Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-2020216605-A1
Application number	US-201816625276-A
Country	US
Kind code	A1
Filing date	Jun 18, 2018
Priority date	Jun 21, 2017
Publication date	Jul 9, 2020
Grant date	—

Abstract

The present application relates to a polymer containing at least one structural unit of a formula (I). The polymer is suitable for use in an electronic device.

First claim

1 - 18 . (canceled)

19 . A polymer comprising at least one structural unit of formula (I):

wherein
U is the same or different in each instance and is C(R 1 ) 2 , CR 1 ═CR 1 , Si(R 1 ) 2 , O, or S, wherein the groups CR 1 ═CR 1 , O, and S are not bonded directly to one another;
Z is the same or different in each instance and is N or CR 2 when no group is bonded thereto, and is C when a group is bonded thereto;
Ar 1 , Ar 2 , Ar 3 , Ar 4 , and Ar 5
are the same or different and are selected from the group consisting of heteroaromatic ring systems, which have 5 to 40 aromatic ring atoms and which are optionally substituted by one or more R 3 radicals, and aromatic ring systems which have 6 to 40 aromatic ring atoms and are optionally substituted by one or more R 3 radicals;

R 1 is the same or different in each instance and is selected from the group consisting of H, D, F, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R 1 or R 2 or R 3 radicals are optionally joined to one another and optionally define a ring; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each optionally substituted by one or more R 4 radicals; and wherein one or more CH 2 groups in the alkyl, alkoxy, alkenyl, and alkynyl groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 ;
R 2 and R 3
are the same or different in each instance and are selected from the group consisting of H, D, F, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , straight-chain alkyl, or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl, or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R 1 or R 2 or R 3 radicals are optionally joined to one another and optionally define a ring; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each optionally substituted by one or more R 4 radicals; and wherein one or more CH 2 groups in the alkyl, alkoxy, alkenyl, and alkynyl groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 ;

R 4 is the same or different in each instance and is selected from the group consisting of H, D, F, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , OR 5 , S(═O)R 5 , S(═O) 2 R 5 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R 4 radicals are optionally joined to one another and optionally define a ring; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each optionally substituted by one or more R 5 radicals; and wherein one or more CH 2 groups in the alkyl, alkoxy, alkenyl, and alkynyl groups are optionally replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO, or SO 2 ;
R 5 is the same or different in each instance and is selected from the group consisting of H, D, F, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R 5 radicals may be joined to one another and may form a ring; and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by F or CN;
r is 1, 2, or 3 when p is 1, and is 1 when p is 0;
s is 0, 1, 2, or 3 when q is 1, and is 1 when q is 0;
p is 0 or 1; wherein, when p is 0, the groups bonded to the unit between square brackets with index p are bonded directly to one another;
q is 0 or 1; wherein, when q is 0, the groups bonded to the unit between square brackets with index q are bonded directly to one another;
n is 0 or 1, wherein, when n is 0, the groups bonded to the unit between square brackets with index n are bonded directly to one another;
m is 0 or 1, wherein, when m is 0, the groups bonded to the unit between square brackets with index m are bonded directly to one another;
o is 0 or 1, wherein, when o is 0, the groups bonded to the unit between square brackets with index o are bonded directly to one another;
i is the same or different in each instance and is 1, 2, 3, 4, 5, 6, 7, or 8;
wherein at least one U group containing one or more R 1 groups selected from the group consisting of straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms is present; wherein two or more R 1 or R 2 or R 3 radicals are optionally joined to one another and optionally define a ring; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each optionally substituted by one or more R 4 radicals; and wherein one or more CH 2 groups in the alkyl, alkoxy, alkenyl, and alkynyl groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 .

20 . The polymer of claim 19 , wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , and Ar 5 are the same or different in each instance and are selected from the group consisting of benzene, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, indenofluorene, spirobifluorene, dibenzofuran, dibenzothiophene, carbazole, indenocarbazole, and indolocarbazole, each of which is optionally substituted by one or more R 1 radicals.

21 . The polymer of claim 19 , wherein R 1 is the same or different in each instance and is selected from from the group consisting of H, D, F, straight-chain alkyl groups having 1 to 10 carbon atoms, and branched alkyl groups having 3 to 10 carbon atoms.

22 . The polymer of claim 19 , wherein the two U groups directly adjacent to the bridgehead carbon atom are each substituted with an R 1 radical selected from the group consisting of F, CN, Si(R 4 ) 3 , OR 4 , straight-chain alkyl and alkoxy groups having 1 to 10 carbon atoms, branched alkyl and alkoxy groups having 3 to 10 carbon atoms, and aromatic ring systems having 6 to 20 aromatic ring atoms, wherein two or more R 1 or R 2 or R 3 radicals are optionally joined to one another and optionally define a ring; and wherein the alkyl and alkoxy groups and the aromatic ring systems are each optionally substituted by one or more R 4 radicals.

Assignees

• Merck Patent Gmbh

Inventors

• Burkhart Beate
• Scheible Katja
• Koenen Nils
• Heil Holger

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07C2603/78

  containing seven-membered rings · CPC title

• C07D407/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07C2603/10

  containing five-membered rings · CPC title