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Organic Semiconductors of Phthalocyanine Compounds for Field Effect Transistors (FETs)

  • Yuexing Zhang
  • Xue Cai
  • Yongzhong Bian
  • Jianzhuang JiangEmail author
Chapter
Part of the Structure and Bonding book series (STRUCTURE, volume 135)

Abstract

Various functional phthalocyanines as well as their tetrapyrrole analogs, porphyrins, have been extensively studied as organic semiconductors since the first report of organic field effect transistors (OFETs) in 1986. The large conjugated π system, excellent photoelectric characteristics, intriguing and unique optical properties, high thermal and chemical stability, and most importantly the easy functionalization of phthalocyanines render them ideal organic semiconductor materials as active layers for OFETs. In this chapter, the semiconducting properties of monomeric phthalocyanines as well as monomeric porphyrins, bis(phthalocyaninato) rare earth double-deckers, and tris(phthalocyaninato) rare earth triple-deckers in terms of their semiconducting nature (p-type, n-type, or ambipolar), carrier mobility, and current modulation reported in the past two decades have been summarized. Theoretical studies toward understanding the relationship between molecular structures as well as molecular electronic structures of phthalocyanines and their semiconducting properties have also been included.

Keywords

Field effect transistors (FETs) Organic semiconductor Phthalocyanine Porphyrin Tetrapyrrole 

Abbreviations

TC/BG

Top contact/bottom gate

BC/BG

Bottom contact/bottom gate

SC/BG

Sandwich contact/bottom gate

BC/TG

Bottom contact/top gate

PR-TRMC

Pulse-radiolysis time-resolved microwave conductivity technique

ITO

Indium tin oxide

OTS

Octadecyltrichlorosilane

GMA

Glycidyl methacrylate

PBMA

Poly(butyl methacrylate)

PMMA

Poly(methylmethacrylate)

P(MMA-co-GMA)

Poly(methylmethacrylate-co-glycidylmethacrylate)

PVP

Poly(4-vinylphenol)

C6

1,6-bis(trichlorosilyl)hexane

CPVP-C6

Poly[1,6-(4-vinylphenol)-bis(bichlorosilyl)hexane]

Parylene-C

Dichloro-[2,2]-paracyclophane

Parylene-N

[2,2]-paracyclophane

CyEPL

Cyanoethylpullulan

HMDS

Hexamethyldisilazane

PZT

PbZr0.5Ti0.5O3

P1

Polyimide-1

P2

Poly(amic acid)

PI

Polyimide-2

PVC

Poly(vinylchloride)

PVDF

Poly(vinylidenefluoride)

PAN

Poly(acrylonitrile)

PNVP

Poly(N-vinylpyrrolidone)

PS

Poly(styrene)

PVPy

Poly(4-vinylpyridine)

PVK

Poly(N-vinylcarbazole)

p-6P

Para-sexiphenyl

MPc

Monomeric phthalocyaninate metal complex

H2Pc

Metal free phthalocyanine

VOPc

Vanadyl phthalocyanine

TiOPc

Titanyl phthalocyanine

H2PcAmBu

2(3)-amino-9(10),16(17),23(24)-tri(tert-butyl)-phthalocyanine

H2PcNT

2(3)-(1,8-naphthalimide)-9(10),16(17),23(24)-tri(tert-butyl)-phthalocyanine

CuPc-i-Pro

Tetra-iso-propoxy-phthalocyaninato copper (II)

CuPcTSNa

Copper phthalocyanine tetrasulfonic acid tetrasodium salt

ZnPcTO

Tetra-{4-[5-(4-tert-butyl-phenyl)-[1,3,4]oxadiazol-2-yl]-phenoxy}-zincphthalocyanine

H2PcT(t-Bu)(OCOH)

2,9,16-tri(tert-butyl)-23-(10-hydroxydecyloxy) phthalocyanine

CuPcT(t-Bu)(OCOH)

2,9,16-tri(tert-butyl)-23-(10-hydroxydecyloxy) copper phthalocyanine

M(Pc)2

Bis(phthalocyaninato) rare earth complex

MPc[Pc(OC8H17)8]

Heteroleptic (phthalocyaninato) [2,3,9,10,16,17,23,24-octakis(octyloxy)-phthalocyaninato] rare earth double-decker complex

MOEP

2,3,7,8,12,13,17,18-octaethyl-porphyrinate metal complex

H2OEP

2,3,7,8,12,13,17,18-ocataethyl-21H,23H-porphyrin

H2TPP

5,10,15,20-tetra-phenyl-21H,23H-porphyrin

H2TBP

Tetrabenzoporphyrin

NiTBP

Nickel tetrabenzoporphyrin

CuTBP

Copper tetrabenzoporphyrin

H2EP-I

Etioporphyrin-I

MEP-I

Metal etioporphyrin-I

H2TPrP

2,7,12,17-tetra-(n-propyl)-porphycene

PtTPrP

2,7,12,17-tetra-(n-propyl)-porphycene platinum

H2TBuP

5,10,15,20-tetra-(n-butyl)-porphyrin

PtTBuP

5,10,15,20-tetra-(n-butyl)-porphyrin platinum

MPcF16

Metal hexadecafluorophthalocyanine

FePcCl16

Iron hexadecachlorinphthalocyanine

FePc(CN)16

Copper hexadecacyanophthalocyanine

SnCl2Pc

Phthalocyanato tin(IV) dichloride

SnOPc

Tin (IV) phthalocyanine oxide

DH-α6T

α, α’-dihexylsexithiophene

TCNQ

7,7,8,8-tetracyano-p-quinodimethane

BBL

Poly(benzobisimidazobenzophenanthroline)

BP2T

2,5-bis(4-biphenylyl) bithiophene

AB

Copper(II) phthalocyanine tetrakis(methyl pyridinium) chloride

Notes

Acknowledgements

The authors thank the National Natural Science Foundation of China, Education Ministry of China, University of Science and Technology Beijing, and Shandong University for financial support.

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Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • Yuexing Zhang
    • 1
  • Xue Cai
    • 1
  • Yongzhong Bian
    • 1
  • Jianzhuang Jiang
    • 1
    Email author
  1. 1.Department of ChemistryUniversity of Science and Technology BeijingBeijingChina

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