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EP-3824500-B1 - COMPOUND AND ORGANIC SEMICONDUCTING LAYER, ORGANIC ELECTRONIC DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE COMPRISING THE SAME

EP3824500B1EP 3824500 B1EP3824500 B1EP 3824500B1EP-3824500-B1

Inventors

  • GALAN, Elena
  • SCHULZE, Benjamin
  • WUTKE, JENS
  • HARTMANN, HORST

Dates

Publication Date
20260506
Application Date
20190716

Claims (17)

  1. A compound according to formula 1: wherein R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, substituted or unsubstituted C 6 to C 38 aryl, substituted or unsubstituted C 3 to C 36 heteroaryl or C 1 to C 16 alkyl group, -PO(R') 2 , D, F, CN, or formula 2; wherein the substituents are selected from C 6 to C 18 aryl, C 3 to C 25 heteroaryl, -PO(R') 2 , D, F or CN, partially or perfluorinated C 1 to C 16 alkyl, C 1 to C 16 alkoxy, partially or perfluorinated C 1 to C 16 alkoxy, partially or perdeuterated C 1 to C 16 alkoxy; R' is independently selected from alkyl, aryl or heteroaryl; a, b, c, d and e are independently 0, 1 or 2, wherein at least one of a, b, c or d is 1 or 2; wherein at least one of R 1 , R 2 , R 3 or R 4 is formula 2; Ar 1 is selected from substituted or unsubstituted C 6 to C 38 arylene, substituted or unsubstituted C 3 to C 36 heteroarylene or C 1 to C 16 alkylene group, wherein the substituents are selected from C 6 to C 18 aryl, C 3 to C 25 heteroaryl, -PO(R') 2 , D, F or CN, partially or perfluorinated C 1 to C 16 alkyl, C 1 to C 16 alkoxy, partially or perfluorinated C 1 to C 16 alkoxy, partially or perdeuterated C 1 to C 16 alkoxy; Ar 2 is selected from F1, F2, F4, F5 and F7 to F13: wherein R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are independently selected from single bond, hydrogen, substituted or unsubstituted phenyl, naphthyl, biphenyl, pyridinyl, dibenzofuryl, benzofuranyl, dibenzothienyl, benzothiophenyl, anthracenyl, phenanthryl, carbazolyl, wherein the substituents are selected from C 6 to C 18 aryl, C 3 to C 25 heteroaryl, - PO(R') 2 , D, F or CN, partially or perfluorinated C 1 to C 16 alkyl, C 1 to C 16 alkoxy, partially or perfluorinated C 1 to C 16 alkoxy, partially or perdeuterated C 1 to C 16 alkoxy; and wherein one of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 represents a single bond only, and the single bond is the single bond that bonds Ar 2 to Ar 1 . wherein Ar 1 does not contain one or more CN substituents when Ar 2 is substituted or unsubstituted C 6 to C 38 aryl; wherein the following compound 3, and compound 7 are excluded:
  2. The compound of formula 1 according to claim 1, wherein - at least two of a, b, c or d are 0, 1 or 2, preferably at least two of a, b, c or d are 0 or 1; or - a and b are 0 and c or d is independently selected from 1 or 2, preferably a and b are 0 and c or d is 1; or - c and d are 0 and a or b is independently selected from 1 or 2, preferably c and d are 0 and a or b is 1; or - a and c are 0 and b or d is independently selected from 1 or 2, preferably a and c are 0 and b or d is 1; or - b and d are 0 and a or c is independently selected from 1 or 2, preferably b and d are 0 and a or c is 1; or - at least three selected from a, b, c and d are 0 and one selected from a, b, c or d is 1; or - at least three selected from a, b, c and d are 1 or 2, preferably at least two of a, b, c and d is 1.
  3. The compound of formula 1 according to claim 1 or 2, wherein e is 0, 1 or 2, further preferred 0 or 1 and more preferred 0.
  4. The compound of formula 1 according to any of claims 1 to 3, wherein at least two of R 1 , R 2 , R 3 and R 4 are selected same when a+b+c+d ≥ 2, preferably R 1 and R 2 or R 3 and R 4 are selected same when a+b+c+d ≥ 2, further preferred R 1 and R 3 or R 2 and R 4 are selected same when a+b+c+d ≥ 2.
  5. The compound of formula 1 according to any of claims 1 to 4, wherein R 1 , R 2 , R 3 and R 4 are independently selected from H, nitrile, phenyl, naphthyl, biphenyl, pyridinyl, dibenzofuran, dibenzothiophene or carbazole; preferably at least one of R 1 , R 2 , R 3 or R 4 is independently selected from nitrile, phenyl, naphthyl, biphenyl, pyridinyl, dibenzofuran, dibenzothiophene or carbazole; preferably at least two of R 1 , R 2 , R 3 and R 4 are independently selected from nitrile, phenyl, naphthyl, biphenyl, pyridinyl, dibenzofuran, dibenzothiophene or carbazole; further preferred at least three of R 1 , R 2 , R 3 and R 4 are independently selected from nitrile, phenyl, naphthyl, biphenyl, pyridinyl, dibenzofuran, dibenzothiophene or carbazole; in addition preferred at least three of R 1 , R 2 , R 3 and R 4 are independently selected from nitrile, phenyl, naphthyl, biphenyl, pyridinyl, dibenzofuran, dibenzothiophene or carbazole.
  6. The compound of formula 1 according to any of claims 1 to 5, wherein at most one of R 1 , R 2 , R 3 or R 4 is H; preferably at most two of R 1 , R 2 , R 3 and R 4 are H; and more preferred at most three of R 1 , R 2 , R 3 and R 4 are H.
  7. The compound of formula 1 according to any of claims 1 to 6, wherein two of R 1 , R 2 , R 3 and R 4 are formula 2, preferably one of R 1 , R 2 , R 3 or R 4 is formula 2.
  8. The compound of formula 1 according to any of claims 1 to 7, wherein Ar 1 is selected from substituted or unsubstituted phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, triphenylene, anthracenylene, wherein the substituents are selected from C 6 to C 18 aryl, C 3 to C 25 heteroaryl, - PO(R') 2 , D, F or CN, partially or perfluorinated C 1 to C 16 alkyl, C 1 to C 16 alkoxy, partially or perfluorinated C 1 to C 16 alkoxy, partially or perdeuterated C 1 to C 16 alkoxy.
  9. The compound of formula 1 according to any of claims 1 to 8, wherein R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, CN, or D1 to D54:
  10. The compound of formula 1 according to any of claims 1 to 9, wherein Ar 1 is selected from E1 to E14:
  11. The compound of formula 1 according to any of claims 1 to 10, wherein R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are independently selected from G1 to G72:
  12. The compound of formula 1 according to any of claims 1 to 11, wherein the compound of formula 1 is selected from J1 to J47, J49 to J51, and J53:
  13. An organic semiconductor layer comprising at least one compound of formula 1 according to any of the preceding claims 1 to 12.
  14. The organic semiconductor layer according to claim 13, wherein the organic semiconductor layer further comprises a metal, metal salt or organic metal complex, preferably an organic monovalent or divalent metal complex, more preferably LiQ or alkali borate.
  15. An organic electronic device (100) comprising an anode layer (120), a cathode layer (190) and at least one organic semiconductor layer according to claim 13 or 14, wherein the at least one organic semiconductor layer comprises a compound of formula 1 according to any of the preceding claims 1 to 12.
  16. An organic electronic device according to claim 15 further comprising at least one emission layer (150), wherein the organic semiconductor layer is arranged between the at least one emission layer (150) and the cathode layer (190).
  17. The organic electronic device according to claim 15 or 16, wherein the organic electronic device is a light emitting device, thin film transistor, a battery, a display device or a photovoltaic cell, and preferably a light emitting device.

Description

Technical Field The present invention relates to an organic compound of formula 1, suitable for use as a layer material for electronic devices, and it relates to an organic semiconductor layer comprising at least one compound thereof, as well as to an organic electronic device comprising at least one organic semiconductor layer, and a method of manufacturing the same. Background Art Organic electronic devices, such as organic light-emitting diodes OLEDs, which are self-emitting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, the EML, and the ETL are thin films formed from organic compounds. When a voltage is applied to the anode and the cathode, holes injected from the anode move to the EML, via the HTL, and electrons injected from the cathode move to the EML, via the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced, so that an OLED having the above-described structure has excellent efficiency and/or a long lifetime. WEN-LIANG GONG, BO WANG, MATTHEW. P., ALDRED, CHONG LI GUO-FENG ZHANG, TAO CHEN, LEI WANG AND MING-QIANG ZHU: "Tetraphenylethene-decorated carbazoles:synthesis, aggregation-induced emission, photo-oxidation and electroluminescence", JOURNAL OFMATERIALS CHEMISTRY C, vol. 2, 17 July 2814 (2014-07-17). Pages 7001-7012, XP002788483. MATTHEW P. ALDRED, ET AL.: "Fluorescence quenching and enhancement of vitrifiable oligofluorenesend-capped with tetraphenylethene",JOURNAL OF MATERIALS CHEMISTRY, vol. 22, 15 February 2012 (2012-02-15), pages 7515-7528, XP002788484. US 2006/024525 A1 refers to an organic electroluminescent device including an organic green emission layer comprising a green emission material and a blue emission material. The green emission layer is interposed between a pair of electrodes. US 2021/319568 A1 refers to an organic electroluminescence device having a low drive voltage and excellent durability. Provided also is an organic electroluminescence device having low dependency of voltage increment after driving on temperature of usage environment. Komatsu Koichi ET AL: "Syntheses and Properties of the Polymethylenebis-( diphenylcyclopropenium) Dications", Bull. Chem. Jpn., vol. 55, no. 8, 1 August 1982 (1982-08-01 ), pages 2470-2479, XP093040342. KR 2016 0082067 A refers to a compound and an organic light-emitting device using the same. The compound can play a role as a hole injecting material, a hole transporting material, a light-emitting material, a hole blocking material, an electron transporting material, and an electron injecting material in the organic light-emitting device. WO 2017/036573 A1 relates to phenanthrene compounds of a particular formula (I), their use in electronic devices, electronic devices comprising such phenanthrene compounds, as well as processes for the synthesis of such phenanthrene compounds. Performance of an organic light emitting diode may be affected by characteristics of the organic semiconductor layer, and among them, may be affected by characteristics of an organic material of the organic semiconductor layer. There is a need for organic compounds having improved melting point, improved glass transition temperature (Tg) and a rate onset temperature (TRO) in a range suitable for mass production. Additionally, there is a need for improved performance of organic electronic devices. In particular, there is a need for organic electronic devices having a high efficiency and long lifetime at lower operating voltages. Thereby the power consumption may be decreased and battery life improved, for example of mobile electronic devices. DISCLOSURE The present invention is represented by the claims. An aspect of the present invention provides in accordance with claim 1 a compound of formula 1: wherein R1, R2, R3 and R4 are independently selected from hydrogen, substituted or unsubstituted C6 to C38 aryl, substituted or unsubstituted C3 to C36 heteroaryl or C1 to C16 alkyl group, -PO(R') 2, D, F, CN, or formula 2; wherein the substituents are selected from C6 to C18 aryl, C3 to C25 heteroaryl, -PO(R')2, D, F or CN, partially or perfluorinated C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkoxy;R' is independently selected from alkyl, aryl or heteroaryl;a, b, c, d and e are independently 0, 1 or 2, wherein at least one of a, b, c or d is 1 or 2; wherein at least one of R1, R2, R3 or R4 is formula 2;Ar1 is selected from substituted or unsubstituted C6 to C38 arylene, substituted or unsubstituted C3 to C36 heteroaryl