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EP-3670507-B1 - ORGANIC MOLECULES FOR USE IN OPTOELECTRONIC DEVICES

EP3670507B1EP 3670507 B1EP3670507 B1EP 3670507B1EP-3670507-B1

Inventors

  • DANZ, MICHAEL
  • MUHAMMAD, ASHRAF

Dates

Publication Date
20260506
Application Date
20191204

Claims (10)

  1. Organic molecule, comprising or consisting of a structure of formula Illaa, formula Illab, formula Illac: R I is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, C 1 -C 5 -alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C 2 -C 8 -alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C 2 -C 8 -alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; R 11 , R 12 , R 13 , R 14 and R 15 is at each occurrence independently selected from the group consisting of hydrogen, deuterium, CN, C 1 -C 5 -alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C 2 -C 8 -alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C 2 -C 8 -alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; R a is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I, C 1 -C 40 -alkyl, which is optionally substituted with one or more substituents R 5 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; C 1 -C 40 -alkoxy, which is optionally substituted with one or more substituents R 5 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; C 1 -C 40 -thioalkoxy, which is optionally substituted with one or more substituents R 5 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; C 2 -C 40 -alkenyl, which is optionally substituted with one or more substituents R 5 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; C 2 -C 40 -alkynyl, which is optionally substituted with one or more substituents R 5 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; C 6 -C 60 -aryl, which is optionally substituted with one or more substituents R 5 ; and C 3 -C 57 -heteroaryl, which is optionally substituted with one or more substituents R 5 ; R 5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br, I, C 1 -C 40 -alkyl, which is optionally substituted with one or more substituents R 6 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; C 1 -C 40 -alkoxy, which is optionally substituted with one or more substituents R 6 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; C 1 -C 40 -thioalkoxy, which is optionally substituted with one or more substituents R 6 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; C 2 -C 40 -alkenyl, which is optionally substituted with one or more substituents R 6 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; C 2 -C 40 -alkynyl, which is optionally substituted with one or more substituents R 6 and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; C 6 -C 60 -aryl, which is optionally substituted with one or more substituents R 6 ; and C 3 -C 57 -heteroaryl, which is optionally substituted with one or more substituents R 6 ; R 6 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 5 -alkyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -alkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -thioalkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkenyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkynyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF 3 , or F; C 6 -C 18 -aryl, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents; C 3 -C 17 -heteroaryl, which is optionally substituted with one or more C 1 -C 5 -alkyl substituents; N(C 6 -C 18 -aryl) 2 ; N(C 3 -C 17 -heteroaryl) 2 , and N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl); wherein, optionally, the substituents R a or R 5 independently form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more other substituents R a or R 5 .
  2. The organic molecule according to claim 1, wherein R I , R 11 , R 12 , R 13 , R 14 , R 15 is at each occurrence independently selected from the group consisting of H and methyl.
  3. A method for preparing an organic molecule according to one or more of claims 1 or 2, wherein a R 11 -R 15 -substituted 2,4-dichloro-6-phenyltriazine is used as reactant.
  4. Use of an organic molecule according to one or more of claims 1 or 2 as a luminescent emitter and/or a host material and/or an electron transport material and/or a hole injection material and/or a hole blocking material in an optoelectronic device.
  5. The use according to claim 4, wherein the optoelectronic device is selected from the group consisting of: • organic light-emitting diodes (OLEDs), • light-emitting electrochemical cells, • OLED-sensors, • organic diodes, • organic solar cells, • organic transistors, • organic field-effect transistors, • organic lasers, and • down-conversion elements.
  6. Composition, comprising: (a) an organic molecule according to one or more of claims 1 or 2, in particular in the form of an emitter and/or a host, and (b) an emitter and/or a host material, which differs from the organic molecule according to claims 1 or 2, and (c) optionally, one or more dyes and/or one or more solvents.
  7. The composition according to claim 6, comprising: (i) 1-50 % by weight, preferably 5-40 % by weight, in particular 10-30 % by weight, of one organic molecule according to the invention; (ii) 5-98 % by weight, preferably 30-93.9 % by weight, in particular 40-88% by weight, of one host compound H; (iii) 1-30 % by weight, in particular 1-20 % by weight, preferably 1-5 % by weight, of at least one further emitter molecule with a structure differing from the structure of the organic molecule according to claims 1 or 2; and (iv) optionally, 0-94 % by weight, preferably 0.1-65 % by weight, in particular 1-50 % by weight, of at least one further host compound D with a structure differing from the structure of the organic molecules according to claims 1 or 2; and (v) optionally, 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent.
  8. Optoelectronic device, comprising an organic molecule according to one or more of claims 1 or 2 or a composition according to claim 6 or claim 7, in particular in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser, and down-conversion element.
  9. The optoelectronic device according to claim 8, comprising - a substrate, - an anode, and - a cathode, wherein the anode or the cathode are disposed on the substrate, and - a light-emitting layer, which is arranged between the anode and the cathode and which comprises an organic molecule or the composition.
  10. A method for producing an optoelectronic device, wherein an organic molecule according to one or more of claims 1 or 2 or a composition according to claim 6 or 7 is used, in particular comprising the processing of the organic molecule using a vacuum evaporation method or from a solution.

Description

The invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices. Prior art EP 3 275 968 A1 describes a light-emitting material which is, for example, represented by the following Chemical Formula 12: wherein R34 to R45, Sub1 and Sub2 are defined as disclosed in EP 3 275 968 A1.KR 2017 0113808 discloses a heat-active delayed fluorescent material, for example, represented by chemical formula 3 which is identical to chemical formula 12 of EP 3 275 968 A1, wherein R34 to R45, Sub1 and Sub2 are defined as disclosed in KR 2017 0113808. KR 2016 0059733 relates to an organic light emitting compound represented by chemical formula 1 and an organic electroluminescent device comprising the same: wherein Z1, Z2, Z3, L, X, and HTU are defined as disclosed in KR 2016 0059733. Description The object of the present invention is to provide molecules which are suitable for use in optoelectronic devices. This object is achieved by the invention which provides a new class of organic molecules. The object is solved by the subject-matter of the independent claims. Further advantageous embodiments of the present invention are described in the respective sub-claims. The invention is defined by the claims. Embodiments not covered by the claimed subject-matter do not form part of the invention. The organic molecules of the invention are purely organic molecules, i.e. they do not contain any metal ions in contrast to metal complexes known for use in optoelectronic devices. The organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range. The photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 26 % or more. The molecules of the invention exhibit in particular thermally activated delayed fluorescence (TADF). The use of the molecules according to the invention in an optoelectronic device, for example, an organic light-emitting diode (OLED), leads to higher efficiencies of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color. In particular, the molecules can be used in combination with a fluorescence emitter to enable so-called hyperfluorescence. The organic molecules according to the invention comprise or consist of a structure of formula Illaa, formula Illab, formula Illac: RI is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium,C1-C5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C2-C8-alkenyl,wherein one or more hydrogen atoms are optionally substituted by deuterium; and C2-C8-alkynyl,wherein one or more hydrogen atoms are optionally substituted by deuterium.R11, R12, R13, R14 and R15 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, CN,C1-C5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium;C2-C8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; andC2-C8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium..Ra is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, N(R5)2, Si(R5)3, B(OR5)2, OSO2R5, CF3, CN, F, Br, I, C1-C40-alkyl, which is optionally substituted with one or more substituents R5 andwherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=O, C=S, C=Se, C=NR5, P(=O)(R5), SO, SO2, NR5, O, S or CONR5;C1-C40-alkoxy, which is optionally substituted with one or more substituents R5 andwherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=O, C=S, C=Se, C=NR5, P(=O)(R5), SO, SO2, NR5, O, S or CONR5;C1-C40-thioalkoxy, which is optionally substituted with one or more substituents R5 andwherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=O, C=S, C=Se, C=NR5, P(=O)(R5), SO, SO2, NR5, O, S or CONR5;C2-C40-alkenyl, which is optionally substituted with one or more substituents R5 andwherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=O, C=S, C=Se, C=NR5, P(=O)(R5), SO, SO2, NR5, O, S or CONR5;C2-C40-alkynyl, which is optionally substituted with one or more substituents R5 andwherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C=O, C=S, C=Se, C=NR5, P(=O)(R5), SO, SO2, NR5, O, S or CONR5;C6-C60-aryl, which is optionally substituted with one or more substituents R5; andC3-C57-heteroaryl, which is optionally substituted with one or more substituents R5.R5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, N(R6)2, OR6, Si(R6)3, B(OR6)2, OSO2R6, C