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EP-4392427-B1 - ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

EP4392427B1EP 4392427 B1EP4392427 B1EP 4392427B1EP-4392427-B1

Inventors

  • ZINK, DANIEL
  • THIRION, DAMIEN

Dates

Publication Date
20260506
Application Date
20220729

Claims (15)

  1. Organic molecule, comprising a structure represented by formula I: wherein X is selected from N and CR a ; R d and R e is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R d ) 2 , OR d , Si(R a ) 3 , B(OR a ) 2 , B(R a ) 2 , OSO 2 R a , CF 3 , CN, F, Cl, Br, I, C 1 -C 40 -alkyl, which is optionally substituted with one or more substituents R a and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R a C=CR a , C≡C, Si(R a ) 2 , Ge(R a ) 2 , S n (R a ) 2 , C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO 2 , NR a , O, S or CONR a ; C 1 -C 40 -alkoxy, which is optionally substituted with one or more substituents R a and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R a C=CR a , C≡C, Si(R a ) 2 , Ge(R a ) 2 , S n (R a ) 2 , C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO 2 , NR a , O, S or CONR a ; C 1 -C 40 -thioalkoxy, which is optionally substituted with one or more substituents R a and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R a C=CR a , C≡C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO 2 , NR a , O, S or CONR a ; C 2 -C 40 -alkenyl, which is optionally substituted with one or more substituents R a and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R a C=CR a , C≡C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO 2 , NR a , O, S or CONR a ; C 2 -C 40 -alkynyl, which is optionally substituted with one or more substituents R a and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R a C=CR a , C≡C, Si(R a ) 2 , Ge(R a ) 2 , S n (R a ) 2 , C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO 2 , NR a , O, S or CONR a ; C 6 -C 60 -aryl, which is optionally substituted with one or more substituents R a ; and C 2 -C 57 -heteroaryl, which is optionally substituted with one or more substituents R a ; 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 57 -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 5 -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 5 -alkyl substituents; C 2 -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 2 -C 17 -heteroaryl) 2 , and N(C 2 -C 17 -heteroaryl)(C 6 -C 18 -aryl); wherein any of the substituents R a , R d , R e , R 5 , and R 6 optionally independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more substituents R a , R d , R e , R 5 and/or R 6 ; wherein alkyl, alkenyl, alkynyl, alkoxy, thioalkoxy are linear, branched or cyclic.
  2. The organic molecule according to claim 1, comprising a structure formula II:
  3. The organic molecule according to claim 1 or 2, comprising a structure formula III: wherein A is selected from the group consisting of O, S, and NR 5 .
  4. The organic molecule according any of claims 1 to 3, comprising a structure of formula IIb: wherein R b is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R 5 ) 2 , OR 5 , 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 2 -C 57 -heteroaryl, which is optionally substituted with one or more substituents R 5 .
  5. The organic molecule according to any of claims 1 to 4, comprising a structure of formula VIa, formula VIb, formula VIc or formula IVd: wherein R c is at each occurrence selected from the group of hydrogen and R f , wherein R f is at each occurrence selected from the group consisting of: Me, i Pr, t Bu, 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.
  6. The organic molecule according to any of claims 1 to 5, comprising a structure of formula IVc:
  7. The organic molecule according to claim 1 to 6, wherein R a 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 Me, i Pr, t Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  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, comprising a material selected from the group consisting of a TADF material and a phosphorescence material.
  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 phosphorescence material comprising iridium.
  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 510 nm to 550 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

The invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices. WO 2020/135953 A1 discloses an organic compound with boron-nitrogen heterocycles and their use in OLEDs. 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 invention is defined as by the features of independent claims 1 and 15. The dependent claims provide preferred embodiments. 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 op- toelectronic 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 below 560 nm, more preferably below 550 nm, even more preferably below 545 nm or even below 540 nm. It will typically be above 500 nm, more preferably above 510 nm, even more preferably above 515 nm or even above 520 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 X is selected from the group consisting of N and CRa;Rd and Re is independently from each other selected from the group consisting of:is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(Ra)2, ORa, Si(Ra)3, B(ORa)2, B(Ra)2, OSO2Ra, CF3, CN, F, Cl, Br, I,C1-C40-alkyl,which is optionally substituted with one or more substituents Ra andwherein one or more non-adjacent CH2-groups are optionally substituted by RaC=CR a, C≡C, Si(Ra)2, Ge(Ra)2, Sn(Ra)2, C=O, C=S, C=Se, C=NRa, P(=O)(Ra), SO, SO2, NRa, O, S or CONRa;C1-C40-alkoxy,which is optionally substituted with one or more substituents Ra andwherein one or more non-adjacent CH2-groups are optionally substituted by RaC=CR a, C≡C, Si(Ra)2, Ge(Ra)2, Sn(Ra)2, C=O, C=S, C=Se, C=NRa, P(=O)(Ra), SO, SO2, NRa, O, S or CONRa;C1-C40-thioalkoxy,which is optionally substituted with one or more substituents Ra andwherein one or more non-adjacent CH2-groups are optionally substituted by RaC=CR a, C≡C, Si(Ra)2, Ge(Ra)2, Sn(Ra)2, C=O, C=S, C=Se, C=NRa, P(=O)(Ra), SO, SO2, NRa, O, S or CONRa;C2-C40-alkenyl,which is optionally substituted with one or more substituents Ra andwherein one or more non-adjacent CH2-groups are optionally substituted by RaC=CR a, C≡C, Si(Ra)2, Ge(Ra)2, Sn(Ra)2, C=O, C=S, C=Se, C=NRa, P(=O)(Ra), SO, SO2, NRa, O, S or CONRa;C2-C40-alkynyl,which is optionally substituted with one or more substituents Ra andwherein one or more non-adjacent CH2-groups are optionally substituted by RaC=CR a, C≡C, Si(Ra)2, Ge(Ra)2, Sn(Ra)2, C=O, C=S, C=Se, C=NRa, P(=O)(Ra), SO, SO2, NRa, O, S or CONRa;C6-C60-aryl,which is optionally substituted with one or more substituents Ra; andC2-C37-heteroaryl,which is optionally substituted with one or more substituents Ra;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