Highly phosphorescent bis-cyclometalated iridium complexes

Synthesis, photophysical characterization, and use in organic light emitting diodes

S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H. E. Lee, Chihaya Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson

Research output: Contribution to journalArticle

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Abstract

The synthesis and photophysical study of a family of cyclometalated iridium(III) complexes are reported. The iridium complexes have two cyclometalated (ĈN) ligands and a single monoanionic, bidentate ancillary ligand (LX), i.e., ĈN2Ir(LX). The ĈN ligands can be any of a wide variety of organometallic ligands. The LX ligands used for this study were all β-diketonates, with the major emphasis placed on acetylacetonate (acac) complexes. The majority of the ĈN2Ir(acac) complexes phosphoresce with high quantum efficiencies (solution quantum yields, 0.1-0.6), and microsecond lifetimes (e.g., 1-14 μs). The strongly allowed phosphorescence in these complexes is the result of significant spin-orbit coupling of the Ir center. The lowest energy (emissive) excited state in these ĈN2Ir(acac) complexes is a mixture of 3MLCT and 3(π-π*) states. By choosing the appropriate ĈN ligand, ĈN2Ir(acac) complexes can be prepared which emit in any color from green to red. Simple, systematic changes in the ĈN ligands, which lead to bathochromic shifts of the free ligands, lead to similar bathochromic shifts in the Ir complexes of the same ligands, consistent with "ĈN2-Ir"-centered emission. Three of the ĈN2Ir(acac) complexes were used as dopants for organic light emitting diodes (OLEDs). The three Ir complexes, i.e., bis(2-phenylpyridinato-N,C2′)iridium(acetylacetonate) [ppy2Ir(acac)], bis(2-phenyl benzothiozolato-N,C2′)iridium(acetylacetonate) [bt2Ir(acac)], and bis(2-(2′-benzothienyl)-pyridinato-N,C3′)iridium (acetylacetonate) [btp2Ir(acac)], were doped into the emissive region of multilayer, vapor-deposited OLEDs. The ppy2Ir(acac)-, bt2Ir(acac)-, and btp2Ir(acac)-based OLEDs give green, yellow, and red electroluminescence, respectively, with very similar current-voltage characteristics. The OLEDs give high external quantum efficiencies, ranging from 6 to 12.3%, with the ppy2Ir(acac) giving the highest efficiency (12.3%, 38 lm/W, >50 Cd/A). The btp2Ir(acac)-based device gives saturated red emission with a quantum efficiency of 6.5% and a luminance efficiency of 2.2 lm/W. These C∧N2Ir(acac)-doped OLEDs show some of the highest efficiencies reported for organic light emitting diodes. The high efficiencies result from efficient trapping and radiative relaxation of the singlet and triplet excitons formed in the electroluminescent process.

Original languageEnglish
Pages (from-to)4304-4312
Number of pages9
JournalJournal of the American Chemical Society
Volume123
Issue number18
DOIs
Publication statusPublished - Oct 8 2001

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Iridium
Organic light emitting diodes (OLED)
Ligands
Light
Quantum efficiency
acetyl acetonate
Phosphorescence
Electroluminescence
Organometallics
Quantum yield
Current voltage characteristics
Excited states
Excitons
Luminance
Multilayers
Orbits
Vapors
Doping (additives)
Color
Orbit

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Highly phosphorescent bis-cyclometalated iridium complexes : Synthesis, photophysical characterization, and use in organic light emitting diodes. / Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razzaq, F.; Lee, H. E.; Adachi, Chihaya; Burrows, P. E.; Forrest, S. R.; Thompson, M. E.

In: Journal of the American Chemical Society, Vol. 123, No. 18, 08.10.2001, p. 4304-4312.

Research output: Contribution to journalArticle

Lamansky, S. ; Djurovich, P. ; Murphy, D. ; Abdel-Razzaq, F. ; Lee, H. E. ; Adachi, Chihaya ; Burrows, P. E. ; Forrest, S. R. ; Thompson, M. E. / Highly phosphorescent bis-cyclometalated iridium complexes : Synthesis, photophysical characterization, and use in organic light emitting diodes. In: Journal of the American Chemical Society. 2001 ; Vol. 123, No. 18. pp. 4304-4312.
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abstract = "The synthesis and photophysical study of a family of cyclometalated iridium(III) complexes are reported. The iridium complexes have two cyclometalated (ĈN) ligands and a single monoanionic, bidentate ancillary ligand (LX), i.e., ĈN2Ir(LX). The ĈN ligands can be any of a wide variety of organometallic ligands. The LX ligands used for this study were all β-diketonates, with the major emphasis placed on acetylacetonate (acac) complexes. The majority of the ĈN2Ir(acac) complexes phosphoresce with high quantum efficiencies (solution quantum yields, 0.1-0.6), and microsecond lifetimes (e.g., 1-14 μs). The strongly allowed phosphorescence in these complexes is the result of significant spin-orbit coupling of the Ir center. The lowest energy (emissive) excited state in these ĈN2Ir(acac) complexes is a mixture of 3MLCT and 3(π-π*) states. By choosing the appropriate ĈN ligand, ĈN2Ir(acac) complexes can be prepared which emit in any color from green to red. Simple, systematic changes in the ĈN ligands, which lead to bathochromic shifts of the free ligands, lead to similar bathochromic shifts in the Ir complexes of the same ligands, consistent with {"}ĈN2-Ir{"}-centered emission. Three of the ĈN2Ir(acac) complexes were used as dopants for organic light emitting diodes (OLEDs). The three Ir complexes, i.e., bis(2-phenylpyridinato-N,C2′)iridium(acetylacetonate) [ppy2Ir(acac)], bis(2-phenyl benzothiozolato-N,C2′)iridium(acetylacetonate) [bt2Ir(acac)], and bis(2-(2′-benzothienyl)-pyridinato-N,C3′)iridium (acetylacetonate) [btp2Ir(acac)], were doped into the emissive region of multilayer, vapor-deposited OLEDs. The ppy2Ir(acac)-, bt2Ir(acac)-, and btp2Ir(acac)-based OLEDs give green, yellow, and red electroluminescence, respectively, with very similar current-voltage characteristics. The OLEDs give high external quantum efficiencies, ranging from 6 to 12.3{\%}, with the ppy2Ir(acac) giving the highest efficiency (12.3{\%}, 38 lm/W, >50 Cd/A). The btp2Ir(acac)-based device gives saturated red emission with a quantum efficiency of 6.5{\%} and a luminance efficiency of 2.2 lm/W. These C∧N2Ir(acac)-doped OLEDs show some of the highest efficiencies reported for organic light emitting diodes. The high efficiencies result from efficient trapping and radiative relaxation of the singlet and triplet excitons formed in the electroluminescent process.",
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TY - JOUR

T1 - Highly phosphorescent bis-cyclometalated iridium complexes

T2 - Synthesis, photophysical characterization, and use in organic light emitting diodes

AU - Lamansky, S.

AU - Djurovich, P.

AU - Murphy, D.

AU - Abdel-Razzaq, F.

AU - Lee, H. E.

AU - Adachi, Chihaya

AU - Burrows, P. E.

AU - Forrest, S. R.

AU - Thompson, M. E.

PY - 2001/10/8

Y1 - 2001/10/8

N2 - The synthesis and photophysical study of a family of cyclometalated iridium(III) complexes are reported. The iridium complexes have two cyclometalated (ĈN) ligands and a single monoanionic, bidentate ancillary ligand (LX), i.e., ĈN2Ir(LX). The ĈN ligands can be any of a wide variety of organometallic ligands. The LX ligands used for this study were all β-diketonates, with the major emphasis placed on acetylacetonate (acac) complexes. The majority of the ĈN2Ir(acac) complexes phosphoresce with high quantum efficiencies (solution quantum yields, 0.1-0.6), and microsecond lifetimes (e.g., 1-14 μs). The strongly allowed phosphorescence in these complexes is the result of significant spin-orbit coupling of the Ir center. The lowest energy (emissive) excited state in these ĈN2Ir(acac) complexes is a mixture of 3MLCT and 3(π-π*) states. By choosing the appropriate ĈN ligand, ĈN2Ir(acac) complexes can be prepared which emit in any color from green to red. Simple, systematic changes in the ĈN ligands, which lead to bathochromic shifts of the free ligands, lead to similar bathochromic shifts in the Ir complexes of the same ligands, consistent with "ĈN2-Ir"-centered emission. Three of the ĈN2Ir(acac) complexes were used as dopants for organic light emitting diodes (OLEDs). The three Ir complexes, i.e., bis(2-phenylpyridinato-N,C2′)iridium(acetylacetonate) [ppy2Ir(acac)], bis(2-phenyl benzothiozolato-N,C2′)iridium(acetylacetonate) [bt2Ir(acac)], and bis(2-(2′-benzothienyl)-pyridinato-N,C3′)iridium (acetylacetonate) [btp2Ir(acac)], were doped into the emissive region of multilayer, vapor-deposited OLEDs. The ppy2Ir(acac)-, bt2Ir(acac)-, and btp2Ir(acac)-based OLEDs give green, yellow, and red electroluminescence, respectively, with very similar current-voltage characteristics. The OLEDs give high external quantum efficiencies, ranging from 6 to 12.3%, with the ppy2Ir(acac) giving the highest efficiency (12.3%, 38 lm/W, >50 Cd/A). The btp2Ir(acac)-based device gives saturated red emission with a quantum efficiency of 6.5% and a luminance efficiency of 2.2 lm/W. These C∧N2Ir(acac)-doped OLEDs show some of the highest efficiencies reported for organic light emitting diodes. The high efficiencies result from efficient trapping and radiative relaxation of the singlet and triplet excitons formed in the electroluminescent process.

AB - The synthesis and photophysical study of a family of cyclometalated iridium(III) complexes are reported. The iridium complexes have two cyclometalated (ĈN) ligands and a single monoanionic, bidentate ancillary ligand (LX), i.e., ĈN2Ir(LX). The ĈN ligands can be any of a wide variety of organometallic ligands. The LX ligands used for this study were all β-diketonates, with the major emphasis placed on acetylacetonate (acac) complexes. The majority of the ĈN2Ir(acac) complexes phosphoresce with high quantum efficiencies (solution quantum yields, 0.1-0.6), and microsecond lifetimes (e.g., 1-14 μs). The strongly allowed phosphorescence in these complexes is the result of significant spin-orbit coupling of the Ir center. The lowest energy (emissive) excited state in these ĈN2Ir(acac) complexes is a mixture of 3MLCT and 3(π-π*) states. By choosing the appropriate ĈN ligand, ĈN2Ir(acac) complexes can be prepared which emit in any color from green to red. Simple, systematic changes in the ĈN ligands, which lead to bathochromic shifts of the free ligands, lead to similar bathochromic shifts in the Ir complexes of the same ligands, consistent with "ĈN2-Ir"-centered emission. Three of the ĈN2Ir(acac) complexes were used as dopants for organic light emitting diodes (OLEDs). The three Ir complexes, i.e., bis(2-phenylpyridinato-N,C2′)iridium(acetylacetonate) [ppy2Ir(acac)], bis(2-phenyl benzothiozolato-N,C2′)iridium(acetylacetonate) [bt2Ir(acac)], and bis(2-(2′-benzothienyl)-pyridinato-N,C3′)iridium (acetylacetonate) [btp2Ir(acac)], were doped into the emissive region of multilayer, vapor-deposited OLEDs. The ppy2Ir(acac)-, bt2Ir(acac)-, and btp2Ir(acac)-based OLEDs give green, yellow, and red electroluminescence, respectively, with very similar current-voltage characteristics. The OLEDs give high external quantum efficiencies, ranging from 6 to 12.3%, with the ppy2Ir(acac) giving the highest efficiency (12.3%, 38 lm/W, >50 Cd/A). The btp2Ir(acac)-based device gives saturated red emission with a quantum efficiency of 6.5% and a luminance efficiency of 2.2 lm/W. These C∧N2Ir(acac)-doped OLEDs show some of the highest efficiencies reported for organic light emitting diodes. The high efficiencies result from efficient trapping and radiative relaxation of the singlet and triplet excitons formed in the electroluminescent process.

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