Phenanthro[9,10-B]furan polymers and small molecules for electronic applications

Patent metadata

Field	Value
Publication number	US-9505877-B2
Application number	US-201314385696-A
Country	US
Kind code	B2
Filing date	Mar 27, 2013
Priority date	Apr 2, 2012
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

Phenanthro[9,10-b]furan polymers and small molecules for electronic applications. The present invention relates to polymers comprising a repeating unit of the formula (I), (II), (VIII), (IX) and compounds of formula (VIII), or (IX), wherein Y, Y 15 , Y 16 and Y 17 are independently of each other a group of formula (I), or (II), and their use as organic semiconductor in organic electronic devices, especially in organic photovoltaics and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers and compounds according to the invention can have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers and compounds according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.

First claim

The invention claimed is:

1. A polymer, comprising a repeating unit of formula (I) or formula (II):

where
R 1 and R 2 are each independently H, F, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E′ and/or interrupted by D′, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G′, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G′, or
R 1 and R 2 form together a group

R 205 , R 206 , R 206′ , R 207 , R 208 , R 208′ , R 209 , and R 210 are each independently H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E′ and/or interrupted by D′, alkoxy, or C 1 -C 18 alkoxy which is substituted by E′ and/or interrupted by D′, C 1 -C 18 fluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G′, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G′, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, C 7 -C 25 aralkyl which is substituted by G′; CN, or —CO—R 28 ,
D′ is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—,
E′ is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, CF 3 , or halogen,
G′ is E′, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by —O—,
R 28 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 63 and R 64 are each independently C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;
R 65 and R 66 are each independently C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—; or
R 65 and R 66 together form a five or six membered ring,
R 67 is C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 68 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 69 is C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 70 and R 71 are each independently C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and
R 72 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl.

2. The polymer according to claim 1 , wherein
R 1 and R 2 are each independently a group of formula

wherein R 400 , R 401 , R 402 , R 403 , R 404 and R 405 are each independently H, CN, F, CF 3 , C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—, or
R 1 and R 2 form together a group

3. The polymer according to claim 1 , wherein the polymer is a polymer of formula

or a polymer comprising repeating units of formulae

wherein
n is of 4 to 1000,
A is a repeating unit of the formula (I), or the formula (II), and
—COM 1 - is a repeating unit

wherein
k is 0, 1, 2, or 3; 1 is 1, 2, or 3; r is 0, 1, 2, or 3; z is 0, 1, 2, or 3;
Ar 4 , Ar 5 , Ar 6 and Ar 7 are each independently selected from the group consisting of the following formulae:

wherein X 1 is —O—, —S—, —NR 8 —, —Si(R 11 )(R 11′ )—, —Ge(R 11 )(R 11′ )—, —C(R 7 )(R 7′ )—, —C(═O)—, —C(═CR 104 R 104′ )—,

wherein X 1′ is S, O, NR 107 —, —Si(R 117 )(R 117′ )—, —Ge(R 117 )(R 117′ )—, —C(R 108 )(R 109 )—, —C(═O)—, —C(═CR 104 R 104′ )—,

R 3 and R 3′ are each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 104 and R 104′ are each independently hydrogen, cyano, COOR 103 , C 1 -C 25 alkyl, or C 6 -C 24 aryl or C 2 -C 20 heteroaryl,
R 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ are each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 7 , R 7′ , R 9 and R 9′ are each independently hydrogen, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 8 and R 8′ are each independently hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; or C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 11 and R 11′ are each independently C 1 -C 25 alkyl, C 7 -C 25 arylalkyl, or a phenyl group, which is optionally substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 12 and R 12′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or

wherein R 13 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group; or
R 104 and R 104′ are each independently hydrogen, C 1 -C 18 alkyl, C 6 -C 10 aryl, which is optionally substituted by G, or C 2 -C 8 heteroaryl, which is optionally substituted by G,
R 105 , R 105′ , R 106 and R 106′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 18 alkoxy,
R 107 is hydrogen, C 7 -C 25 arylalkyl, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 perflu

Assignees

• Basf Se

Inventors

• Welker Matthias
• Schaefer Thomas
• Chebotareva Natalia
• Duebner Matthias
• Turbiez Mathieu G R

Classifications

• C08G2261/411

  Suzuki reactions · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C09K2211/145

  containing oxygen as the only heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H01B1/128

  comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes · CPC title