WO2021008374A1 - Nouveau composé, application de celui-ci et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé, application de celui-ci et dispositif électroluminescent organique l'utilisant Download PDF

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WO2021008374A1
WO2021008374A1 PCT/CN2020/099815 CN2020099815W WO2021008374A1 WO 2021008374 A1 WO2021008374 A1 WO 2021008374A1 CN 2020099815 W CN2020099815 W CN 2020099815W WO 2021008374 A1 WO2021008374 A1 WO 2021008374A1
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formula
butyl
group
cyano
independently selected
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PCT/CN2020/099815
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Chinese (zh)
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段炼
张跃威
张东东
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清华大学
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Priority claimed from CN201910649982.XA external-priority patent/CN110407858B/zh
Priority claimed from CN201911200466.5A external-priority patent/CN110872316B/zh
Application filed by 清华大学 filed Critical 清华大学
Priority to JP2021578163A priority Critical patent/JP7429055B2/ja
Priority to KR1020227000639A priority patent/KR102657477B1/ko
Publication of WO2021008374A1 publication Critical patent/WO2021008374A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a new type of compound, at the same time, it also relates to the application of this type of compound, and to an organic light emitting device using this type of compound.
  • OLED Organic Light Emission Diodes
  • OLED Organic Light Emission Diodes
  • sandwich-like devices including positive and negative electrode film layers and organic functional material layers sandwiched between the electrode film layers.
  • OLED devices have the advantages of high brightness, fast response, wide viewing angle, simple process, and flexibility, they have attracted much attention in the field of new display technology and new lighting technology.
  • this technology has been widely used in the display panels of new lighting fixtures, smart phones and tablet computers, and will further expand to the application fields of large-size display products such as TVs. It is a new type of display with rapid development and high technical requirements. technology.
  • MR-TADF multiple resonance induced thermally activated delayed fluorescence
  • thermally activated delayed fluorescent molecule can have both high radiation transition rate and high color purity, its larger HOMO-LUMO overlap will cause the material's single and triplet energy range ( ⁇ Est) to be larger , Resulting in serious device efficiency roll-off; in addition, there is room for further improvement in the practical requirements of the material's half-width distance.
  • the present invention provides a new thermally activated delayed fluorescent material, which can be applied to the field of organic electroluminescence.
  • the organic compound of the present invention is represented by the following general formula (1-1), (1-2) or (1-3):
  • Y 1 , Y 2 and Y 3 are each independently selected from B;
  • X 1 , X 2 and X 3 are each independently selected from N;
  • n and p are independently selected from 0 or 1;
  • X 4 , X 5 and X 6 are each independently selected from a single bond or CR, and R is selected from one of the following substituted or unsubstituted groups: C1-C30 chain alkyl, C3-C30 cycloalkane Group, C1-C30 haloalkyl, C1-C30 alkoxy, C2-C30 alkenyl, C3-C30 alkynyl, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6 -C60 aryloxy group, C5-C60 monocyclic heteroaryl group or C5-C60 condensed ring heteroaryl group;
  • R 1 to R 20 are each independently selected from hydrogen, deuterium, or substituted or unsubstituted one of the following groups: halogen, C1 to C30 chain alkyl, C3 to C30 cycloalkyl, C1 to C10 Alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 Monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl or C5-C60 fused heteroaryl, and R 1 ⁇ R 20 medium phase Two adjacent groups can be bonded to each other and form one of C5-C30 five- or six-membered aryl ring, C5-C30 five- or six-membered heteroaryl ring together with the adjacent benzene ring , And at
  • R 21 is selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, C1 ⁇ C30 chain alkyl, C3 ⁇ C30 cycloalkyl, C1 ⁇ C10 alkoxy, C1 ⁇ C10 thioalkoxy, carbonyl, carboxy, nitro, cyano, amino, C6 ⁇ C30 arylamino, C3 ⁇ C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 Condensed ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl or C5-C60 condensed heteroaryl;
  • the substituents are independently selected from deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, One of C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.
  • At least one of m, n and p is 0; or at least one of m, n and p is 1; or m is 0, n and p are both 1, or m is 1, n and p are both.
  • R 1 to R 21 each independently have the same defined range as in claim 1.
  • R 1 to R 21 are each independently selected from hydrogen, deuterium or one of the following substituted or unsubstituted substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl Base, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl , Phenanthryl,
  • the two adjacent groups in R 1 to R 20 may be bonded to each other and form a C5-C30 five- or six-membered aryl ring together with the adjacent benzene ring, and C5-C30 five- or six-membered ring
  • One of the heteroaryl rings, and at least one hydrogen in the formed ring can be fused by C6 ⁇ C30 arylamino, C3 ⁇ C30 heteroarylamino, C6 ⁇ C60 monocyclic aryl, C6 ⁇ C60 Cyclic aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 fused-ring heteroaryl, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl , C1 ⁇ C10 alkoxy group, C1 ⁇ C10 thioalkoxy group, carbonyl group, carboxyl group, nitro group, cyano group, amino group substituted by any one;
  • the substituents are independently selected from deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6 One of ⁇ C30 arylamino, C3 to C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.
  • R 2 , R 5 , R 8 , R 11 , R 14 , and R 17 are each independently selected from a hydrogen atom or a substituted or unsubstituted following substituent Group: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, cyclohexyl, fluorine atom, trifluoromethyl, Cyano, tert-butylbenzene, methylphenyl, phenyl, triarylamino, carbazolyl, pyridyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzene Othienyl, isobenzothienyl, dibenzothienyl, adamantane, tetrahydropyrrole, pipe
  • the R 2 , R 5 , R 8 , and R 19 are each independently selected from a hydrogen atom or substituted or unsubstituted following substituent groups: methyl, ethyl Group, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, cyclohexyl, fluorine atom, trifluoromethyl, cyano, tert-butylbenzene , Methylphenyl, phenyl, triarylamino, carbazolyl, pyridyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzene And thienyl, dibenzothienyl, adamantane, tetrahydropyrrole, piperidine, sily
  • R 2 , R 5 , R 8 , R 11 , R 16 , and R 19 are each independently selected from a hydrogen atom or a substituted or unsubstituted following substituent Group: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, cyclohexyl, fluorine atom, trifluoromethyl, Cyano, tert-butylbenzene, methylphenyl, phenyl, triarylamino, carbazolyl, pyridyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzene Othienyl, isobenzothienyl, dibenzothienyl, adamantane, tetrahydropyrrole, pipe
  • the expression of Ca to Cb means that the number of carbon atoms of the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituent.
  • the substituted or unsubstituted C6-C60 aryl group is preferably a C6-C30 aryl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, an indenyl group, Fluorenyl and its derivatives, fluoranthene, triphenylene, pyrenyl, perylene, A group in the group consisting of a tetraphenyl group and a tetraphenyl group.
  • biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, P-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl and 2-naphthyl; anthracenyl is selected from 1-anthryl, 2-anthryl and 9-anthryl; said fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from 9,9'-dimethylfluorene, 9,9'-spirobifluorene and benzofluorene; the pyrenyl is selected from 1-
  • the heteroatom in the present invention generally refers to an atom or group of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O, and S.
  • the substituted or unsubstituted C5-C60 heteroaryl group is preferably a C5-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc.
  • examples may include: furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and
  • the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
  • the above C1 to C30 chain alkyl group is preferably a C1 to C10 chain alkyl group, more preferably a C1 to C6 chain alkyl group, for example, methyl, ethyl, n-propyl , N-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl, etc.
  • C3-C30 cycloalkyl includes monocycloalkyl and polycyclic alkyl, preferably C3-C10 cycloalkyl.
  • the compounds described by the general formula (1) of the present invention may preferably be the following specific structure compounds P-1 to P-405, and these compounds are only representative:
  • the present invention simultaneously protects any of the above general formula (1-1), formula (1-2), formula (1-3), formula (2-1), formula (2-2) and formula (2-3)
  • the application of the compound shown is as a light-emitting layer material in an organic electroluminescence device, preferably as a light-emitting dye and/or sensitizer.
  • the present invention also provides an organic electroluminescent device, including a substrate, including a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein
  • the organic layer includes any of the above general formula (1-1), formula (1-2), formula (1-3), formula (2-1), formula (2-2) and formula (2-3) The compound shown.
  • one embodiment of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer Including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer.
  • the hole injection layer is formed on the anode layer, and the hole transport layer is formed on the hole injection layer.
  • the cathode layer is formed on the electron transport layer, and the light emitting layer is formed between the hole transport layer and the electron transport layer; wherein, the light emitting layer contains the above formula (1 -1), formula (1-2), formula (1-3), formula (2-1), formula (2-2) and formula (2-3) any of the general formula compounds of the present invention .
  • the OLED device prepared by using the compound of the invention has low starting voltage, high luminous efficiency, high color purity and better service life.
  • the compound of the present invention has a long service life under the premise of ensuring that the device has a suitable driving voltage and efficiency. It is not only suitable for use as a luminescent material in organic electroluminescence devices, but also can be applied to optical sensors and solar cells. , Lighting components, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels and other technical fields.
  • the structure design of the new compounds of the present invention preferably introduces more rigid donors such as carbazole and its derivatives at the 1, 3 and 5 positions of the central benzene ring, which not only makes the entire BN
  • the resonance framework is more rigid (helps to further reduce its vibration relaxation and narrow the spectrum), and the preferred carbazole unit can also participate in the front-line orbital distribution, which increases the overlap of the HOMO and LUMO orbitals (further increases the intensity of its radiation transition oscillator , That is, luminous efficiency); at the same time, the ortho and para positions of the nitrogen atoms at positions 1, 3, and 5 correspond to the electron-withdrawing boron atom.
  • This special structure can make the N atom and the B atom have both electron donating and withdrawing capabilities Different degrees of reduction, so the spectrum will blue shift.
  • this special multi-donor-multi-acceptor structure is also conducive to introducing more intermediate triplet states between the singlet state S1 and the triplet state T1, thereby promoting the reverse gap between the singlet state and the triplet state.
  • Increase the proportion of delayed components and reduce the delayed fluorescence lifetime, and ultimately reduce the efficiency roll-off and increase the stability of the electroluminescent device; further, it is more preferable to introduce R 21 groups with a certain steric hindrance , And buckling the Ph-B-Ph group into a five-membered ring, a six-membered ring, etc. will more stabilize the rigid structure of the molecule. While maintaining the above-mentioned excellent characteristics, the half-value width of the material is further reduced.
  • the compound of the present invention can be used as a light-emitting layer material in an organic electroluminescence device, and can also be used as a fluorescent sensitizer in an organic electroluminescence device.
  • the preparation process of the compound of the present invention is simple and feasible, and the raw materials are easily available, which is suitable for mass production and scale-up.
  • FIG. 1 is a schematic diagram of the structure of an organic electroluminescent device prepared by the present invention.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole transport layer
  • 4 is an organic light-emitting layer
  • 5 is an electron transport layer
  • 6 is a cathode ;
  • FIG. 2 is a comparison diagram of the electroluminescence spectra of the device D1 prepared in the embodiment of the present invention and the device DD1 prepared in the comparative example;
  • FIG. 3 is a comparison diagram of the photoluminescence spectra of the device D1 prepared in the embodiment of the present invention and the device DD1 prepared in the comparative example;
  • FIG. 4 is a comparison diagram of the photoluminescence lifetime of a device D1 prepared in an embodiment of the present invention and a device DD1 prepared in a comparative example;
  • Fig. 5 is the electroluminescence spectrum of a TTA-type device T1 prepared in an embodiment of the present invention.
  • the synthesis method of the compound of the present invention is briefly described below.
  • the hydrogen and Cl atoms between X 1 , X 2 and X 3 are ortho-metalized using n-butyl lithium or tert-butyl lithium.
  • a Bronsted base such as N,N-diisopropylethylamine is added.
  • the Tandem Bora-Friedel-Crafts Reaction is carried out to obtain the target.
  • a pentane solution of tert-butyllithium (18.96mL, 1.60M, 30.34mmol) was slowly added to a solution of the Br generation precursor (13.83g, 13.79mmol) in tert-butylbenzene (150mL) at 0°C, Then, the temperature was raised to 80°C, 100°C, and 120°C for 1 hour each. After the reaction, the temperature was lowered to -30°C, boron tribromide (7.6 g, 30.34 mmol) was slowly added, and stirring was continued for 0.5 hours at room temperature.
  • N,N-diisopropylethylamine (5.35g, 41.37mmol) was added at room temperature, and the reaction was continued at 145°C for 5 hours before stopping.
  • MALDI-TOF-MS results molecular ion peak: 925.92 elemental analysis results: theoretical value: C: 85.62%; H: 7.61%; B: 2.30%; N: 4.47%; experimental value: C: 85.72%; H: 7.66 %; B: 2.83%; N: 3.79%.
  • This example is basically the same as Synthesis Example 1, with the difference that: in this example, P-1-1 needs to be replaced with P-300-1 in the same amount.
  • the target compound P-300 (0.81 g, 10% yield, HPLC analytical purity 99.66%) is a yellow solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: P-1-1 needs to be replaced with P-334-1 of the same amount in this example.
  • the target compound P-334 (1.27 g, 10% yield, HPLC analytical purity 99.36%), is a yellow solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: P-1-1 needs to be replaced with P-301-1 in the same amount in this example. .
  • the target compound P-301 (1.02 g, 11% yield, HPLC analytical purity 99.55%) is a yellow solid.
  • This example is basically the same as Synthesis Example 1, and the difference is that: in this example, P-1-1 needs to be replaced with an equivalent amount of P-303-1. .
  • the target compound P-303 (1.42 g, 10% yield, HPLC analytical purity 99.35%), is a yellow solid.
  • This example is basically the same as Synthesis Example 1, and the difference lies in: in this example, P-1-1 needs to be replaced with P-330-1 in the same amount.
  • the target compound P-330 (1.29 g, 10% yield, HPLC analytical purity 99.36%), is a yellow solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: P-1-1 needs to be replaced with P-334-1 of the same amount in this example.
  • the target compound P-334 (1.27 g, 10% yield, HPLC analytical purity 99.36%), is a yellow solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: in this example, P-1-1 needs to be replaced with P-497-1 in the same amount.
  • the target compound P-497 (0.92 g, 10% yield, HPLC analytical purity 99.55%) is a yellow solid.
  • MALDI-TOF-MS results molecular ion peak: 665.62 elemental analysis results: theoretical value: C, 86.65%; H, 3.79%; B, 3.25%; N, 6.32%; experimental value: C, 86.85%; H, 3.59 %; B, 3.05%; N, 6.52%.
  • This example is basically the same as Synthesis Example 1, and the difference is that: in this example, P-1-1 needs to be replaced with P-499-1 in the same amount.
  • the target compound P-499 (0.62 g, 6% yield, HPLC analytical purity 99.75%) is a yellow solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: in this example, P-1-1 needs to be replaced with P-7-1 of the same amount.
  • the target compound P-7 (0.60 g, 4.4% yield, HPLC analytical purity 99.55%) is a green solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: in this example, P-1-1 needs to be replaced with P-39-1 of the same amount.
  • the target compound P-39 (0.60 g, 4.4% yield, HPLC analytical purity 99.55%) is a green solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: P-1-1 needs to be replaced with P-46-1 in the same amount in this example.
  • the target compound P-46 (1.78 g, 12% yield, HPLC analytical purity 99.55%) is a green solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: in this example, P-1-1 needs to be replaced with P-64-1 in the same amount.
  • the target compound P-64 (1.65 g, 12% yield, HPLC analytical purity 99.35%) is a green solid.
  • MALDI-TOF-MS results molecular ion peak: 721.48 elemental analysis results: theoretical value: C, 86.57%; H, 4.61%; B, 3.00%; N, 5.82%; experimental value: C, 86.64%; H, 4.51 %; B, 3.09%; N, 5.76%;
  • This example is basically the same as Synthesis Example 1, and the difference is that: in this example, P-1-1 needs to be replaced with P-88-1 in the same amount.
  • the target compound P-88 (0.78 g, 8% yield, HPLC analytical purity 99.55%) is a green solid.
  • This example is basically the same as Synthesis Example 1, with the difference that: P-1-1 needs to be replaced with P-92-1 in the same amount in this example.
  • the target compound P-92 (0.90 g, 8% yield, HPLC analytical purity 99.75%) is a green solid.
  • This example is basically the same as Synthesis Example 1, and the difference lies in: in this example, P-1-1 needs to be replaced with P-206-1 in the same amount.
  • the target compound P-206 (0.86 g, 6% yield, HPLC analytical purity 99.55%) is a green solid.
  • MALDI-TOF-MS results molecular ion peak: 1089.65; elemental analysis results: theoretical value: C, 85.95%; H, 7.21%; B, 2.98%; N, 3.86%; experimental value: C, 85.91%; H, 7.25%; B, 2.94; N, 3.90.
  • a pentane solution of tert-butyllithium (18.96mL, 1.60M, 30.34mmol) was slowly added to a solution of Br generation precursor (8.84g, 13.79mmol) in tert-butylbenzene (150mL) at 0°C, Then, the temperature was raised to 80°C, 100°C, and 120°C for 1 hour each. After the reaction, the temperature was lowered to -30°C, boron tribromide (7.6 g, 30.34 mmol) was slowly added, and stirring was continued for 0.5 hours at room temperature.
  • N,N-diisopropylethylamine (5.35g, 41.37mmol) was added at room temperature, and the reaction was continued at 145°C for 5 hours, and then it was cooled to room temperature.
  • a tetrahydrofuran solution of phenyl magnesium chloride (30 mL, 1.0 M, 30 mmol) was added at room temperature, and the reaction was continued for 12 h before stopping.
  • MALDI-TOF-MS results molecular ion peak: 588.09 elemental analysis results: theoretical value: C, 85.78%; H, 3.94%; B, 5.51%; N, 4.76%; experimental value: C, 85.68%; H, 3.94 %; B, 5.61%; N, 4.76%.
  • This example is basically the same as Synthesis Example 23, and the difference is that: in this example, P-114-1 and phenyl magnesium chloride need to be replaced with equivalent amounts of P-110-1 and tert-butyl magnesium chloride.
  • the target compound P-110 (0.75 g, 6% yield, HPLC analysis purity 99.45%), is a green solid.
  • the following demonstrates and verifies the technical effects and advantages of the present invention by specifically applying the compound of the present invention to organic electroluminescent devices to test actual use performance.
  • the organic electroluminescence device includes a first electrode, a second electrode, and an organic material layer between the two electrodes.
  • the organic material can be divided into multiple regions.
  • the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.
  • the material of the anode can be indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and other oxide transparent conductive materials and any combination thereof.
  • the cathode material can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) ) And other metals or alloys and any combination between them.
  • the hole transport region is located between the anode and the light-emitting layer.
  • the hole transport region may be a single-layered hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds.
  • the hole transport region may also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • the material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecyl benzene sulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4 -Styrene sulfonate) (Pani/PSS), aromatic amine derivatives, etc.
  • phthalocyanine derivatives such as CuPc
  • conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecyl benzene sulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythioph
  • the light-emitting layer includes light-emitting dyes (ie, dopants) that can emit different wavelength spectra, and may also include a host material (Host) at the same time.
  • the light-emitting layer may be a monochromatic light-emitting layer emitting a single color such as red, green, and blue.
  • the monochromatic light-emitting layers of multiple different colors can be arranged in a plane according to the pixel pattern, or stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other.
  • the light-emitting layer may also be a single-color light-emitting layer capable of emitting red, green, and blue at the same time.
  • the electron transport region can be a single-layered electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds.
  • the electron transport region may also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the preparation process of the organic electroluminescent device is described with reference to FIG. 1 as follows: an anode 2, a hole transport layer 3, an organic light emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on the substrate 1, and then packaged.
  • the organic light-emitting layer 4 is formed by a method of co-evaporating a wide band gap material source, an electron donor type material source, an electron acceptor type material source and a resonance type TADF material source.
  • the preparation method of the organic electroluminescent device of the present invention includes the following steps:
  • the glass plate coated with anode material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, degreasing ultrasonically in a mixed solvent of acetone and ethanol, and baked in a clean environment until the water is completely removed. Light and ozone cleaning, and bombard the surface with low-energy cation beams;
  • Vacuum evaporation of hole transport material on the hole injection layer to form a hole transport layer the evaporation rate is 0.1-0.5nm/s
  • Vacuum vapor deposition of an electron blocking layer on the hole transport layer the vapor deposition rate is 0.1-0.5nm/s;
  • the organic light-emitting layer of the device is vacuum-evaporated on the electron blocking layer.
  • the material of the organic light-emitting layer includes the host material and TADF dye.
  • the method of multi-source co-evaporation is used to adjust the evaporation rate of the host material and the sensitizer material.
  • the vapor deposition speed and the vapor deposition rate of the dye make the dye reach the preset doping ratio;
  • the electron transport material of the device is vacuum evaporated on the hole blocking layer to form an electron transport layer, and the evaporation rate is 0.1-0.5nm/s;
  • a 0.1-0.5nm/s vacuum deposition of LiF on the electron transport layer is used as the electron injection layer, and a 0.5-1nm/s vacuum deposition of Al layer is used as the cathode of the device.
  • An embodiment of the present invention also provides a display device, which includes the organic electroluminescent device provided above.
  • the display device may specifically be a display device such as an OLED display, and any product or component with a display function, such as a TV, a digital camera, a mobile phone, a tablet computer, and the like including the display device.
  • This display device has the same advantages as the aforementioned organic electroluminescent device over the prior art, and will not be repeated here.
  • organic electroluminescent device of the present invention will be further introduced below through specific examples.
  • the anode material is ITO;
  • the hole injection layer material is HI, generally the total thickness is 5-30nm, this embodiment is 10nm;
  • the hole transport layer material is HT, the total thickness is generally 5-500nm, this embodiment is 40nm;
  • Host is the host material for the wide band gap of the organic light-emitting layer, the compound P-1 of the present invention is a dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm;
  • the material is ET, and the thickness is generally 5-300 nm. In this embodiment, it is 30 nm;
  • the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).
  • the preparation method is the same as that of device embodiment 1, except that the wide band gap host material used in the light-emitting layer is replaced with a TADF host TD.
  • the specific device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced from P-1 to P-4.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 2, except that the dye in the light-emitting layer is replaced from P-1 to P-4.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the dye in the light-emitting layer is replaced from P-1 to P-7.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 2, except that the dye in the light-emitting layer is replaced from P-1 to P-7.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced from P-1 to P-39.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 2, except that the dye in the light-emitting layer is replaced from P-1 to P-39.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the dye in the light-emitting layer is replaced from P-1 to P-95.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 2, except that the dye in the light-emitting layer is replaced from P-1 to P-95.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the dye in the light-emitting layer is replaced from P-1 to P-110.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 2, except that the dye in the light-emitting layer is replaced from P-1 to P-110.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced from P-1 to P-114.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 2, except that the dye in the light-emitting layer is replaced from P-1 to P-114.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the dye in the light-emitting layer is replaced with P-206 from P-1.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 2, except that the dye in the light-emitting layer is replaced from P-1 to P-206.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced from P-1 to P-308.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 2, except that the dye in the light-emitting layer is replaced from P-1 to P-308.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the dye in the light-emitting layer is replaced with P-300 from P-1.
  • the device structure is as follows:
  • the preparation method is the same as that of device example 2, except that the dye in the light-emitting layer is replaced from P-1 to P-300.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the dye in the light-emitting layer is replaced from P-1 to P-334.
  • the device structure is as follows:
  • the preparation method is the same as that of device embodiment 2, except that the dye in the light-emitting layer is replaced from P-1 to P-334.
  • the device structure is as follows:
  • a TTA-type body AN is used to prepare a triplet-triplet annihilation upconversion (TTA) type organic electroluminescent device, that is, a T1 device.
  • TTA triplet-triplet annihilation upconversion
  • the anode material is ITO;
  • the hole injection layer material is HI, generally the total thickness is 5-30nm, this embodiment is 10nm;
  • the hole transport layer material is HT, the total thickness is generally 5-500nm, this embodiment is 40nm;
  • Host is TTA type host material AN, the compound P-1 of the present invention is a dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30nm;
  • the material of the electron transport layer is ET , The thickness is generally 5-300nm, this embodiment is 30nm;
  • the electron injection layer and cathode materials choose LiF (0.5nm) and metal aluminum (150nm).
  • the preparation method is the same as that of device embodiment 1, except that the compound P-1 of the present invention used in the light-emitting layer is replaced with the compound P1 in the prior art.
  • the specific device structure is as follows:
  • the preparation method is the same as that of device embodiment 2, except that the compound P-1 of the present invention used in the light-emitting layer is replaced with the compound P1 in the prior art.
  • the specific device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the compound P-1 of the present invention used in the light-emitting layer is replaced with the compound P2 in the prior art.
  • the specific device structure is as follows:
  • the preparation method is the same as that of device example 2, except that the compound P-1 of the present invention used in the light-emitting layer is replaced with the compound P2 in the prior art.
  • the specific device structure is as follows:
  • the preparation method is the same as that of device embodiment 1, except that the compound P-1 of the present invention used in the light-emitting layer is replaced with the compound P3 in the prior art.
  • the specific device structure is as follows:
  • the preparation method of device embodiment 2 in the specification of this application is the same, except that the compound P-1 of the present invention used in the light-emitting layer is replaced with the compound P3 in the prior art.
  • the specific device structure is as follows:
  • the specific performance data of the organic electroluminescent devices D1 to D16 and T1 prepared in the foregoing device embodiments, and the devices DD1 to DD4 prepared in the comparative example are shown in Table 1 below. Especially in the half-width of the luminescence spectrum, the examples confirm that it has an effective effect, and the color purity of the device is more excellent; in addition, the external quantum efficiency of the device is also significantly improved and the efficiency roll-off is also significantly improved.
  • novel compounds of the present invention are organic light-emitting functional materials with good performance and are expected to be promoted for commercial applications.

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  • Chemical & Material Sciences (AREA)
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  • High Energy & Nuclear Physics (AREA)
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Abstract

L'invention concerne un nouveau composé organique, une application de celui-ci et un dispositif électroluminescent organique l'utilisant, le composé ayant une structure telle que représentée dans la formule (1-1), (1-2) ou (1-3) suivante : dans laquelle : Y1, Y2 et Y3 sont chacun indépendamment choisis parmi B; X1, X2 et X3 sont chacun indépendamment choisis parmi N; X4, X5 et X6 sont chacun indépendamment choisis parmi une liaison simple ou CR, R est choisi parmi l'un des groupes substitués ou non substitués ci-dessous : un groupe alkyle à chaîne en C1 à C30, un groupe cycloalkyle en C3 à C30, un groupe halogénoalkyle en C1 à C30, un groupe alcoxy en C1 à C30, un groupe alcényle en C2 à C30, un groupe alcynyle en C3 à C30, un groupe aryle monocyclique en C6 à C60, un groupe aryle à cycles condensés en C6 à C60, un groupe aryloxy en C6 à C60, un groupe hétéroaryle monocyclique en C5 à C60 ou un groupe hétéroaryle à cycles condensés en C5 à C60. Le composé présente d'excellentes performances et stabilité de dispositif lorsqu'il est utilisé en tant que matériau de couche luminescente dans un dispositif OLED.
PCT/CN2020/099815 2019-07-18 2020-07-02 Nouveau composé, application de celui-ci et dispositif électroluminescent organique l'utilisant WO2021008374A1 (fr)

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CN113292584A (zh) * 2021-05-31 2021-08-24 上海天马有机发光显示技术有限公司 一种含硼和氮的有机化合物及其电致发光的应用
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