# US 10,370,484 B2 · Polymer compound and light emitting device using the same

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- Number: US 10,370,484 B2
- Document ID: US10370484B2
- Status: Granted
- Kind: B2
- Application number: 15/322,851
- Filed: 2015-06-26
- Published: 2017-05-18
- Granted: 2019-08-06
- Earliest claimed: 2014-07-03
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Sumitomo Chemical Company, Limited
- Inventors: Motoaki Usui; Daisuke Fukushima; Shin-ya Tanaka
- Web page: https://patentgrep.com/patent/US10370484B2

## CPC

- C07D 487/04: Ortho-condensed systems
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G 61/124: {with a five-membered ring containing one nitrogen atom in the ring}
- C09K 11/06: containing organic luminescent materials
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/151: {Copolymers}
- C08G 2261/12: Copolymers
- C08G 2261/148: Side-chains having aromatic units
- C08G 2261/3241: containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
- C08G 2261/95: Use in organic luminescent diodes
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

Provided is a polymer compound which is useful for production of a light emitting device excellent in light emission efficiency is provided. The polymer compound contains a constitutional unit represented by the formula (1) and a constitutional unit represented by the formula (Y) as follows: wherein R1 to R8 represent a hydrogen atom, an alkyl group, an aryl group or the like, and RA and RB represent an aryl group or a monovalent heterocyclic group, and ArY1 (Y) wherein ArY1 represents an arylene group or the like.

## Claims

### Claim 1

A polymer compound comprising a constitutional unit represented by the following formula (1-1) and a constitutional unit represented by the following formula (Y):
wherein
R1, R2, R3, R4, R5, R6, R7 and R8 represent a hydrogen atom
R10 and R13 each independently represent a methyl group, a methoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, each having no substituent,
R9, R11, R12 and R14 represent a hydrogen atom, and
Ra, Rb, Rc and Rd each independently represent a methyl group, a methoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, each having no substituent:
ArY1 (Y)
wherein ArY1 represents an arylene group, a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly to each other, the foregoing groups each optionally having a substituent.

### Claim 2 (depends on 1)

The polymer compound according to claim 1, wherein Ra, Rb, Rc and Rd are each a methyl group having no substituent.

### Claim 3 (depends on 1)

The polymer compound according to claim 1, wherein the constitutional unit represented by the formula (Y) is a constitutional unit represented by the following formula (Y-2):
wherein
each RY1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and the plurality of RY1 may be the same or different, with the proviso that adjacent groups RY1 may be combined together to form a ring together with the carbon atoms to which they are attached, and
XY1 represents a group represented by —C(RY2)2—, a group represented by —C(RY2)═C(RY2)— or a group represented by —C(RY2)2—C(RY2)2—, wherein each RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and the plurality of RY2 may be the same or different, with the proviso that groups RY2 may be combined together to form a ring together with the carbon atoms to which they are attached.

### Claim 4 (depends on 1)

The polymer compound according to claim 1, wherein the constitutional unit represented by the formula (Y) is a constitutional unit represented by the following formula (Y-5), (Y-6) or (Y-7):
wherein
each RY1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and the plurality of RY1 may be the same or different, with the proviso that adjacent groups RY1 may be combined together to form a ring together with the carbon atoms to which they are attached, and
RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent.

### Claim 5 (depends on 1)

The polymer compound according to claim 1, further comprising a constitutional unit represented by the following formula (X):
wherein
aX1 and aX2 each independently represent an integer of 0 or more,
ArX1 and ArX3 each independently represent an arylene group or a divalent heterocyclic group, these groups each optionally having a substituent,
ArX2 and ArX4 each independently represent an arylene group, a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly to each other, and these groups each optionally having a substituent, and
RX1, RX2 and RX3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent.

### Claim 6 (depends on 1)

The polymer compound according to claim 1, wherein the content of the constitutional unit represented by the formula (1) is 0.1 to 50 mol % with respect to the total content of constitutional units contained in the polymer compound.

### Claim 7

A compound represented by the following formula (M-1-2):
wherein
R1 , R2, R3, R4, R5, R6, R7 and R8 represent a hydrogen atom,
R10 and R13 each independently represent a hydrogen atom, a methyl group, a methoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, each having no substituent,
R9, R11, R12, and R14 represent a hydrogen atom,
Ra′, Rb′, Rc′ and Rd′ each independently represent a methyl group, a methoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, each having no substituent, and
ZC1 and ZC2 each independently represent a group selected from the group consisting of the following Group A of substituents and Group B of substituents:
wherein the Group A substituents are selected from a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, and a group represented by —O—S(═O)2 RC1, wherein RC1 represents an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, and
wherein the Group B substituents are selected from:
a group represented by —B(ORC2)2, wherein each RC2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, with the proviso that the plurality of RC2 may be the same or different and may be combined together to form a cyclic structure together with the oxygen atoms to which they are attached;
a group represented by —BF3 Q′, wherein Q′ represents Li, Na, K, Rb or Cs;
a group represented by —MgY′, wherein Y′ represents a chlorine atom, a bromine atom or an iodine atom;
a group represented by —ZnY″, wherein Y″ represents a chlorine atom, a bromine atom or an iodine atom; and
a group represented by —Sn(RC3)3, wherein each RC3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, with the proviso that the plurality of RC3 may be the same or different and may be combined together to form a cyclic structure together with the tin atom to which they are attached.

### Claim 8 (depends on 1)

A composition comprising
the polymer compound according to claim 1 and
at least one material selected from the group consisting of a hole transporting material, a hole injection material, an electron transporting material, an electron injection material, a light emitting material, an antioxidant, and a solvent.

### Claim 9 (depends on 1)

A light emitting device produced by using the polymer compound according to claim 1.

### Claim 10

A method for producing a compound represented by the following formula (M-1′), the method comprising:
a step of making a compound represented by the following formula (Z) and a compound represented by the following formula (2) undergo amination in the presence of a transition metal complex having a phosphine ligand, a base and a solvent:
RC—NH2 (Z)
wherein RC represents an aryl group or a monovalent heterocyclic group, these groups each optionally having a substituent:
wherein
R1, R2, R3, R4, R5, R6, R7 and R8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent,
R15 and R16 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a group selected from the group consisting of the following Group A of substituents and Group B of sub stituents, the foregoing groups each optionally having a substituent,
with the proviso that R1 and R2, R2 and R15, R15 and R3, R3 and R4, R5 and R6, R6 and R16, R16 and R7, and R7 and R8 each may be combined together to form a ring together with the carbon atoms to which they are attached, and
each Ya represents a chlorine atom, a bromine atom, an iodine atom or —O—S(═O)2RC1, and RC1 represents an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, and the plurality of Ya may be the same or different:
wherein the Group A substituents are selected from a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, and a group represented by —O—S(═O)2RC1, wherein RC1 represents an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, and
wherein the Group B substituents are selected from:
a group represented by —B(ORC2)2, wherein each RC2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, with the proviso that the plurality of RC2 may be the same or different and may be combined together to form a cyclic structure together with the oxygen atoms to which they are attached;
a group represented by —BF3Q′, wherein Q′ represents Li, Na, K, Rb or Cs;
a group represented by —MgY′, wherein Y′ represents a chlorine atom, a bromine atom or an iodine atom;
a group represented by —ZnY″, wherein Y″ represents a chlorine atom, a bromine atom or an iodine atom; and
a group represented by —Sn(RC3)3, wherein each RC3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, the foregoing groups each optionally having a substituent, with the proviso that the plurality of RC3 may be the same or different and may be combined together to form a cyclic structure together with the tin atom to which they are attached:
wherein R1, R2, R3, R4, R5, R6, R7, R8, R15, R16 and each RC are as defined above, and the plurality of RC may be the same or different.

### Claim 11 (depends on 10)

The method for producing a compound according to claim 10, wherein the compound represented by the formula (M-1′) is a compound represented by the following formula (M-1′-1):
wherein
R1, R2, R3, R4, R5, R6, R7, R8, R15 and R16 are as defined above, and
R9, R10, R11, R12, R13, R14, Ra, Rb,Rc and Rd each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, the foregoing groups each optionally having a sub stituent, with the proviso that R9 and R10, R10 and R11, R12 and R13, and R13 and R14 each may be combined together to form a ring together with the carbon atoms to which they are attached.

### Claim 12 (depends on 11)

The method for producing a compound according to claim 11, wherein Ra, Rb, Rc and Rd are each an alkyl group optionally having a substituent.

### Claim 13

A compound represented by the following formula (M-1-2):
wherein
R1, R2, R3, R4, R5, R6, R7 and R8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, each optionally having a substituent, with the proviso that R1 and R2, R3 and R4, R5 and R6, and R7 and R8 each may be combined together to form a ring together with the carbon atoms to which they are attached,
R9, R10, R11, R12, R13 and R14 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, each optionally having a substituent, with the proviso that R9 and R10, R10 and R11, R12 and R13, and R13 and R14 each may be combined together to form a ring together with the carbon atoms to which they are attached,
Ra′, Rb′, Rc′ and Rd′ each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group, each optionally having a substituent, and
ZC1 and ZC2 represent a hydrogen atom.