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Functional Phthalocyanine Molecular Materials pp 275–321Cite as

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

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Part of the book series: Structure and Bonding ((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.

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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

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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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  1. Department of Chemistry, University of Science and Technology Beijing, Beijing, 100083, China

    Yuexing Zhang, Xue Cai, Yongzhong Bian & Jianzhuang Jiang

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  1. Yuexing Zhang
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  2. Xue Cai
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  3. Yongzhong Bian
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  4. Jianzhuang Jiang
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Correspondence to Jianzhuang Jiang .

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  1. Dept. Chemistry, Shandong University, Jinan, 250100, China, People's Republic

    Jianzhuang Jiang

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Zhang, Y., Cai, X., Bian, Y., Jiang, J. (2010). Organic Semiconductors of Phthalocyanine Compounds for Field Effect Transistors (FETs). In: Jiang, J. (eds) Functional Phthalocyanine Molecular Materials. Structure and Bonding, vol 135. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-04752-7_9

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