Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Patent metadata

Field	Value
Publication number	US-12012389-B2
Application number	US-202318329687-A
Country	US
Kind code	B2
Filing date	Jun 6, 2023
Priority date	Nov 5, 2020
Publication date	Jun 18, 2024
Grant date	Jun 18, 2024

Abstract

A compound represented by the following formula (1):

The R 1 to R 9 , L 1 to L 3 , and Ar 1 to Ar 2 in the formula (1) are as defined in the description. An organic electroluminescence device contains the compound, and an electronic instrument includes the organic electroluminescence device.

First claim

The invention claimed is:

1. A compound represented by the following formula (1):

wherein
R 1 to R 9 are each independently a hydrogen atom, 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 halogen atom, a cyano group, a nitro group, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
provided that adjacent two selected from R 1 to R 9 are not bonded to each other, thus forming no ring structure,
L 1 is an arylene group represented by the following formula (TEMP-43) or (TEMP-44);

wherein
each * represents a bonding site to the carbon atom or the central nitrogen atom, and
Q 1 to Q 5 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms,
combinations of adjacent two selected from Q 1 to Q 5 may or may not each independently be bonded to each other to form a substituted or unsubstituted ring structure, and
L 2 and L 3 are each independently a single bond, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a group represented by any of the following formulae (i) to (iii):

wherein
*a is bonded to one selected from the carbon atoms *1 to *3,
*b is bonded to one selected from the carbon atoms *4 to *6,
*c is bonded to one selected from the carbon atoms *7 to *9,
*d is bonded to one selected from the carbon atoms *10 to *17, *e is bonded to another one selected from the carbon atoms *10 to *17,
* represents a bonding site to the central nitrogen atom, and
** represents a bonding site to Ar 1 or Ar 2 ,

Ar 1 and Ar 2 are each independently a group represented by any of the following formulae (a) to (e):

in the formula (a),
R 10 to R 25 are each independently a hydrogen atom, 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 halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms constituted only of 6-membered rings, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
provided that
one selected from R 10 to R 14 is a single bond bonded to *f,
one selected from R 15 to R 20 is a single bond bonded to *g, another one selected from R 15 to R 20 is a single bond bonded to *h,
*** represents a bonding site to L 2 or L 3 ,
m1 is 0 or 1, n1 is 0 or 1,
when m1 is 0 and n1 is 0, *h is bonded to L 2 or L 3 ,
when m1 is 0 and n1 is 1, *f is bonded to L 2 or L 3 ,
when m1 is 1 and n1 is 0, one selected from R 10 to R 14 is a single bond bonded to *h,
k1 is 1 or 2, and
adjacent two selected from R 10 to R 14 at are not the single bond are, and adjacent two selected from R 15 to R 20 that are not either of the single bonds are, not bonded to each other, thus forming no ring structure;

in the formula (b),
R 10 to R 20 , *f *g, *h, and *** are the same as described above,
R 26 to R 33 are each independently a hydrogen atom, 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 halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms constituted only of 6-membered rings, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
provided that one selected from R 26 to R 33 is a single bond bonded to *i,
m2 is 0 or 1, n2 is 0 or 1,
when m2 is 0 and n2 is 0, *h is bonded to L 2 or L 3 ,
when m2 is 0 and n2 is 1, *f is bonded to L 2 or L 3 ,
when m2 is 1 and n2 is 0, one selected from R 10 to R 14 is a single bond bonded to *h, and
adjacent two selected from R 10 to R 14 that are not the single bond are, and adjacent two selected from R 15 to R 20 that are not either of the single bonds are, not bonded to each other, thus forming no ring structure;

in the formula (c),
R 10 to R 20 , *f, *g, *h, and *** are the same as described above,
R 34 to R 43 are each independently a hydrogen atom, 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 halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms constituted only of 6-membered rings, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
provided that one selected from R 34 to R 43 is a single bond bonded to *j,
m3 is 0 or 1, n3 is 0 or 1,
when m3 is 0 and n3 is 0, *h is bonded to L 2 or L 3 ,
when m3 is 0 and n3 is 1, *f is bonded to L 2 or L 3 ,
when m3 is 1 and n2 is 0, one selected from R 10 to R 14 is a single bond bonded to *h, and
adjacent two selected from R 10 to R 14 that are not the single bond are, adjacent two selected from R 15 to R 20 that are not either of the single bonds are, and R 34 and R 35 are, not bonded to each other, thus forming no ring structure;

in the formula (d),
R 10 to R 14 , *f, and *** are the same as described above,
R 44 to R 51 are each independently a hydrogen atom, 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 halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms constituted only of 6-membered rings, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
X is an oxygen atom, a sulfur atom, CR a R b , or NR c ,
R a , R b , and R c are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
provided that one selected from R 44 to R 51 and R c is a single bond bonded to *k,
m4 is 0 or 1,
when m4 is 0, *f is bonded to L 2 or L 3 ,
combinations of adjacent two selected from R 44 to R 51 that are not the single bond may each independently be bonded to each other to form a substituted or unsubstituted ring structure,
R 46 and R 47 , and R 48 and R 49 , are not bonded to each other, thus forming no ring structure, and
R a and R b are not crosslinked;

in the formula (e),
R 10 to R 14 , *f, and *** are the same as described above,
R 52 to R 66 are each independently a hydrogen atom, 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 halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms constituted only of 6-membered rings, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
provided that
one selected from R 52 to R 56 is a single bond bonded to *l, another one sel

Assignees

• Idemitsu Kosan Co

Inventors

• Takahashi Yusuke
• Haketa Tasuku
• Tanaka Shota

Classifications

• H10K50/15

  Hole transporting layers · CPC title

• C07D307/91 Primary

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C07D407/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/14 Primary

  containing three or more hetero rings · CPC title