# US 2014/0151660 A1 · Polymer and organic electronic device

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- Number: US 2014/0151660 A1
- Document ID: US20140151660A1
- Status: Published application
- Kind: A1
- Application number: 14/091,163
- Filed: 2013-11-26
- Published: 2014-06-05
- Earliest claimed: 2012-11-30
- Assignees: Sumitomo Chemical Company, Limited; Cambridge Display Technology Limited
- Applicants: Sumitomo Chemical Company Limited; Cambridge Display Technology
- Inventors: Kiran Kamtekar; Annette Steudel
- Web page: https://patentgrep.com/patent/US20140151660A1

## CPC

- C07F 5/025: {Boronic and borinic acid compounds}
- C08G 61/02: Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08K 5/3472: Five-membered rings
- C08K 5/56: Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers
- C09D 165/00: Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers
- H10K 85/151: {Copolymers}
- C08G 2261/122: statistical
- C08G 2261/1412: Saturated aliphatic units
- C08G 2261/19: partially conjugated
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3162: Arylamines
- C08G 2261/3424: non-conjugated, e.g. paracyclophanes or xylenes
- C08G 2261/411: Suzuki reactions
- C08G 2261/5242: electrophosphorescent
- C08G 2261/76: crosslinking
- C08G 2261/95: Use in organic luminescent diodes
- H10K 50/12: comprising dopants
- H10K 50/125: specially adapted for multicolour light emission, e.g. for emitting white light
- H10K 71/00: Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K 71/12: using liquid deposition, e.g. spin coating
- Y02E 10/549: Organic PV cells
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A polymer comprising repeat units of formula (I) and one or more co-repeat units: Ar1 in each occurrence independently represent an aryl or heteroaryl group; R1 and R2 in each occurrence independently represent a substituent; p independently in each occurrence is 0 or a positive integer; Sp represents a spacer group comprising at least one carbon or silicon atom spacing the two groups Ar1 apart; and each group Ar1 is bound to an aromatic group of a co-repeat unit. The polymer may form a charge-transporting layer of an OLED or may be a host material used with a luminescent dopant in a light-emitting layer of an OLED.

## Claims

### Claim 1

A polymer comprising repeat units of formula (I) and one or more co-repeat units:
Ar1 in each occurrence independently represent an aryl or heteroaryl group;
R1 and R2 in each occurrence independently represent a substituent;
p independently in each occurrence is 0 or a positive integer;
Sp represents a spacer group comprising at least one carbon or silicon atom spacing the two groups Ar1 apart; and
each group Ar1 is bound to an aromatic group of a co-repeat unit.

### Claim 2 (depends on 1)

A polymer according to claim 1 wherein Ar1 is an aryl group and the Ar1 groups may be the same or different.

### Claim 3 (depends on 2)

A polymer according to claim 2 wherein each Ar1 is phenyl.

### Claim 4 (depends on 3)

A polymer according to claim 3 wherein the repeat unit of formula (I) has formula (Ia):

### Claim 5 (depends on 4)

A polymer according to claim 4 wherein the repeat unit of formula (I) has formula (Ib):

### Claim 6 (depends on 1)

A polymer according to claim 1 wherein Sp represents a C1-20 alkyl chain wherein one or more non-adjacent C atoms of the chain may be replaced with O, S, —NR11—, —SiR112—, —C(═O)— or —COO— and wherein R11 in each occurrence is independently H or a substituent.

### Claim 7 (depends on 1)

A polymer according to claim 1 wherein R1 in each occurrence is independently a C1-20 alkyl.

### Claim 8 (depends on 1)

A polymer according to claim 1 wherein the one or more co-repeat units include a charge-transporting repeat unit.

### Claim 9 (depends on 8)

A polymer according to claim 8 wherein the charge-transporting repeat unit has formula (VII):
wherein Ar8 and Ar9 in each occurrence are independently selected from substituted or unsubstituted aryl or heteroaryl, g is greater than or equal to 1, R13 is H or a substituent, c and d are each independently 1, 2 or 3; and any two of Ar8, Ar9 and R13 directly linked to the same N atom may be linked by a direct bond or a divalent linking group.

### Claim 10 (depends on 9)

A polymer according to claim 9 wherein the charge-transporting repeat unit has formula (VIII):
wherein Ar8, Ar9 and Ar10 are in each occurrence independently selected from substituted or unsubstituted aryl or heteroaryl; z in each occurrence is independently at least 1, optionally 1, 2 or 3, preferably 1, and Y is N or CR14, wherein R14 is H or a substituent, preferably H or C1-10 alkyl.

### Claim 11 (depends on 1)

A monomer of formula (Im):
wherein LG is a leaving group capable of leaving in a coupling reaction to form a carbon-carbon bond between Ar1 and an aromatic or heteroaromatic group, and Ar1, R1, R2, p and Sp are as defined in claim 1.

### Claim 12 (depends on 11)

A monomer according to claim 11 wherein each LG is independently selected from the group consisting of halogens; boronic acids; boronic esters; sulfonic acids; and sulfonic esters.

### Claim 13 (depends on 11, 12)

A method of forming a polymer comprising the step of polymerising a monomer according to claim 11 or 12 and one or more co-monomers for forming the one or more respective co-repeat units.

### Claim 14 (depends on 1)

A composition comprising a polymer according to claim 1 and at least one light-emitting dopant.

### Claim 15 (depends on 14)

A composition according to claim 14 wherein the dopant is a phosphorescent dopant.

### Claim 16 (depends on 14, 15)

A formulation comprising a polymer or a composition according to claim 14 or 15 and at least one solvent.

### Claim 17 (depends on 15)

An organic light-emitting device comprising an anode, a cathode and one or more organic layers between the anode and cathode including a light-emitting layer wherein at least one of the one or more organic layers comprises a polymer according to claim 15.

### Claim 18 (depends on 17)

An organic light-emitting device wherein the organic light-emitting layer comprises a composition according to claim 17.

### Claim 19 (depends on 18)

An organic light-emitting device wherein the organic layers comprise a hole-transporting layer between the anode and the light-emitting layer, the hole-transporting layer comprising a polymer according to claim 18.

### Claim 20 (depends on 18)

A method of forming an organic light-emitting device according to claim 18 comprising the step of forming the light-emitting layer over one of the anode and the cathode and forming the other of the anode and the cathode over the light-emitting layer.