Organic electroluminescent compounds and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-11527728-B2
Application number	US-201916701319-A
Country	US
Kind code	B2
Filing date	Dec 3, 2019
Priority date	Oct 13, 2015
Publication date	Dec 13, 2022
Grant date	Dec 13, 2022

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.

First claim

The invention claimed is:

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

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;
R 11 and R 12 , 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 are 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;
a and d, each independently, represent an integer of 1 to 4; b and c, each independently, represent an integer of 1 or 2; 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 R 1 to R 4 , each independently, represents hydrogen, deuterium, a substituted or unsubstituted mono or di-(C6-C25)arylamino, a substituted or unsubstituted (C6-C25)aryl selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, and spirobifluorenyl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl selected from furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl;
X, R 11 to R 12 , a, b, c and are as defined in claim 1 .

3. 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 1 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.

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

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

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

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Ahn Hee-Choon

Classifications

• C07D409/14 Primary

  containing three or more hetero rings · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D409/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title