Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same

Patent metadata

Field	Value
Publication number	US-9837615-B2
Application number	US-201514716429-A
Country	US
Kind code	B2
Filing date	May 19, 2015
Priority date	Jun 4, 2013
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

A nitrogen-containing heterocyclic derivative in which an indole structure is fused to a benzophenanthrene ring is a novel material useful as a material for organic electroluminescence devices for the production of organic electroluminescence devices and electronic equipment.

First claim

What is claimed is:

1. A nitrogen-containing heterocyclic derivative represented by formula (6) or (7):

wherein R 1 to R 4 and R 7 to R 12 each represent a hydrogen atom; each of R 13 to R 16 independently represents a hydrogen atom or a substituent group, wherein the substituent group represented by R 13 to R 16 is independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 61 carbon atoms, an amino group, a mono- or disubstituted amino group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 ring carbon atoms, a mono-, di-, or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a sulfonyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a disubstituted phosphoryl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, an alkylsulfonyloxy group, an arylsulfonyloxy group, an alkylcarbonyloxy group, an arylcarbonyloxy group, a boron-containing group, a zinc-containing group, a tin-containing group, a silicon-containing group, a magnesium-containing group, a lithium-containing group, a hydroxyl group, an alkyl- or aryl-substituted carbonyl group, a carboxyl group, a vinyl group, a (meth)acryloyl group, an epoxy group, and an oxetanyl group; R 18 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted nitrogen-containing heterocyclic group having 5 to 30 ring atoms; and a pair of adjacent two groups selected from R 13 to R 16 and R 18 may be bonded to each other to form a saturated or unsaturated divalent group which completes a ring, with the proviso that the following compound is excluded from the nitrogen-containing heterocyclic derivative:

2. The nitrogen-containing heterocyclic derivative according to claim 1 , wherein the nitrogen-containing heterocyclic derivative is represented by formula (10) or (11):

wherein each of X 1 to X 3 independently represents C(R 21 ) or a nitrogen atom; R 1 to R 4 and R 7 to R 16 are as defined in formula (6) and formula (7); a pair of adjacent two groups selected from R 13 to R 16 may be bonded to each other to form a saturated or unsaturated divalent group which completes a ring; each of R 19 to R 21 independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted nitrogen-containing heterocyclic group having 5 to 30 ring atoms; and a pair of adjacent two groups selected from R 19 to R 21 may be bonded to each other to form a saturated or unsaturated divalent group which completes a ring.

3. The nitrogen-containing heterocyclic derivative according to claim 2 , wherein the nitrogen-containing heterocyclic derivative is represented by formula (12) or (13):

wherein X 1 , R 1 to R 4 , R 7 to R 16 , R 19 , and R 20 are each as defined in formula (10) and formula (11).

4. A nitrogen-containing heterocyclic derivative represented by formula (14) or (15):

wherein:
each of X 2 to X 3 independently represents C(R 21 ) or a nitrogen atom;
each of R 1 to R 4 and R 7 to R 16 independently represents a hydrogen atom or a substituent group;
the substituent group represented by R 1 to R 4 and R 7 to R 16 is independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 61 carbon atoms, an amino group, a mono- or disubstituted amino group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 ring carbon atoms, a mono-, di-, or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a sulfonyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a disubstituted phosphoryl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, an alkylsulfonyloxy group, an arylsulfonyloxy group, an alkylcarbonyloxy group, an arylcarbonyloxy group, a boron-containing group, a zinc-containing group, a tin-containing group, a silicon-containing group, a magnesium-containing group, a lithium-containing group, a hydroxyl group, an alkyl- or aryl-substituted carbonyl group, a carboxyl group, a vinyl group, a (meth)acryloyl group, an epoxy group, and an oxetanyl group;
a pair of adjacent two groups selected from R 1 to R 4 and R 7 to R 12 is not bonded to each other to form a ring structure;
a pair of adjacent two groups selected from R 13 to R 16 may be bonded to each other to form a saturated or unsaturated divalent group which completes a ring;
each of R 19 , R 21 to R 25 independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted nitrogen-containing heterocyclic group having 5 to 30 ring atoms; and
a pair of adjacent two groups selected from R 19 and R 21 to R 25 may be bonded to each other to form a saturated or unsaturated divalent group which completes a ring.

5. A nitrogen-containing heterocyclic derivative represented by formula (16) or (17):

wherein X 1 represents C(R 21 ) or a nitrogen atom

Assignees

• Idemitsu Kosan Co

Inventors

• Kawamura Masahiro
• Mizuki Yumiko
• Ito Hirokatsu
• HAYAMA Tomoharu
• Haketa Tasuku

Classifications

• H01L51/5092

  Electricity · mapped topic

• H01L51/5096

  Electricity · mapped topic

• C07D403/04 Primary

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

• H01L51/5072

  Electricity · mapped topic

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title