Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes

Jian Yang Cho, Benoit Domercq, Stephen Barlow, Kyrill Yu Suponitsky, Jennifer Li, Tatiana V. Timofeeva, Simon C. Jones, Lauren E. Hayden, Alpay Kimyonok, Clinton R. South, Marcus Weck, Bernard Kippelen, Seth R. Marder

Research output: Contribution to journalArticle

Abstract

A norbornene-functionalized derivative of acetylacetone has been used to synthesize a series of new polymerizable norbornene-derivatized phosphorescent platinum complexes of the form Pt(C∧N)(O∧O*) where C∧N represents a cyclometalated ligand and O∧O* represents the functionalized acetylacetonate ligand. The complexes have been fully characterized, and the structures of three examples have been determined by X-ray diffraction. Solution absorption and luminescence spectra and electrochemical data are very similar to those for analogues without these polymerizable groups. A 9,9-dialkyl-2,7-di(carbazol-9-yl)fluorene material, in which one of the alkyl groups bears a norbornene group, has been synthesized and copolymerized with the Pt(C∧N)(O∧O*) complexes using Grubbs ruthenium catalysts, resulting in copolymers with broad molecular weight distributions. The copolymers have been used as lumophores in organic light-emitting diodes, thus demonstrating that platinum phosphors can be successfully integrated into the "hybrid" approach to organic light-emitting diodes, in which molecules with transport or luminescent properties are covalently attached to electronically inert polymer backbones to give solution-processible materials. Emission from aggregate states appears to play a similar role in these copolymers to that seen in vapor-deposited devices based on small phosphor and host molecules; in particular, considerable aggregate emission is observed when a phosphor with blue solution emission is used in the devices.

Original languageEnglish (US)
Pages (from-to)4816-4829
Number of pages14
JournalOrganometallics
Volume26
Issue number19
DOIs
StatePublished - Sep 10 2007

Fingerprint

Organic light emitting diodes (OLED)
Platinum
Phosphors
phosphors
copolymers
platinum
light emitting diodes
Copolymers
synthesis
Ligands
acetylacetone
ligands
Molecules
Ruthenium
Molecular weight distribution
bears
ruthenium
Luminescence
molecules
molecular weight

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Cho, J. Y., Domercq, B., Barlow, S., Suponitsky, K. Y., Li, J., Timofeeva, T. V., ... Marder, S. R. (2007). Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes. Organometallics, 26(19), 4816-4829. https://doi.org/10.1021/om700373c

Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes. / Cho, Jian Yang; Domercq, Benoit; Barlow, Stephen; Suponitsky, Kyrill Yu; Li, Jennifer; Timofeeva, Tatiana V.; Jones, Simon C.; Hayden, Lauren E.; Kimyonok, Alpay; South, Clinton R.; Weck, Marcus; Kippelen, Bernard; Marder, Seth R.

In: Organometallics, Vol. 26, No. 19, 10.09.2007, p. 4816-4829.

Research output: Contribution to journalArticle

Cho, JY, Domercq, B, Barlow, S, Suponitsky, KY, Li, J, Timofeeva, TV, Jones, SC, Hayden, LE, Kimyonok, A, South, CR, Weck, M, Kippelen, B & Marder, SR 2007, 'Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes', Organometallics, vol. 26, no. 19, pp. 4816-4829. https://doi.org/10.1021/om700373c
Cho, Jian Yang ; Domercq, Benoit ; Barlow, Stephen ; Suponitsky, Kyrill Yu ; Li, Jennifer ; Timofeeva, Tatiana V. ; Jones, Simon C. ; Hayden, Lauren E. ; Kimyonok, Alpay ; South, Clinton R. ; Weck, Marcus ; Kippelen, Bernard ; Marder, Seth R. / Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes. In: Organometallics. 2007 ; Vol. 26, No. 19. pp. 4816-4829.
@article{d3b807290e794c7fb609b20904841c4e,
title = "Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes",
abstract = "A norbornene-functionalized derivative of acetylacetone has been used to synthesize a series of new polymerizable norbornene-derivatized phosphorescent platinum complexes of the form Pt(C∧N)(O∧O*) where C∧N represents a cyclometalated ligand and O∧O* represents the functionalized acetylacetonate ligand. The complexes have been fully characterized, and the structures of three examples have been determined by X-ray diffraction. Solution absorption and luminescence spectra and electrochemical data are very similar to those for analogues without these polymerizable groups. A 9,9-dialkyl-2,7-di(carbazol-9-yl)fluorene material, in which one of the alkyl groups bears a norbornene group, has been synthesized and copolymerized with the Pt(C∧N)(O∧O*) complexes using Grubbs ruthenium catalysts, resulting in copolymers with broad molecular weight distributions. The copolymers have been used as lumophores in organic light-emitting diodes, thus demonstrating that platinum phosphors can be successfully integrated into the {"}hybrid{"} approach to organic light-emitting diodes, in which molecules with transport or luminescent properties are covalently attached to electronically inert polymer backbones to give solution-processible materials. Emission from aggregate states appears to play a similar role in these copolymers to that seen in vapor-deposited devices based on small phosphor and host molecules; in particular, considerable aggregate emission is observed when a phosphor with blue solution emission is used in the devices.",
author = "Cho, {Jian Yang} and Benoit Domercq and Stephen Barlow and Suponitsky, {Kyrill Yu} and Jennifer Li and Timofeeva, {Tatiana V.} and Jones, {Simon C.} and Hayden, {Lauren E.} and Alpay Kimyonok and South, {Clinton R.} and Marcus Weck and Bernard Kippelen and Marder, {Seth R.}",
year = "2007",
month = "9",
day = "10",
doi = "10.1021/om700373c",
language = "English (US)",
volume = "26",
pages = "4816--4829",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "19",

}

TY - JOUR

T1 - Synthesis and characterization of polymerizable phosphorescent platinum(II) complexes for solution-processible organic light-emitting diodes

AU - Cho, Jian Yang

AU - Domercq, Benoit

AU - Barlow, Stephen

AU - Suponitsky, Kyrill Yu

AU - Li, Jennifer

AU - Timofeeva, Tatiana V.

AU - Jones, Simon C.

AU - Hayden, Lauren E.

AU - Kimyonok, Alpay

AU - South, Clinton R.

AU - Weck, Marcus

AU - Kippelen, Bernard

AU - Marder, Seth R.

PY - 2007/9/10

Y1 - 2007/9/10

N2 - A norbornene-functionalized derivative of acetylacetone has been used to synthesize a series of new polymerizable norbornene-derivatized phosphorescent platinum complexes of the form Pt(C∧N)(O∧O*) where C∧N represents a cyclometalated ligand and O∧O* represents the functionalized acetylacetonate ligand. The complexes have been fully characterized, and the structures of three examples have been determined by X-ray diffraction. Solution absorption and luminescence spectra and electrochemical data are very similar to those for analogues without these polymerizable groups. A 9,9-dialkyl-2,7-di(carbazol-9-yl)fluorene material, in which one of the alkyl groups bears a norbornene group, has been synthesized and copolymerized with the Pt(C∧N)(O∧O*) complexes using Grubbs ruthenium catalysts, resulting in copolymers with broad molecular weight distributions. The copolymers have been used as lumophores in organic light-emitting diodes, thus demonstrating that platinum phosphors can be successfully integrated into the "hybrid" approach to organic light-emitting diodes, in which molecules with transport or luminescent properties are covalently attached to electronically inert polymer backbones to give solution-processible materials. Emission from aggregate states appears to play a similar role in these copolymers to that seen in vapor-deposited devices based on small phosphor and host molecules; in particular, considerable aggregate emission is observed when a phosphor with blue solution emission is used in the devices.

AB - A norbornene-functionalized derivative of acetylacetone has been used to synthesize a series of new polymerizable norbornene-derivatized phosphorescent platinum complexes of the form Pt(C∧N)(O∧O*) where C∧N represents a cyclometalated ligand and O∧O* represents the functionalized acetylacetonate ligand. The complexes have been fully characterized, and the structures of three examples have been determined by X-ray diffraction. Solution absorption and luminescence spectra and electrochemical data are very similar to those for analogues without these polymerizable groups. A 9,9-dialkyl-2,7-di(carbazol-9-yl)fluorene material, in which one of the alkyl groups bears a norbornene group, has been synthesized and copolymerized with the Pt(C∧N)(O∧O*) complexes using Grubbs ruthenium catalysts, resulting in copolymers with broad molecular weight distributions. The copolymers have been used as lumophores in organic light-emitting diodes, thus demonstrating that platinum phosphors can be successfully integrated into the "hybrid" approach to organic light-emitting diodes, in which molecules with transport or luminescent properties are covalently attached to electronically inert polymer backbones to give solution-processible materials. Emission from aggregate states appears to play a similar role in these copolymers to that seen in vapor-deposited devices based on small phosphor and host molecules; in particular, considerable aggregate emission is observed when a phosphor with blue solution emission is used in the devices.

UR - http://www.scopus.com/inward/record.url?scp=34748891756&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34748891756&partnerID=8YFLogxK

U2 - 10.1021/om700373c

DO - 10.1021/om700373c

M3 - Article

VL - 26

SP - 4816

EP - 4829

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 19

ER -