzoperimidine ring of the structure:

and

is a site bonding to L1 of Chemical Formula 1.

2. The compound of claim 1 , wherein Chemical Formula 1 is one of the following Chemical Formula 1-1 or 1-2:

wherein in Chemical Formulae 1-1 and 1-2:
Ar1 has the same definition as in Chemical Formula 1;
one of L1 and L2 is a phenylene group that is unsubstituted or substituted with an aryl group substituted with a cyano group, an aryl group substituted with a fluoroalkoxy group, a heteroaryl group substituted with an alkyl group, an aryl group, or a heteroaryl group; a biphenylene group; a divalent naphthyl group that is unsubstituted or substituted with a cyano group; a divalent fluorenyl group that is unsubstituted or substituted with an alkyl group or an aryl group; a divalent dibenzofuranyl group; a divalent dibenzothiophenyl group; a divalent carbazolyl group that is unsubstituted or substituted with an aryl group, a heteroaryl group, or an arylheteroaryl group; or a divalent s

Assignees

• Lg Chemical Ltd

Inventors

• Huh Jungoh
• Lee Dong Hoon
• Heo Dong Uk
• Han Miyeon
• Lee Jae Tak
• Yang Junghoon
• Yun Heekyung

Classifications

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K85/622

  containing four rings, e.g. pyrene · CPC title