Spiro-Based Thermally Activated Delayed Fluorescence Emitters with Reduced Nonradiative Decay for High-Quantum-Efficiency, Low-Roll-Off, Organic Light-Emitting Diodes.
Sharma, Nidhi; Maciejczyk, Michal; Hall, David; Li, Wenbo; Liégeois, Vincent; Beljonne, David; Olivier, Yoann; Robertson, Neil; Samuel, Ifor D. W.; Zysman-Colman, Eli; ACS applied materials & interfaces 13 (2021) 44628–44640; doi:10.1021/acsami.1c12234

data_4519038
_publ_section_title
;
 Spiro-Based Thermally Activated Delayed Fluorescence Emitters with
 Reduced Nonradiative Decay for High-Quantum-Efficiency, Low-Roll-Off,
 Organic Light-Emitting Diodes.
;
_journal_issue                   37
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              44628
_journal_page_last               44640
_journal_paper_doi               10.1021/acsami.1c12234
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         '2(C H2 Cl2), C77 H60 N2 O3 P2, C6 H14'
_chemical_formula_sum            'C85 H78 Cl4 N2 O3 P2'
_chemical_formula_weight         1379.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.014(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9417(11)
_cell_length_b                   9.4035(4)
_cell_length_c                   33.0239(19)
_cell_measurement_reflns_used    4732
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      24.7400
_cell_measurement_theta_min      3.4100
_cell_volume                     7109.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -25.00  23.00   1.00   30.00    --  -15.82 -99.00-150.00   48
  2  \w     -2.00  87.00   1.00   30.00    --   17.38  37.00 -90.00   89
  3  \w      1.00  85.00   1.00   30.00    --   17.38  57.00 -90.00   84
  4  \w    -50.00  44.00   1.00   30.00    --   17.38 -77.00 -30.00   94
  5  \w    -66.00 -29.00   1.00   30.00    --  -15.82 119.00 172.51   37
  6  \w     -2.00  87.00   1.00   30.00    --   17.38  37.00  90.00   89
  7  \w    -50.00  34.00   1.00   30.00    --   17.38 -57.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0304306000
_diffrn_orient_matrix_UB_12      -0.0055974000
_diffrn_orient_matrix_UB_13      -0.0101130000
_diffrn_orient_matrix_UB_21      -0.0055052000
_diffrn_orient_matrix_UB_22      0.0089507000
_diffrn_orient_matrix_UB_23      0.0198185000
_diffrn_orient_matrix_UB_31      -0.0016208000
_diffrn_orient_matrix_UB_32      0.0747061000
_diffrn_orient_matrix_UB_33      -0.0031248000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23812
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        20.814
_diffrn_reflns_theta_max         20.814
_diffrn_reflns_theta_min         2.905
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             2896
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of hexane and dichloromethane by evaporation'
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1202P)^2^+32.5089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2912
_reflns_number_total             3710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c12234_si_002.cif
_cod_data_source_block           nr17026
_cod_database_code               4519038
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C86 H77 Cl4 N2 O2 P2'
_chemical_oxdiff_usercomment     '@ 120 K SFX-POMeDPA'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.885
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16),
 C17(H17), C19(H19), C20(H20), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              11045
_shelx_hkl_checksum              49194
_olex2_date_sample_submission    2017-11-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id SFX-POMeDPA
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.133
_oxdiff_exptl_absorpt_empirical_full_min 0.884