An unprecedented roll-off ratio in high-performing red TADF OLED emitters featuring 2,3-indole-annulated naphthalene imide and auxiliary donors.
Grzelak, Magdalena; Kumar, Dharmendra; Kochman, Michał Andrzej; Morawiak, Maja; Wiosna-Sałyga, Gabriela; Kubas, Adam; Data, Przemysław; Lindner, Marcin; Chemical science 15 (2024) 8404–8413; doi:10.1039/d4sc01391c

data_1571530
_publ_section_title
;
 An unprecedented roll-off ratio in high-performing red TADF OLED emitters
 featuring 2,3-indole-annulated naphthalene imide and auxiliary donors.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              8404
_journal_page_last               8413
_journal_paper_doi               10.1039/d4sc01391c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C43 H35 N3 O3, C H2 Cl2'
_chemical_formula_sum            'C44 H37 Cl2 N3 O3'
_chemical_formula_weight         726.66
_chemical_name_common            'JW 156'
_chemical_name_systematic        'MMG 156'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-11
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-02-16 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5023(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9323(4)
_cell_length_b                   11.41330(17)
_cell_length_c                   13.3857(2)
_cell_measurement_reflns_used    9456
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.8830
_cell_measurement_theta_min      4.2900
_cell_volume                     3624.96(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_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    -60.00 -35.00   0.50    0.20    --    0.00 121.00 -81.00   50
  2  \w    -73.00 -47.00   0.50    0.20    --    0.00 153.00  77.00   52
  3  \w    -12.00  14.00   0.50    0.20    --    0.00  57.00   0.00   52
  4  \w    -15.00  78.00   0.50    0.20    --    0.00  57.00-150.00  186
  5  \w     36.00  62.00   0.50    0.20    --    0.00  57.00   0.00   52
  6  \w   -130.00-105.00   0.50    2.00    --  -54.00-121.00-164.00   50
  7  \w    -99.00 -54.00   0.50    2.00    --  -54.00-153.00  36.00   90
  8  \w   -133.00 -86.00   0.50    2.00    --  -54.00 -99.00-120.00   94
  9  \w   -127.00 -91.00   0.50    2.00    --  -54.00 -99.00 -60.00   72
 10  \w   -138.00 -93.00   0.50    2.00    --  -54.00 -99.00 -90.00   90
 11  \w   -140.00-112.00   0.50    2.00    --  -54.00 -99.00  60.00   56
 12  \w   -140.00 -90.00   0.50    2.00    --  -54.00 -99.00-150.00  100
 13  \w     36.00 110.00   0.50    2.00    --   55.77-121.00-164.00  148
 14  \w     93.00 126.00   0.50    2.00    --   55.77 153.00  77.00   66
 15  \w     35.00 134.00   0.50    2.00    --   55.77  57.00 -90.00  198
 16  \w     83.00 110.00   0.50    5.00    --  111.55-121.00-164.00   54
 17  \w     99.00 167.00   0.50    5.00    --  111.55 121.00 -81.00  136
 18  \w     74.00 132.00   0.50    5.00    --  111.55-153.00  36.00  116
 19  \w     76.00 116.00   0.50    5.00    --  111.55 153.00  77.00   80
 20  \w     77.00 117.00   0.50    5.00    --  111.55  61.00 -90.00   80
 21  \w     85.00 177.00   0.50    5.00    --  111.55  61.00 -30.00  184
 22  \w     83.00 116.00   0.50    5.00    --  111.55 -61.00 150.00   66
 23  \w     80.00 105.00   0.50    5.00    --  111.55 -94.00-150.00   50
 24  \w     77.00 156.00   0.50    5.00    --  111.55  61.00-150.00  158
 25  \w     27.00  69.00   0.50    5.00    --  111.55 -94.00-150.00   84
 26  \w     49.00 102.00   0.50    5.00    --  111.55-111.00  90.00  106
 27  \w    116.00 149.00   0.50    5.00    --  111.55  77.00 -90.00   66
 28  \w     70.00 112.00   0.50    5.00    --  111.55  77.00 -90.00   84
 29  \w    139.00 168.00   0.50    5.00    --  111.55  61.00-120.00   58
 30  \w     70.00 159.00   0.50    5.00    --  111.55  77.00   0.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0265972000
_diffrn_orient_matrix_UB_12      0.0737324000
_diffrn_orient_matrix_UB_13      0.0902946000
_diffrn_orient_matrix_UB_21      -0.0097377000
_diffrn_orient_matrix_UB_22      0.1120939000
_diffrn_orient_matrix_UB_23      -0.0640214000
_diffrn_orient_matrix_UB_31      -0.0584272000
_diffrn_orient_matrix_UB_32      0.0148552000
_diffrn_orient_matrix_UB_33      0.0349340000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.201
_diffrn_reflns_theta_min         3.726
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         7095
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0588P)^2^+1.3822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5724
_reflns_number_total             7095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01391c2.cif
_cod_data_source_block           2023_08_10_dt_jw-156_n_auto
_cod_depositor_comments
'Adding full bibliography for 1571528--1571532.cif.'
_cod_original_cell_volume        3624.94(10)
_cod_database_code               1571530
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H37 Cl2 N3 O3'
_chemical_oxdiff_usercomment     '100 K'
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.749
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1A-C49 \\sim Cl1B-C49
 with sigma of 0.02
 Cl1B-C49 \\sim Cl1A-C49
 with sigma of 0.01
3. Others
 Sof(H49C)=Sof(H49D)=Sof(Cl1B)=1-FVAR(1)
 Sof(H49A)=Sof(H49B)=Sof(Cl1A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C49(H49A,H49B), C49(H49C,H49D)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C17(H17), C23(H23),
 C25(H25), C33(H33), C34(H34), C35(H35), C36(H36), C40(H40), C41(H41), C42(H42),
  C43(H43)
4.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C48(H48A,H48B,
 H48C)
;
_shelx_res_checksum              54161
_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.833