Polymeric material comprising N, P, S, As, or Se and composition for charge transport material

• US 6,630,566 B1
• Filed: 10/02/2001
• Issued: 10/07/2003
• Est. Priority Date: 12/19/1997
• Status: Expired due to Term

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Avecia Limited
• Inventors: Thomas, Mark, Leeming, Stephen William, Morgan, John Dylan, Allen, Joanne Victoria, Fergus, Julie Anne
• Primary Examiner(s): Truong, Duc
• Application Number:
  US09/581,914
• Time in Patent Office: 735 Days
• Field of Search: 528/422, 528/373, 528/398, 525/328.5, 428/690, 428/914, 250/462.1
• US Class Current: 528/422
• CPC Class Codes: C08G 2261/312 Non-condensed aromatic systems, e.g. benzene
• CPC Class Codes: C08G 61/12 Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
• CPC Class Codes: C08G 73/00 Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00 polycarbodiimides prepared from isocyanates C08G18/025, C08G18/797
• CPC Class Codes: C08G 73/026 Wholly aromatic polyamines
• CPC Class Codes: G03G 5/0764 triarylamine
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

A polymeric material comprises at least one repeat unit consisting substantially of a moiety of Formula 1:

in which Y¹ represents N, P, S, As and/or Se, Ar¹ and Ar², which may the same or different, represent independently a multivalent, optionally substituted aromatic group, and Ar³ represents independently a mono or multivalent, optionally substituted aromatic group. At least one terminal group is attached in the polymer to the Ar¹, Ar² and optionally Ar³ groups located at the end of the polymer chains, so as to cap the polymer chains and prevent further polymer growth. At least one terminal group is derived from at least one end capping reagent used in the polymerisation to form the polymeric material to control the molecular weight thereof. A charge transport material comprising such polymers is useful in electroreprographic and electroluminescent devices. These polymers may be made by controlling their molecular weight with an end capping reagent.

Claims

1. A polymeric material comprising at least one repeat unit, the or each (if more than one) repeat unit consisting substantially of a moiety of Formula I:

in which;

Y¹ represents, independently if in different repeat units, N, P, S, As and/or Se;

Ar¹ and Ar² which may be the same or different, represent, independently if in different repeat units, a multivalent aromatic group optionally substituted by at least one optionally substituted C_1-40carbyl-derived groups and/or at least one other optional substituent, and

Ar³ represents, independently if in different repeat units, a mono or multivalent aromatic group optionally substituted by at least one;

optionally substituted C_1-40carbyl-derived group and/or at least one other optional substituent;

except when Y¹ is divalent S or divalent Se, Ar³ and the arrow therefrom are not present;

the arrow from Ar³ indicates, in the case where Ar³ is monovalent, a bond to a terminal group inert to coupling in the polymerisation to form said polymeric material, or, in the case where Ar³ is multivalent, a bond to another said repeat unit;

where at least one terminal group is attached in the polymer to the Ar¹, Ar² and optionally Ar³ groups located at the end of the polymer chains, so as to cap the polymer chains and prevent further polymer growth, and at least one terminal group is derived from at least one end capping reagent used in the polymerisation to form said polymeric material to control the molecular weight thereof.

2. A polymeric material as claimed in claim 1, which comprises a substance represented by Formula 2:

where

Ar¹, Ar², Ar³ and Y¹ and the arrow from Ar³, are defined above;

n represents and integer from 3 to about 500;

R¹, R² and R³ represents, independently, a terminal group as described herein, R³ only being present when Ar³ is not attached to another repeat unit.

3. A polymeric material as claimed in claim 1, in which Ar¹, Ar², and Ar³ comprises independently if in different repeat units, at least one optionally substituted heterocyclic and/or benzenoid ring which comprises an aromatic moiety.

4. A polymeric material as set forth in claim 1, in which Ar¹, Ar², and Ar³ comprise, independently if in different repeat units, a bivalent aromatic C_6-40 hydrocarbyl.

5. A polymeric material as claimed in claim 1, which comprises a substance represented by Formula 3:

where

R¹, R², R³ and n represent, independently if in different repeat units, those groups or values described herein, R³ only being present when the ring to which it is attached is not itself attached to another repeat unit;

a and b represent, independently in each case, 0 or an integer from 1 to 4;

c represents, independently in each case, 0 or an integer from 1 to d (where d is 6 minus the valence of the aromatic group);

n represents an integer from 4 to about 200; and

R⁴, R⁵ and R⁶ represent, independently in each case, optionally substituted C_1-15 alkyl and/or at least one optional substituent.

6. A polymeric material as claimed in claim 1, in which the terminal group(s) comprise, independently if in different repeat units, at least one optionally substituted C_1-40 hydrocarbyl group each of which is substantially incapable of undergoing chain extension or cross-linking under the conditions of polymerization.

7. A polymeric material as claimed in claim 1, in which the terminal group(s) comprise, independently if in different repeat units, at least one group selected from C_1-30 alkyl, C_6-36 aryl and C_7-36 aralkyl, each of which is substantially incapable of undergoing chain extension or cross-linking under the conditions of polymerization.

8. A polymeric material as claimed in claim 1 which is obtained by process for preparing an end capped polymeric material, the process comprising the steps of:

a) performing polymerization of at least one polymer precursor of Formula 4;

in which;

Y² independently represents, N, P, S, As and/or Se;

Ar⁴, Ar⁵, and Ar⁶ which may be the same or different, each independently, represent at least one mononuclear or polynuclear aromatic group optionally substituted by a substituent which does not react with other groups on the polymer precursor(s) under the conditions of polymerisation;

X¹, X² which may be the same or different, each independently represent a leaving group which, under the conditions of polymerisation, permits coupling between the aromatic groups to which they are attached and an aromatic group not linked thereto, directly via a bond {this provides chain extension and optional cross-linking, optionally with another of the or each polymer precursor(s)}; and

X³ independently represents H, another group inert to coupling or a leaving group which, under the conditions of polymerization, permits coupling between the aromatic group to which it is attached and an aromatic group not linked thereto, directly via a bond {this provides chain extension and optional cross-linking, optionally with another of the or each polymer precursor(s)}; and

then;

b) adding an end capping reagent of Formula 5 in an amount sufficient to reduce substantially polymerization (optionally the end capping reagent is added in excess), and where in Formula 5;

9. A process for preparing the polymeric material as set forth in claim 8, comprising a) performing polymerization of at least one polymer precursor of Formula 4:

in which;

Y² independently represents N, P, S, As and/or Se;

Ar⁴, Ar⁵, and Ar⁶ which may be the same or different, each independently represent at least one mononuclear or polynuclear aromatic group optionally substituted by a substituent which does not react with other groups on the polymer precursor(s) under the condition of polymerisation;

X¹, and X² which may be the same or different, each independently represent a leaving group which, under the conditions of polymerisation, permits coupling between the aromatic groups to which they are attached and an aromatic group not linked thereto, directly via a bond {this provides chain extension and optional cross-linking, optionally with another of the or each polymer precursor(s)}; and

X³ independently represents H, another group intert to coupling or a leaving group which, under the conditions of polymerization, permits coupling between the aromatic group to which it is attached and an aromatic group not linked thereto, directly via a bond {this provides chain extension and optional cross-linking, optionally with another of the or each polymer precursor(s)}; and

then;

b) adding an end capping reagent of Formula 5 in an amount sufficient to reduce substantially polymerization (optionally the end capping reagent is added in excess), and where in Formula 5;

10. A charge transport material comprising a polymeric material as claimed in claim 1.

11. A method which comprises transporting charge and/or improving electroreprographic and/or electroluminescent performance with a polymeric material according to claim 1.

12. A polymeric material as claimed in claim 5, wherein c represents 0 to 5.

13. A polymeric material as claimed in claim 8, wherein Y² represents N.