Material for organic electroluminescent element, and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-9266865-B2
Application number	US-201113637988-A
Country	US
Kind code	B2
Filing date	Mar 29, 2011
Priority date	Mar 31, 2010
Publication date	Feb 23, 2016
Grant date	Feb 23, 2016

Abstract

Provided is a material for an organic electroluminescence device having a specific structure in which a dibenzothiophenyl group or a carbazolyl group is bonded to a carbazolyl group at its N-position (9-position) directly or through a linking group. Further provided is an organic electroluminescence device including one or more organic thin film layers including a light emitting layer between a cathode and an anode, in which at least one organic thin film layer contains the material for an organic electroluminescence device of the present invention.

First claim

The invention claimed is:

1. A material represented by formula (1):

wherein:
G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or formula (A):

* represents a bond to L 3 ;
X 1 represents a sulfur atom or N—R 9 ;
X 2 represents a sulfur atom or N—R 10 ;
provided that, when X 1 represents a sulfur atom, G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
and, when X 1 represents N—R 9 ; G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms or formula (A);
R 1 to R 8 each independently represent a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, such that alkyl groups represented by R 1 to R 8 optionally form a ring;
when G and R 1 to R 8 have substituents, the substituents R's each independently represent an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 18 ring carbon atoms;
a, d, and f each independently represent an integer of any one of 0 to 4, and b, c, and e represent 0, such that a relationship of 0≦(a+b+c+d+e+f)≦4 is established;
R 9 and R 10 each independently represent an alkyl group having 1 to 5 carbon atoms, a phenyl group, a toluyl group, a dimethylphenyl group, a trimethylphenyl group, or a biphenyl group;
g represents 0, and h represents an integer of any one of 0 to 4, such that a relationship of 0≦(g+h)≦4 is established;
provided that when X 1 and X 2 each represent nitrogen, and the substituent R 9 represents a phenyl group, a case where the substituent R 10 represents a phenyl group is excluded;
L 1 represents a single bond, a divalent linking group including N, a divalent linking group including O, a divalent linking group including Si, a divalent linking group including P, a divalent linking group including S, or an alkylene group having 1 to 5 carbon atoms; and
L 2 and L 3 represent a single bond.

2. The material according to claim 1 , wherein in the formula (1), X 1 represents N—R 9 and G represents the formula (A) where the X 2 represents a sulfur atom.

3. The material according to claim 1 , wherein:
the formula (1) is represented by formula (2):

G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or formula (A):

* represents a bond to L 3 ;
X 1 represents a sulfur atom or N—R 9 ;
X 2 represents a sulfur atom or N—R 10 ;
provided that, when X 1 represents a sulfur atom, G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
and, when X 1 represents N—R 9 ; G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms or formula (A);
R 1 to R 8 each independently represent a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, such that alkyl groups represented by R 1 to R 8 optionally form a ring;
when G and R 1 to R 8 have substituents, the substituents R's each independently represent an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 18 ring carbon atoms;
a, d, and f each independently represent an integer of any one of 0 to 4, and b, c, and e represent 0, such that a relationship of 0≦(a+b+c+d+e+f)≦4 is established;
R 9 and R 10 each independently represent an alkyl group having 1 to 5 carbon atoms, a phenyl group, a toluyl group, a dimethylphenyl group, a trimethylphenyl group, or a biphenyl group;
g represents 0, and h represents an integer of any one of 0 to 4, such that a relationship of 0≦(g+h)≦4 is established;
provided that when X 1 and X 2 each represent nitrogen, and the substituent R 9 represents a phenyl group, a case where the substituent R 10 represents a phenyl group is excluded;
L 1 represents a single bond, a divalent linking group including N, a divalent linking group including O, a divalent linking group including Si, a divalent linking group including P, a divalent linking group including S, or an alkylene group having 1 to 5 carbon atoms; and
L 2 and L 3 represent a single bond.

4. The material according to claim 1 , wherein:
the formula (1) is represented by formula (3):

R 1 , R 4 , and R 6 each independently represent an aryl group having 6 to 18 ring carbon atoms, and the aryl group is optionally further substituted with the substituent R;
G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or formula (A):

* represents a bond to L 3 ;
X 1 represents a sulfur atom or N—R 9 ;
X 2 represents a sulfur atom or N—R 10 ;
provided that, when X 1 represents a sulfur atom, G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
and, when X 1 represents N—R 9 ; G represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms or formula (A);
R 1 , R 2 , R 3 , R 5 , R 7 and R 8 each independently represent a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, such that alkyl groups represented by R 1 to R 8 optionally form a ring;
when G and R 1 to R 8 have substituents, the substituents R's each independently represent an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 18 ring carbon atoms;
a, d, and f each independently represent an integer of any one of 0 to 4, and b, c, and e represent 0, such that a relationship of 0≦(a+b+c+d+e+f)≦4 is established;
R 9 and R 10 each independently represent an alkyl group having 1 to 5 carbon atoms, a phenyl group, a toluyl group, a dimethylphenyl group, a trimethylphenyl group, or a biphenyl group;
g represents 0, and h represents an integer of any one of 0 to 4, such that a relationship of 0≦(g+h)≦4 is established;
provided that when X 1 and X 2 each represent nitrogen, and the substituent R 9 represents a phenyl group, a case where the substituent R 10 represents a phenyl group is excluded;
L 1 represents a single bond, a divalent linking group including N, a divalent linking group including O, a divalent linking group including Si, a divalent linking group including P, a divalent linking group including S, or an alkylene group having 1 to 5 carbon atoms; and
L 2 and L 3 represent a single bond.

5. The material according to claim 1 , wherein in the formula (1), the L 1 represents one selected from the group consisting of a single bond, a divalent linking group including O, a divalent linking group including S, and an alkylene group having 1 to 5 carbon atoms.

6. The material according to claim 1 , wherein the material has a molecular weight of 1,000 or less.

7. The material according

Assignees

• Numata Masaki
• Nagashima Hideaki
• Idemitsu Kosan Co

Inventors

• Numata Masaki
• Nagashima Hideaki

Classifications

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D405/04

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

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• H01L51/0072

  Electricity · mapped topic

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title