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EP-4185591-B1 - ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

EP4185591B1EP 4185591 B1EP4185591 B1EP 4185591B1EP-4185591-B1

Inventors

  • ZINK, DANIEL
  • THIRION, DAMIEN
  • SEIFERMANN, STEFAN
  • DÜCK, Sebastian
  • PASHAZADEH, Ramin

Dates

Publication Date
20260513
Application Date
20210722

Claims (14)

  1. Organic molecule, comprising a structure of formula la: wherein R A is a moiety comprising a structure of formula II, III, or IV: which is bonded to the structure of formula la via the position marked by the dotted line; one Q of Formula II is N and the other Q of Formula II is CR 3 ; R 1 , R 2 , and R 3 are at each occurrence independently selected from the group consisting of: hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 3 , C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently substituted by C 1 -C 5 -alkyl, CN, CF 3 and Ph; R I , R II , R III , R IV , R VI , R VII , and R VIII are at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R 6 ) 2 , OR 6 , SR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , CF 3 , CN, halogen, 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 ; wherein the substituents R I , R II , R III , R IV , R VI , R VII , and R VIII independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more adjacent substituents R I , R II , R III , R IV , R VI , R VII or R VIII . R 6 is at each occurrence selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF 3 , CN, F, Si(C 1 -C 5 -alkyl) 3 , Si(Ph) 3 , C 1 -C 5 -alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -alkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkenyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkynyl, wherein optionally one or more hydrogen atoms are 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 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), whereby the term alkyl group is understood as linear, branched, or cyclic alkyl substituent; the term alkenyl comprises linear, branched, and cyclic alkenyl substituents; the term alkynyl comprises linear, branched, and cyclic alkynyl substituents; the term alkoxy comprises linear, branched, and cyclic alkoxy substituents; and the term thioalkoxy comprises linear, branched, and cyclic thioalkoxy substituents.
  2. Organic molecule according to claim 1, wherein R A is a moiety represented by one of the formulas IIa, IIb, Illa, and IVa: which is bonded to the structure of formula I or la via the position marked by the dotted line.
  3. Organic molecule according to any of claims 1 or 2, wherein the molecule comprises a structure of formula Ib or Ic:
  4. Organic molecule according to any of claims 1 to 3, wherein the molecule comprises a structure of formula Ib-1or Ib-2:
  5. Organic molecule according to any of claims 1 to 4, wherein R 1 , R", R III , R IV , R VI , R VII , and R VIII are at each occurrence independently selected from the group consisting of: hydrogen, deuterium, halogen, CN, CF 3 , SiMe 3 , SiPh 3 , C 1 -C 5 -alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently substituted C 1 -C 5 -alkyl, C 6 -C 18 -aryl, C 3 -C 17 -heteroaryl, CN or CF 3 ; C 3 -C 15 -heteroaryl, wherein optionally one or more hydrogen atoms are independently substituted by C 1 -C 5 -alkyl, C 6 -C 18 -aryl, C 3 -C 17 -heteroaryl, CN or CF 3 ; and N(Ph) 2 .
  6. Organic molecule according to any of claims 1 to 4, wherein R I , R I , R III , R IV , R VI , R VII , and R VIII are at each occurrence independently selected from the group consisting of: hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 3 , Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and N(Ph) 2 .
  7. Organic molecule according to any of claims 1 to 6, wherein R 6 is at each occurrence selected from the group consisting of: hydrogen, deuterium, halogen, CN, CF 3 , SiMe 3 , SiPh 3 , C 1 -C 5 -alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently substituted C 1 -C 5 -alkyl, C 6 -C 18 -aryl, C 3 -C 17 -heteroaryl, CN or CF 3 ; C 3 -C 15 -heteroaryl, wherein optionally one or more hydrogen atoms are independently substituted by C 1 -C 5 -alkyl, C 6 -C 18 -aryl, C 3 -C 17 -heteroaryl, CN or CF 3 ; and N(Ph) 2 .
  8. Use of an organic molecule according to any of claims 1 to 7 as a luminescent emitter in an optoelectronic device.
  9. Use according to claim 8, 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.
  10. Composition, comprising: (a) an organic molecule according to any of claims 1 to 7, 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, and (c) optionally, a dye and/or a solvent.
  11. Optoelectronic device, comprising an organic molecule according to any of claims 1 to 7 or a composition according to claim 10.
  12. Optoelectronic device according to claim 11 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.
  13. Optoelectronic device according to claim 11 or 12, comprising: - a substrate, - an anode, and - a cathode, wherein the anode or the cathode is 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.
  14. Method for producing an optoelectronic device, wherein an organic molecule according to any one of claims 1 to 7 or a composition according to claim 10 is used, in particular comprising the processing of the organic molecule by 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 CN 110 407 859 A describes an organic electroluminescent device containing the compound, wherein the compound has a structure represented by the following formula wherein X1, X2, and R21 to R30, and R40 are defined as disclosed in CN 110 407 859. CN 112 898 324 A, which is only relevant for novelty, discloses a compound, application thereof and an organic electroluminescent device. The compound has a structure as follows: wherein A, M, Z, X, Y, Ra, Rb, and Rn are defined as disclosed in CN 112 898 324 A. Xiao Liang et al: "Peripheral Amplification of Multi-Resonance Induced Thermally Activated Delayed Fluorescence for Highly Efficient OLEDs," Angewandte Chemie International Edition, Verlag Chemie, Hoboken, USA, vol. 57, no. 35, July 30, 2018, pages 11316-11320 describes compounds such as DABNA-1 and DABNA-2 that show high external quantum efficiency and good color purity, but the devices fabricated with these emitters exhibit poor stability with a sharp drop in efficiency roll-off. 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. Organic electroluminescent devices containing one or more light-emitting layers based on organics such as, e.g., organic light emitting diodes (OLEDs), light emitting electrochemical cells (LECs) and light-emitting transistors gain increasing importance. In particular, OLEDs are promising devices for electronic products such as screens, displays and illumination devices. In contrast to most electroluminescent devices essentially based on inorganics, organic electroluminescent devices based on organics are often rather flexible and producible in particularly thin layers. The OLED-based screens and displays already available today bear either good efficiencies and long lifetimes or good color purity and long lifetimes, but do not combine all three properties, i.e. good efficiency, long lifetime, and good color purity. Thus, there is still an unmet technical need for organic electroluminescent devices which have a high quantum yield, a long lifetime, and good color purity. The color purity or color point of an OLED is typically provided by CIEx and CIEy coordinates, whereas the color gamut for the next display generation is provided by so-called BT-2020 and DCPI3 values. Generally, in order to achieve these color coordinates, top emitting devices are needed to adjust the color coordinates by changing the cavity. In order to achieve high efficiency in top emitting devices while targeting this color gamut, a narrow emission spectrum in bottom emitting devices is required. The organic molecules according to the invention exhibit emission maxima in the sky blue, green or yellow spectral range. The organic molecules exhibit in particular emission maxima between 490 and 600 nm, more preferably between 500 and 560 nm, and even more preferably between 520 and 540 nm. Additionally, the molecules of the invention exhibit in particular a narrow - expressed by a small full width at half maximum (FWHM) - emission. The emission spectra of the organic molecules preferably show a full width at half maximum (FWHM) of less than or equal to 0.25 eV (≤ 0.25 eV), if not stated otherwise measured with 2% by weight of emitter in poly(methyl methacrylate) PMMA at room temperature. The photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 10 % 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 a narrow emission and high efficiency of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color and/or by employing the molecules according to the invention in an OLED display, a more accurate reproduction of visible colors in nature, i.e. a higher resolution in the displayed image, is achieved. In particular, the molecules can be used in combination with an energy pump to achieve hyper-fluorescence or hyper-phosphorescence. In these cases, another species comprised in an organic electroluminescent device transfers energy to the organic molecules of the invention which then emit light. The organic molecules according to the invention comprise or consist a structure of formula la wherein RA is a moiety comprising a structure of formula II, III, or IV: which is bonded to the structure of Formula la via the position marked by the dotted line. One Q of Formula II is N and the other Q of Formula II is CR3. R1, R2, and R3 are at each occurrence independently selected from the group consisting of: hydrogen, deuterium, halogen, Me, iPr, tBu, CN, CF3, SiMe3, SiPh3,C6-C18-aryl, wherein optionally