Electronic device, polymer compound, organic compound, and method of producing polymer compound

Patent metadata

Field	Value
Publication number	US-9306169-B2
Application number	US-201214007668-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 (7) as a charge injection layer and/or a charge transport layer:

Wherein R 1 , R 2 , R 6 and R 7 represent certain groups; m1 and m5 represent an integer of 0 or more; when R 2 and R 7 are plurally present, they may be the same or different; and a hydrogen atom in formula (1) or (7) may be replaced with a substituent other than the certain groups.

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 (7) as a charge injection layer and/or a charge transport layer,
wherein the structural unit represented by formula (1) is:

wherein
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 0 or more;
when R 2 is plurally present, they may be the same or different; and
a hydrogen atom in formula (1) may be replaced with a substituent other than R 1 or R 2 ;
wherein the group represented by formula (2) is:
—R 3 -{(Q 1 ) n1 -Y 1 (M 1 ) a1 (Z 1 ) b1 } m2   (2)

wherein
R 3 represents a single bond, or a (1+m2)-valent organic group that optionally has a substituent;
Q 1 represents a divalent organic group;
Y 1 represents —CO 2 − , —SO 3 − , —SO 2 − , —PO 3 2− or —B(R α ) 3 − ;
M 1 represents Cs + ;
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;
m2 represents an integer of 1 or more, and when R 3 is a single bond, m2 represents 1; and
when Q 1 , Y 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 } m3   (3)

wherein
R 4 represents a single bond, or a (1+m3)-valent organic group that optionally has a substituent;
Q 2 represents 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;
m3 represents an integer of 1 or more, and when R 4 is a single bond, m3 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 } m4   (4)

wherein
R 5 represents a single bond, or a (1+m4)-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 formula (5) or formula (6);
n3 represents an integer of 0 or more;
m4 represents an integer of 1 or more, and when R 5 is a single bond, m4 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 formula (5) or formula (6) are:
—O—(R′O) a3 —R″  (5)

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 in formula (5) represents an integer of 3 to 10;
a3 in formula (6) represents an integer of 1 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 (7) is:

wherein
R 6 represents a group represented by formula (8) or formula (9);
R 7 represents the group represented by formula (4), wherein
R 5 , Q 3 , n3, and m4 are represented as defined above, Y 3 represents a cyano group or a group represented by formula (5) or formula (6), wherein a3 in formula (5) or formula (6) represents an integer of 1 or more, R′, R″, R′″, and Rc are represented as defined above, and when Q 3 , Y 3 , n3, R′, R″, and R′″ are plurally present, they may each be the same or different;

m5 represents an integer of 0 or more;
when R 7 is plurally present, they may be the same or different; and
a hydrogen atom in formula (7) may be replaced with a substituent other than R 6 or R 7 ;
wherein the group represented by formula (8) is:

wherein
R 8 represents a (1+m6+m7)-valent organic group that optionally has a substituent;
M 1 represents a metallic cation, or represents an ammonium cation that optionally has a substituent;
Y 3 represents a cyano group or a group represented by formula (5) or formula (6), wherein a3 in formula (5) or formula (6) represents an integer of 1 or more, R′, R″, R′″, and Rc are represented as defined above, and when R′, R″, and R′″ are plurally present, they may each be the same or different;
Q 1 , Q 3 , Y 1 , Z 1 , n1, n3, a1 and b1 are the same as the corresponding definitions above;
m6 and m7 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 (9) is:

wherein
R 9 represents a (1+m8+m9)-valent organic group that optionally has a substituent;
Y 3 represents a cyano group or a group represented by formula (5) or formula (6), wherein a3 in formula (5) or formula (6) represents an integer of 1 ore more, R′, R″, R′″, and Rc are represented as defined above, and when R′, R″, and R′″ are plurally present, they may each be the same or different;
Q 2 , Q 3 , Y 2 , M 2 , Z 2 , n2, n3, a2 and b2 are the same as the corresponding definitions above;
m8 and m9 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, b2 are each plurally present, they each may be the same or di

Assignees

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

Inventors

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

Classifications

• H10K85/115

  Polyfluorene; Derivatives thereof · CPC title

• C07C69/94 Primary

  of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings · CPC title

• H01L51/5088

  Electricity · mapped topic

• C08G2261/124

  alternating · CPC title

• C08G2261/3142

  fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene · CPC title