Electronic device and polymer compound

Patent metadata

Field	Value
Publication number	US-9306170-B2
Application number	US-201214007854-A
Country	US
Kind code	B2
Filing date	Mar 27, 2012
Priority date	Mar 28, 2011
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

An electronic device that serves as a high-brightness electroluminescent device includes a layer containing a polymer compound having one or more structural units selected from a structural unit represented by formula (1) and a structural unit represented by formula (14) as a charge injection layer and/or a charge transport layer:

wherein Ar 1 and Ar 2 represent certain fused polycyclic aromatic groups; R 1 , R 2 , R 6 and R 7 represent certain organic groups; m1, m2 and m6 represent an integer of 1 or more; m7 represents an integer of 0 or more; and when R 1 , R 2 , R 6 and R 7 are each plurally present, they each may be the same or different.

First claim

The invention claimed is:

1. An electronic device including a layer comprising a polymer compound comprising one or more structural units selected from the group consisting of a structural unit represented by formula (1) and a structural unit represented by formula (14) as a charge injection layer and/or a charge transport layer,
wherein the structural unit represented by formula (1) is:

wherein
Ar 1 represents a (2+m1+m2)-valent fused polycyclic aromatic group that optionally has a substitutent;
R 1 represents a group represented by formula (2) or formula (3);
R 2 represents a group represented by formula (4);
m1 represents an integer of 1 or more;
m2 represents an integer of 1 or more;
Y 1 represents —CO 2 − , —SO 3 − , —SO 2 − , —PO 3 2− or —B(R α ) 3 ;
M 1 represents a metallic cation, or represents an ammonium cation that optionally has a substituent;
Z 1 represents F − , Cl − , Br − , I − , OH − , B(R a ) 4 − , R a SO 3 − , R a COO − , ClO − , ClO 2 − , ClO 3 − , ClO 4 − , SCN − , CN − , NO 3 − , SO 4 2− , HSO 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , BF 4 − or PF 6 − ;
n1 represents an integer of 0 or more;
a1 represents an integer of 1 or more, and b1 represents an integer of 0 or more, wherein a1 and b1 are selected such that a charge of the group represented by formula (2) is zero;
R α represents an alkyl group having 1 to 30 carbon atoms that optionally has a substituent, or an aryl group having 6 to 50 carbon atoms that optionally has a substituent;
R a represents an alkyl group having 1 to 30 carbon atoms that optionally has a substituent, or an aryl group having 6 to 50 carbon atoms that optionally has a substituent;
m3 represents an integer of 1 or more, and when R 3 is, a single bond, m3 represents 1; and
when Q 1 , Y 1 , M 1 , Z 1 , n1, a1 and b1 are each plurally present, they each may be the same or different;

wherein the group represented by formula (3) is:
—R 4 -{(Q 2 ) n2 -Y 2 (M 2 ) a2 (Z 2 ) b2 } m4   (3)

wherein
R 4 represents a single bond, or a (1+m4)-valent organic group that optionally has a substituent;
Q 2 represent a divalent organic group;
Y 2 represents a carbocation, an ammonium cation, a phosphonium cation, a sulfonium cation, or an iodonium cation;
M 2 represents F − , Cl − , Br − , I − , OH − , B(R b ) 4 − , R b SO 3 − , R b COO − , ClO − , ClO 2 − , ClO 3 − , ClO 4 − , SCN − , CN − , NO 3 − , SO 4 2− , HSO 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , BF 4 − or PF 6 + ;
Z 2 represents a metallic cation, or represents an ammonium cation that optionally has a substituent;
n2 represents an integer of 0 or more;
a2 represents an integer of 1 or more, and b2 represents an integer of 0 or more, wherein a2 and b2 are selected such that a charge of the group represented by formula (3) is zero;
R b represents an alkyl group having 1 to 30 carbon atoms that optionally has a substituent, or an aryl group having 6 to 50 carbon atoms that optionally has a substituent;
m4 represents an integer of 1 or more, and when R 4 is a single bond, m4 represents 1; and
when Q 2 , Y 2 , M 2 , Z 2 , n2, a2 and b2 are each plurally present, they each may be the same or different;

wherein the group represented by formula (4) is:
—R 5 -{(Q 3 ) n3 -Y 3 } m5   (4)

wherein
R 5 represents a single bond, or a (1+m5)-valent organic group that optionally has a substituent;
Q 3 represents a divalent organic group;
Y 3 represents a cyano group, or a group represented by any one of formulae (5), (6), (7), and (12);
n3 represents an integer of 0 or more;
m5 represents an integer of 1 or more, and when R 5 is a single bond, m5 is 1; and
when Q 3 , Y 3 and n3 are each plurally present, they each may be the same or different;
wherein the group represented by any one of formulae (5), (6), (7), and (12) is:
—O—(R′O) a3 —R″  (5)

—S—(R′S) a4 —R″  (7)

—C(═O)O—(R′O) a4 —R″  (12)

wherein
R′ represents a divalent hydrocarbon group that optionally has a substituent;
R″ represents a hydrogen atom, a monovalent hydrocarbon group that optionally has a substituent, a carboxyl group, a sulfo group, a hydroxy group, a mercapto group, —NR C 2 , a cyano group or —C(═O)NR c 2 ;
R′″ represents a trivalent hydrocarbon group that optionally has a substituent;
a3 represents an integer of 1 or more;
a4 represents an integer of 0 or more;
R c represents an alkyl group having 1 to 30 carbon atoms that optionally has a substituent, or an aryl group having 6 to 50 carbon atoms that optionally has a substituent; and
when R′, R″ and R′″ are each plurally present, they each may be the same or different;

and
wherein the structural unit represented by formula (14) is:

wherein
Ar 2 represents a (2+m6+m7)-valent fused polycyclic aromatic group that optionally has a substituent;
R 6 represents a group represented by formula (15) or formula (16);
R 7 represents the group represented by formula (4);
m6 represents an integer of 1 or more;
m7 represents an integer of 0 or more;
when R 6 and R 7 are each plurally present, they each may be the same or different; and
a hydrogen atom in formula (14) may be replaced with a substituent other than R 6 or R 7 ;
wherein the group represented by formula (15) is:

wherein
R 8 represents a (1+m8+m9)-valent organic group that optionally has a substituent;
Y 3 represents a cyano group, or a group represented by any one of formulae (5) to (13);
wherein each of formulae (8), (9), (10), (11) and (13) is represented by the following:
—C(═O)—(R′—C(═O)) a4 —R″  (8)

—C(═S)—(R′—C(═S)) a4 —R″  (9)

—N{(R′) a4 R″} 2   (10)

—C(═O)O—(R′—C(═O)O) a4 —R″  (11)

—NHC(═O)—(R′NHC(═O)) a4 —R″  (13)

wherein R′, R″, and a4 are the same as the corresponding definitions above;

Q 1 , Q 3 , Y 1 , M 1 , Z 1 , n1, n3, a1 and b1 are the same as the corresponding definitions above;
m8 and m9 each independently represent an integer of 1 or more; and
when Q 1 , Q 3 , Y 1 , Y 3 , M 1 , Z 1 , n1, n3, a1 and b1 are each plurally present, they each may be the same or different;

wherein the group represented by formula (16) is:

wherein
R 9 represents a (1+m10+m11)-valent organic group that optionally has a substituent;
Q 2 , Q 3 , Y 2 , Y 3 , M 2 , Z 2 , n2, n3, a2 and b2 are the same as the corresponding definitions above;
m10 and m11 each independently represent an integer of 1 or more; and
when Q 2 , Q 3 , Y 2 , Y 3 , M 2 , Z 2 , n2, n3, a2 and b2 are each plurally present, they each may be the same or different.

2. The electronic device according to claim 1 , wherein the (2+m1+m2)-valent fused polycyclic aromatic group that optionally has a substituent which is represented by Ar 1 is a group remaining after removing (2+m1+m2) hydrogen atoms from a ring represented by any one of the following formulae:

3. The electronic device according to claim 1 , wherein the (2+m6+m7)-valent fused polycyclic aromatic group that optionally has a substituent which is represented by Ar 2 is a group remaining after removing (2+m6+m7) hydrogen atoms from a ring represented by any one of the following formulae:

Assignees

• Tanaka Masanobu
• Ishikawa Rui
• Kobayashi Norifumi
• Sakakibara Ken
• Higashimura Hideyuki
• Sumitomo Chemical Co

Inventors

• Tanaka Masanobu
• Ishikawa Rui
• Kobayashi Norifumi
• Sakakibara Ken
• Higashimura Hideyuki

Classifications

• H10K85/151

  Copolymers · CPC title

• C08G61/10 Primary

  only aromatic carbon atoms, e.g. polyphenylenes · CPC title

• C08G2261/3162

  Arylamines · CPC title

• C08G2261/1426

  containing carboxy groups (COOH) and/or -C(=O)O-moieties · CPC title

• C08G61/12

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title