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Conjugated Organosilicon Materials for Organic Electronics and Photonics

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Silicon Polymers

Part of the book series: Advances in Polymer Science ((POLYMER,volume 235))

Abstract

In this chapter different types of conjugated organosilicon materials possessing luminescent and/or semiconducting properties will be described. Such macromolecules have various topologies and molecular structures: linear, branched and hyperbranched oligomers, polymers, and dendrimers. Specific synthetic approaches to access these structures will be discussed. Special attention is devoted to the role of silicon in these structures and its influence on their optical and electrical properties, leading to their potential application in the emerging areas of organic and hybrid electronics.

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Notes

  1. 1.

    Coordinated within the CIE 1931 color space chromaticity diagram. CIE – the International Commission on Illumination (abbreviation comes from French “Commission internationale de l’éclairage”).

  2. 2.

    An optical limitation is an optical transmittance that sharply decreases at high light levels and strongly attenuates the optical power of intense laser pulses.

Abbreviations

[C70]PCBM:

([6,6]-Phenyl C71-butyric acid methyl ester)

2T:

2, 2′-Bithiophene

3AC:

Anthracene

3D:

Three-dimensional

3T:

2, 2′ : 5′,2′′-Terthiophene

4AC:

Tetracene

4T:

2, 2′:5′, 2′′:5′′, 2′′′-Quaterthiophene

5AC:

Pentacene

5T:

2, 2′:5′, 2′′ : 5′′, 2′′′:5′′′, 2′′′′-Quinquethiophene

6T:

2, 2′:5′, 2:5′′, 2′′′:5′′′, 2′′′′:5′′′′, 2′′′′′-Sexithiophene

7T:

2, 2′:5′, 2′′:5′′, 2′′′:5′′′, 2′′′′:5′′′′, 2′′′′′:5′′′′′, 2′′′′′′-Septithiophene

ηEL :

External electroluminescence quantum efficiency

Φ F :

Luminescence quantum yield

Ac:

Acetyl

ADT:

Anthradithiophene

AFM:

Atomic force microscopy

AIE:

Aggregation induced emission

Alq3 :

Tris(8-quinolinolato) aluminum(III) complex

BS:

Dibenzosilole

Bu:

n-Butyl

tBu:

tert-Butyl

n-BuLi:

n-Butyl lithium

t-BuLi:

tert-Butyl lithium

CEE:

Cooling-enhanced emission

CIE:

International Commission on Illumination

CV:

Cyclic voltammogram

Cz:

Carbazolyl

D–A complex:

Donor–acceptor complex

Dec:

n-Decyl

DFT:

Density functional theory

DMS:

Dimethylsilyl

DMSO:

Dimethyl sulfoxide

DSC:

Differential scanning calorimetry

EDOT:

3,4-Ethylenedioxythiophene

EL:

Electroluminescence

Et:

Ethyl

ET:

Electron transport

eV:

Electron volt

Fe(acac)3 :

Iron(III) acetylacetonate

FET:

Field-effect transistor

FF:

Fill factor

HB:

Hyperbranched

Hex:

n-Hexyl

HOMO:

Highest occupied molecular orbital

HTL:

Hole-transporting layer

IP:

Ionization potential

I sc :

Short circuit current

ITO:

Indium tin oxide

LDA:

Lithium di(iso-propyl)amide

LEC:

Light-emitting electrochemical cell

LOPV:

Ladder oligo(p-phenylenevinylene)

LUMO:

Lowest unoccupied molecular orbital

MALDI–TOF:

Matrix assisted laser desorption ionization–time-of-flight mass spectrometry

Me:

Methyl

MEH-PPV:

Poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene vinylene]

M n :

Number-averaged molecular weight

M w :

Weight-averaged molecular weight

NiCl2(dppe):

1,2-Bis(diphenylphosphino)ethane nickel(II) chloride

NIR:

Near infrared

NPB:

N, N ′-Bis(1-naphthyl)-N, N ′-diphenylbenzidine

NPD:

4, 4′-Bis[N-1-naphthyl-N-phenylamino]-biphenyl

Oct:

n-Octyl

OEt:

Ethoxy

OFET:

Organic field-effect transistor

OLED:

Organic light-emitting diode

OligoT:

Oligothiophene

OMe:

Methoxy

OPV:

Organic photovoltaics

OTFT:

Organic thin film transistor

P3HT:

Poly(3-hexylthiophene)

PBD:

2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole

PCBM:

[6,6]-Phenyl C61-butyric acid methyl ester

PCE:

Power conversion efficiency

PEDOT:

Poly(3,4-ethylenedioxythiophene)

PF:

Polyfluorene

Ph:

Phenyl

PL:

Photoluminescence

PMMA:

Poly(methyl methacrylate)

PPV:

Poly(1,4-phenylene vinylene)

ppy:

2-Phenylpyridine

PS:

Polystyrene

PSS:

Poly(styrene sulfonate)

PTV:

Polythiophenevinylene

PVK:

Poly(N-vinyl carbazole)

Py:

Pyridyl

SAM:

Self-assembled monolayer

SAMFET:

Self-assembled monolayer field-effect transistor

SBAr:

Silicon-bridged biaryl

SCE:

Saturated calomel electrode

SiF:

Silafluorene

T:

Thienyl

TES:

Triethylsilyl

TGA:

Thermal gravimetric analysis

TIPS:

Triisopropylsilyl

TMS:

Trimethylsilyl

TPD:

N, N ′-Diphenyl-N, N ′-di(m-tolyl)biphenyl-4, 4′-diamine

TPS:

Triphenylsilyl

TPSppy:

2-(4′-(Triphenylsilyl)biphenyl-3-yl)pyridine

TS:

Dithienosilole

TVS:

Trivinylsilyl

Und:

n-Undecyl

UV-vis:

Ultraviolet-visible

V oc :

Open-circuit voltage

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  1. Enikolopov Institute of Synthetic Polymeric Materials of Russian Academy of Sciences (ISPM RAS), Profsoyuznaya st. 70, Moscow, 117393, Russia

    Sergei A. Ponomarenko

  2. H.C. Starck Clevios GmbH, Chempark Leverkusen, Building B 202, Leverkusen, 51368, Germany

    Stephan Kirchmeyer

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  1. Moscow State University, Inst. Synthetic Polymeric Materials, Russian Academy of Sciences, ul. Profsoyuznaya 70, Moskva, 117393, Russian Federation

    Aziz M. Muzafarov

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Ponomarenko, S.A., Kirchmeyer, S. (2010). Conjugated Organosilicon Materials for Organic Electronics and Photonics. In: Muzafarov, A. (eds) Silicon Polymers. Advances in Polymer Science, vol 235. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2009_48

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