# US 2014/0191160 A1 · Composition containing borane compound and conjugated polymer compound, and element

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- Number: US 2014/0191160 A1
- Document ID: US20140191160A1
- Status: Published application
- Kind: A1
- Application number: 14/240,905
- Filed: 2012-08-23
- Published: 2014-07-10
- Earliest claimed: 2011-08-31
- Assignees: National University Corporation Hokkaido University; Sumitomo Chemical Company, Limited
- Inventors: Yusuke Ishii; Noboru Kitamura; Eri Sakuda; Akitaka Ito; Kazuyoshi Kawanishi
- Web page: https://patentgrep.com/patent/US20140191160A1

## CPC

- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C08K 5/0091: {Complexes with metal-heteroatom-bonds}
- C08K 5/55: Boron-containing compounds {(C08K5/0091 takes precedence)}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/791: {Starburst compounds}
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3162: Arylamines
- C08G 2261/411: Suzuki reactions
- C08G 2261/5242: electrophosphorescent
- C08G 2261/95: Use in organic luminescent diodes
- 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
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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)

## Abstract

Provided is an organic material which can be employed for manufacturing an organic electroluminescent device having a long luminance half-lifetime. The organic material is a composition containing: a borane compound represented by Formula (B1): wherein three ArB1 represent an arylene group or a divalent aromatic heterocyclic group; and three XB1 represent an aromatic amino group, a monovalent aromatic heterocyclic group, an alkyl group, or a hydrogen atom; and a conjugated polymer compound represented by Formula (P1): wherein Arp1 represents an arylene group, with the proviso that Arp1 is different from Flup1; Flup1 represents a fluorenediyl group; Hetp1 represents a divalent aromatic heterocyclic group; Amp1 represents a divalent aromatic amine residue; nAr, nFlu, nHet and nAm are numbers representing molar ratios of Arp1, Flup1, Hetp1 and Amp1, respectively, and numbers satisfying 0.4≦nFlu≦1, 0≦nAr≦0.6, 0≦nHet≦0.6 and 0≦nAm≦0.6 when defining nAr+nFlu+nHet+nAm=1.

## Claims

### Claim 1

A composition comprising:
a borane compound represented by Formula (B1):
wherein three ArB1 each independently represent an arylene group optionally having a substituent or a divalent aromatic heterocyclic group optionally having a substituent; and three XB1 each independently represent an aromatic amino group optionally having a substituent, a monovalent aromatic heterocyclic group optionally having a substituent, an alkyl group optionally having a substituent, or a hydrogen atom; and
a conjugated polymer compound represented by Formula (P1):
wherein a structural unit Arp1 represents an arylene group optionally having a substituent, with the proviso that the structural unit Arp1 is different from a structural unit Flup1; a structural unit Flup1 represents a fluorenediyl group optionally having a substituent; a structural unit Hetp1 represents a divalent aromatic heterocyclic group optionally having a substituent; a structural unit Amp1 represents a divalent aromatic amine residue optionally having a substituent; nAr, nFlu, nHet and nAm are numbers representing molar ratios in the conjugated polymer compound for the structural unit Arp1, the structural unit Flup1, the structural unit Hetp1 and the structural unit Amp1, respectively, and nAr, nFlu, nHet and nAm are numbers satisfying 0.4≦nFlu≦1, 0 23 nAr≦0.6, 0≦nHet≦0.6 and 0≦nAm≦0.6 when defining nAr+nFlu+nHet+nAm=1; polymerization type of the structural unit Arp1, the structural unit Flup1, the structural unit Hetp1 and the structural unit Amp1 in the conjugated polymer compound may be any of alternating polymerization, random polymerization, block polymerization and graft polymerization; when the structural unit Arp1 is plurally present, they may be the same as or different from each other; when the structural unit Flup1 is plurally present, they may be the same as or different from each other; when the structural unit Hetp1 is plurally present, they may be the same as or different from each other; and when the structural unit Amp1 is plurally present, they may be the same as or different from each other.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein at least one of the three ArB1 is an arylene group optionally having a substituent.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein the three ArB1 are each independently a group represented by Formula (Ar-001):
wherein two R0 and two R1 each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; and a symbol “*” represents a binding position to a boron atom and a symbol “**” represents a binding position to XB1.

### Claim 4 (depends on 3)

The composition according to claim 3, wherein the two R1 are an alkyl group.

### Claim 5 (depends on 1)

The composition according to claim 1, wherein the three ArB1 are each independently a group represented by Formula (Ar-007):
wherein a plurality of R0 each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; and a symbol “*” represents a binding position to a boron atom and a symbol “**” represents a binding position to XB1.

### Claim 6 (depends on 1)

The composition according to claim 1, wherein at least one of the three XB1 is an aromatic amino group optionally having a substituent.

### Claim 7 (depends on 1)

The composition according to claim 1, wherein the three XB1 are each independently a group represented by Formula (X-001):
wherein a plurality of R0 each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; and a symbol “**” represents a binding position to ArB1.

### Claim 8 (depends on 1)

The composition according to claim 1, wherein at least one of the three XB1 is a monovalent aromatic heterocyclic group optionally having a substituent.

### Claim 9 (depends on 1)

The composition according to claim 1, wherein the three XB1 are each independently a group represented by Formula (X-101):
wherein a plurality of R0 each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; and a symbol “**” represents a binding position to ArB1.

### Claim 10 (depends on 3)

The composition according to claim 3, wherein the plurality of R0 are each independently a hydrogen atom or an alkyl group.

### Claim 11 (depends on 1)

The composition according to claim 1, wherein the nHet and the nAm are 0.

### Claim 12 (depends on 1)

The composition according to claim 1, wherein the nAr and the nHet are 0.

### Claim 13 (depends on 1)

The composition according to claim 1, further comprising a phosphorescent light-emitting metal complex.

### Claim 14 (depends on 1)

The composition according to claim 1, further comprising a solvent or a dispersion medium.

### Claim 15 (depends on 1)

A film manufactured using the composition of claim 1.

### Claim 16 (depends on 15)

A device comprising the film of claim 15.

### Claim 17 (depends on 16)

The device according to claim 16, wherein the device is an organic electroluminescent device.