Compound, organic electroluminescence element material, ink composition, organic electroluminescence element, electronic device, and method for producing compound

Patent metadata

Field	Value
Publication number	US-10032991-B2
Application number	US-201414911606-A
Country	US
Kind code	B2
Filing date	Dec 17, 2014
Priority date	Dec 18, 2013
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

A compound represented by formula (1):

wherein *a, *b, R 1 , X 1 , L 1 , L 2 , n, A 1 , and A 2 are as defined in the description, and a production method of the compound represented by formula (1) are provide. In the production method, A 1 is introduced under a reaction condition in which the reactivity of Hal 2 in a compound represented by formula (I):

wherein *c, *d, R 1 , X 1 , L 1 , L 2 , n, A 1 , A 2 , Hal 1 , and Hal 2 are as defined in the description,

is extremely low as compared with that of Hal 1 and then A 2 which is different from A 1 is introduced under a reaction condition in which the reactivity of Hal 2 is high. The compound represented by formula (1) is formed into a layer by a coating method and meets various performance requirements of an organic EL device.

First claim

What is claimed is:

1. A compound represented by formula (1):

wherein one of *a and *b is bonded to a carbon atom *c1, and the other is bonded to a carbon atom *c2;
R 1 represents a hydrogen atom or a substituent;
X 1 represents N or CR 2 , R 2 represents a hydrogen atom or a substituent, and R 2 may be bonded to R 1 to form a ring;
when *b is bonded to the carbon atom *c2, X 1 represents CR 2 , and R 2 is bonded to R 1 to form a ring, —R 1 R 2 — represents X a ═X b —X c ═X d —;
X a to X d each independently represent N or CR a , R a represents a hydrogen atom or a substituent, and adjacent two groups R a may be bonded to each other to form a ring;
L 1 represents a linking group;
L 2 represents a divalent linking group;
n represents an integer of 0 to 3 and when n is 0, L 2 represents a single bond;
A 1 and A 2 are different from each other and each represent a group represented by any of formulae (2), (2′), (3), (3′), (3″), and (4):

wherein *2 is bonded to the carbon atom *c1, the carbon atom *c2, L 1 when n is 0, or L 2 when n is an integer of 1 to 3, each described in formula (1);
one of X 7 to X 11 is a carbon atom bonded to *3;
one of X 12 to X 16 is a carbon atom bonded to *4;
a rest of X 7 to X 11 , a rest of X 12 to X 16 , X 2 to X 6 , and X 17 to X 21 each independently represent N or CR 3 ;
R 3 represents a hydrogen atom or a substituent and groups R 3 may be bonded to each other to form a ring;
X 6 and X 11 may be carbon atoms which are bonded to each other, and X 16 and X 21 may be carbon atoms which are bonded to each other;
X 22 represents NR 4 , CR 5 R 6 , O, S, Se, or SiR 7 R 8 ; and
R 4 to R 8 each independently represent a hydrogen atom or a substituent, and R 5 and R 6 , and R 7 and R 8 may be bonded to each other to form a ring;

wherein *2, X 7 to X 11 , X 12 to X 16 , X 17 to X 21 , and X 22 are as defined above;
one of X 2′ to X 6′ represents a carbon atom bonded to *3′;
one of X 12′ to X 16′ represents a carbon atom bonded to *4′;
a rest of X 2′ to X 6′ , a rest of X 12′ to X 16′ , and X 17′ to X 21′ each independently represent N or CR 3 ;
R 3 is as defined above;
X 6′ and X 11 may be carbon atoms which are bonded to each other, X 16 and X 21 may be carbon atoms which are bonded to each other, and X 16′ and X 21′ may be carbon atoms which are bonded to each other;
X 22′ represents NR 4 , CR 5 R 6 , O, S, Se, or SiR 7 R 8 ; and
R 4 to R 8 are as defined above;

wherein *5 is bonded to the carbon atom *c1, the carbon atom *c2, L 1 when n is 0, or L 2 when n is an integer of 1 to 3, each described in formula (1);
one of X 37 to X 41 represents a carbon atom bonded to *6;
a rest of X 37 to X 41 , X 32 to X 36 , and X 42 to X 51 each independently represent N or CR 9 ;
R 9 represents a hydrogen atom or a substituent and groups R 9 may be bonded to each other to form a ring; and
X 36 and X 41 may be carbon atoms which are bonded to each other and X 46 and X 51 may be carbon atoms which are bonded to each other;

wherein *5, X 37 to X 41 , and X 42 to X 51 are as defined above;
one of X 32′ to X 36′ represents a carbon atom bonded to *6′
a rest of X 32′ to X 36′ and X 42′ to X 51′ each independently represent N or CR 9 ;
R 9 is as defined above; and
X 36′ and X 41 may be carbon atoms which are bonded to each other, X 46 and X 51 may be carbon atoms which are bonded to each other, and X 46′ and X 51′ may be carbon atoms which are bonded to each other;

wherein *5, X 37 to X 41 , and X 42 to X 51 are as defined above;
one of X 32″ to X 36″ represents a carbon atom bonded to 3″;
one of X 12″ to X 16″ represents a carbon atom bonded to *4″;
a rest of X 32″ to X 36″ , a rest of X 12″ to X 16″ , and X 17″ to X 21″ each independently represent N or CR 3 ;
R 3 is as defined above;
X 36″ and X 41 may be carbon atoms which are bonded to each other, X 46 and X 51 may be carbon atoms which are bonded to each other, X 16″ and X 21″ may be carbon atoms which are bonded to each other;
X 22″ represents NR 4 , CR 5 R 6 , O, S, Se, or SiR 7 R 8 ; and
R 4 to R 8 are as defined above;

wherein *7 is bonded to the carbon atom *c1, the carbon atom *c2, L 1 when n is 0, or L 2 when n is an integer of 1 to 3, each described in formula (1);
one of adjacent two selected from X 67 to X 71 represents a carbon atom bonded to *8 and the other represents a carbon atom bonded to *9;
a rest of X 67 to X 71 , X 62 to X 66 , and X 72 to X 75 each independently represent N or CR 10 ;
R 10 represents a hydrogen atom or a substituent, and groups R 10 may be bonded to each other to form a ring;
X 66 and X 71 may be carbon atoms which are bonded to each other;
X 76 represents NR 11 , CR 12 R 13 , O, S, Se, or SiR 14 R 15 ; and
R 11 to R 15 each independently represent a hydrogen atom or a substituent, and R 11 and R 12 , and R 13 and R 14 may be bonded to each other to form a ring.

2. The compound according to claim 1 , wherein
when *b is bonded to the carbon atom *c1, L 1 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a group of atoms which completes a ring together with R 2 ;
when L 1 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and n is 1, L 1 and L 2 may be the same or different and may be crosslinked together; and
when L 1 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and n is 2 or 3, L 1 and two or three groups L 2 may be the same or different, and L 1 and L 2 , and two groups L 2 may be crosslinked together.

3. The compound according to claim 1 , wherein
when *b is bonded to the carbon atom *c2 and n is 1, L 1 and L 2 may be the same or different and may be crosslinked together; and
when *b is bonded to the carbon atom *c2 and n is 2 or 3, L 1 and two or three groups L 2 may be the same or different, and L 1 and L 2 , and two groups L 2 may be crosslinked together.

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

wherein R 1 , X 1 , L 1 , L 2 , n, A 1 , and A 2 are as defined above.

5. The compound according to claim 1 , wherein the compound is represented by formula (1b):

wherein R 1 , X 1 , L 1 , L 2 , n, A 1 , and A 2 are as defined above.

6. The compound according to claim 1 , wherein the co

Assignees

• Idemitsu Kosan Co

Inventors

• Ikeda Kiyoshi
• Kawakami Hironori

Classifications

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B69/109

  containing other specific dyes · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09D11/50

  Sympathetic, colour changing or similar inks · CPC title