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EP-4387975-B1 - ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

EP4387975B1EP 4387975 B1EP4387975 B1EP 4387975B1EP-4387975-B1

Inventors

  • ZINK, DANIEL
  • DANZ, MICHAEL
  • THIRION, DAMIEN

Dates

Publication Date
20260506
Application Date
20220819

Claims (15)

  1. Organic molecule, comprising a structure represented by formula I wherein R a is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Cl, 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 2 -C 37 -heteroaryl, which is optionally substituted with one or more substituents R 5 ; R 5 is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , B(R 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 2 -C 37 -heteroaryl, which is optionally substituted with one or more substituents R 6 ; R 6 is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 3 -alkyl, wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; C 1 -C 3 -alkoxy, wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; C 1 -C 3 -thioalkoxy, wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkenyl, wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; C 2 -C 3 -alkynyl, wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; C 6 -C 18 -aryl, which is optionally substituted with one or more C 1 -C 3 -alkyl substituents; C 2 -C 17 -heteroaryl, which is optionally substituted with one or more C 1 -C 3 -alkyl substituents; N(C 6 -C 18 -aryl) 2 ; N(C 2 -C 17 -heteroaryl) 2 , and N(C 2 -C 17 -heteroaryl)(C 6 -C 18 -aryl); wherein optionally, any of the substituents R a , R 5 , and R 6 independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more substituents R a , R 5 and/or R 6 .
  2. The organic molecule according to claim 1, comprising a structure of formula Id:
  3. The organic molecule according to claim 1 or 2, comprising a structure of formula II: wherein, R e is selected from the group consisting of hydrogen, Me, i Pr, t Bu, and Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph.
  4. The organic molecule according any of claims 1 to 3, comprising a structure of formula II-1: wherein, R e# is independently selected from the group consisting of a C 1 -C 6 -alkyl substituent and phenyl, which is optionally substituted with one or more C 1 -C 6 -alkyl substituents.
  5. The organic molecule according to any of claims 1 to 4, comprising a structure formula IIIa, formula IIIb, formula IIIc or formula IIId: wherein R c is at each occurrence independently from another selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF 3 , Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of M e , i Pr, t Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  6. The organic molecule according to any of claims 1 to 5, comprising a structure of formula IV-1 wherein R f is at each occurrence independently from each other selected from the group consisting of hydrogen, Me, i Pr, t Bu, CN, CF 3 , Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  7. The organic molecule according to any of claims 1 to 5, comprising a structure of formula IV-2 wherein R f is at each occurrence selected from the group consisting of R a and both R f together form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system.
  8. Composition, comprising: (a) an organic molecule according to any of claims 1 to 7, in particular in the form of an emitter, and (b) a host material, which differs from the organic molecule, and (c) optionally, a dye and/or a solvent.
  9. The composition according to claim 8 containing 0.1-30% by weight, preferably 0.8-15% by weight, in particular 1.5-5% by weight, of the organic molecule.
  10. The composition according to claim 8 or 9, wherein the host material comprises a structure represented by formula 4 wherein each Ar is independently selected from the group consisting of C 6 -C 60 -aryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 -heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; and C 3 -C 57 -heteroaryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 - heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; and each A 1 is independently selected from the group consisting of consisting of hydrogen; deuterium; C 6 -C 60 -aryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 -heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; C 3 -C 57 -heteroaryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 - heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; and C 1 -C 40 -(hetero)alkyl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 - heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl.
  11. Optoelectronic device, comprising an organic molecule according to any of claims 1 to 7, in particular as a luminescent emitter, or a composition according to any of claims 8 to 10.
  12. The optoelectronic device according to claim 11, which is selected from the group consisting of: · organic diodes, · organic light-emitting diodes (OLEDs), · light-emitting electrochemical cells, · OLED-sensors, · organic solar cells, · organic transistors, · organic field-effect transistors, · organic lasers, and down-conversion elements.
  13. The optoelectronic device according to claim 11 or 12, comprising: a host material comprising a structure represented by formula 4 wherein each Ar is independently selected from the group consisting of C 6 -C 60 -aryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 -heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; and C 3 -C 57 -heteroaryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 - heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; and each A 1 is independently selected from the group consisting of consisting of hydrogen; deuterium; C 6 -C 60 -aryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 -heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; C 3 -C 57 -heteroaryl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 - heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl; and C 1 -C 40 -(hetero)alkyl, which is optionally substituted with one or more residues selected from the group consisting of C 6 -C 60 -aryl, C 3 -C 57 - heteroaryl, halogen, and C 1 -C 40 -(hetero)alkyl.
  14. The optoelectronic device according to any of claims 11 to 13, 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 the organic molecule or the composition.
  15. A method for generating light at a wavelength from 440 nm to 470 nm, comprising the steps of: (i) providing an optoelectronic device according to any of claims 11 to 14; and (ii) applying an electrical current to the optoelectronic device.

Description

Technical Field The invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices. Background Light-emitting organic molecules and their use in optoelectronic devices are disclosed in, e.g., WO2020135953A1. Disclosure of Invention Technical Problem The object of the present invention is to provide molecules which are suitable for use in optoelectronic devices. Solution to Problem This object is achieved by the invention which provides a new class of organic molecules. According to the invention the organic molecules are purely organic molecules, i.e. they do not contain any metal ions in contrast to metal complexes known for use in optoelectronic devices. According to the present invention, the organic molecules exhibit emission maxima in the blue or sky-blue spectral range. The organic molecules exhibit in particular emission maxima between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm. The photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 50 % or more. 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 or higher color purity, expressed by the full width at half maximum (FWHM) of emission, of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color. The organic light-emitting molecule of the invention comprises or consists of a structure of formula I wherein Ra is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, B(R5)2, OSO2R5, CF3, CN, F, Br, I, Cl,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=CR 5, 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=CR 5, 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=CR 5, 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=CR 5, 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=CR 5, 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; andC2-C37-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, B(R6)2, OSO2R6, CF 3, CN, F, Br, I,C1-C40-alkyl,which is optionally substituted with one or more substituents R6 andwherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR 6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=O, C=S, C=Se, C=NR6, P(=O)(R6), SO, SO2, NR6, O, S or CONR6;C1-C40-alkoxy,which is optionally substituted with one or more substituents R6 andwherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR 6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=O, C=S, C=Se, C=NR6, P(=O)(R6), SO, SO2, NR6, O, S or CONR6;C1-C40-thioalkoxy,which is optionally substituted with one or more substituents R6 andwherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR 6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=O, C=S, C=Se, C=NR6, P(=O)(R6), SO, SO2, NR6, O, S or CONR6;C2-C40-alkenyl,which is optionally substituted with one or more substituents R6 andwherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR 6, C=C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=O, C=S, C=Se, C=NR6, P(=O)(R6), SO, SO2, NR6, O, S or CONR6;C2-C40-alkynyl,which is optionally substituted with one or more substituents R6 andwherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR 6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C=O, C=S, C=Se, C=NR6, P(=O)(R6), SO, SO2, NR6, O, S or CONR6;C6-C60-aryl,which is optionally substituted with one or more substituents R6; andC2-C57-heteroaryl,which is optionally substituted with one or more substituents R6;R6 is at each occurrence independently from another selected from the gro