# US 2014/0193937 A1 · Method and compound

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- Number: US 2014/0193937 A1
- Document ID: US20140193937A1
- Status: Published application
- Kind: A1
- Application number: 14/151,639
- Filed: 2014-01-09
- Published: 2014-07-10
- Earliest claimed: 2013-01-09
- Assignees: Sumitomo Chemical Company, Limited; Cambridge Display Technology Limited
- Applicants: Sumitomo Chemical Company Limited; Cambridge Display Technology, Ltd.
- Inventors: Martin Humphries; Florence Bourcet
- Web page: https://patentgrep.com/patent/US20140193937A1

## CPC

- H10K 85/624: {containing six or more rings}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 50/15: Hole transporting layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A method of forming a layer of an electronic device, for example an organic light-emitting device, the method comprising the step of depositing a precursor layer comprising a compound of formula (I) and reacting the compound of formula (I) in a ring-opening addition reaction: Core-(Reactive Group)n (I) wherein Core is a non-polymeric core group; and each Reactive Group, which may be the same or different in each occurrence, is a group of formula (II): wherein Sp1 independently in each occurrence represents a spacer group; w independently in each occurrence is 0 or 1; Ar in each occurrence independently represents an aryl or heteroaryl group; R1 in each occurrence independently represents H or a substituent, with the proviso that at least one R1 is a substituent; n is at least 1; and * is a point of attachment of the group of formula (II) to the Core; and wherein the compound of formula (I) reacts with itself or with a non-polymeric co-reactant.

## Claims

### Claim 1

A method of forming a layer of an electronic device, the method comprising the step of depositing a precursor layer comprising a compound of formula (I) and reacting the compound of formula (I) in a ring-opening addition reaction:
Core-(Reactive Group)n (I)
wherein Core is a non-polymeric core group; and each Reactive Group, which may be the same or different in each occurrence, is a group of formula (II):
wherein:
Sp1 independently in each occurrence represents a spacer group;
w independently in each occurrence is 0 or 1;
Ar in each occurrence independently represents an aryl or heteroaryl group that is unsubstituted or substituted with one or more substituents;
R1 in each occurrence independently represents H or a substituent, with the proviso that at least one R1 is a substituent;
n is at least 1; and
* is a point of attachment of the group of formula (II) to the Core;
and wherein the compound of formula (I) reacts with itself or with a non-polymeric co-reactant.

### Claim 2 (depends on 1)

A method according to claim 1 wherein w of at least one group of formula (II) is 1, and Sp1 is selected from the group consisting of a C1-20 n-alkyl chain wherein one or more non-adjacent C atoms of the n-alkyl chain may be replaced with optionally substituted aryl or heteroaryl, O, S, substituted N, substituted Si—C═O and —COO—, and one or more H atoms of the n-alkyl chain may be replaced with C1-5 alkyl, F or an aryl or heteroaryl group.

### Claim 3 (depends on 1)

A method according to claim 1 wherein at least one R1 is selected from the group consisting of linear or branched C1-20 alkyl; C1-20 alkoxy; aryl or heteroaryl that may be unsubstituted or substituted with one or more substituents; and silyl.

### Claim 4 (depends on 1)

A method according to claim 1 wherein at least one group of formula (II) carries only one R1 substituent group.

### Claim 5 (depends on 1)

A method according to according to claim 1 wherein Ar is phenyl that may be unsubstituted or substituted with one or more substituents.

### Claim 6 (depends on 1)

A method according to according to claim 1 wherein the core is a group of formula (III):
wherein:
Ar1 in each occurrence independently represents an aryl or heteroaryl group that is unsubstituted or substituted with one or more substituents;
Ar3 in each occurrence independently represents an aryl or heteroaryl group that is unsubstituted or substituted with one or more substituents;
R8 in each occurrence independently represent represents a substituent, and R8 and Ar3 directly attached to the same N atom may be linked to form a ring;
x is a positive integer, optionally 1, 2 or 3;
y in each occurrence is independently 0 or a positive integer, optionally 1 or 2;
m in each occurrence is a positive integer, optionally 1 or 2;
and wherein the or each group of formula (II) is independently in each occurrence bound to one of: Ar1; Ar3 in the case where y is a positive integer; and N in the case where y is 0.

### Claim 7 (depends on 6)

A method according to claim 6 wherein R8 is a group of formula (II).

### Claim 8 (depends on 6, 7)

A method according to claim 6 or 7 wherein Ar1 is selected from the group consisting of phenyl that may be unsubstituted or substituted with one or more substituents, and a fused aryl or heteroaryl group that may be unsubstituted or substituted with one or more substituents.

### Claim 9 (depends on 1)

A method according to claim 1 wherein Ar1 is selected from groups of formulae (IV)-(IX), each of which may be unsubstituted or substituted with one or more substituents:

### Claim 10 (depends on 1)

A method according to claim 1 wherein the compound of formula (I) is an ionic compound and Core is a cation or anion.

### Claim 11 (depends on 10)

A method according to claim 10 wherein the compound of formula (I) is an optionally substituted compound of formula (Id):
wherein X− is an anion.

### Claim 12 (depends on 1)

A method according to claim 1 wherein the compound of formula (I) is reacted with itself to form the layer.

### Claim 13 (depends on 1)

A method according to claim 1 wherein the compound of formula (I) is reacted with a dienophile co-reactant of formula (X):
wherein:
Core, Sp1 and w are as defined in any preceding claim;
R7 is H or a substituent;
R6 is H or a substituent; and
q is at least 1.

### Claim 14 (depends on 1)

A method according to claim 1 wherein the electronic device is an organic light-emitting device comprising a light-emitting layer between an anode and a cathode, and wherein.
the reacted layer is a hole-transporting layer between the anode and the light-emitting layer.

### Claim 15

A compound of formula (I):
Core-(Reactive Group)n (I)
wherein Core is a non-polymeric core group; and each Reactive Group, which may be the same or different in each occurrence, is a group of formula (II):
wherein:
Sp1 independently in each occurrence represents a spacer group;
w independently in each occurrence is 0 or 1;
Ar in each occurrence independently represents an aryl or heteroaryl group that is unsubstituted or substituted with one or more substituents;
R1 in each occurrence independently represents H or a substituent, with the proviso that at least on R1 is a substituent;
n is at least 1; and
* is a point of attachment of the group of formula (II) to the Core.