WO2021121230A1 - Composé, son application et dispositif électroluminescent organique le contenant - Google Patents

Composé, son application et dispositif électroluminescent organique le contenant Download PDF

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WO2021121230A1
WO2021121230A1 PCT/CN2020/136595 CN2020136595W WO2021121230A1 WO 2021121230 A1 WO2021121230 A1 WO 2021121230A1 CN 2020136595 W CN2020136595 W CN 2020136595W WO 2021121230 A1 WO2021121230 A1 WO 2021121230A1
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compound
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group
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黄金华
曾礼昌
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北京鼎材科技有限公司
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Priority to KR1020227024930A priority Critical patent/KR20220115617A/ko
Publication of WO2021121230A1 publication Critical patent/WO2021121230A1/fr

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Definitions

  • the present invention relates to the field of organic light-emitting compounds and organic electroluminescence technology, in particular to a compound and its application, and an organic electroluminescence device containing the compound.
  • OLED organic light-emitting diodes
  • OLED organic field effect tubes
  • organic photovoltaic cells organic sensors
  • OLED has developed particularly rapidly and has achieved commercial success in the field of information display.
  • OLED can provide high-saturation red, green, and blue colors.
  • the full-color display device made with it does not require an additional backlight source, and has the advantages of dazzling colors, light, thin and soft.
  • the core of the OLED device is a thin film structure containing a variety of organic functional materials.
  • Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and luminescent host materials and luminescent guests (dyes). When energized, electrons and holes are respectively injected and transported to the light-emitting area and recombined there, thereby generating excitons and emitting light.
  • TADF Thermally excited delayed fluorescence
  • Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the luminous body through energy transfer, which can also achieve higher luminous efficiency.
  • the object of the present invention is to provide a compound which can further reduce the driving voltage of the device, improve the luminous efficiency of the device and prolong the service life of the device when used in an organic electroluminescent device.
  • the present invention adopts the following technical solutions:
  • the present invention provides a compound having a structure represented by formula (I);
  • the m is an integer of 1 to 7, such as 2, 3, 4, 5, 6, etc., and the a is an integer of 1 to m;
  • n is an integer of 1 to 6, such as 2, 3, 4, 5, etc.
  • b is an integer of 1 to n;
  • the Y a and Z b are independently selected from hydrogen atom, halogen, cyano, nitro, hydroxyl, silyl, ether, substituted or unsubstituted C 1 -C 12 alkyl, substituted Or one of an unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, and a substituted or unsubstituted C 3 -C 30 heteroaryl group;
  • Y a and Z b independently represent a type of group, rather than a specific group.
  • a is 1 or 2
  • Y a can be Y 1
  • Y 2 can be Y 2 , that is, when two Y a are substituted on the two-membered five-membered ring, the two Y a may be the same or different
  • Z b is the same.
  • the X is selected from NR 3 , S or O;
  • the R 1 , R 2 and R 3 are independently selected from a hydrogen atom, a substituted or unsubstituted C 1 -C 12 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C One of 6 -C 30 aryl and substituted or unsubstituted C 3 -C 30 heteroaryl;
  • the L 1 , L 2 and L 3 are independently selected from a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 3 -C 30 heteroarylene group One of the bases;
  • the Ar 1 and Ar 2 are independently selected from one of substituted or unsubstituted C 6 -C 30 aryl groups and substituted or unsubstituted C 3 -C 30 heteroaryl groups;
  • the R 1 , the R 2 , the R 3 , the L 1 , the L 2 , the L 3 , the Ar 1 and the Ar 2 each independently selected groups have substituents
  • the substituent is selected from halogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 1 -C 6 alkoxy or thioalkoxy, C 6 -C 30 mono One or a combination of at least two of a ring aryl group or a condensed ring aryl group, a C 3 -C 30 monocyclic heteroaryl group or a condensed ring heteroaryl group.
  • C 6 -C 30 represents the number of carbon atoms in the group, for example, 6, 10, 12, 15, 18, 20, 23, 25, 28, 30 carbon atoms; similarly, substituted or unsubstituted C 3 -C 30 heteroarylene and substituted or unsubstituted C 3 -C
  • the number of carbon atoms in the 30 heteroaryl group can be 4, 6, 8, 12, 15, 18, 20, 23 , 25, 28 or 30; the number of carbon atoms in the C 1 -C 20 alkyl group can be 1, 3, 5, 8, 10, 12, 15, 18, or 20.
  • the number of carbon atoms of the group can be any integer within the numerical range. Unless otherwise specified, in general, the number of carbon atoms does not include the number of carbon atoms of the substituent.
  • the expression of chemical elements includes the concept of isotopes with the same chemical properties, for example, the expression of "hydrogen” also includes the concepts of “deuterium” and “tritium” with the same chemical properties.
  • the heteroatom of the heteroaryl group is usually selected from N, O, and S.
  • the expression of the ring structure crossed by "—" means that the connection site is at any position on the ring structure that can form a bond.
  • the above-mentioned substituted or unsubstituted C 1 -C 12 alkyl group is preferably a C 1 -C 10 alkyl group, more preferably a C 1 -C 6 alkyl group, for example, methyl, ethyl, n-propyl, Isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • the above-mentioned substituted or unsubstituted C 6 -C 30 aryl group is preferably C 6 -C 20 aryl group, preferably the aryl group is composed of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, Indenyl, fluorenyl and its derivatives, fluoranthene, triphenylene, pyrenyl, perylene, One or a combination of a tetraphenyl group and a tetraphenyl group.
  • the biphenyl group is selected from 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; said terphenyl group includes p-terphenyl-4-yl and p-terphenyl-3-yl , P-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl includes 1-naphthyl Or 2-naphthyl; the anthryl group is selected from one or a combination of 1-anthryl, 2-anthryl and 9-anthryl groups; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3 -One or a combination of fluorenyl, 4-fluorenyl and 9-fluorenyl groups; the fluorenyl derivative is selected from 9,9'-dimethylfluorene, 9,9'-spirobiflu
  • the above-mentioned substituted or unsubstituted C 3 -C 30 heteroaryl groups are preferably C 6 -C 20 heteroaryl groups, preferably the heteroaryl groups are furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl , Isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9 -Naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole.
  • the introduction of the dibenzo five-membered ring at the 1-position of the naphthalene ring can not only adjust the size of the ortho steric hindrance, but also effectively control the twist of the molecule to reduce the molecular crystallinity; secondly, the 1-position of the naphthalene ring
  • the introduction of the five-membered dibenzo ring can effectively control the energy level and transmission properties of the aromatic amine molecules, thereby enabling the designed material to meet the material requirements of the device.
  • the present invention is a naphthalene ring by the five-membered ring and dibenzofuran core structure linked together with Ar 1, Ar 2, Y a and Z b substituent such that the material as a hole transport layer of the organic electroluminescent device In the case of materials or electron blocking layers, it can improve the luminous efficiency, reduce the starting voltage and extend the service life of the device.
  • the driving voltage is as low as 5.0V and below, and the current efficiency is as high as 11.5 cd/A and above.
  • 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.
  • the compound has any one of the structures shown in formulas (1-1) to (1-4):
  • the compound has any one of the structures shown in formulas (2-1) to (2-4):
  • the Y a and Z b are independently selected from hydrogen atoms, or one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, n-butyl, Tert-butyl, n-pentyl, n-butyl, methyl ether, ethyl ether, butyl ether, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, tertphenyl, Phenanthryl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl;
  • the substituent is selected from halogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 1 -C 6 One or at least two of alkoxy or thioalkoxy, C 6 -C 30 monocyclic aryl or fused ring aryl, C 3 -C 30 monocyclic heteroaryl or fused ring heteroarylkind of combination.
  • the Y a and Z b are independently selected from hydrogen atoms.
  • L 1 and L 2 of said at least one group selected from a single bond are selected from a single bond.
  • the L 3 is selected from single bonds.
  • the X is And said R 1 and R 2 are independently selected from C 1 -C 12 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl; more preferably, said R 1 and R 2 are independently selected from Methyl or phenyl.
  • said R 1 and R 2 are independently selected from C 1 -C 12 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl; more preferably, said R 1 and R 2 are independently Selected from methyl or phenyl.
  • the X is NR 3
  • the R 3 is selected from a substituted or unsubstituted C 6 -C 30 aryl group; more preferably, the R 3 is selected from a phenyl group; when the R 3 has a substituent , The substituent is selected from halogen, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 1 -C 6 alkoxy or thioalkoxy, C 6 -C 30 monocyclic ring One or a combination of at least two of an aryl group or a condensed ring aryl group, a C 3 -C 30 monocyclic heteroaryl group or a condensed ring heteroaryl group.
  • said R 3 is selected from substituted or unsubstituted C 6 -C 30 aryl groups; more preferably, said R 3 is selected from phenyl; when said R 3 has a substituent, said substituent is selected from halogen , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 1 -C 6 alkoxy or thioalkoxy, C 6 -C 30 monocyclic aryl or condensed ring aryl, One or a combination of at least two C 3 -C 30 monocyclic heteroaryl groups or condensed ring heteroaryl groups.
  • the Ar 1 and Ar 2 are independently selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, carbazolyl , Dibenzofuranyl, dibenzothienyl; when the group independently selected by Ar 1 and Ar 2 has a substituent, the substituent is selected from halogen, C 1 -C 10 alkyl, C 2- C 10 alkenyl, C 1 -C 6 alkoxy or thioalkoxy, C 6 -C 30 monocyclic aryl or condensed ring aryl, C 3 -C 30 monocyclic heteroaryl Or one or a combination of at least two of the fused ring heteroaryl groups.
  • the substituents are selected from the following groups: methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl Base, n-pentyl, n-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, 9,9-dimethylfluorene
  • the group 9,9-diphenylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothienyl.
  • the Ar 1 and Ar 2 are independently selected from one of the following groups:
  • the dotted line represents the access point of the group.
  • the dotted line crosses the representation method of the benzene ring, and the connection point of the representative group can be any bondable position on the benzene ring.
  • *-L 1 -Ar 1 is dibenzofuran; or said *-L 1 -Ar 1 is biphenyl; or said *-L 1 -Ar 1 is naphthalene; or said *-L 1 -Ar 1 is 9,9-dimethyl fluorenyl; or said *-L 1 -Ar 1 is 9,9-diphenyl fluorenyl; wherein * represents the bond of the group, which has the same meaning as the dotted line , The following is the same, not repeating them one by one.
  • the *-L 1 -Ar 1 is
  • the compound has one of the following structures shown in P1-P209, P230-P298 and P299-P304:
  • the second object of the present invention is to provide an application of the compound described in the first object, and the compound is applied to an organic electronic device.
  • the organic electronic device includes an organic electroluminescence device, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, electronic paper or
  • the organic EL panel is preferably an organic electroluminescence device.
  • the compound is used as a hole transport material or electron blocking material of an organic electroluminescent device.
  • the third object of the present invention is to provide an organic electroluminescent device, the organic electroluminescent device comprising a substrate, a first electrode, a second electrode, and at least one layer located between the first electrode and the second electrode
  • the organic layer contains at least one compound according to one of the objectives.
  • an organic electroluminescent device including a substrate, and an anode layer, a plurality of light-emitting function layers, and a cathode layer sequentially formed on the substrate; the light-emitting function
  • the layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, and an electron transport layer, wherein at least one of the hole transport layer or the electron blocking layer contains one of the objectives described in Compound.
  • the OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes.
  • the organic material can be divided into multiple regions.
  • the organic material layer may include a hole transport region, a light-emitting layer, and an electron transport region.
  • a substrate may be used below the first electrode or above the second electrode.
  • the substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance, and transparency.
  • thin film transistors (TFT) may also be provided on the substrate used as a display.
  • the first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate.
  • transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof can be used.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • SnO 2 tin dioxide
  • ZnO zinc oxide
  • magnesium (Mg) silver
  • silver (Ag) aluminum
  • Al-lithium (Al-Li) aluminum-lithium (Al-Li)
  • magnesium-silver can be used (Mg-Ag) and other metals or alloys and any combination between them.
  • the organic material layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, and printing.
  • the compound used as the organic material layer may be organic small molecules, organic macromolecules, and polymers, and combinations thereof.
  • 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 hole transport region material may be selected from one or more compounds represented by formula (I) of the present invention, and the electron blocking layer of the hole transport region may not exist, or may have and be selected from, but Not limited to phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polyphenylene vinylene, polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly(3,4 ethylene) Dioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4-styrene sulfonate) (Pani/PSS) , Aromatic amine derivatives such as the following compounds HT-1 to HT-34; or any combination thereof.
  • phthalocyanine derivatives such as CuPc
  • conductive polymers or conductive dopant-containing polymers
  • the hole transport layer of the hole transport zone is selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzene 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 such as the following compounds HT-1 to HT-34, or any combination thereof; the electron blocking layer of the hole transport region is selected from One or any combination of the above-mentioned compounds.
  • phthalocyanine derivatives such as CuPc
  • conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene,
  • the hole injection layer is located between the anode and the hole transport layer.
  • the hole injection layer may be a single compound material or a combination of multiple compounds.
  • the hole injection layer may use one or more of the above-mentioned HT-1 to HT-34 compounds, or use one or more of the following HI-1 to HI-3 compounds; or HT-1
  • One or more compounds to HT-34 are doped with one or more compounds in the following HI-1 to HI-3.
  • 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 can also be a single-color light-emitting layer capable of emitting red, green, and blue at the same time.
  • the light-emitting layer material can use different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent luminescent materials.
  • a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used.
  • These different luminescent materials classified by technology can emit light of the same color or different colors of light.
  • the light-emitting layer adopts fluorescent electroluminescence technology.
  • the fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
  • the light-emitting layer adopts fluorescent electroluminescence technology.
  • the fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or a combination of BFD-1 to BFD-12 listed below.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the host material of the light-emitting layer is selected from, but not limited to, one or a combination of GPH-1 to GPH-80.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or a combination of GPD-1 to GPD-47 listed below.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or a combination of RPD-1 to RPD-28 listed below.
  • the light-emitting layer adopts phosphorescence electroluminescence technology.
  • the phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.
  • the light-emitting layer adopts thermally activated delayed fluorescent light emission technology.
  • the fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or a combination of TDE-1 to TDE-39 listed below.
  • the light-emitting layer adopts thermally activated delayed fluorescent light emission technology.
  • the fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or a combination of TDE-1 to TDE-39 listed below.
  • the OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode.
  • 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 electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-57 listed below.
  • the device may also include an electron injection layer located between the electron transport layer and the cathode.
  • the materials of the electron injection layer include but are not limited to one or a combination of the following: LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li or Ca.
  • the present invention has the following beneficial effects:
  • the introduction of a dibenzo five-membered ring at the 1-position of the naphthalene ring can not only adjust the size of the ortho steric hindrance to reduce molecular crystallinity, and secondly, the dibenzo five-membered ring can effectively regulate the HOMO energy of the molecule.
  • Grade improve the hole injection ability, and then enable the designed compound to meet the requirements of the device for the compound.
  • the core structure formed by connecting the naphthalene ring and the dibenzo five-membered ring is matched with substituents such as Ar1, Ar2, Ya and Zb, which can achieve the best effect, and make the compound as the empty of the organic electroluminescent device.
  • substituents such as Ar1, Ar2, Ya and Zb, which can achieve the best effect, and make the compound as the empty of the organic electroluminescent device.
  • the hole transport layer material or the electron blocking layer is used, the luminous efficiency of the organic electroluminescent device using the compound can be improved, the starting voltage can be reduced, and the service life of the device can be prolonged.
  • the driving voltage is as low as 5.0 V or less, and the current efficiency is as high as 11.5 cd/A or more.
  • the following synthesis examples of the present invention exemplarily provide specific synthesis methods of representative compounds, the solvents and reagents used in the following synthesis examples, such as aryl bromide, 2-bromo-9,9'-dimethylfluorene, 2-bromodibenzofuran, 2-bromodibenzothiophene, 4-bromobiphenyl, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride, tris(diethylene) Benzylacetone) two palladium, toluene, petroleum ether, n-hexane, dichloromethane, acetone, sodium sulfate, ethyl acetate, ethanol, tri-tert-butyl phosphine, potassium tert-butylate/sodium and other chemical reagents, all available from Domestic chemical products are purchased or customized on the market, for example, purchased from Sinopharm Reagent Company, Sigma-Aldrich Company
  • This embodiment provides an organic electroluminescent device, and the specific preparation method is as follows:
  • the glass plate coated with the transparent conductive layer of ITO 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;
  • the compound P1 prepared in Synthesis Example 1 was vacuum evaporated on the hole injection layer as the hole transport layer of the device, the evaporation rate was 0.1 nm/s, and the total evaporation film thickness was 60 nm;
  • HT-14 is vacuum-evaporated as the electron blocking layer of the device, the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 60nm;
  • the light-emitting layer of the device is vacuum-evaporated on the electron blocking layer.
  • the light-emitting layer includes the host material and the dye material.
  • the evaporation rate of the host material GPH-59 is adjusted to 0.1nm/s, and the dye RPD-8
  • the evaporation rate is set at a ratio of 3%, and the total film thickness of the evaporation is 40nm;
  • the electron transport layer material ET-46 of the vacuum vapor deposition device on the light-emitting layer is set at a ratio of 50% and ET-57 at a ratio of 50%.
  • the vapor deposition rate is 0.1nm/s, and the total vapor deposition film The thickness is 25nm;
  • ETL electron transport layer
  • LiF with a thickness of 0.5 nm was vacuum-evaporated as the electron injection layer
  • Al layer with a thickness of 150 nm was used as the cathode of the device.
  • Example 2-13 The difference between Example 2-13 and Example 1 is only that the hole transport layer compound P1 is replaced with the corresponding compound in Table 1.
  • Example 1 The difference from Example 1 is that compound P1 is replaced with compound R-1, and the structure of compound R-1 is as follows:
  • Example 1 The difference from Example 1 is that the compound P1 is replaced with the compound R-2, and the structure of the compound R-2 is as follows:
  • Example 1 The difference from Example 1 is that the compound P1 is replaced with the compound R-3, and the structure of the compound R-3 is as follows:
  • Example 1 The difference from Example 1 is that the compound P1 is replaced with the compound R-4, and the structure of the compound R-4 is as follows:
  • the life test of LT95 is as follows: use a luminance meter to maintain a constant current at a luminance of 5000 cd/m 2 and measure the time for the luminance of the organic electroluminescent device to drop to 4750 cd/m 2 in hours.
  • the compounds of the present invention is used for an organic electroluminescent device hole transport material, the device luminance of 5000cd / m 2, the driving voltage as low as 5.0V, and the current efficiency as high as 11.5 cd / Above A, it can effectively reduce the driving voltage, improve the current efficiency, and prolong the service life of the device. It is a hole transport material with good performance.
  • the compound R-1 of Comparative Example 1 differs only in that the dibenzofuran group is substituted at the 2-position of the naphthalene ring, and the aromatic amine is substituted at the 3-position.
  • This compound is used as an organic electron
  • the driving voltage of the device is 5.8V
  • the current efficiency is 8cd/A.
  • the data is worse than that of Example 10. This is due to the triarylamine molecule substituted at the 2-position of the naphthalene ring.
  • the triarylamine molecules substituted at the 3-position they have better regularity during film formation, which can effectively reduce the device's turn-on voltage and improve the transport of holes between molecules, thereby increasing the efficiency and life of the entire device.
  • the compound R-2 of Comparative Example 2 differs only in that the group substituted at the 1-position of the naphthalene ring is a phenanthrene group substituted with a phenyl group.
  • the driving voltage of the device is 5.7V
  • the current efficiency is 8.4cd/A
  • the current efficiency and lifetime data are both deteriorated. This is because the naphthalene ring is connected to the 9,9-dimethylfluorenyl group at the second position. It can effectively reduce the HOMO energy level of the molecule, thereby improving the exciton injection ability. Therefore, the compound P5 will have a better turn-on voltage, better luminous efficiency and service life than R-2.
  • the compound R-3 of Comparative Example 3 differs in that the dibenzothiophene group is substituted with two diarylamine groups, and the compound is used as a hole in an organic electroluminescent device.
  • the driving voltage of the device is 6.1V
  • the current efficiency is 7.9cd/A
  • the current efficiency and lifetime data are both worsened; the compound P174 has better regularity during film formation, which can effectively reduce the turn-on voltage of the device. Improve the transmission of holes between molecules, thereby improving the efficiency and life of the entire device.
  • the compound R-4 of Comparative Example 4 differs in that the group substituted at the 1-position of the naphthalene ring is a spirofluorenyl group.
  • the driving voltage of the device is 6.5V, the current efficiency is 7.3cd/A, and all the data are worse than those in the examples; the 9,9-dimethylfluorenyl group at the 2-position of compound P13 is better than the spirofluorenyl group.
  • the spirofluorenyl group is larger than the 9,9-dimethylfluorenyl group at position 2, which causes a certain degree of distortion of the molecule and is not conducive to the formation of a film
  • the orderly arrangement at times affects the hole transport performance of the film. Therefore, the turn-on voltage, current efficiency and lifetime of the device prepared based on R-4 are poor.
  • the dibenzo five-membered ring group in the compound provided by the present invention, the dibenzo five-membered ring group, its substitution position on the naphthalene ring, and the substituents on the dibenzo five-membered ring group all make the compound applicable Organic electroluminescent devices are an important factor that can bring excellent performance, and none of them are indispensable.
  • This embodiment provides an organic electroluminescent device, and the specific preparation process is as follows:
  • the glass plate coated with the transparent conductive layer of ITO 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 evaporate HT-4 on the hole injection layer as the hole transport layer of the device the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 60nm;
  • the compound P1 synthesized in Synthesis Example 1 was vacuum vapor-deposited on the hole transport layer as the electron blocking layer material of the device, the vapor deposition rate was 0.1 nm/s, and the total vapor deposition film thickness was 60 nm;
  • the light-emitting layer of the device is vacuum-evaporated on the electron blocking layer.
  • the light-emitting layer includes the host material and the dye material.
  • the evaporation rate of the host material GPH-59 is adjusted to 0.1nm/s, and the dye RPD-8
  • the evaporation rate is set at a ratio of 3%, and the total film thickness of the evaporation is 40nm;
  • the electron transport layer material ET-46 of the vacuum vapor deposition device on the light-emitting layer is set at a ratio of 50% and ET-57 at a ratio of 50%.
  • the vapor deposition rate is 0.1nm/s, and the total vapor deposition film The thickness is 25nm;
  • ETL electron transport layer
  • LiF with a thickness of 0.5 nm was vacuum-evaporated as the electron injection layer
  • Al layer with a thickness of 150 nm was used as the cathode of the device.
  • Example 15-31 The difference between Examples 15-31, Comparative Examples 5-8 and Example 14 is only that the electron blocking layer material compound P1 is replaced with the corresponding compound in Table 2.
  • the compounds of the present invention a barrier layer material for the organic electroluminescent electronic device, the device luminance of 5000cd / m 2, the driving voltage as low as 4.5V, and the current efficiency of up to 12cd / Above A, it can effectively reduce the driving voltage, improve the current efficiency, and prolong the service life of the device. It is an electronic barrier material with good performance. From the above results, it can be seen that the above compound can be used as a hole transport material, and can also be used as an electron blocking layer material in combination with other hole transport materials.
  • the devices prepared by using the above materials have the characteristics of low starting voltage, high performance and long life. The improvement of these properties is closely related to the coordination of the core and specific substituents of the special structure of the compound provided by the present invention.
  • Examples 32-37 and Comparative Examples 1-4 are different from Example 1 only in that the hole transport layer compound P1 is replaced with the corresponding compound in Table 3.
  • Example 38-43 The difference between Examples 38-43 and Comparative Examples 5-8 and Example 14 is only that the electron blocking layer material compound P1 is replaced with the corresponding compound in Table 4.
  • the compounds of the present application P299 to P304 when the electron blocking layer material for the organic electroluminescent device, and the device luminance of 5000cd / m 2, drive The voltage is as low as 4.6V and the current efficiency is as high as 12cd/A or more, which can effectively reduce the driving voltage, improve the current efficiency, and prolong the service life of the device. Therefore, it is also a good electronic barrier material.
  • the five-membered dibenzo ring group in the compounds provided by the present invention, the five-membered dibenzo ring group, its substitution position on the naphthalene ring and the substituents on the five-membered dibenzo ring group are all used in these compounds. It has a positive impact on the excellent performance of organic electroluminescent devices.
  • the present invention uses the above embodiments to illustrate the detailed methods of the present invention, but the present invention is not limited to the above detailed methods, which does not mean that the present invention must rely on the above detailed methods to be implemented.
  • Those skilled in the art should understand that any improvement of the present invention, the equivalent replacement of each raw material of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., fall within the scope of protection and disclosure of the present invention.

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Abstract

L'invention concerne un composé représenté par la formule (I), son application, et un dispositif électroluminescent organique le contenant. Lorsque le composé est utilisé dans un dispositif électroluminescent organique, l'efficience lumineuse peut être améliorée, la tension de démarrage peut être réduite et la durée de vie peut être prolongée.
PCT/CN2020/136595 2019-12-18 2020-12-15 Composé, son application et dispositif électroluminescent organique le contenant WO2021121230A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO2023075134A1 (fr) * 2021-10-28 2023-05-04 엘티소재주식회사 Composé amine et dispositif électroluminescent organique le comprenant

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