WO2022100634A1 - Dispositif électroluminescent organique et appareil d'affichage le comprenant - Google Patents

Dispositif électroluminescent organique et appareil d'affichage le comprenant Download PDF

Info

Publication number
WO2022100634A1
WO2022100634A1 PCT/CN2021/129912 CN2021129912W WO2022100634A1 WO 2022100634 A1 WO2022100634 A1 WO 2022100634A1 CN 2021129912 W CN2021129912 W CN 2021129912W WO 2022100634 A1 WO2022100634 A1 WO 2022100634A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
heteroaryl
independently selected
aryl
independently
Prior art date
Application number
PCT/CN2021/129912
Other languages
English (en)
Chinese (zh)
Inventor
陈跃
丰佩川
邢其锋
邱创弘
陈义丽
孙伟
王鹏程
Original Assignee
烟台海森大数据有限公司
烟台显华光电材料研究院有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 烟台海森大数据有限公司, 烟台显华光电材料研究院有限公司 filed Critical 烟台海森大数据有限公司
Publication of WO2022100634A1 publication Critical patent/WO2022100634A1/fr

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D269/00—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00
    • C07D269/02—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00 having the hetero atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses

Definitions

  • the present application relates to the technical field of organic light-emitting displays, and in particular, to an organic electroluminescent device and a display device including the device.
  • the organic electroluminescent device is a multilayer organic thin film structure in which the light-emitting layer is located between the cathode and the anode. After electrification, the light emitted by the light-emitting layer is transmitted from the transparent electrode side, and the light is lost due to the waveguide effect such as total reflection between each film layer. Adding a high refractive index light extraction layer on the transparent electrode can greatly improve the light extraction efficiency.
  • the light extraction layer may be an inorganic compound or an organic compound.
  • Inorganic compounds are characterized by a high refractive index, which is beneficial for light extraction, but the coating temperature is very high (>1000 degrees), which can cause damage to organic components.
  • the evaporation temperature of organic thin films is low, and the technology has greater advantages than inorganic compounds.
  • Organic electroluminescent diode (OLED) elements basically use organic light extraction materials that can improve the light extraction efficiency of OLEDs. Refractive index is the most important indicator of light extraction materials. Generally, the higher the refractive index of the light extraction layer, the higher the light extraction efficiency from the electrode to the light extraction layer, and the higher the luminous efficiency of the OLED.
  • the material mainly used for the light extraction layer of OLED is an aromatic amine compound (CN103828485A) from Hodogaya, Japan.
  • the refractive index of such compounds eg compounds 1-1 and 1-2
  • a first aspect of the present application provides an organic electroluminescence device, comprising:
  • the light extraction layer includes a compound of general formula (I):
  • Ar 1 and Ar 2 are each independently selected from H atom, deuterium atom, halogen, C 6 -C 30 aryl group or C 3 -C 30 heteroaryl group, the hydrogen on the aryl group and the heteroaryl group
  • Each atom can be independently substituted with Ra
  • the heteroatoms on the heteroaryl group are each independently selected from O, S and N
  • the Ra is each independently selected from deuterium, halogen, C 1 -C 6 alkyl, phenyl, biphenyl, terphenyl or naphthyl;
  • L 1 , L 2 and L 3 are each independently selected from phenylene or pyridylene.
  • a second aspect of the present application provides a display device comprising the organic electroluminescent device provided by the present application.
  • the organic electroluminescent device provided by the present application includes a light extraction layer with a high refractive index, and takes advantage of the high refractive index of the light extraction layer to more effectively promote light extraction, thereby improving the luminous efficiency of the organic electroluminescent device.
  • the display device provided by the present application has excellent display effect.
  • FIG. 1 is a schematic diagram of an organic electroluminescent device according to an embodiment of the present application.
  • a first aspect of the present application provides an organic electroluminescence device, comprising:
  • the light extraction layer includes a compound of general formula (I):
  • Ar 1 and Ar 2 are each independently selected from H atom, deuterium atom, halogen, C 6 -C 30 aryl group or C 3 -C 30 heteroaryl group, the hydrogen on the aryl group and the heteroaryl group
  • Each atom can be independently substituted with Ra
  • the heteroatoms on the heteroaryl group are each independently selected from O, S and N
  • the Ra is each independently selected from deuterium, halogen, C 1 -C 6 alkyl, phenyl, biphenyl, terphenyl or naphthyl;
  • L 1 , L 2 and L 3 are each independently selected from phenylene or pyridylene.
  • said L 1 , L 2 and L 3 are each independently selected from the following groups:
  • said Ar 1 and Ar 2 are each independently selected from the following groups:
  • R 1 and R 2 are each independently selected from C 1 -C 6 alkyl, C 6 -C 12 aryl, or C 3 -C 12 heteroaryl.
  • the Ar 1 is selected from the following groups:
  • R 01 and R 02 are each independently selected from a C 1 -C 6 alkyl group, a C 6 -C 12 aryl group or a C 3 -C 12 heteroaryl group, and the heteroatom in the heteroaryl group is selected from O or S.
  • the compound of general formula (I) may be selected from the following compounds:
  • the hole transport layer comprises a compound of general formula (II):
  • Ar 3 and Ar 4 are each independently selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group may each independently be substituted by Rb;
  • R 3 -R 6 are each independently selected from hydrogen, deuterium, C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl base, the hydrogen atoms on the aryl group and the heteroaryl group can be independently substituted by Rb, and the two adjacent groups in the R 3 -R 6 can be connected to form a ring;
  • R 7 and R 8 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl, said The hydrogen atoms on the aryl group and the heteroaryl group can each independently be replaced by Rb, and the R7 and R8 can be connected to form a ring;
  • X is selected from O, S, CR 9 R 10 , NR 11 , R 9 and R 10 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 alkyl Aryl or C 3 -C 30 heteroaryl, the R 11 is selected from C 6 -C 30 aryl or C 3 -C 30 heteroaryl, the aryl and the hydrogen atom on the heteroaryl Each independently can be substituted by Rb, and said R 9 and R 10 can be linked to form a ring;
  • L is selected from a chemical bond, a C 6 -C 30 arylene group or a C 3 -C 30 heteroarylene group, and each of the hydrogen atoms on the arylene group and the heteroarylene group independently may be substituted by Rb;
  • heteroatoms on the heteroaryl or heteroarylene are each independently selected from O, S, N;
  • the Rbs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
  • the compound of general formula (II) may be selected from the following compounds:
  • the electron transport layer comprises a compound of general formula (III):
  • R 12 -R 17 are each independently selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, said aryl and heteroaryl
  • the hydrogen atoms on each independently can be substituted by Rc, the adjacent two groups in the R 12 -R 14 can be connected to form a ring, and the R 16 and R 17 can be connected to form a ring;
  • A is selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc;
  • Y is selected from O, S, CR 18 R 19 , R 18 and R 19 are each independently selected from C 1 -C 6 alkyl, C 5 -C 20 cycloalkyl, C 6 -C 30 aryl or
  • the heteroaryl group of C 3 -C 30 , the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc, and the R 18 and R 19 can be connected to form a ring;
  • X 1 -X 4 are each independently selected from CR 20 or N, and R 20 is selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl , the hydrogen atoms on the aryl group and the heteroaryl group can be substituted by Rc independently, and the adjacent R 20 can be connected to form a ring;
  • L 1 and L 2 are each independently selected from a chemical bond, a C 6 -C 30 arylene group, or a C 3 -C 30 heteroarylene group, and the hydrogen atoms on the arylene group and the heteroarylene group are each independently Can be replaced by Rc;
  • heteroatoms on the heteroaryl group or the heteroarylene group are each independently selected from O, S, N;
  • the Rcs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
  • the compound of general formula (III) may be selected from the following compounds:
  • organic electroluminescence device which may be organic electroluminescence devices of various types and structures known in the art.
  • the organic electroluminescence device of the present application may be a light-emitting device with a top emission structure, and may include an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, Transparent or translucent cathodes and light extraction layer structures.
  • the organic electroluminescent device of the present application may be a light-emitting device with a bottom-emitting structure, which may include a light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron Transport layer, electron injection layer and cathode electrode.
  • the organic electroluminescent device of the present application may also be a light-emitting device with a double-sided light-emitting structure, which may include a light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, and a light-emitting layer on the substrate in this order. , electron transport layer, electron injection layer, transparent or semi-transparent cathode and light extraction layer.
  • an electron blocking layer may also be provided between the hole transport layer and the light-emitting layer, and a hole blocking layer may be provided between the light-emitting layer and the electron transport layer.
  • the above-mentioned layers may be added or omitted as long as the purpose of the present application is satisfied.
  • FIG. 1 shows a schematic diagram of an organic electroluminescent device according to an embodiment of the present application, wherein, from bottom to top, a substrate 1, an anode electrode 2, a hole injection layer 3, a hole transport layer 4, and a light-emitting layer 5 are arranged in sequence. , an electron transport layer 6 , an electron injection layer 7 , a cathode electrode 8 and a light extraction layer 9 .
  • FIG. 1 only schematically shows the structure of a typical organic electroluminescence device, and the present application is not limited to this structure.
  • the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the prior art can be used, such as glass, polymer materials, glass and polymer materials with TFT components, and the like.
  • the anode electrode 2 is not particularly limited, and can be selected from known anode electrodes in the prior art.
  • metals, alloys or conductive compounds have a high work function (4 eV or greater).
  • the metal may be metals such as Au and Ag.
  • the conductive transparent material can be selected from materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO, or an amorphous material such as IDIXO (In 2 O 3 -ZnO) that can form a transparent conductive film is used.
  • the thickness of the anode is in the range of 10 to 1,000 nm. Here, the thickness of the anode electrode varies depending on the material used.
  • the material of the hole injection layer 3 is not particularly limited, and can be made of hole injection layer materials known in the art, for example, hole transport material (HTM) is selected as the hole injection material.
  • HTM hole transport material
  • the hole injection layer 3 may further include a p-type dopant.
  • the type of the p-type dopant is not particularly limited, and various p-type dopants known in the art can be used. Dopants such as the following p-type dopants can be used:
  • the amount of the p-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
  • the hole transport layer 4 is not limited, and hole transport materials known to those skilled in the art can be used.
  • the hole transport layer 4 may comprise at least one of the hole transport materials of the present application, or at least one of the hole transport materials of the present application and the following known hole transport materials A combination of at least one of HT-1 to HT-32.
  • the material for the host of the hole injection layer and the material for the hole transport layer may be selected from at least one of the following HT-1 to HT-32 compounds:
  • the light-emitting layer 5 may include a blue light-emitting layer, a green light-emitting layer or a red light-emitting layer.
  • the light-emitting material in the light-emitting layer 5 is not particularly limited, and various light-emitting materials known to those skilled in the art can be used. Materials, for example, the luminescent material may comprise a host material and a luminescent dye.
  • the blue light host material may be selected from at least one of the following BH-1 to BH-36 compounds:
  • the green host material may be selected from at least one of the following GPH-1 to GPH-82 compounds:
  • the red host material may be selected from at least one of the following RH-1 to RH-10 compounds:
  • the light-emitting layer 5 adopts electroluminescence technology.
  • the luminescent dye in its luminescent layer 5 is a fluorescent or phosphorescent dopant, and the dopant can be selected from, but not limited to, at least one of the following blue-light dyes BD01 to BD04 compounds, and at least one of green dyes GD01 to GD04 compounds.
  • the amount of the dopant used is not particularly limited, and can be the amount known to those skilled in the art.
  • the electron transport layer 6 is not particularly limited, and electron transport materials known to those skilled in the art can be used.
  • the electron transport layer 6 contains at least one of the electron transport materials of the present application, and in another preferred embodiment, the electron transport layer 6 may also contain at least one of the electron transport materials of the present application A combination with at least one of the following known electron transport materials ET-1 to ET-58:
  • the electron transport layer 6 may further include n-type dopants, the types of the n-type dopants are not particularly limited, and various n-type dopants known in the art can be used , for example the following n-type dopants can be used:
  • the amount of the n-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
  • the electron injection layer 7 is not particularly limited, and electron injection materials known in the art can be used, for example, including but not limited to LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 in the prior art At least one of CO 3 , BaO, Na, Li, Ca and other materials.
  • the cathode electrode 8 is not particularly limited, and can be selected from, but not limited to, magnesium-silver mixture, LiF/Al, ITO, Al and other metals, metal mixtures, oxides and other materials.
  • the light extraction layer 9 includes at least one of the light extraction layers of the present application, and the light extraction layer 9 may also include at least one of the light extraction layers of the present application and known light extraction layers.
  • known light extraction layers are mainly light extraction layers containing aromatic amine compounds.
  • the light extraction layer of the present application is arranged on the transparent electrode on the light extraction side. It is required that the refractive index of the light extraction layer is larger than that of the electrode and can transmit visible light.
  • the light extraction layer of the present application has a higher refractive index, and thus can provide a high light extraction rate.
  • the refractive index of the light extraction layer of the present application is >1.85.
  • the refractive index of red light of the above-mentioned light extraction layer is greater than or equal to 1.85, the refractive index of green light is greater than or equal to 1.90, and the refractive index of blue light is greater than or equal to 2.00.
  • the thickness of the light extraction layer is 50-90 nm, preferably 60-80 nm.
  • the present application also provides a display device comprising the organic electroluminescent device of the present application.
  • the display device includes, but is not limited to, a display, a television, a mobile communication terminal, a tablet computer, and the like.
  • the method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art can be used.
  • the present application can be prepared by the following preparation method:
  • An electron injection material is vacuum-evaporated on the electron transport layer 6 as the electron injection layer 7, and the electron injection material is selected from LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca at least one of the other materials;
  • vacuum evaporation cathode material is used as cathode electrode 8 on electron injection layer 7;
  • a reflective anode electrode is arranged on the glass substrate, the anode electrode is an ITO electrode, and the thickness of the electrode is 130 nm;
  • a hole injection layer with a thickness of 10 nm was vacuum evaporated on the anode electrode.
  • the material of the hole injection layer was HT-11 and a p-type dopant p-1 with a mass ratio of 3%, wherein the evaporation rate was 0.1 nm/s, the selected hole injection layer materials and p-type dopants are the following materials:
  • a hole transport layer with a thickness of 112 nm was vacuum evaporated on the hole injection layer, and the material of the hole transport layer was the above-mentioned HT-32, wherein the evaporation rate was 0.1 nm/s;
  • a light-emitting layer is vacuum-evaporated on the hole transport layer, and the light-emitting layer includes a host material BH-1 and a light-emitting dye BD-1, and is vapor-deposited by a multi-source co-evaporation method, wherein the host material BH-1 is adjusted
  • the evaporation rate is 0.1nm/s
  • the evaporation rate of dye BD-1 is 3% of the evaporation rate of the host material
  • the total film thickness of evaporation is 20nm
  • the host material and the luminescent dye are the following materials:
  • the electron transport layer contained an electron transport material ET-58 and an n-type dopant n-1, wherein the content of the n-type dopant was 50 mol%.
  • the electron transport materials and n-type dopants are the following materials:
  • an electron injection layer with a thickness of 40 nm is vacuum-evaporated on the electron transport layer, and the material of the electron injection layer is Liq (8-hydroxyquinoline-lithium), and the evaporation rate is 0.1 nm/s;
  • a cathode electrode with a thickness of 18 nm is vacuum-evaporated on the electron injection layer, and the cathode electrode is composed of a cathode material with a Mg:Ag molar ratio of 1:9, and the evaporation rate is 1 nm/s;
  • a light extraction layer with a thickness of 50 nm was vacuum evaporated on the cathode electrode, and the material of the light extraction layer was LEM-1.
  • the organic electroluminescent device of this embodiment emits blue light.
  • the organic electroluminescent device of this embodiment emits green light.
  • Example 2 The rest is the same as Example 1, except that the light-emitting host material and the light-emitting dye are replaced by RH-10 and RPD-1, respectively.
  • the organic electroluminescent device of this embodiment emits red light.
  • Example 31 The same as in Example 31, except that the hole transport material was replaced by B6 and the electron transport material was replaced by C27 as shown in Table 1.
  • the measuring instrument is Version-1.0.1.4 spectroscopic ellipsometer of _Radiation technology company; the size of the glass substrate is 200mm ⁇ 200mm, and the thickness of the material film is 80nm. The refractive index of the compound was measured at different wavelengths.
  • the BJV test system was used to test the current efficiency and CIE color coordinates of the organic electroluminescent device.
  • the blue light index (BI) is used to investigate the luminous efficiency, and the CIEy value mainly evaluates the saturation of the blue light color.
  • the blue light index is obtained by dividing the current efficiency of the blue light device by the CIEy value. The larger the CIEy value, the red shift of the blue color. , the decrease of CIEy value indicates the blue shift of blue color; the current efficiency is used to evaluate the luminous efficiency of green and red devices; the color change of green and red devices is mainly evaluated by the CIEx value, and the increase of CIEx indicates the red shift of luminescence , CIEx becomes smaller, indicating a blue-shift of luminescence.
  • the blue light index changed from 92 to 76, which decreased by 16, and the CIEy changed from 0.050 to 0.070, which increased by 0.020, indicating that the blue light changed to red.
  • the blue light index changes from 96 to 83, a decrease of 7, and the CIEy changes from 0.051 to 0.063, an increase of 7.
  • the blue light index of compound 1-1 is smaller than that of compound LEM-1, and the CIEy of compound 1-1 is larger than that of compound LEM-1, indicating that the blue light of the blue light device of LEM-1 Color saturation is higher.
  • the thickness of the light extraction layer is increased from 50nm to 90nm, the current efficiency is changed from 97cd/A to 101cd/A, an increase of 4cd/A, and the CIEx is changed from 0.235 to 0.250, an increase of 0.015
  • the current efficiency changed from 99cd/A to 106cd/A, an increase of 7cd/A, and the CIEx changed from 0.234 to 0.243, an increase of 0.009.
  • the thickness of the light extraction layer increased from 50nm to 90nm
  • the current efficiency increased from 46cd/A to 53cd/A, an increase of 7cd/A
  • the CIEx increased from 0.665 to 0.675, an increase of 0.010
  • the current efficiency changed from 48cd/A to 61cd/A, an increase of 13cd/A
  • the CIEx changed from 0.665 to 0.676, an increase of 0.011.
  • compound LEM-1 as a light extraction material can make the device emit light. Higher color saturation and greater current efficiency.
  • Examples 40-46 used the compounds provided in this application as hole injection materials and electron transport materials, respectively.
  • the blue light devices using these materials were compared with the comparative examples with the same thickness of the light extraction layer. It can be seen that the blue light index increased significantly. , CIEy decreases.
  • the compounds provided by the present application are used in the light extraction layer of organic electroluminescent devices, and the refractive indices of blue light, green light and red light are significantly improved, Therefore, light extraction can be more effectively promoted, a high light extraction rate can be provided, and the luminous efficiency of the organic electroluminescent device can be greatly improved.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique et un appareil d'affichage le comprenant. Le dispositif électroluminescent organique comprend un substrat, une électrode d'anode, une couche d'injection de trous, une couche de transport de trous, une couche d'émission de lumière, une couche de transport électronique, une couche d'injection électronique, une électrode de cathode et une couche d'extraction de lumière ; et la couche d'extraction de lumière comprend un composé de formule générale (I), a un indice de réfraction élevé, et peut améliorer l'efficacité d'émission de lumière du dispositif électroluminescent organique.
PCT/CN2021/129912 2020-11-12 2021-11-10 Dispositif électroluminescent organique et appareil d'affichage le comprenant WO2022100634A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN202011260930 2020-11-12
CN202011260930.2 2020-11-12
CN202110034259.8 2021-01-12
CN202110034259.8A CN112687797B (zh) 2020-11-12 2021-01-12 一种有机电致发光器件及包含该器件的显示装置

Publications (1)

Publication Number Publication Date
WO2022100634A1 true WO2022100634A1 (fr) 2022-05-19

Family

ID=75457446

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2021/129912 WO2022100634A1 (fr) 2020-11-12 2021-11-10 Dispositif électroluminescent organique et appareil d'affichage le comprenant

Country Status (2)

Country Link
CN (1) CN112687797B (fr)
WO (1) WO2022100634A1 (fr)

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014104500A1 (fr) * 2012-12-31 2014-07-03 제일모직 주식회사 Composé pour dispositif optoélectronique organique, diode électroluminescente organique le comprenant, et appareil d'affichage comprenant une diode électroluminescente organique
CN104662010A (zh) * 2012-08-30 2015-05-27 出光兴产株式会社 芳香族胺衍生物以及使用其的有机电致发光元件
KR20160111780A (ko) * 2015-03-17 2016-09-27 주식회사 엘지화학 유기 발광 소자
KR20160142918A (ko) * 2015-06-03 2016-12-14 머티어리얼사이언스 주식회사 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자
KR20170093270A (ko) * 2016-02-03 2017-08-16 주식회사 동진쎄미켐 캡핑층을 구비하는 유기발광소자 및 이를 이용한 전자장치
CN107223122A (zh) * 2015-02-16 2017-09-29 默克专利有限公司 用于电子器件的基于螺二芴衍生物的材料
CN108250189A (zh) * 2016-12-26 2018-07-06 株式会社Lg化学 新型杂环化合物及利用其的有机发光元件
CN110938063A (zh) * 2018-09-21 2020-03-31 东进世美肯株式会社 新颖的覆盖层用化合物及包含其的有机发光器件
CN111217778A (zh) * 2018-11-27 2020-06-02 东进世美肯株式会社 覆盖层用有机化合物及包含其的有机发光器件
CN111808042A (zh) * 2020-07-31 2020-10-23 长春海谱润斯科技有限公司 一种三芳胺化合物及其有机电致发光器件
CN111869326A (zh) * 2017-12-21 2020-10-30 保土谷化学工业株式会社 有机电致发光元件及其制造方法
CN111995532A (zh) * 2019-05-27 2020-11-27 东进世美肯株式会社 覆盖层用有机化合物及包含其的有机发光器件
CN112538060A (zh) * 2019-09-23 2021-03-23 东进世美肯株式会社 全新的覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
CN112745264A (zh) * 2019-10-31 2021-05-04 东进世美肯株式会社 新型覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
WO2021093377A1 (fr) * 2019-11-12 2021-05-20 广州华睿光电材料有限公司 Dispositif électroluminescent organique contenant un matériau de couche d'extraction de lumière

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100441434B1 (ko) * 2001-08-01 2004-07-22 삼성에스디아이 주식회사 유기 화합물 유도체 박막을 포함하는 유기 전계 발광 소자및 그 소자의 제조 방법
KR20170074652A (ko) * 2015-12-22 2017-06-30 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
US20180093962A1 (en) * 2016-10-05 2018-04-05 Sfc Co., Ltd. Novel organic compound and oranic light-emitting diode comprising same background of the invention
KR102393153B1 (ko) * 2017-07-27 2022-05-02 에스에프씨주식회사 저전압 구동이 가능하며, 고효율 및 장수명 특성을 가지는 유기 발광 소자
KR20200065952A (ko) * 2018-11-30 2020-06-09 주식회사 엘지화학 유기 발광 소자
CN109721540A (zh) * 2018-12-18 2019-05-07 阜阳欣奕华材料科技有限公司 二氢苯并吲唑类化合物、有机电致发光器件及显示装置
KR102583027B1 (ko) * 2019-03-13 2023-09-26 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20200122117A (ko) * 2019-04-17 2020-10-27 엘지디스플레이 주식회사 유기전계 발광소자
CN111533678B (zh) * 2019-07-19 2021-07-20 南京高光半导体材料有限公司 高效率电子阻挡材料及使用该种材料的有机电致发光器件
CN111533716B (zh) * 2019-12-30 2021-03-26 南京高光半导体材料有限公司 一种芴基有机电致发光化合物及有机电致发光器件
CN111440135B (zh) * 2020-04-16 2023-06-23 烟台显华化工科技有限公司 一种化合物、光提取材料和有机电致发光器件
CN111440159B (zh) * 2020-04-16 2023-12-15 烟台显华化工科技有限公司 一种化合物、光提取材料和有机电致发光器件
CN111606812B (zh) * 2020-05-25 2021-07-06 长春海谱润斯科技股份有限公司 一种三芳胺衍生物及其有机电致发光器件
CN111635392A (zh) * 2020-06-04 2020-09-08 烟台显华化工科技有限公司 一种化合物、空穴传输材料和有机电致发光器件

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104662010A (zh) * 2012-08-30 2015-05-27 出光兴产株式会社 芳香族胺衍生物以及使用其的有机电致发光元件
WO2014104500A1 (fr) * 2012-12-31 2014-07-03 제일모직 주식회사 Composé pour dispositif optoélectronique organique, diode électroluminescente organique le comprenant, et appareil d'affichage comprenant une diode électroluminescente organique
CN107223122A (zh) * 2015-02-16 2017-09-29 默克专利有限公司 用于电子器件的基于螺二芴衍生物的材料
KR20160111780A (ko) * 2015-03-17 2016-09-27 주식회사 엘지화학 유기 발광 소자
KR20160142918A (ko) * 2015-06-03 2016-12-14 머티어리얼사이언스 주식회사 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자
KR20170093270A (ko) * 2016-02-03 2017-08-16 주식회사 동진쎄미켐 캡핑층을 구비하는 유기발광소자 및 이를 이용한 전자장치
CN108250189A (zh) * 2016-12-26 2018-07-06 株式会社Lg化学 新型杂环化合物及利用其的有机发光元件
CN111869326A (zh) * 2017-12-21 2020-10-30 保土谷化学工业株式会社 有机电致发光元件及其制造方法
CN110938063A (zh) * 2018-09-21 2020-03-31 东进世美肯株式会社 新颖的覆盖层用化合物及包含其的有机发光器件
CN111217778A (zh) * 2018-11-27 2020-06-02 东进世美肯株式会社 覆盖层用有机化合物及包含其的有机发光器件
CN111995532A (zh) * 2019-05-27 2020-11-27 东进世美肯株式会社 覆盖层用有机化合物及包含其的有机发光器件
CN112538060A (zh) * 2019-09-23 2021-03-23 东进世美肯株式会社 全新的覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
CN112745264A (zh) * 2019-10-31 2021-05-04 东进世美肯株式会社 新型覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
WO2021093377A1 (fr) * 2019-11-12 2021-05-20 广州华睿光电材料有限公司 Dispositif électroluminescent organique contenant un matériau de couche d'extraction de lumière
CN111808042A (zh) * 2020-07-31 2020-10-23 长春海谱润斯科技有限公司 一种三芳胺化合物及其有机电致发光器件

Also Published As

Publication number Publication date
CN112687797B (zh) 2023-03-24
CN112687797A (zh) 2021-04-20

Similar Documents

Publication Publication Date Title
WO2022166623A1 (fr) Dispositif électroluminescent organique et appareil d'affichage le comprenant
JP6955610B2 (ja) 複素環化合物、および有機エレクトロルミネッセンス素子
TWI580666B (zh) Aromatic amine derivatives, organic electroluminescent elements and electronic machines
CN111606813B (zh) 化合物、包含其的有机电子发光器件及其应用
TW201300499A (zh) 新穎有機電場發光化合物及包含該化合物之有機電場發光裝置
CN111440135B (zh) 一种化合物、光提取材料和有机电致发光器件
CN112250640B (zh) 一种化合物、发光层主体材料和有机电致发光器件
JP2021504876A (ja) 有機発光素子
CN111440159A (zh) 一种化合物、光提取材料和有机电致发光器件
WO2009066808A1 (fr) Composés aromatiques électroluminescents à haut rendement et dispositif électroluminescent utilisant ces composés
WO2022100634A1 (fr) Dispositif électroluminescent organique et appareil d'affichage le comprenant
CN112939959B (zh) 一种化合物、光提取材料和有机电致发光器件
CN117263893A (zh) 一种含有二甲基芴结构的有机化合物及包含其的有机电致发光器件
CN112952019B (zh) 一种有机电致发光器件及包含该器件的显示装置
KR20130133518A (ko) 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
CN113725383B (zh) 一种有机电致发光器件及包含该器件的显示装置
CN115611891B (zh) 一种喹啉取代菲啰啉化合物及其应用
CN113972337B (zh) 包含封盖层的有机电致发光器件以及其制备方法
CN115521253B (zh) 一种双联喹啉衍生物化合物及其应用
CN115521292B (zh) 一种喹啉取代吡啶化合物及其应用
CN113851599A (zh) 一种有机电致发光器件及包含该器件的显示装置
CN115594599B (zh) 一类双联萘化合物及其应用
CN113823750A (zh) 一种有机电致发光器件及包含该器件的显示装置
CN115696960A (zh) 一种有机电致发光器件及包含该器件的显示装置
KR20220067943A (ko) 다환고리 화합물을 포함하는 유기전계발광소자 및 이의 제조방법

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21891154

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21891154

Country of ref document: EP

Kind code of ref document: A1