• 专利标题:   New substituted indacenetetrone compounds used in e.g. photoelectric conversion layer, organic and/or hybrid module for optoelectronic application e.g. image sensor and organic photovoltaics comprising organic photoelectric conversion layer.
  • 专利号:   WO2022207312-A1
  • 发明人:   DANNER D, DEICHMANN V A F, ROBERTS A, CHERCKA D, ROSSELLI S, WEGNER B, KNORR N, YAKUTKIN V, MITEVA T, NELLES G
  • 专利权人:   SONY GROUP CORP, SONY EURO BV
  • 国际专利分类:   C07C001/00, C07D201/00, C09B057/00, H01L027/146, H01L027/30, H01L051/00
  • 专利详细信息:   WO2022207312-A1 06 Oct 2022 C09B-057/00 202293 Pages: 49 English
  • 申请详细信息:   WO2022207312-A1 WOEP056719 15 Mar 2022
  • 优先权号:   EP165612

▎ 摘  要

NOVELTY - Substituted indacenetetrone compounds (I) are new. USE - (I) are useful: in photoelectric conversion layer; in an organic and/or hybrid module for optoelectronic application e.g. image sensor, photodiode, organic photovoltaics, comprising organic photoelectric conversion layer(s), organic light-emitting diodes and organic thin film transistor organic modules; in a buffer layer, e.g. a hole blocking layer, an electron blocking layer, a hole transport layer, or an electron transport layer; and in hybrid Silicon-organic image sensor or organic image sensor (all claimed). ADVANTAGE - (I) exhibit absorption in the visible absorption (400-700 nm), absorbs in the blue absorption range or absorbs in the green absorption range or absorbs in the red absorption range, preferably shows an extinction coefficient of less than 104LmoH/cm. DETAILED DESCRIPTION - Substituted indacenetetrone compounds of formula (I) are new. R=e.g. linear or branched alkyl, cycloalkyl, aryl, alkylamine, arylamine, biaryl, heteroaryl, furanyl, thienyl, thieno3,2-bthienyl, benzo1,2-b:4,5-b'dithienyl, selenophenyl, naphthyl, quinolinyl, pyrrolyl, indolyl, and substituted heterocyclyl moieties of formulae (a1)-(a10); R1, R2=H, halo, CF , CN, alkoxy, cycloalkoxy, alkyl (preferably -CH ), cycloalkyl, alkenyl, alkynyl, -NH , benzyl, heteroaryl or aryl; X1, Y1=O, S, Se, Te, NR1A1, CR1B1, or SiR1c; and R3, R1A1, R1B1, R1c=alkyl, cycloalkyl, alkenyl, alkynyl, -NH , benzyl, heteroaryl or aryl. Provided that, (I) is not (2E,6E)-2,6-bis(4-(dinonylamino)benzylidene)-s-indacene-1,3,5,7(2H,6H)-tetraone, (2E,6E)-2,6-bis((5-(4-(dinonylamino)phenyl)thiophen-2-yl)methylene)-s-indacene-1,3,5,7(2H,6H)-tetraone, (2E,6E)-2,6-bis(4-(dipentylamino)benzylidene)-s-indacene-1,3,5,7(2H,6H)-tetraone, (2E,6E)-2-((E)-3-(5-(dipentylamino)thiophen-2-yl)allylidene)-6-((5-(dipentylamino)thiophen-2-yl)methylene)-s-indacene-1,3,5,7(2H,6H)-tetraone, (2E,6E)-2,6-bis((E)-2-(1-heptyl-3,3-dimethylindolin-2-ylidene)ethylidene)-s-indacene-1,3,5,7(2H,6H)-tetraone, (2E,6E)-2,6-bis(thiophen-2-ylmethylene)-s-indacene-1,3,5,7(2H,6H)-tetraone and (2E,6E)-2,6-bis(4-(diphenylamino)benzylidene)-s-indacene-1,3,5,7(2H,6H)-tetraone. INDEPENDENT CLAIMS are also included for: a photoelectric conversion layer comprising (I), and optionally comprising further compound(s); a buffer layer comprising (I) and optionally comprising further compound(s), where the buffer layer is an n-buffer layer and/or p-buffer layer; an organic module (OM1) comprising the photoelectric conversion layer; an organic material or organic module comprising the photoelectric conversion layer(s), and optionally comprising further compound(s), where (I) exhibits absorption in the visible absorption 480-600 nm of more than 104 cm; an organic module (OM2) comprising the photoelectric conversion layer and optionally comprising further compound(s), where (I) exhibits absorption in the infrared absorption range, preferably 700-900 nm, with an absorption coefficient 700-900 nm; a device, comprising at least one (I), the photoelectric conversion layer, buffer layer, organic module, and organic material or organic module, where the device is preferably an organic image sensor, an hybrid image sensor, photodiode, organic photovoltaics, organic light-emitting diode, organic thin-film transistor; an organic image sensor, comprising the organic photoelectric conversion unit, at least one electrode, a substrate, and optionally, a second electrode on top of the photoelectric conversion layer(s), preferably not comprising color filter(s); and a hybrid silicon-organic image sensor or organic image sensor, comprising the an organic photoelectric conversion unit or units, optionally, a silicon based photoelectric conversion unit, metal wiring, a complementary metal-oxide-semiconductor substrate, and insulating layer(s), preferably oxide.