# US 11,910,697 B2 · Copolymer, electroluminescence device material including copolymer, and electroluminescence device

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- Number: US 11,910,697 B2
- Document ID: US11910697B2
- Status: Granted
- Kind: B2
- Application number: 17/470,884
- Filed: 2021-09-09
- Published: 2022-03-10
- Granted: 2024-02-20
- Earliest claimed: 2020-09-09
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Fumiaki Kato; Masashi Tsuji; Takao Motoyama; Yusaku Konishi; Keigo Furuta; Takahiro Fujiyama; Tae Ho Kim; Won Sik Yoon; Ha Il Kwon; Dae Young Chung; Eun Joo Jang
- Web page: https://patentgrep.com/patent/US11910697B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C08G 61/10: only aromatic carbon atoms, e.g. polyphenylenes
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- 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
- C08L 65/02: Polyphenylenes
- 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 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/151: {Copolymers}
- C08G 2261/11: Homopolymers
- C08G 2261/12: Copolymers
- C08G 2261/124: alternating
- C08G 2261/1412: Saturated aliphatic units
- C08G 2261/143: Side-chains containing nitrogen
- C08G 2261/1434: containing triarylamine moieties
- C08G 2261/148: Side-chains having aromatic units
- C08G 2261/149: Side-chains having heteroaromatic units
- C08G 2261/312: Non-condensed aromatic systems, e.g. benzene
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3162: Arylamines
- C08G 2261/411: Suzuki reactions
- C08G 2261/52: Luminescence
- C08G 2261/95: Use in organic luminescent diodes
- H10K 50/115: comprising active inorganic nanostructures, e.g. luminescent quantum dots
- H10K 50/15: Hole transporting layers
- H10K 50/17: Carrier injection layers
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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

## Abstract

A copolymer having a structural unit represented by Chemical Formula 1 is provided. The copolymer may improve performance, e.g., luminous efficiency, of an electroluminescence device. In Chemical Formula 1, the definition of each substituent is as described in the detailed description.

## Claims

### Claim 1

A copolymer having a structural unit represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
Ar1 and Ar2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms,
L1 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 carbon atoms,
each R1 is independently a hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms, wherein two R1's are optionally linked to provide a ring structure,
a is an integer of 0, 1, 2, or 3, and
Y is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 3 to 60 ring-member atoms.

### Claim 2 (depends on 1)

The copolymer of claim 1, wherein at least one of Ar1 or Ar2 is a group represented by Chemical Formula 1-2:
wherein, in Chemical Formula 1-2,
L2 is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms,
each R2 and each R3 are independently a hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms, wherein optionally, two adjacent R2, or two adjacent R3, join to form a ring structure,
X is ═CR4R5—, —O—, or —S—, wherein R4 and R5 are independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or R4 and R5 join to form a ring structure,
b is an integer of 0, 1, 2, or 3, and
c is an integer of 0, 1, 2, 3, or 4.

### Claim 3 (depends on 2)

The copolymer of claim 2, wherein the group represented by Chemical Formula 1-2 is a group of Chemical Formulas 3 to 18:
wherein, in Chemical Formulas 3 to 18,
L2 is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms,
each R2 and each R3 are independently a hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms,
R4 and R5 are independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
b is an integer of 0, 1, 2, or 3, and
c is an integer of 0, 1, 2, 3, or 4.

### Claim 4 (depends on 1)

The copolymer of claim 1, wherein Ar2 is of Chemical Formulas 3 to 6 or Chemical Formulas 11 to 14, and Ar2 is of Chemical Formulas 7 to 14, or an aromatic hydrocarbon group having 6 to 25 carbon atoms that is optionally substituted with a linear alkyl group having 1 to 8 carbon atoms or a branched alkyl group having 3 to 8 carbon atoms:
wherein, in Chemical Formulas 3 to 14,
L2 is a single bond or a phenylene group,
each R2 and each R3 are independently a hydrogen, or an alkyl group having 1 to 10 carbon atoms,
b is an integer of 0, 1, 2, or 3, and
c is an integer of 0, 1, 2, 3, or 4.

### Claim 5 (depends on 1)

The copolymer of claim 1, wherein Y is one of Chemical Formulas 19 to 34:
wherein, in Chemical Formulas 19 to 34,
each R4 is independently a hydrogen, substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 60 ring-member atoms, or an alkyl group having 1 to 60 carbon atoms,
Q is each independently O, S, Se, CR17R18, or SiR17R18, wherein R17 and R18 are independently a hydrogen, a deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Z is each independently CR19, N, or SiR19, wherein R19 is a hydrogen, a deuterium, substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and
* indicates a linking position.

### Claim 6 (depends on 1)

A polymer composition comprising the copolymer of claim 1 and a polymeric material having a HOMO level of greater than about −5.6 eV and less than or equal to about −5.3 eV.

### Claim 7 (depends on 6)

The polymer composition of claim 6, wherein the polymeric material is represented by Chemical Formula 35:
wherein, in Chemical Formula 35,
R6 to R9 are independently a hydrogen, or a hydrocarbon group having 1 to 16 carbon atoms, L3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 ring-member atoms,
d is 0, 1, or 2, and if d is 0, L3 is a single bond, and if d is 2, each L3 is the same or different,
L4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 ring-member atoms, wherein L4 optionally forms a ring with Ar3,
Ar3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 ring-member atoms, wherein Ar3 optionally forms a ring with Ar4 or L4, and
Ar4 is an aromatic hydrocarbon group having 6 to 25 carbon atoms which is substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, a branched hydrocarbon group having 3 to 12 carbon atoms, or an aromatic heterocyclic group having 3 to 24 ring-member atoms which is substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, or a branched hydrocarbon group having 3 to 12 carbon atoms, wherein Ar4 optionally forms a ring with Ar3.

### Claim 8 (depends on 1)

An electroluminescence device material, comprising the copolymer of claim 1.

### Claim 9 (depends on 6)

An electroluminescence device material, comprising the polymer composition of claim 6.

### Claim 10 (depends on 1)

An electroluminescence device, comprising
a first electrode and a second electrode, and
one or more organic layers disposed between the first electrode and the second electrode,
wherein at least one layer of the one or more organic layers includes the copolymer of claim 1.

### Claim 11 (depends on 10)

The electroluminescence device of claim 10, wherein the at least one organic layer including the copolymer is a hole transport layer or a hole injection layer.

### Claim 12 (depends on 10)

The electroluminescence device of claim 10, wherein the one or more organic layers is a light emitting layer comprising a semiconductor nanoparticle or an organometal complex.

### Claim 13 (depends on 6)

An electroluminescence device comprising
a first electrode and a second electrode, and
one or more organic layers disposed between the first electrode and the second electrode,
wherein at least one layer of the one or more organic layers includes the polymer composition of claim 6.

### Claim 14 (depends on 13)

The electroluminescence device of claim 13, wherein the at least one organic layer including the polymer composition is a hole transport layer or a hole injection layer.

### Claim 15 (depends on 13)

The electroluminescence device of claim 13, wherein the one or more organic layers is a light emitting layer comprising a semiconductor nanoparticle or an organometal complex.

### Claim 16 (depends on 1)

The copolymer of claim 1, further comprising a structural unit represented by Chemical Formula 1-1
wherein in Chemical Formula 1-1, L1, Ar1, Ar2, R1, and a are as defined, and are independently the same or different than L1, Ar1, Ar2, R1, and a, of Chemical Formula 1.

### Claim 17 (depends on 16)

The copolymer of claim 16, wherein at least one of Ar1 or Ar2 of Chemical Formula 1-1 is a group represented by Chemical Formula 1-2:
wherein, in Chemical Formula 1-2,
L2 is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms,
each R2 and each R3 are independently a hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 ring-member atoms,
X is ═CR4R5—, —O—, or —S—, wherein R4 and R5 are independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or R4 and R5 join to form a ring structure
b is an integer of 0, 1, 2, or 3, and
c is an integer of 0, 1, 2, 3, or 4.