Near-infrared organic light-emitting diodes with very high external quantum efficiency and radiance
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1 In the format provided by the authors and unedited. SUPPLEMENTARY INFORMATION DOI: /NPHOTON Near-infrared organic light-emitting diodes with very high external quantum efficiency and radiance Kiet Tuong Ly, a Ren-Wu Chen-Cheng, b Hao-Wu Lin,*,b Yu-Jeng Shiau, b Shih-Hung Liu, c Pi-Tai Chou,*,c Cheng-Si Tsao, d,e Yu-Ching Huang, d and Yun Chi*,a a Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan; ychi@mx.nthu.edu.tw b Department of Materials Science and Engineering, National Tsing Hua University, Hsinchu 30013, Taiwan, hwlin@mx.nthu.edu.tw c Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan; chop@ntu.edu.tw d Institute of Nuclear Energy Research, Taoyuan 32546, Taiwan e Department of Materials Science and Engineering, National Taiwan University, Taipei 10617, Taiwan NATURE PHOTONICS Macmillan Publishers Limited, part of Springer Nature. All rights reserved.
2 Contents Figure S1. GISAXS profiles reduced along in-plane direction of 1, 2 and 3. Figure S2. Angle-dependent PL of the 2-pyrazinyl pyrazolate Pt(II) complexes. Figures S3 S5. Frontier molecular orbitals pertinent to the optical transitions for of Pt(II) complexes 1 3. Figure S6. The Pt-Pt distance and emission character of dimeric Pt(II) complex 1 in S1 and T1 states. Figure S7. Frontier molecular orbitals HOMO and LUMO of S1 excited states for dimer and trimer excimers of 1. Figure S8 S9. Frontier molecular orbitals HOMO and LUMO of S1 and T1 excited states for dimer and trimer excimers of 2 and 3. Figure S10. The device structure and material energy band diagram of the OLEDs. Figure S11. EL spectra and external quantum efficiency of 1 as a function of the current density vs. ETL materials and layer thicknesses. Figure S12. EL spectra of the OLED fabricated using Pt complexes 1 3. Figure S13. Calculated Φair as a function of the HTL and ETL thicknesses for the 1-based device. Figure S14. Schematic diagram of the integrating sphere measurement setup and the light out-coupling half-sphere attachment on the OLED substrate. Figure S15. External quantum efficiency and power conversion efficiency as a function of the current density with a hemi-sphere light out-coupling structure. Tables S1-S3. The calculated wavelengths, transition probabilities and charge transfer character of the optical transitions for monomer of Pt(II) complexes 1 3 in THF. Table S4 S6. The calculated wavelengths, transition probabilities and charge transfer character of the emission for hypothetical dimer and trimer excimers of Pt(II) complex 1 3. Table S7. HOMO, LUMO and energy gap of 1 3 with thin film PL and device EL. Table S8. Comparative device performances of our red-nir-emitting OLEDs vs. literature examples. page S3 S4 S5 S8 S9 S10 S12 S13 S14 S15 S16 S17 S18 S21 S22 S23 S2
3 I(q) (cm -1 ) 1E-3 1E q (Å -1 ) Figure S1. GISAXS profiles along in-plane direction of 1, 2 and 3-based thin films. S3
4 Normalized PL Intensity (a.u.) Simulation isotropic ( =0.67) Simulation horizontal ( =1) Experimental 1 ( =0.87) Experimental 2 ( =0.88) Experimental 3 ( =0.77) Angle (degree) Figure S2. Angle-dependent PL of the 2-pyrazinyl pyrazolate Pt(II) complexes. Emission signals were measured from 0 to 90 in 2 increments. The dashed lines are simulated values. S4
5 HOMO-7 ( 7.87 ev) Pt: 4.45% HOMO-6 ( 7.83 ev) Pt: 0.34% HOMO-4 ( 7.50 ev) Pt: 1.31% HOMO-3 ( 7.06 ev) Pt: 95.31% HOMO-2 ( 6.79 ev) Pt: 9.2% HOMO-1 ( 6.72 ev) Pt: 0.01% HOMO ( 6.32 ev) Pt: 32.03% LUMO ( 3.47 ev) Pt: 4.15% LUMO+1 ( 2.20 ev) Pt: 5.10% optimized structure Figure S3. Frontier molecular orbitals pertinent to the optical transitions for monomer of Pt(II) complex 1 and the percentage of electron density from the Pt atom. For the clarity, the optimized structure without involvement of frontier orbitals is shown at the last figure. S5
6 HOMO-10 ( 8.48 ev) Pt: 48.91% HOMO-6 ( 7.78 ev) Pt: 2.57% HOMO-3 ( 6.93 ev) Pt: 95.84% HOMO-2 ( 6.69 ev) Pt: 8.48% HOMO-1 ( 6.57 ev) Pt: 2.45% HOMO ( 6.22 ev) Pt: 32.08% LUMO ( 3.26 ev) Pt: 4.7% LUMO+1 ( 1.79 ev) Pt: 4.59% LUMO+4 ( 0.95 ev) Pt: 56.05% optimized structure Figure S4. Frontier molecular orbitals pertinent to the optical transitions for monomer of Pt(II) complex 2 and the percentage of electron density from the Pt atom. For the clarity, the optimized structure without involvement of frontier orbitals is shown at the last figure. S6
7 HOMO-6 ( 7.77 ev) Pt: 2.62% HOMO-4 ( 7.21 ev) Pt: 53.73% HOMO-3 ( 6.90 ev) Pt: 95.86% HOMO-2 ( 6.67 ev) Pt: 8.44% HOMO-1 ( 6.52 ev) Pt: 3.28% HOMO ( 6.19 ev) Pt: 31.64% LUMO ( 3.22 ev) Pt: 4.77% LUMO+1 ( 1.68 ev) Pt: 4.61% LUMO+2 ( 1.42 ev) Pt: 0.68% LUMO+4 ( 0.91 ev) optimized structure Pt: 56.03% Figure S5. Frontier molecular orbitals pertinent to the optical transitions for monomer of Pt(II) complex 3 and the percentage of electron density from the Pt atom. For the clarity, the optimized structure without involvement of frontier orbitals is shown at the last figure. S7
8 emission wavelength (nm) T S Pt-Pt initial distance (Å ) Pt-Pt final distance (Å ) Figure S6. The calculated Pt-Pt distance and emission character of dimeric Pt(II) complex 1 in S1 and T1 states. S8
9 optimized structure of dimer HOMO ( 5.83 ev) Pt: 87.70% LUMO ( 2.99 ev) Pt: 5.66% optimized structure of trimer HOMO ( 5.81 ev) Pt: 89.55% LUMO ( 3.07 ev) Pt: 6.96% Figure S7. Frontier molecular orbitals HOMO and LUMO in S1 excited state for dimer (top) and trimer (bottom) excimers of Pt(II) complex 1. The electron density distributions summation of the Pt atoms in HOMO and LUMO are also shown. S9
10 optimized structure of dimer in T1 state HOMO ( 5.61 ev) Pt: 87.30% LUMO ( 2.72 ev) Pt: 6.46% optimized structure of dimer in S1 state HOMO ( 5.61 ev) Pt: 87.52% LUMO ( 2.71 ev) Pt: 6.28% optimized structure of trimer in T1 state HOMO ( 5.50 ev) Pt: 88.32% LUMO ( 2.76 ev) Pt: 7.54% optimized structure of trimer in S1 state HOMO ( 5.56 ev) Pt: 87.84% LUMO ( 2.72 ev) Pt: 7.01% Figure S8. Frontier molecular orbitals HOMO and LUMO in S1 and T1 excited states for dimer and trimer excimers of Pt(II) complex 2. The electron density distributions summation of the Pt atoms in HOMO and LUMO are also shown. S10
11 optimized structure of dimer in T1 state HOMO ( 5.60 ev) Pt: 86.70% LUMO ( 2.68 ev) Pt: 6.69% optimized structure of dimer in S1 state HOMO ( 5.61 ev) Pt: 86.90% LUMO ( 2.68 ev) Pt: 6.48% optimized structure of trimer in T1 state HOMO ( 5.69 ev) Pt: 90.17% LUMO ( 2.73 ev) Pt: 7.64% optimized structure of trimer in S1 state HOMO ( 5.56 ev) Pt: 87.96% LUMO ( 2.70 ev) Pt: 7.11% Figure S9. Frontier molecular orbitals HOMO and LUMO in S1 and T1 excited states for dimer and trimer excimers of Pt(II) complex 3. The electron density distributions summation of the Pt atoms in HOMO and LUMO are also shown. S11
12 Figure S10. The device structure and material energy band diagram of the OLEDs. S12
13 Normalized Intensity (a.u.) (a) TPBi (20 nm) TPBi (30 nm) TPBi (40 nm) Bphen (20 nm) Bphen (30 nm) Bphen (40 nm) Wavelength (nm) Quantum Efficiency ext % (b) TPBi (20 nm) TPBi (30 nm) TPBi (40 nm) Bphen (20 nm) Bphen (30 nm) Bphen (40 nm) Current Density (ma/cm 2 ) Figure S11. (a) EL spectra and (b) external quantum efficiency of Pt(II) complex 1 as a function of the current density vs. ETL materials and layer thicknesses. S13
14 Normalized Intensity (a.u.) Wavelength (nm) Figure S12. EL spectra of the OLEDs fabricated using Pt(II) complexes 1 3. S14
15 HTL Thickness (nm) % (60, 75) ETL Thickness (nm) out (%) Figure S13. Calculated Φair as a function of the HTL and ETL thicknesses for the Pt(II) complex 1-based device. The HTL thickness represents the total thickness of the hole transporting structure (HATCN thickness + NPB thickness + mcp thickness). S15
16 (a) (b) Figure S14. (a) Schematic diagram of the integrating sphere measurement setup. (b) Schematic of the light out-coupling half-sphere attachment on the OLED substrate. S16
17 70 (a) Quantum Efficiency ext % Current Density (ma/cm 2 ) Power Conversion Efficiency (%) (b) Current Density (ma/cm 2 ) Figure S15. (a) External quantum efficiency and (b) power conversion efficiency as a function of the current density and with hemi-sphere attached on device. S17
18 Table S1. The calculated wavelengths, transition probabilities and charge transfer character of the optical transitions for monomer of Pt(II) complex 1 in THF. State λ (nm) f Assignments MLCT T HOMO LUMO (70%) HOMO-2 LUMO (14%) 19.66% HOMO-1 LUMO+1 (11%) T HOMO-1 LUMO (66%) HOMO LUMO+1 (14%) 1.61% HOMO-2 LUMO+1 (14%) S HOMO LUMO (99%) 27.60% T HOMO-2 LUMO (59%) HOMO LUMO (24%) 9.21% HOMO-1 LUMO+1 (9%) T HOMO LUMO+1 (74%) HOMO-1 LUMO (8%) HOMO-2 LUMO+1 (7%) 19.71% HOMO-4 LUMO (6%) T HOMO-3 LUMO (84%) HOMO-7 LUMO (7%) 76.26% HOMO-6 LUMO+1 (7%) S HOMO LUMO+1 (70%) HOMO-1 LUMO (26%) 17.77% S HOMO-3 LUMO (100%) 91.16% S HOMO-1 LUMO (72%) HOMO LUMO+1 (27%) 4.29% S HOMO-2 LUMO (97%) 4.90% S18
19 Table S2. The calculated wavelengths, transition probabilities and charge transfer character of the optical transitions for monomer of Pt(II) complex 2 in THF. State λ (nm) f Assignments MLCT T HOMO LUMO (53%) HOMO-2 LUMO (29%) 15.41% HOMO-1 LUMO (9%) T HOMO LUMO (27%) HOMO-1 LUMO (23%) HOMO-2 LUMO (19%) 10.15% HOMO LUMO+1 (10%) HOMO-1 LUMO+1 (9%) S HOMO LUMO (98%) 26.83% T HOMO-2 LUMO (34%) HOMO-1 LUMO (17%) HOMO-1 LUMO+1 (17%) 6.30% HOMO LUMO (13%) HOMO LUMO+1 (8%) T HOMO LUMO+4 (82%) HOMO-10 LUMO+4 (9%) 20.30% T HOMO-3 LUMO (68%) HOMO-6 LUMO (23%) 61.49% S HOMO-1 LUMO (97%) 3.67% S HOMO-3 LUMO (99%) 90.23% S HOMO-2 LUMO (95%) 3.59% S HOMO LUMO+1 (95%) 26.12% S19
20 Table S3. The calculated wavelengths, transition probabilities and charge transfer character of the optical transitions for monomer of Pt(II) complex 3 in THF. State λ (nm) f Assignments MLCT T HOMO LUMO (51%) HOMO-2 LUMO (31%) 14.71% HOMO-1 LUMO (9%) T HOMO LUMO (37%) HOMO-2 LUMO (31%) HOMO-1 LUMO (12%) 12.25% HOMO LUMO+1 (5%) S HOMO LUMO (97%) 26.06% T HOMO-1 LUMO (28%) HOMO-2 LUMO (21%) HOMO-1 LUMO+1 (20%) 3.33% HOMO LUMO+1 (12%) T HOMO LUMO+4 (81%) 19.76% T HOMO-3 LUMO (38%) HOMO-6 LUMO (12%) HOMO-2 LUMO+2 (11%) 41.47% HOMO-4 LUMO (9%) HOMO LUMO+2 (6%) S HOMO-1 LUMO (97%) 1.45% S HOMO-3 LUMO (99%) 90.18% S HOMO-2 LUMO (95%) 3.49% S HOMO LUMO+1 (95%) 25.68% S20
21 Table S4. The calculated wavelengths, transition probabilities and charge transfer character of the emission for hypothetical dimer and trimer excimers of Pt(II) complex 1. State λ (nm) f Assignments MMLCT dimer trimer T1 S LUMO HOMO (99%) 82.04% S1 S LUMO HOMO (100%) 80.80% T1 S LUMO HOMO (70%) 56.81% S1 S LUMO HOMO (70%) 57.81% Table S5. The calculated wavelengths, transition probabilities and charge transfer character of the emission for hypothetical dimer and trimer excimers of Pt(II) complex 2. State λ (nm) f Assignments MMLCT dimer trimer T1 S LUMO HOMO (99%) 80.03% S1 S LUMO HOMO (99%) 80.43% T1 S LUMO HOMO (70%) 57.59% S1 S LUMO HOMO (70%) 56.58% Table S6. The calculated wavelengths, transition probabilities and charge transfer character of the emission for hypothetical dimer and trimer excimers of Pt(II) complex 3. State λ (nm) f Assignments MMLCT dimer trimer T1 S LUMO HOMO (99%) 79.21% S1 S LUMO HOMO (99%) 79.62% T1 S LUMO HOMO (70%) 57.77% S1 S LUMO HOMO (70%) 56.60% S21
22 Table S7. HOMO, LUMO and energy gap of Pt(II) complex 1 3 with thin film PL and device EL. HOMO (ev) LUMO (ev) Eg (ev) PL λmax (nm) EL λmax (nm) S22
23 Table S8. Comparative device performances of our red-nir-emitting OLEDs vs. literature examples. EL λmax (nm) NIR fraction (%) [a] Red fraction (%) [b] EQEmax (%) (without lens/with lens) EL PL EL PL Total NIR [a] Radiancemax (mw s r 1 m 2 ) (without lens/with lens) [c] Total (x 10 5 ) NIR [a] (x 10 5 ) PCEmax (%) (without lens/with lens) Total NIR [a] Φ (%) Θ (%) ηout (%) Φ x ηout (%) ±1 / 19±1 / 3.6±0.2 / 2.8±0.2 / 6.4±0.3 / 5.0±0.2 / ±3 44±2 8.7± ±0.3 15±1 12± ±1 / 9.4±0.5 / 4.2±0.2 / 1.8±0.1 / 6.8±0.3 / 2.9±0.1 / ±2 21±1 9.7± ±0.2 15±1 6.2± ±1 / 8.5±0.4 / 4.1±0.2 / 1.4±0.1 / 10±0.5 / 3.3±0.2 / ±3 18±1 8.9± ±0.2 21±1 6.8±0.3 Ref /NA 7.3/NA 0.8/NA 0.4/NA 6/NA 3/NA NA NA NA NA Ref NA 0 NA 9.2/NA 9.2/NA 0.14/NA 0.14/NA 5/NA 5/NA 33 [d] NA NA NA [a] Wavelength > 700 nm. [b] Wavelength 700 nm. [c] Assuming Lambertian emission. [d] Measured in toluene. S23
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