WO2019114769A1 - Composé contenant du pyridoindole et son utilisation dans un dispositif électroluminescent organique - Google Patents

Composé contenant du pyridoindole et son utilisation dans un dispositif électroluminescent organique Download PDF

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WO2019114769A1
WO2019114769A1 PCT/CN2018/120716 CN2018120716W WO2019114769A1 WO 2019114769 A1 WO2019114769 A1 WO 2019114769A1 CN 2018120716 W CN2018120716 W CN 2018120716W WO 2019114769 A1 WO2019114769 A1 WO 2019114769A1
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thickness
group
layer
compound
pyridoindole
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PCT/CN2018/120716
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Chinese (zh)
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王芳
李崇
张兆超
庞羽佳
蔡啸
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江苏三月光电科技有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

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  • the present invention relates to the field of semiconductor technology, and more particularly to a compound containing pyridoindole and its use in an organic electroluminescent device.
  • OLED Organic Light Emission Diodes
  • the OLED light-emitting device is like a sandwich structure, including an electrode material film layer and an organic functional material sandwiched between different electrode film layers, and various functional materials are superposed on each other according to the purpose to form an OLED light-emitting device.
  • OLED display technology has been applied in the fields of smart phones, tablet computers, etc., and will further expand to large-size applications such as televisions.
  • OLED devices have luminous efficiency and service life. Further improvement is needed.
  • Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device.
  • OLED photoelectric functional materials applied to OLED devices can be divided into two categories, namely, charge injection transport materials and luminescent materials, and further, charge injection transport materials can be divided into electron injection transport materials, electron blocking materials, and holes. The transport material and the hole blocking material are injected, and the luminescent material can also be divided into a host luminescent material and a dopant material.
  • various organic functional materials are required to have good photoelectric characteristics. For example, as a charge transport material, it is required to have good carrier mobility, high glass transition temperature, etc., as a main body of the light-emitting layer. Materials require materials with good bipolarity, appropriate HOMO/LUMO energy levels, and the like.
  • the OLED photoelectric functional material film layer constituting the OLED device includes at least two or more layers, and the industrially applied OLED device structure includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron.
  • a plurality of film layers such as a transport layer and an electron injection layer, that is, an optoelectronic functional material applied to an OLED device includes at least a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material, etc., and the material type and the collocation form are rich. Characteristics of sex and diversity.
  • the optoelectronic functional materials used have strong selectivity, and the performance of the same materials in different structural devices may be completely different. Therefore, in view of the industrial application requirements of current OLED devices, and the different functional film layers of OLED devices, the photoelectric characteristics of the devices must be selected to be more suitable, and high-performance OLED functional materials or material combinations can achieve high efficiency and long device. Comprehensive characteristics of life and low voltage. As far as the actual demand of the current OLED display lighting industry is concerned, the development of OLED materials is still far from enough. It is lagging behind the requirements of panel manufacturers, and it is especially important to develop higher performance organic functional materials as material enterprises.
  • the present application provides a pyridinium-containing compound and its use in an organic electroluminescent device.
  • the compound of the invention has high glass transition temperature and molecular thermal stability, suitable HOMO and LUMO energy levels, high hole mobility, and can be effectively used to improve the luminous efficiency of the device and the service life of the OLED device after being fabricated by the OLED device. .
  • A is represented by a single bond, an oxygen atom, a C 1-10 linear or branched alkyl substituted alkylene group, an aryl substituted alkylene group, an alkyl substituted imido group or an aryl substituted imido group.
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 are each independently represented as CH or N atom, and the number of N atoms is 0, 1 or 2;
  • n, p, q are equal to 0 or 1; and m + n + p + q ⁇ 1;
  • E is a pyridoindole group optionally substituted with one or more R 1 ;
  • R 1 represents one of a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 5 to C 30 heteroaryl group; the hetero atom is nitrogen, oxygen or sulfur.
  • the present invention can also make the following improvements.
  • a compound containing pyridoindole the E being represented by the formula (2);
  • Ar 1 is represented by one of a mono-, substituted or unsubstituted C 6 - 30 arylene, a substituted or unsubstituted C 5 - 30 heteroarylene; the hetero atom is nitrogen, oxygen or sulfur ;
  • Ar 2 is represented by one of a substituted or unsubstituted C 6 - 30 aryl group, a substituted or unsubstituted C 5 - 30 heteroaryl group; the hetero atom is nitrogen, oxygen or sulfur;
  • Z is represented by a C-H or N atom, and at least one Z represents an N atom.
  • a compound containing pyridoindole in the formula (1) Expressed as: Any of them.
  • a compound containing a pyridoindole the structure of the formula (2) can be expressed as: Any of them.
  • said Ar 1 represents a single bond, phenylene, naphthylene group, biphenylene group, anthracenyl group, a furyl group, a carbazolyl group, a naphthylene Of pyridine, quinolinol, thienylene, pyridylene, fluorenylene, 9,9-dimethylindenyl, phenanthrylene, dibenzofuranyl, dibenzothiophenyl One type;
  • the Ar 2 is represented by phenyl, naphthyl, biphenyl, anthracenyl, furyl, oxazolyl, naphthyridinyl, quinolyl, thienyl, pyridyl, fluorenyl, 9,9-dimethyl
  • a mercapto group a phenanthryl group, a dibenzofuranyl group, and a dibenzothiophene group.
  • a compound containing pyridoindole the specific structural formula of the compound is:
  • the invention also provides a preparation method of a compound containing pyridoindole, the preparation method relates to a reaction equation:
  • the raw material A and the intermediate M are dissolved in a mixed solution of toluene and ethanol, and after deoxidation, Pd(PPh 3 ) 4 and K 2 CO 3 are added , and the reaction is carried out at 95 to 110 ° C for 10 to 24 hours in an inert atmosphere until the raw materials are used. After the reaction is completed, the mixture is cooled and filtered, and the filtrate is evaporated to remove the solvent, and the crude product is passed through a silica gel column to obtain the target compound;
  • the amount of the toluene and the ethanol is 30 to 50 mL of toluene and 5 to 10 mL of ethanol per gram of the raw material A, and the molar ratio of the intermediate M to the raw material A is 1 to 3:1, Pd(PPh 3 ) 4 and the raw material.
  • the molar ratio of A is from 0.006 to 0.03:1, and the molar ratio of K 2 CO 3 to the raw material A is from 1.5 to 4.5:1.
  • the present invention also provides an organic electroluminescent device comprising at least one functional layer containing the pyridinium-containing compound.
  • an organic electroluminescent device comprises a hole transport layer/electron barrier layer, the hole transport layer/electron barrier layer containing the pyridinium-containing compound.
  • an organic electroluminescent device comprises a light-emitting layer containing the pyridinium-containing compound.
  • the invention also provides an illumination or display element comprising the organic electroluminescent device.
  • the compound of the present invention has asymmetry and avoids aggregation between molecules.
  • the compound of the present invention has strong rigidity, is incapable of crystallization, is difficult to aggregate, has good film forming property, and has high glass transition temperature and heat. Stability, therefore, when the compound of the present invention is applied to an OLED device, the film stability after film formation can be maintained, and the service life of the OLED device can be improved.
  • the structure of the compound of the invention makes the distribution of electrons and holes in the luminescent layer more balanced, and improves the hole injection/transport performance at the appropriate HOMO level; and at the appropriate LUMO level, it acts as an electron blocking. Enhancing the recombination efficiency of the excitons in the luminescent layer; when used as a luminescent functional layer material of the OLED illuminating device, the pyridine ruthenium combined with the branch within the scope of the invention can effectively improve the exciton utilization and the high fluorescence radiation efficiency, and the high Efficiency roll-off at current density reduces device voltage and increases current efficiency and lifetime of the device.
  • the compound of the invention has good application effects in OLED light-emitting devices and has good industrialization prospects.
  • FIG. 1 is a schematic structural view of a material exemplified in the present invention applied to an OLED device;
  • 1 is a transparent substrate layer
  • 2 is an ITO anode layer
  • 3 is a hole injection layer
  • 4 is a hole transport or electron blocking layer
  • 5 is a light emitting layer
  • 6 is an electron transport or hole blocking layer
  • 7 is an electron injection layer.
  • Layer, 8 is a cathode reflective electrode layer;
  • Figure 2 is a plot of current efficiency as a function of temperature.
  • the amount of the toluene and the ethanol is 30 to 50 mL of toluene and 5 to 10 mL of ethanol per gram of the raw material C
  • the molar ratio of the raw material B to the raw material C is (1 to 1.5): 1
  • Pd(PPh 3 ) 4 and The molar ratio of the raw material C was (0.006 to 0.02): 1
  • the molar ratio of K 2 CO 3 to the raw material C was (1.5 to 2): 1.
  • the molar ratio of the intermediate S to n-butyllithium is 1:1 to 1.5; and the molar ratio of the intermediate S to triisopropyl borate is 1:1 to 1.5.
  • the intermediate M was prepared by the synthesis method of the intermediate M-1, and the specific structure is shown in Table 1.
  • Compound 42 was prepared in the same manner as in Example 2 except that the starting material A-1 was replaced with the starting material A-2 and the starting material B-1 was replaced with the intermediate M-2. Elemental analysis structure (Molecular formula C 52 H 34 N 2 ): Theory C, 90.93; H, 4.99; N, 4.08; ⁇ / RTI> C, 90.97; H, 5.05; N, 4.12. ESI-MS (m/z) (M + ): calc. 686.27.
  • Compound 64 was prepared in the same manner as in Example 2 except that the starting material A-1 was replaced with the starting material A-4 and the starting material B-1 was replaced with the starting material B-4. Elemental analysis structure (Molecular formula C 42 H 28 N 2 ): calcd. C, 89.97; H, 5.03; N, 5.00; ⁇ / RTI> ⁇ /RTI> C, 90.03; H, 5.07; N, 5.02. ESI-MS (m/z) (M + ): 550.21.
  • Compound 70 was prepared in the same manner as in Example 2 except that the starting material A-1 was replaced with the starting material A-4 and the starting material B-1 was replaced with the intermediate M-1. Elemental Analysis Structure (Molecular Formula C 48 H 32 N 2 ): Theory C, 90.54; H, 5.07; N, 4.40; Tests: C, 90.57; H, 5.11; N, 4.48. ESI-MS (m/z) (M + ): calc.
  • Compound 134 was prepared in the same manner as in Example 10 except that the starting material A-6 was replaced with the starting material A-5 and the intermediate material M-1 was used to replace the starting material B-1.
  • Elemental analysis structure (Molecular Formula C 48 H 30 N 2 ): Theory C, 90.82; H, 4.76; N, 4.41; Tests: C, 90.85; H, 4.79; N, 4.44.
  • Compound 140 was prepared in the same manner as in Example 10 except that the starting material B-1 was replaced with the intermediate M-3. Elemental Analysis Structure (Molecular Formula C 51 H 31 N 3 ): Theory C, 89.32; H, 4.56; N, 6.13; Tests: C, 89.34; H, 4.59; N, 6.17. ESI-MS (m/z) (M + ): calc. 685.
  • Compound 182 was prepared in the same manner as in Example 10 except that the starting material A-5 was replaced with the starting material A-8 and the starting material B-1 was replaced with the intermediate M-4. Elemental analysis structure (Molecular formula C 51 H 36 N 2 ): Theory C, 90.50; H, 5.36; N, 4.14; ⁇ / RTI> C, 90.54; H, 5.38; N, 4.17. ESI-MS (m/z) (M + ): s.
  • Compound 201 was prepared in the same manner as in Example 2 except that the starting material A-1 was replaced with the starting material A-11. Elemental analysis structure (Molecular formula C 45 H 34 N 2 ): calcd. C, 89.67; H, 5.69; N, 4.65; ⁇ / RTI> ⁇ /RTI> C, 89.69; H, 5.71; N, 4.68. ESI-MS (m/z) (M + ): calc. 602.
  • Compound 215 was prepared in the same manner as in Example 10 except that the starting material A-5 was replaced with starting material A-12. Elemental analysis structure (Molecular formula C 41 H 25 N 3 ): calcd. C, 87.99; H, 4.50; N, 7.51; ⁇ / RTI> ⁇ /RTI> C, 88.05; H, 4.53; N, 7.54. ESI-MS (m/z) (M + ): 553.
  • Compound 223 was prepared in the same manner as in Example 10 except that the starting material A-5 was replaced with the starting material A-13 and the starting material B-1 was replaced with the intermediate M-2. Elemental analysis structure (Molecular formula C 51 H 31 N 3 ): Theory C, 89.32; H, 4.56; N, 6.13; Tests: C, 89.34; H, 4.62; N, 6.15. ESI-MS (m/z) (M + ): calc. 685.
  • the compound 243 was prepared in the same manner as in Example 10 except that the starting material A-5 was replaced with the starting material A-14 and the starting material B-1 was replaced with the intermediate M-5. Elemental Analysis Structure (Molecular Formula C 52 H 32 N 4 ): Theory C, 87.62; H, 4.52; N, 7.86; Found: C, 87.65; H, 4.55; N, 7.89. ESI-MS (m/z) (M + ): s.
  • the organic compound is used in a light-emitting device, has a high Tg (glass transition temperature) temperature and a triplet level (T1), and a suitable HOMO, LUMO energy level can be used as a hole blocking/electron transport material, or as a The luminescent layer material is used.
  • Tg glass transition temperature
  • T1 triplet level
  • HOMO HOMO
  • LUMO energy level can be used as a hole blocking/electron transport material, or as a The luminescent layer material is used.
  • the thermal performance, T1 energy level and HOMO energy level test were carried out on the compound of the present invention and the existing materials, and the results are shown in Table 2.
  • the triplet energy level T1 is tested by Hitachi's F4600 fluorescence spectrometer.
  • the test conditions of the material are 2*10 -5 toluene solution;
  • the glass transition temperature Tg is by differential scanning calorimetry (DSC, Germany Benz DSC204F1 differential scanning) The calorimeter was measured at a heating rate of 10 ° C/min;
  • the thermogravimetric temperature Td was a temperature at which the weight loss was 1% in a nitrogen atmosphere, and was measured on a TGA-50H thermogravimetric analyzer of Shimadzu Corporation, Japan, and the flow rate of nitrogen was 20 mL/ Min;
  • the highest occupied molecular orbital HOMO level is tested by the ionization energy test system (IPS3) and tested as the atmospheric environment.
  • IPS3 ionization energy test system
  • the organic compound of the invention has high glass transition temperature, can improve the phase stability of the material film, further improve the service life of the device, and has a high triplet energy level, compared with the currently applied CBP and TPBi materials.
  • the energy loss of the luminescent layer can be blocked, thereby improving the luminous efficiency of the device.
  • the materials of the invention and the materials of application have similar HOMO levels. Therefore, the organic material containing pyridinium in the invention can effectively improve the luminous efficiency and the service life of the device after being applied to different functional layers of the OLED device.
  • the device examples 1 to 21 and the device comparative example 1 have the same fabrication process, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also maintained. Consistently, the difference between the device embodiments 2 and 13 is that the material of the light-emitting layer in the device is changed; the device embodiments 14 to 21 change the material of the hole blocking/electron transport layer of the device, and the devices obtained by the respective embodiments are The performance test results are shown in Table 3.
  • an electroluminescent device is prepared by: a) cleaning an ITO anode layer 2 on a transparent substrate layer 1 and ultrasonically cleaning each with deionized water, acetone, and ethanol for 15 minutes, respectively, and then plasma.
  • the body cleaner is treated for 2 minutes; b) on the ITO anode layer 2, the hole injection layer material HAT-CN is deposited by vacuum evaporation, the thickness is 10 nm, this layer serves as the hole injection layer 3; c) is empty On the hole injecting layer 3, a hole transporting material NPB is deposited by vacuum evaporation to a thickness of 80 nm, the layer is a hole transporting layer/electron blocking layer 4; d) is steamed on the hole transporting/electron blocking layer 4
  • the luminescent layer 5 is plated, the host material is the compound 2 and the compound GH of the invention, the doping material is Ir(ppy) 3 , and the compound 2, GH and Ir(ppy) 3 have a mass ratio of 50:50:10 and a thickness of 40 nm.
  • the electron transporting material TPBI is evaporated by vacuum evaporation to a thickness of 35 nm, and this organic material is used as the hole blocking/electron transporting layer 6; f) in hole blocking/electron transport Above the layer 6, vacuum-evaporating the electron-injecting layer LiF to a thickness of 1 nm, the layer is an electron injecting layer 7; g) in the electron injection On the layer 7, a cathode Al (100 nm) is vacuum-deposited, and the layer is a cathode reflective electrode layer 8; after the fabrication of the electroluminescent device is completed according to the above steps, the driving voltage and current efficiency of the device are measured, and the results are shown in Table 3. Show.
  • the molecular organization of the relevant material is as follows:
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (Thickness: 40 nm, material: compound 15, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: compound 38, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10)/hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / luminescent layer 5 (Thickness: 40 nm, material: Compound 42 and Ir(ppy) 3 are mixed by weight ratio of 90:10) / Hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / Electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: compound 58, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10)/hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (Thickness: 40 nm, material: compound 64, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: compound 70 and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (Thickness: 40 nm, material: compound 98, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10)/hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: compound 102 and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: compound 134, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10)/hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (Thickness: 40 nm, material: compound 197, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10)/hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (Thickness: 40 nm, material: compound 199, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / luminescent layer 5 (Thickness: 40 nm, material: compound 201, GH, and Ir(ppy) 3 are mixed by weight ratio of 50:50:10)/hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection Layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 140) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 143) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 155) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 182) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 215) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 223) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 234) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / luminescent layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: compound 243) / electron injection layer 7 (thickness) : 1 nm, material: LiF) / Al (thickness: 100 nm).
  • ITO anode layer 2 (thickness: 150 nm) / hole injection layer 3 (thickness: 10 nm, material: HAT-CN) / hole transport layer 4 (thickness: 80 nm, material: NPB) / light-emitting layer 5 (thickness: 40 nm, material: CBP and Ir(ppy) 3 are mixed by weight ratio of 90:10) / hole blocking/electron transport layer 6 (thickness: 35 nm, material: TPBI) / electron injection layer 7 (thickness: 1 nm, material: LiF) / Al (thickness: 100 nm).
  • the detection data of the obtained electroluminescent device is shown in Table 3.
  • the OLED device prepared by the material of the invention is more stable when operating at a low temperature, and the device examples 2, 9, and 17 and the device comparative example 1 are tested in the range of -10 to 80 ° C, and the results are shown in Table 4 and Figure 2 shows.
  • device examples 2, 9, and 17 are device structures in which the materials of the present invention and known materials are matched, and compared with the device comparative example 1, not only the low temperature efficiency but also the temperature rise process. In the middle, efficiency has increased steadily.

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

Abstract

La présente invention concerne un composé contenant du pyridoindole et son utilisation dans un dispositif électroluminescent organique. Le composé selon l'invention est constitué de groupes pyridoindole, a un niveau d'énergie HOMO profond et une mobilité des trous et est approprié en tant que matériau de transport de trous ou matériau de blocage d'électrons ; De plus, le groupe dans le composé selon l'invention a une forte résistance, et a des caractéristiques qui ne sont pas faciles à cristalliser et à agréger et présente une bonne propriété de formation de film. L'invention utilise un matériau de couche fonctionnelle électroluminescente organique dans un dispositif OLED, ce qui permet d'améliorer de manière considérable l'efficacité du courant, l'efficacité énergétique et le rendement quantique externe du dispositif ; en même temps, l'amélioration de la durée de vie du dispositif est très significative.
PCT/CN2018/120716 2017-12-13 2018-12-12 Composé contenant du pyridoindole et son utilisation dans un dispositif électroluminescent organique WO2019114769A1 (fr)

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CN112876465B (zh) * 2019-11-29 2023-07-04 上海和辉光电股份有限公司 一种噁二唑取代的有机发光材料及oled器件
CN112574045B (zh) * 2020-12-08 2022-04-01 武汉华星光电半导体显示技术有限公司 空穴传输材料及其制备方法、电致发光器件

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006131783A (ja) * 2004-11-08 2006-05-25 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
KR20130106520A (ko) * 2012-03-20 2013-09-30 엘지디스플레이 주식회사 인광 화합물 및 이를 이용한 유기발광다이오드소자
KR20150030309A (ko) * 2013-09-11 2015-03-20 엘지디스플레이 주식회사 형광 화합물 및 이를 이용한 유기발광다이오드소자
CN104892578A (zh) * 2015-05-19 2015-09-09 苏州大学 芴螺三苯胺衍生物及其用途
CN104953037A (zh) * 2014-03-31 2015-09-30 乐金显示有限公司 有机发光二极管
KR20170075645A (ko) * 2015-12-23 2017-07-03 솔브레인 주식회사 신규한 유기화합물 및 이를 포함하는 유기전계발광소자
CN107501302A (zh) * 2017-08-11 2017-12-22 长春海谱润斯科技有限公司 一种1,3,5‑三嗪衍生物及其应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106831581B (zh) * 2017-02-10 2021-07-09 上海大学 一种氮杂螺二芴衍生物及其制备方法
CN107033167B (zh) * 2017-05-22 2019-03-15 上海大学 具有热活化延迟荧光的亚铜离子配合物及其制备和应用
CN107021926B (zh) * 2017-06-12 2020-12-11 中节能万润股份有限公司 一种含有氮杂螺芴和含氮六元杂环的化合物及其在oled上的应用

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006131783A (ja) * 2004-11-08 2006-05-25 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
KR20130106520A (ko) * 2012-03-20 2013-09-30 엘지디스플레이 주식회사 인광 화합물 및 이를 이용한 유기발광다이오드소자
KR20150030309A (ko) * 2013-09-11 2015-03-20 엘지디스플레이 주식회사 형광 화합물 및 이를 이용한 유기발광다이오드소자
CN104953037A (zh) * 2014-03-31 2015-09-30 乐金显示有限公司 有机发光二极管
CN104892578A (zh) * 2015-05-19 2015-09-09 苏州大学 芴螺三苯胺衍生物及其用途
KR20170075645A (ko) * 2015-12-23 2017-07-03 솔브레인 주식회사 신규한 유기화합물 및 이를 포함하는 유기전계발광소자
CN107501302A (zh) * 2017-08-11 2017-12-22 长春海谱润斯科技有限公司 一种1,3,5‑三嗪衍生物及其应用

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