Tetraaryl biphenyl diamine hole transport materials: a structural study utilizing both single crystal and high resolution powder diffraction

A.R. Kennedy, W.E. Smith, D.R. Tackley, W.I.F. David, K. Shankland, B. Brown, S.J. Teat

Research output: Contribution to journalArticle

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Abstract

The use of synchrotron based instruments has allowed the crystal structures of the triarylamine based hole transport materials N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD) and N,N-diphenyl-N,N-bis(4-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD-4) to be determined for the first time. The structure of TPD, based on a single crystal experiment using a microcrystal, has profound implications for work on elucidating the hole transport mechanism of these materials as it is shown to contain two disordered but distinct molecular conformations. Neither conformation corresponds to previous predictions from density functional theory. Further complicating the system is the presence of a second polymorph detected in bulk TPD. The crystal structure of TPD-4, derived from high resolution powder diffraction techniques, is also presented and is discussed with reference to that of TPD.
LanguageEnglish
Pages168-172
Number of pages4
JournalJournal of Materials Chemistry
Volume12
DOIs
Publication statusPublished - 20 Dec 2001

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Diamines
Temperature programmed desorption
Single crystals
Conformations
Crystal structure
Microcrystals
Polymorphism
Synchrotrons
Density functional theory
Powder Diffraction
diphenyl
Experiments

Keywords

  • synchrotron
  • crystal structures
  • triarylamine
  • microcrystal
  • molecular conformations
  • TPD

Cite this

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title = "Tetraaryl biphenyl diamine hole transport materials: a structural study utilizing both single crystal and high resolution powder diffraction",
abstract = "The use of synchrotron based instruments has allowed the crystal structures of the triarylamine based hole transport materials N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD) and N,N-diphenyl-N,N-bis(4-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD-4) to be determined for the first time. The structure of TPD, based on a single crystal experiment using a microcrystal, has profound implications for work on elucidating the hole transport mechanism of these materials as it is shown to contain two disordered but distinct molecular conformations. Neither conformation corresponds to previous predictions from density functional theory. Further complicating the system is the presence of a second polymorph detected in bulk TPD. The crystal structure of TPD-4, derived from high resolution powder diffraction techniques, is also presented and is discussed with reference to that of TPD.",
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Tetraaryl biphenyl diamine hole transport materials: a structural study utilizing both single crystal and high resolution powder diffraction. / Kennedy, A.R.; Smith, W.E.; Tackley, D.R.; David, W.I.F.; Shankland, K.; Brown, B.; Teat, S.J.

In: Journal of Materials Chemistry, Vol. 12, 20.12.2001, p. 168-172.

Research output: Contribution to journalArticle

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T1 - Tetraaryl biphenyl diamine hole transport materials: a structural study utilizing both single crystal and high resolution powder diffraction

AU - Kennedy, A.R.

AU - Smith, W.E.

AU - Tackley, D.R.

AU - David, W.I.F.

AU - Shankland, K.

AU - Brown, B.

AU - Teat, S.J.

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N2 - The use of synchrotron based instruments has allowed the crystal structures of the triarylamine based hole transport materials N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD) and N,N-diphenyl-N,N-bis(4-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD-4) to be determined for the first time. The structure of TPD, based on a single crystal experiment using a microcrystal, has profound implications for work on elucidating the hole transport mechanism of these materials as it is shown to contain two disordered but distinct molecular conformations. Neither conformation corresponds to previous predictions from density functional theory. Further complicating the system is the presence of a second polymorph detected in bulk TPD. The crystal structure of TPD-4, derived from high resolution powder diffraction techniques, is also presented and is discussed with reference to that of TPD.

AB - The use of synchrotron based instruments has allowed the crystal structures of the triarylamine based hole transport materials N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD) and N,N-diphenyl-N,N-bis(4-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD-4) to be determined for the first time. The structure of TPD, based on a single crystal experiment using a microcrystal, has profound implications for work on elucidating the hole transport mechanism of these materials as it is shown to contain two disordered but distinct molecular conformations. Neither conformation corresponds to previous predictions from density functional theory. Further complicating the system is the presence of a second polymorph detected in bulk TPD. The crystal structure of TPD-4, derived from high resolution powder diffraction techniques, is also presented and is discussed with reference to that of TPD.

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