WO2019206292A1 - Dispositif électroluminescent organique et afficheur le comprenant - Google Patents

Dispositif électroluminescent organique et afficheur le comprenant Download PDF

Info

Publication number
WO2019206292A1
WO2019206292A1 PCT/CN2019/084629 CN2019084629W WO2019206292A1 WO 2019206292 A1 WO2019206292 A1 WO 2019206292A1 CN 2019084629 W CN2019084629 W CN 2019084629W WO 2019206292 A1 WO2019206292 A1 WO 2019206292A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
atom
alkyl
branched
carbon atoms
Prior art date
Application number
PCT/CN2019/084629
Other languages
English (en)
Chinese (zh)
Other versions
WO2019206292A9 (fr
Inventor
李崇
唐丹丹
张兆超
张小庆
Original Assignee
江苏三月光电科技有限公司
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 江苏三月光电科技有限公司 filed Critical 江苏三月光电科技有限公司
Publication of WO2019206292A1 publication Critical patent/WO2019206292A1/fr
Publication of WO2019206292A9 publication Critical patent/WO2019206292A9/fr

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/35—Devices specially adapted for multicolour light emission comprising red-green-blue [RGB] subpixels
    • 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
    • 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
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers

Definitions

  • the present invention relates to the field of semiconductor technology, and more particularly to an organic electroluminescent device and a display including the same.
  • the organic electroluminescent device technology can be used for manufacturing new display products as well as for preparing new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect.
  • An organic electroluminescent device is used as a current device. When a voltage is applied to electrodes at both ends thereof and an electric field acts on the positive and negative charges in the organic layer functional material film layer, the positive and negative charges are further recombined in the organic light-emitting layer, that is, Electroluminescence.
  • Organic electroluminescent devices are generally multilayer in structure, and various auxiliary functional layers other than the luminescent layer also play a vital role in device performance.
  • a reasonable device structure can effectively improve the performance of the device, and an electron injecting layer, an electron transporting layer, a hole blocking layer, an emitting layer, an electron blocking layer, a hole transporting layer, and a hole injecting layer are widely used to improve the performance of the device.
  • the carriers (holes and electrons) in the organic electroluminescent device are respectively injected into the device by the two electrodes of the device under the driving of the electric field, and are combined to emit light in the luminescent layer.
  • Hole transport materials used in existing organic electroluminescent devices are known, for example There is a large HOMO level difference between the HOMO level and the electron blocking layer material, and it is easy to form an accumulated charge at the material interface, which affects the lifetime of the OLED device.
  • a reasonable energy level structure facilitates the formation of a step barrier for the energy levels in each layer of the device, reduces the potential barrier of hole injection, and reduces the driving voltage of the device, thereby improving the luminous efficiency and lifetime of the device.
  • the present invention is directed to an organic electroluminescent device having improved luminous efficiency, heat resistance and service life, and a display including the same.
  • An object of the present invention is achieved by providing an organic electroluminescence device which is provided with a substrate, a first electrode, an organic functional material layer and a second electrode in this order from bottom to top,
  • the organic functional material layer includes:
  • a light emitting layer over the hole transporting region, comprising a host material and a guest material
  • An electron transport region located above the light emitting layer,
  • the hole transporting region includes a hole injecting layer, a hole transporting layer and an electron blocking layer in this order from bottom to top.
  • the hole transport layer includes first and second organic materials, wherein the first organic material has a HOMO level of from -5.2 eV to -5.6 eV, preferably from -5.3 eV to -5.5 eV, more preferably from -5.35 eV to -5.5 eV, and the HOMO level of the second organic material is -5.4 eV to -5.9 eV, preferably -5.4 eV to -5.7 eV, more preferably -5.48 eV to -5.68 eV, and
  • an organic electroluminescent device comprising a hole transport layer comprising the first and second organic materials of the present invention
  • a HOMO of the first and second organic materials is defined, the level matching of the anode and the electron blocking The barrier between the layer interfaces is reduced, which facilitates the injection of holes from the anode into the electron blocking layer, improves the hole injection efficiency, reduces the driving voltage of the device, reduces the accumulated charge at the interface contact, and improves the device.
  • Stability and service life in addition, the higher glass transition temperature of the hole transport layer of the present invention improves the heat resistance of the device.
  • the organic film layer composed of two different materials can effectively improve the molecular arrangement and the intermolecular interaction force, so that the film layer has higher stability, reduces the leakage current of the device, and improves the service life of the device.
  • Another object of the present invention is achieved by providing a display comprising the above organic electroluminescent device.
  • Fig. 1 schematically shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • Fig. 2 is a view schematically showing an energy transfer mechanism diagram of an organic electroluminescent device according to an embodiment of the present invention.
  • 3 to 7 are schematic views showing a combination structure of light-emitting layers in an organic electroluminescence device comprising the hole transport layer of the present invention.
  • any numerical range recited herein is intended to include all sub-ranges that have the For example, "1.0 to 10.0" means including all subranges (and 1.0 and 10.0) between the listed minimum value of 1.0 and the listed maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and equal to Or all subranges of values less than 10.0. Any of the maximum numerical limits set forth herein are meant to include all of the smaller numerical limits that are included herein, and any minimum numerical limitation listed herein is meant to include all of the greater numerical limitations included herein. The Applicant reserves the right to modify the present specification, including the claims, to clearly describe any sub-ranges that fall within the scope of the invention.
  • HT means an organic material constituting a hole transporting layer
  • HT-I means a first organic material
  • HT-II means a second organic material
  • Fig. 1 schematically shows a cross-sectional view of an organic electroluminescent device of one embodiment of the present invention.
  • an organic electroluminescent device according to an embodiment of the present invention is provided with a substrate 1, a first electrode 2, a hole transporting region A, a light emitting layer 6, an electron transporting region B, and a second electrode 10 in this order from bottom to top.
  • the hole transporting region A includes a hole injecting layer 3, a hole transporting layer 4, and an electron blocking layer 5 in this order from bottom to top
  • the electron transporting region B includes a hole blocking layer 7, an electron transporting layer 8, and electrons in order from bottom to top.
  • Inject layer 9 is provided with a substrate 1, a first electrode 2, a hole transporting region A, a light emitting layer 6, an electron transporting region B, and a second electrode 10 in this order from bottom to top.
  • the hole transporting region A includes a hole injecting layer 3, a hole transporting layer 4, and an electron blocking layer 5 in this order from bottom to top
  • any substrate commonly used for an organic electroluminescence device can be selected.
  • transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates; flexible PI film substrates.
  • Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency, and the direction of use is different depending on the nature.
  • a transparent substrate is preferably used.
  • the thickness of the substrate is not particularly limited.
  • a first electrode is formed on the substrate, and the first electrode and the second electrode may face each other.
  • the first electrode can be an anode.
  • the first electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode.
  • the first electrode may be formed using a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide ( ITZO) and so on.
  • the first electrode may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals.
  • the thickness of the first electrode layer depends on the material used, and is usually from 50 to 500 nm, preferably from 70 to 300 nm and more preferably from 100 to 200 nm.
  • the organic functional material layer disposed between the first electrode and the second electrode includes a hole transporting region, a light emitting layer, and an electron transporting region in order from bottom to top.
  • the hole transporting region may be disposed between the first electrode and the light emitting layer.
  • the hole transporting region may include a hole injecting layer, a hole transporting layer, and an electron blocking layer, but is not limited thereto.
  • the hole transporting region may include a hole injecting layer, a hole transporting layer, and an electron blocking layer disposed on the first electrode in order from bottom to top.
  • an organic material having a p-type property which is easily oxidized and electrochemically stabilized when it is oxidized, is mainly used as a hole injecting material or a hole transporting material.
  • an organic material having an n-type property which is easily reduced and electrochemically stabilized when it is reduced, is used as an electron injecting material or an electron transporting material.
  • a material having both a p-type property and an n-type property is preferable, which is stable when it is oxidized and reduced, and preferably has a high luminescence for converting excitons into light when excitons are formed. Efficiency material.
  • the material of the hole injection layer is usually a material preferably having a high work function, so that holes are easily injected into the organic material layer.
  • the material of the hole injection layer contains at least one of the materials represented by the general formula (17), (18) or (19):
  • F 1 -F 3 each independently represent a substituted or unsubstituted C 6-30 aryl group, a substituted or unsubstituted 3 to 30 membered heteroaryl group, and F 1 -F 3 Can be the same or different;
  • G 1 -G 6 each independently represent hydrogen, nitrile group, halogen, amide group, alkoxy group, ester group, nitro group, CR 11 , substituted or unsubstituted a C 6-30 aryl group, a 3 to 30 membered heteroaryl group, wherein R 11 is a linear or branched C 1-20 alkyl group, provided that G 1 -G 6 are not hydrogen at the same time;
  • the hetero atom is selected from at least one of the N, O and S atoms.
  • the material of the hole injection layer used is selected from one of the following (a) to (j):
  • the hole injection layer of the present invention may have a thickness of 5 to 100 nm, preferably 5 to 50 nm, and more preferably 5 to 20 nm.
  • the hole transport layer of the present invention may be disposed over the hole injection layer.
  • the hole transport layer material includes a first organic material and a second organic material, wherein a ratio of the first organic material to the second organic material is 1:99 to 99:1, preferably 10:90 to 90:10, It is preferably from 30:70 to 70:30, based on the mass.
  • the first organic material has a HOMO energy level of from -5.2 eV to -5.6 eV, preferably from -5.3 eV to -5.5 eV, more preferably from -5.35 eV to -5.5 eV, and the HOMO energy of the second organic material
  • the grade is -5.4 eV to -5.9 eV, preferably -5.4 eV to -5.7 eV, more preferably -5.48 eV to -5.68 eV, and
  • FIG. 2 is a view schematically showing an energy transfer mechanism of an organic electroluminescent device according to an embodiment of the present invention, wherein a represents a hole injection layer, b represents a hole transport layer, c represents an electron blocking layer, and d represents a light emitting layer.
  • the absolute value of the difference between the HOMO levels of the second organic material and the electron blocking material is ⁇ 0.4 ev.
  • a small energy barrier between the hole transporting material and the electron blocking layer material allows holes to be easily injected into the electron blocking layer via the hole transport layer and further transported into the light emitting layer.
  • the first and second organic materials of the invention are each independently selected from one of the general formula (1), the general formula (2) and the general formula (3):
  • X, X 1 are each independently selected from a single bond, a carbon atom, an N-(R 5 ), a sulfur atom, an oxygen atom, a vinylidene group, a linear or branched C 1-20 alkyl-substituted alkylene group, One of a linear or branched C 1-20 alkyl substituted silylene group, a C 6-20 aryl substituted alkylene group;
  • R 5 may be the same or differently selected from a hydrogen atom, a halogen atom, a halogen atom, a halogen atom, a fluorine atom, a phosphoric acid or a salt thereof, a linear or branched C 1-20 alkyl-substituted alkyl group.
  • a linear or branched C 1-20 alkyl substituted silylene group an aryl group having 5 to 30 carbon atoms, a hetero atom having 5 to 30 carbon atoms and at least one selected from the group consisting of N, O and S a heteroaryl group, wherein in the case of the latter two, the group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group. ;
  • Z represents a nitrogen atom or CR 6 , wherein R 6 may be the same or differently selected from a hydrogen atom, a ruthenium atom, a ruthenium atom, a ruthenium atom, a fluorine atom, a cyano group, a phosphoric acid or a salt thereof, a linear or branched C 1 - a 20 alkyl-substituted alkyl group, a linear or branched C 1-20 alkyl-substituted silylene group, an aryl group having 5 to 30 carbon atoms, having 5 to 30 carbon atoms, and at least one selected from N a heteroaryl heteroaryl group of O and S, wherein in the case of the latter two, the group may be optionally a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, C a 5-20 heteroaryl substitution wherein two or more R 6 groups may be attached to each other and may form a ring structure;
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 each independently represent a single bond, a linear or branched C 1-20 alkylene group, an arylene group having 5 to 30 carbon atoms, a straight chain or a branched chain. a C 1-20 alkyl-substituted silylene group, a heteroarylene group having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S, wherein in the case of the latter two, the group The group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group, wherein the Ar 1 , Ar 2 groups may also be joined to form a ring;
  • n, p, q, s, and t are equal to 0 or 1; and m+n+p+q ⁇ 1 and m+n+s+t ⁇ 1;
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a structure represented by the formula (4), the formula (5) or the formula (6), provided that R 1 , R 2 , R 3 When it is different from R 4 , it is a hydrogen atom;
  • X 2 and X 3 each independently represent a single bond, an oxygen atom, a sulfur atom, a vinylidene group, a linear or branched C 1-20 alkyl-substituted alkylene group, a linear or branched C 1-20 group.
  • Y 1 may represent N atom or CR identically or differently, wherein R may represent the same or different hydrogen atom, helium atom, rhodium atom, rhodium atom, fluorine atom, cyano group, phosphoric acid or a salt thereof, linear or branched a C 1-20 alkyl-substituted alkyl group, a linear or branched C 1-20 alkyl-substituted silane group, an aryl group having 5 to 30 carbon atoms, having 5 to 30 carbon atoms, and at least one selected a heteroaryl group derived from a hetero atom of N, O and S, wherein in the case of the latter two, the group may be optionally a linear or branched C 1-20 alkyl group, a C 6-20 aryl group a C 5-20 heteroaryl group; wherein two or more R groups may be attached to each other and may form a ring structure;
  • R 6 and R 7 each independently represent a hydrogen atom, a halogen atom, a halogen atom, a halogen atom, a fluorine atom, a phosphoric acid or a salt thereof, a linear or branched C 1-20 alkyl group-substituted alkyl group, a straight chain or a branch.
  • a C 1-20 alkyl-substituted silane group of a chain an aryl group having 5 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S, a structure represented by the formula (7) or the formula (6); wherein, in the case of an aryl group and a heteroaryl group, the group may be optionally a linear or branched C 1-20 alkyl group, C 6- 20 aryl, C 5-20 heteroaryl substituted;
  • Y 2 may represent the N atom or CR 10 identically or differently, wherein R 10 may represent the same or differently a hydrogen atom, a halogen atom, a halogen atom, a halogen atom, a fluorine atom, a cyano group, a phosphoric acid or a salt thereof, a linear chain or a branched C 1-20 alkyl-substituted alkyl group, a linear or branched C 1-20 alkyl-substituted silane group, an aryl group having 5 to 30 carbon atoms, having 5 to 30 carbon atoms, and at least a heteroaryl group selected from heteroatoms of N, O and S, wherein in the case of the latter two, the group may be optionally a linear or branched C 1-20 alkyl group, C 6-20 Aryl, C 5-20 heteroaryl substituted;
  • X 4 and X 5 each independently represent a single bond, an oxygen atom, a sulfur atom, a vinylidene group, a linear or branched C 1-20 alkyl-substituted alkylene group, a linear or branched C 1-20 group.
  • the general formula (7) is linked to the general formula (4) or the general formula (5) by a ring-and-loop method, and * is represented as a linking site.
  • * is represented as a linking site.
  • R 8 and R 9 each independently represent an aryl group having 5 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S, which may be Optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group; R 8 and R 9 may also be bonded to form a ring;
  • L 1 , L 2 , L 3 each independently represent a single bond, an arylene group having 5 to 30 carbon atoms, a hetero atom having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S
  • An aryl group wherein in the case of the latter two, the group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group; 1 , L 2 , L 3 may be connected to each other and may form a ring structure;
  • Ar 5 , Ar 6 and Ar 7 each independently represent an arylene group having 5 to 30 carbon atoms, a heteroarylene group having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S, An imido group of 5 to 30 carbon atoms, which group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group; Ar 5 , Ar 6 , Ar 7 may be connected to each other two-two and may form a ring structure;
  • Each of Ar 5 , Ar 6 and Ar 7 may also be independently represented as one of the formula (4), the formula (5), and the formula (6), wherein the groups X 2 and X 3 in the formula are , Y 1 , R 6 , R 7 and * have the meanings as described above;
  • D 1 , D 2 , D 3 each independently represent a single bond, an arylene group having 5 to 30 carbon atoms, a hetero atom having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S
  • An aryl group wherein in the case of the latter two, the group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group; 1 , L 2 , L 3 may be connected to each other and may form a ring structure;
  • Ar 8 , Ar 9 and Ar 10 each independently represent an arylene group having 5 to 30 carbon atoms, a heteroarylene group having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S, An imino group of 5 to 30 carbon atoms, which group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group; Ar 8 , Ar 9 , Ar 10 may be connected to each other and may form a ring structure;
  • At least one of Ar 8 , Ar 9 and Ar 10 is one of the formula (4), the formula (5), and the formula (6); wherein the group X 2 , X 3 , Y 1 on the formula And R 6 , R 7 and * each have the meanings as described above.
  • the formula (2) is represented by one of the formulae (9) to (12):
  • Ar 5 to Ar 7 represent an arylene group having 5 to 30 carbon atoms, a heteroarylene group having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S, and 5 to 30 carbon atoms.
  • Imino group the group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group;
  • L 1 -L 3 , R 6 -R 9 , Y 1 and X 2 -X 3 all have the meanings described above.
  • the formula (3) is represented by one of the formulae (13) to (16):
  • Ar 8 and Ar 10 represent an arylene group having 5 to 30 carbon atoms, a heteroarylene group having 5 to 30 carbon atoms and at least one hetero atom selected from N, O and S, and 5 to 30 carbon atoms.
  • Imino group the group may be optionally substituted by a linear or branched C 1-20 alkyl group, a C 6-20 aryl group, a C 5-20 heteroaryl group;
  • D 1 -D 3 , R 6 -R 9 , Y 1 and X 2 -X 3 all have the meanings described above.
  • the first organic material is selected from one of the following compounds:
  • the second organic material is selected from one of the following compounds:
  • the hole transport layer material of the present invention has a hole mobility of from 1 ⁇ 10 -5 to 1 ⁇ 10 -2 cm 2 /(V ⁇ s), preferably from 1 ⁇ 10 -4 to 1 ⁇ 10 -2 cm 2 / (V ⁇ s) is more preferably 1 ⁇ 10 -4 to 1 ⁇ 10 -3 cm 2 /(V ⁇ s).
  • the hole transport layer material of the present invention has a glass transition temperature of ⁇ 120 ° C, preferably ⁇ 130 ° C and more preferably ⁇ 140 ° C.
  • the hole transport layer material of the present invention may have a thickness of from 1 to 200 nm, preferably from 10 to 100 nm.
  • the electron blocking layer may be disposed over the hole transport layer; the material of the electron blocking layer is preferably a material having a high T1 and a low LUMO, which is capable of blocking electron loss and energy loss.
  • the electron blocking layer used in the present invention may be
  • the electron blocking layer of the present invention may have a thickness of 5 to 200 nm, preferably 10 to 150 nm, and more preferably 20 to 100 nm.
  • the light emitting layer may be disposed over the hole transporting region.
  • the material of the light-emitting layer is a material which can emit visible light by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the received holes and electrons. Specific examples thereof include metal complexes of hydroxyquinoline derivatives, various metal complexes, anthracene derivatives, bisstyrenebenzene derivatives, anthracene derivatives, oxazole derivatives, and polyparaphenylene derivatives. , but not limited to this.
  • the light emitting layer may include a host material and a guest material.
  • a light-emitting layer material for an organic electroluminescence device which is known in the art may be used, and the host material may be, for example, a thiazole derivative or a benzene. And an imidazole derivative, a polydialkylfluorene derivative or 4,4'-bis(9-carbazolyl)biphenyl (CBP); the guest material may be, for example, quinacridone, coumarin, red fluorescent Alkene, anthracene and derivatives thereof, benzopyran derivatives, rhodamine derivatives or aminostyrene derivatives.
  • the luminescent layer host material used is selected from the group consisting of one or more of EMH-1 to EMH-22 described below:
  • the luminescent material may also comprise a phosphorescent or fluorescent material.
  • the phosphorescent material include phosphorescent materials of metal complexes of ruthenium, platinum, and the like.
  • a green phosphorescent material such as Ir(ppy) 3 [fac-tris(2-phenylpyridine)fluorene]
  • a blue phosphorescent material such as FIrpic or FIr6
  • a red phosphorescent material such as Btp2Ir (acac)
  • the luminescent layer guest material used is selected from one of the following EMD-1 to EMD-23:
  • the ratio of the host material to the guest material used is from 99:1 to 70:30, preferably from 99:1 to 85:15 and more preferably from 97:3 to 87:13, based on the mass. meter.
  • the luminescent layer may be formed of another guest material or a plurality of guest materials, and the guest material may be simple.
  • a fluorescent material, a delayed fluorescent (TADF) material or a phosphorescent material, or a combination of different fluorescent materials, TADF materials, and phosphorescent light the light emitting layer may be a single light emitting layer material, or may be a composite light emitting layer stacked laterally or vertically. material.
  • the light-emitting layers constituting the above organic electroluminescence device are exemplified by the following various structures:
  • the organic light-emitting functional layer includes a light-emitting layer including one or a combination of at least two of blue, green, red, and yellow organic light-emitting layer materials.
  • G represents light
  • 6 represents a light-emitting layer
  • EM1, EM2, and EM3 represent different light-emitting layer materials.
  • 6 represents a light-emitting layer
  • 300 represents an organic light-emitting functional layer
  • 610, 620 and 630 represent a tie layer.
  • the film thickness of the light-emitting layer 6 constituting the OLED light-emitting body can be arbitrarily adjusted as needed, or the light-emitting layers which are not colorable can be alternately superimposed and combined as needed, and adjacent light can be emitted.
  • a charge blocking layer or the like for different functional uses is added to the organic layer of the layer.
  • the light-emitting layer of the present invention may have a thickness of 5 to 60 nm, preferably 10 to 50 nm, more preferably 20 to 45 nm.
  • the electron transporting region may include a hole blocking layer, an electron transporting layer, and an electron injecting layer disposed on the light emitting layer in this order from the bottom to the top, but is not limited thereto.
  • the hole blocking layer is a layer that blocks holes injected from the anode through the light emitting layer and enters the cathode, thereby extending the life of the device and improving the performance of the device.
  • the hole blocking layer of the present invention may be disposed on the light emitting layer to the top.
  • a compound having a hole blocking function known in the art for example, a phenanthroline derivative such as batholine (referred to as BCP), or aluminum can be used.
  • the hole blocking layer of the present invention may have a thickness of 2 to 200 nm, preferably 5 to 150 nm, and more preferably 10 to 100 nm.
  • the electron transport layer can be disposed over the luminescent layer or, if present, the hole blocking layer.
  • the electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light emitting layer. Materials having high electron mobility are preferred.
  • an electron transport layer material for an organic electroluminescence device known in the art for example, a quinolinol derivative typified by Alq 3 or BAlq can be used.
  • Metal complexes various metal complexes, triazole derivatives, 2,4-bis(9,9-dimethyl-9H-indol-2-yl)-6-(naphthalen-2-yl) a triazine derivative such as -1,3,5-triazine (CAS No.: 1459162-51-6), 2-(4-(9,10-di(naphthalen-2-yl)indol-2-yl)benzene Imidazole derivatives such as 1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), triazine derivatives, oxadiazole derivatives, thiadiazole derivatives A carbodiimide derivative, a quinoxaline derivative, a phenanthroline derivative, a silicon-based compound derivative or the like.
  • the electron transport layer of the present invention may have a thickness of 10 to 80 nm, preferably 20 to 60 nm, and more preferably 25 to
  • the electron injection layer may be disposed on the electron transport layer.
  • the electron injecting layer material is generally a material preferably having a low work function such that electrons are easily injected into the organic functional material layer.
  • an electron injecting layer material for an organic electroluminescent device known in the art for example, lithium; a lithium salt such as lithium quinolate, can be used. Lithium fluoride, lithium carbonate or lithium azide; or barium salt, barium fluoride, barium carbonate or barium azide.
  • the electron injecting layer of the present invention may have a thickness of 0.1 to 5 nm, preferably 0.5 to 3 nm, and more preferably 0.8 to 1.5 nm.
  • the second electrode may be disposed over the electron transport region.
  • the second electrode can be a cathode.
  • the second electrode EL2 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
  • the second electrode may include, for example, Li, Yb, Ca, LiF/Ca, LiF/Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is half
  • the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti or a compound or mixture thereof.
  • the organic electroluminescent device of the present invention may be of a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the first electrode may be a reflective electrode and the second electrode may be a transmissive electrode or a semi-transmissive electrode.
  • the first electrode may be a transmissive electrode or a semi-transmissive electrode, and the second electrode may be a reflective electrode.
  • the organic electroluminescent device may further include a package structure.
  • the package structure may be a protective structure for preventing foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device.
  • the package structure may be, for example, a can, such as a glass jar or a metal can; or a film covering the entire surface of the organic layer.
  • the organic electroluminescent device of the present invention can be prepared, for example, by sequentially laminating a first electrode, an organic functional material layer, and a second electrode on a substrate.
  • a physical vapor deposition method such as a sputtering method or an electron beam vapor method, or a vacuum evaporation method may be used, but is not limited thereto.
  • the above compound can be used to form an organic functional material layer by, for example, a vacuum deposition method, a vacuum evaporation method, or a solution coating method.
  • the solution coating method means a spin coating method, a dip coating method, a jet printing method, a screen printing method, a spray method, and a roll coating method, but is not limited thereto.
  • Vacuum evaporation means heating and plating a material onto a substrate in a vacuum environment. In the present invention, it is preferred to form the respective layers using a vacuum evaporation method.
  • the materials for forming the respective layers described in the present invention may be used as a single layer by separately forming a film, or may be formed as a single layer by mixing with other materials, or may be separately formed.
  • a display in another aspect of the invention, includes one or more of the organic electroluminescent devices of the present invention, and where a plurality of devices are included, the devices are stacked in a lateral or longitudinal direction.
  • the display may comprise a device each having a layer of organic light-emitting material of three colors of blue, green, red, and the device has a hole transport layer of the same film thickness and material.
  • the display is comprised of a device that can include layers of organic light-emitting materials each having three colors of blue, green, and red, and that has a hole transport layer of the same material but different film thicknesses.
  • the display may comprise a device having a layer of organic luminescent material each having three colors of blue, green, red, and the device has a hole transport of the same film thickness but at least two combinations of materials thereof Floor.
  • the display may comprise a device each having a layer of organic light-emitting material of three colors of blue, green, red, and the device has an empty film thickness and at least two combinations of materials thereof Hole transport layer.
  • Glass transition temperature Tg measured by differential scanning calorimetry (DSC, Germany NETZSCH DSC204F1 differential scanning calorimeter), heating rate 10 ° C / min;
  • HOMO energy level There are many methods or instruments for testing the HOMO energy level of organic optoelectronic materials, including CV (cyclic voltammetry), UPS (ultraviolet photoelectron spectroscopy), and AC series equipment manufactured by Riken Keiki Co., Ltd. ( Atmospheric photoelectron spectroscopy), IPS series equipment (vacuum photoelectron spectroscopy) produced by Xindi Tianyi Co., Ltd., in addition to the above methods, can also determine the level of HOMO energy level by Gaussian calculation and combined with semi-empirical judgment. The HOMO level is very important for studying the structural matching of OLED devices.
  • the CV method is affected by solvents, and the data accuracy and reproducibility are relatively poor.
  • Others include UPS method, AC method, IPS method, and fundamentally, all are measurement of ultraviolet photoelectron spectroscopy.
  • UPS UPS measurement requires not only ultra-high vacuum, but also expensive equipment, and there are large differences in data analysis results due to the difference in the person being measured and the instrument settings.
  • the AC method requires the sample to be placed in an aerobic dry air environment. The oxygen element has a certain influence on the sample, and the data reproducibility and consistency are relatively poor.
  • the IPS method measures the HOMO level and places the film material in In a vacuum environment, ultraviolet monochromatic light is directly applied to the surface of the sample, and the photoelectron current is measured to determine the magnitude of the HOMO level, which is a direct measurement. Based on the above analysis and practice, the inventors believe that the IPS measurement method has the highest reproducibility, consistency and accuracy when measuring the HOMO level of OLED materials. All HOMO energy levels of the materials involved in the present invention are measurement means of IPS. The specific measurement method is as follows:
  • the evaporation rate is controlled under a vacuum of 1.0E-5Pa.
  • the material is evaporated onto the ITO substrate to a film thickness of 60-80 nm, and then the HOMO level of the sample film is measured by using an IPS3 measuring device, and the measurement environment is a vacuum environment of 10-2 Pa or less;
  • Eg level based on the UV spectrophotometric (UV absorption) baseline of the material single film and the rising side of the first absorption peak, the tangent line is calculated using the tangent and baseline intersection values.
  • LUMO level calculated based on the difference between the aforementioned HOMO level and the Eg level.
  • Hole mobility The material was fabricated into a single charge device and measured by the SCLC method.
  • Elemental analysis structure (Molecular formula C 60 H 42 N 4 ): Theory: C, 87.99; H, 5.17; N, 6.84; Tests: C, 87.97; H, 5.18; N, 6.85.
  • Elemental analysis structure (Molecular formula C 54 H 44 N 2 ): Theory: C, 89.96; H, 6.15; N, 3.89; Tests: C, 89.97; H, 6.13; N, 3.90.
  • Elemental analysis structure (Molecular formula C 42 H 25 NO 3 ): Theory: C, 85.26; H, 4.26; N, 2.37; Tests: C, 85.24; H, 4.24; N, 2.39.
  • Elemental analysis structure (Molecular formula C 72 H 54 N 4 ): Theory: C, 88.67; H, 5.58; N, 5.74; Tests: C, 88.64; H, 5.60; N, 5.73.
  • Elemental analysis structure (Molecular formula C 56 H 40 N 2 ): Theory: C, 90.78; H, 5.44; N, 3.78; ⁇ / RTI> ⁇ /RTI> C, 90.76; H, 5.45; N, 3.79.
  • Elemental analysis structure (Molecular formula C 60 H 44 N 2 ): Theory: C, 90.87; H, 5.59; N, 3.53; ⁇ / RTI> C, 90.86; H, 5.58; N, 3.56.
  • Elemental analysis structure (Molecular formula C 52 H 37 N): Theory: C, 92.41; H, 5.52; N, 2.07; ⁇ / RTI> C, 92.42; H, 5.50; N, 2.08.
  • Elemental analysis structure (Molecular formula C 54 H 39 N): Theory: C, 92.40; H, 5.60; N, 2.00; ⁇ / RTI> C, 92.38; H, 5.61; N, 2.01.
  • Elemental analysis structure (Molecular formula C 52 H 39 N): Theory: C, 92.13; H, 5.80; N, 2.07;
  • Elemental analysis structure (Molecular formula C 55 H 41 NO): Theory: C, 90.25; H, 5.65; N, 1.91; Tests: C, 90.24; H, 5.64; N, 1.90.
  • Elemental analysis structure (Molecular formula C 55 H 43 N): Theory: C, 92.01; H, 6.04; N, 1.95; Tests: C, 92.02; H, 6.02; N, 1.96.
  • Elemental analysis structure (Molecular formula C 54 H 41 NO): Theory: C, 90.09; H, 5.74; N, 1.95; Tests: C, 90.07; H, 5.76; N, 1.97.
  • Elemental analysis structure (Molecular formula C 58 H 47 N): Theory: C, 91.90; H, 6.25; N, 1.85; Test: C, 91.92; H, 6.24; N, 1.84.
  • Elemental analysis structure (Molecular formula C 49 H 41 N): Theory: C, 91.41; H, 6.42; N, 2.18; Tests: C, 91.43; H, 6.41; N, 2.16.
  • Elemental analysis structure (Molecular formula C 60 H 49 N 3 ): Theory: C, 88.74; H, 6.08; N, 5.17; Tests: C, 88.71; H, 6.09; N, 5.20.
  • Elemental analysis structure (Molecular formula C 53 H 41 N 3 ): Theory: C, 88.42; H, 5.74; N, 5.84; Test: C, 88.43; H, 5.75; N, 5.82.
  • Elemental analysis structure (Molecular formula C 54 H 39 N): Theory: C, 92.40; H, 5.60; N, 2.00; ⁇ / RTI> ⁇ /RTI> C, 92.41; H, 5.61; N, 1.98.
  • Elemental analysis structure (Molecular formula C 54 H 35 NO 2 ): Theory: C, 88.86; H, 4.83; N, 1.92; Tests: C, 88.85; H, 4.84; N, 1.91.
  • Elemental analysis structure (Molecular formula C 51 H 37 NO): Theory: C, 90.10; H, 5.49; N, 2.06; ⁇ / RTI> ⁇ /RTI> C, 90.11; H, 5.47; N, 2.07.
  • Elemental analysis structure (Molecular formula C 54 H 36 N 2 O): Theory: C, 88.98; H, 4.98; N, 3.84; Tests: C, 88.96; H, 4.99; N, 3.85.
  • Elemental analysis structure (Molecular formula C 52 H 37 N): Theory: C, 92.41; H, 5.52; N, 2.07; ⁇ / RTI> C, 92.42; H, 5.53; N, 2.05.
  • Elemental analysis structure (Molecular formula C 49 H 35 N): Theory: C, 92.41; H, 5.52; N, 2.07; ⁇ / RTI> ⁇ /RTI> C, 92.42; H, 5.53; N, 2.05.
  • Elemental analysis structure (Molecular formula C 55 H 41 NO): Theory: C, 90.25; H, 5.65; N, 1.91; Tests: C, 90.23; H, 5.66; N, 1.90.
  • Elemental analysis structure (Molecular formula C 52 H 39 NO): Theory: C, 90.01; H, 5.67; N, 2.02; ⁇ / RTI> ⁇ /RTI> C, 90.03; H, 5.64; N, 2.03.
  • Elemental analysis structure (Molecular formula C 55 H 43 N): Theory: C, 92.01; H, 6.04; N, 1.95; Tests: C, 92.02; H, 6.02; N, 1.96.
  • Elemental analysis structure (Molecular formula C 54 H 39 N): Theory: C, 92.40; H, 5.60; N, 2.00; ⁇ / RTI> C, 92.41; H, 5.58; N, 2.01.
  • Elemental analysis structure (Molecular formula C 63 H 57 N): Theory: C, 91.37; H, 6.94; N, 1.69; Test: C, 91.36; H, 6.93; N, 1.70.
  • Elemental analysis structure (Molecular formula C 62 H 55 N): Theory: C, 91.47; H, 6.81; N, 1.72; Tests: C, 91.45; H, 6.82; N, 1.73.
  • Elemental analysis structure (Molecular formula C 45 H 32 N 2 O): Theory: C, 87.63; H, 5.23; N, 4.54; Tests: C, 87.61; H, 5.24; N, 4.55.
  • Elemental analysis structure (Molecular formula C 46 H 31 NO): Theory: C, 90.02; H, 5.09; N, 2.28; ⁇ / RTI> ⁇ /RTI> ⁇ /RTI> C, 90.01; H, 5.07; N, 2.29;
  • Elemental analysis structure (Molecular formula C 46 H 31 NO 2 ): Theory: C, 87.73; H, 4.96; N, 2.22; Test: C, 87.71; H, 4.97; N, 2.23.
  • Elemental analysis structure (Molecular formula C 49 H 37 NO): Theory: C, 89.74; H, 5.69; N, 2.14; Tests: C, 89.74; H, 5.69; N, 2.14.
  • Table 1 shows the prepared first and second organic materials, the electron blocking layer material (EB1) adjacent thereto, the host materials (EMH-1, EMH-7, and EMH-13) of the luminescent material, and the guest material (EMD- 1, EMD-8 and EMD-13) test results of each level.
  • EB1 electron blocking layer material
  • the HOMO energy level of the first organic material of the present invention is between -5.2 eV and -5.6 eV
  • the HOMO energy level of the second organic material is between -5.4 eV and -5.9 eV
  • the absolute value of the difference between the HOMO levels of the second organic material and the electron blocking layer material is ⁇ 0.4 ev.
  • the first organic material HTI-1 and the second organic material HTII-7 were respectively placed in two evaporation sources, and the pressure was controlled under a vacuum of 1.0E -5 Pa.
  • the evaporation rate of the first organic material 1 is Controlling the evaporation rate of the second organic material 1 is
  • the hole transport layer material 1 of the present invention is obtained by co-mixing.
  • Example 1 The preparation process of Example 1 was repeated except that the evaporation rate of the first organic material HTI-1 was The evaporation rate of the second organic material HTII-7 is The hole transport layer material 2 was obtained.
  • Example 1 The preparation process of Example 1 was repeated except that the evaporation rate of the first organic material HTI-1 was The evaporation rate of the second organic material HTII-7 is The hole transport layer material 3 was obtained.
  • Example 1 The preparation process of Example 1 was repeated except that the evaporation rate of the first organic material HTI-1 was The evaporation rate of the second organic material HTII-7 is The hole transport layer material 4 was obtained.
  • Example 1 The preparation process of Example 1 was repeated except that the evaporation rate of the first organic material HTI-1 was The evaporation rate of the second organic material HTII-7 is The hole transport layer material 5 was obtained.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-9 and the second organic material HTII-37 were used to obtain the hole transport layer material 6.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-28 and the second organic material HTII-21 were used to obtain the hole transport layer material 7.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-41 and the second organic material HTII-41 were used to obtain the hole transport layer material 8.
  • Example 3 The preparation process of Example 3 was repeated except that the first organic material HTI-41 and the second organic material HTII-41 were used to obtain the hole transport layer material 9.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-52 and the second organic material HTII-52 were used to obtain the hole transport layer material 10.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-57 and the second organic material HTII-78 were used to obtain the hole transport layer material 11.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-63 and the second organic material HTII-102 were used to obtain the hole transport layer material 12.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-72 and the second organic material HTII-132 were used to obtain the hole transport layer material 13.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-72 and the second organic material HTII-148 were used to obtain the hole transport layer material 14.
  • Example 2 The preparation process of Example 2 was repeated except that the first organic material HTI-72 and the second organic material HTII-164 were used to obtain the hole transport layer material 15.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-86 and the second organic material HTII-164 were used to obtain the hole transport layer material 16.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-101 and the second organic material HTII-192 were used to obtain the hole transport layer material 17.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-114 and the second organic material HTII-192 were used to obtain the hole transport layer material 18.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-124 and the second organic material HTII-232 were used to obtain the hole transport layer material 19.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-134 and the second organic material HTII-243 were used to obtain the hole transport layer material 20.
  • Example 2 The preparation process of Example 2 was repeated except that the first organic material HTI-134 and the second organic material HTII-243 were used to obtain the hole transport layer material 21.
  • Example 2 The preparation process of Example 2 was repeated except that the first organic material HTI-134 and the second organic material HTII-243 were used to obtain the hole transport layer material 22.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-134 and the second organic material HTII-266 were used to obtain the hole transport layer material 23.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-144 and the second organic material HTII-277 were used to obtain the hole transport layer material 24.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-162 and the second organic material HTII-314 were used to obtain the hole transport layer material 25.
  • Example 5 The preparation process of Example 5 was repeated except that the first organic material HTI-162 and the second organic material HTII-314 were used to obtain the hole transport layer material 26.
  • Example 1 The preparation process of Example 1 was repeated except that the first organic material HTI-176 and the second organic material HTII-335 were used to obtain the hole transport layer material 27.
  • vacuum evaporation is performed under the following conditions: using a CIC vapor deposition apparatus (manufactured by Changzhou Industry Co., Ltd.), the vapor deposition rate is controlled under a vacuum of 1.0 E -5 Pa.
  • HAT-CN is deposited by a vacuum evaporation method to a thickness of 10 nm, this layer serves as a hole injection layer;
  • the hole transport layer material 1 obtained in Example 1 was prepared by vacuum evaporation to prepare a hole transport layer material having a thickness of 90 nm, the layer being a hole transport layer;
  • EB1 is deposited by vacuum evaporation, the thickness is 20 nm, the layer is an electron blocking layer;
  • the luminescent layer material is evaporated by vacuum evaporation, the host material is EMH-7 and EMH-9, and the guest material is EMD-8, EMH-7, EMH-9 and EMD-8 mass ratio 45:45:10, thickness 40nm;
  • LG201 and Liq are vapor-deposited by vacuum evaporation, the mass ratio of LG201 and Liq is 50:50, and the thickness is 40 nm, and the layer serves as an electron transport layer;
  • the layer is an electron injection layer
  • Al is vacuum-evaporated to a thickness of 100 nm, and the layer is a second electrode layer.
  • the procedure of Device Preparation Example 1 was carried out except that the film thickness of the hole transport layer in step c) was 160 nm; the host material in step e) was EMH-13, the guest material was EMD-8, and EMH-13 The mass ratio to EMD-8 was 90:10 and the thickness was 40 nm.
  • the procedure of Device Preparation Example 1 was carried out except that the film thickness of the hole transport layer in step c) was 50 nm; the host material in step e) was EMH-1, the guest material was EMD-1, and EMH-1 and The EMD-1 mass ratio was 95:5 and the thickness was 25 nm.
  • Device Preparation Example 1 The procedure of Device Preparation Example 1 was carried out except that only the first organic material or the second organic material listed in Table 2 below was used as the hole transport layer material.
  • Device Preparation Example 11 The procedure of Device Preparation Example 11 was carried out except that only the first organic material or the second organic material listed in Table 3 below was used as the hole transport layer material.
  • Device Preparation Example 21 The procedure of Device Preparation Example 21 was carried out except that only the first organic material or the second organic material listed in Table 4 below was used as the hole transport layer material.
  • Tables 5-7 show the performance results of the fabricated organic electroluminescent device at a current density of 10 mA/cm 2 .
  • LT95 refers to the time it takes for the device brightness to decay to 95% at a current density of 10 mA/cm 2 ;
  • the life test system is the OLED device life tester jointly researched by the owner of the invention and Shanghai University.
  • the driving voltages of the devices prepared in the device preparation examples 1 to 10 of the present invention were remarkably lowered as compared with Comparative Examples 1 to 10 in which the organic materials were used alone as the hole transport layer materials. And the luminance, the luminous efficiency (ie, current efficiency), and the lifetime are both significantly improved.
  • the driving voltages of the devices prepared in the device preparation examples 11 to 20 of the present invention were also significantly lower than those of Comparative Examples 11 to 25, and the luminance and the luminous efficiency (i.e., current) were obtained. Both efficiency) and longevity are significantly improved.
  • the driving voltages of the devices prepared in the device preparation examples 21 to 30 of the present invention were also significantly lower than those of Comparative Examples 26 to 38, and the luminance and the luminous efficiency (i.e., current) were obtained. Both efficiency) and longevity are significantly improved.

Landscapes

  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un dispositif électroluminescent organique, comprenant successivement, de bas en haut, un substrat, une première électrode, une couche de matériau fonctionnel organique et une seconde électrode, la couche de matériau fonctionnel organique comprenant une zone de transport de trous disposée sur la première électrode, une couche lumineuse disposée sur la zone de transport de trous et comprenant des matériaux hôte et invité, et une zone de transport d'électrons disposée sur la couche lumineuse, la zone de transport de trous comprenant successivement, de haut en bas, une couche d'injection de trous, une couche de transport de trous et une couche de blocage d'électrons ; la couche de transport de trous comprend des premier et second matériaux organiques ; et le niveau d'énergie HOMO du premier matériau organique se situe dans la plage de -5,2 eV à -5,6 eV, et le niveau d'énergie HOMO du second matériau organique se situe dans la plage de -5,4 eV à -5,9 eV, où |HOMOpremier matériau organique|< |HOMOsecond matériau organique|.
PCT/CN2019/084629 2018-04-28 2019-04-26 Dispositif électroluminescent organique et afficheur le comprenant WO2019206292A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201810404589.X 2018-04-28
CN201810404589.XA CN110416422B (zh) 2018-04-28 2018-04-28 有机电致发光器件及包括其的显示器

Publications (2)

Publication Number Publication Date
WO2019206292A1 true WO2019206292A1 (fr) 2019-10-31
WO2019206292A9 WO2019206292A9 (fr) 2019-11-28

Family

ID=68293484

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2019/084629 WO2019206292A1 (fr) 2018-04-28 2019-04-26 Dispositif électroluminescent organique et afficheur le comprenant

Country Status (2)

Country Link
CN (1) CN110416422B (fr)
WO (1) WO2019206292A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021112403A1 (fr) * 2019-12-06 2021-06-10 덕산네오룩스 주식회사 Élément électronique organique comprenant un composé organique, et dispositif électronique le comprenant
KR20210086504A (ko) * 2019-12-31 2021-07-08 난징고광반도체재료유한회사 신규한 유기 전계 발광 화합물 및 유기 전계 발광 소자
WO2022003491A1 (fr) * 2020-07-03 2022-01-06 株式会社半導体エネルギー研究所 Composé organique, dispositif électroluminescent, appareil électroluminescent, machine électronique et dispositif d'éclairage
CN114242907A (zh) * 2021-11-03 2022-03-25 阜阳欣奕华材料科技有限公司 一种有机电致发光器件、显示装置
WO2022139445A1 (fr) * 2020-12-22 2022-06-30 덕산네오룩스 주식회사 Élément électrique organique comprenant un composé pour élément électrique organique, et dispositif électronique associé
WO2022173203A1 (fr) * 2021-02-09 2022-08-18 주식회사 엘지화학 Composé et dispositif électronique organique le comprenant
KR20220162113A (ko) 2020-03-31 2022-12-07 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기
US11527722B2 (en) * 2020-08-20 2022-12-13 Samsung Display Co., Ltd. Light-emitting device and electronic apparatus including the same
US11548877B2 (en) 2018-11-30 2023-01-10 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device
US11744149B2 (en) 2019-05-31 2023-08-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110504375A (zh) * 2018-05-18 2019-11-26 江苏三月光电科技有限公司 一种复合空穴传输材料及其oled器件
CN110577509A (zh) * 2018-06-07 2019-12-17 江苏三月光电科技有限公司 一种三芳胺类化合物、制备方法及其应用
CN110655486A (zh) * 2018-06-29 2020-01-07 江苏三月光电科技有限公司 一种以二苯并环庚烯为核心的化合物及其应用
CN111662187A (zh) * 2019-03-08 2020-09-15 江苏三月光电科技有限公司 一种含胺基的有机化合物及其应用
CN112010760B (zh) * 2019-05-29 2021-11-02 南京高光半导体材料有限公司 一种螺二芴类有机电致发光化合物及有机电致发光器件
CN112250585B (zh) * 2019-07-22 2023-11-14 南京高光半导体材料有限公司 一种空穴传输材料及使用该种材料的有机电致发光器件
CN111233674A (zh) * 2019-09-26 2020-06-05 吉林奥来德光电材料股份有限公司 芴类化合物及其制备方法和有机电致发光器件
CN112745229B (zh) * 2019-10-31 2023-12-05 南京高光半导体材料有限公司 一种具有优异性能的空穴传输材料及含有该材料的有机电致发光器件
CN112778253B (zh) * 2019-11-07 2024-02-09 北京鼎材科技有限公司 有机化合物及含有其的有机电致发光器件
CN110885321A (zh) 2019-11-25 2020-03-17 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和电致发光器件
KR20210138825A (ko) * 2020-05-12 2021-11-22 덕산네오룩스 주식회사 유기전기소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치
KR20210142026A (ko) * 2020-05-14 2021-11-24 덕산네오룩스 주식회사 유기전기소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치
CN114122299B (zh) * 2020-06-29 2023-12-29 江苏三月科技股份有限公司 一种有机电致发光器件
CN111848493B (zh) * 2020-08-28 2022-10-14 长春海谱润斯科技股份有限公司 一种含有螺二芴的衍生物及其有机电致发光器件
CN114195747B (zh) * 2020-09-18 2023-06-27 广州华睿光电材料有限公司 芳胺类有机化合物、混合物、组合物及有机电子器件
US20220376199A1 (en) * 2020-12-11 2022-11-24 Boe Technology Group Co., Ltd. Organic Light Emitting Device and Display Apparatus
CN114930561B (zh) * 2020-12-11 2023-12-26 京东方科技集团股份有限公司 有机电致发光器件和显示装置
CN113594395B (zh) * 2021-08-26 2024-04-12 长春海谱润斯科技股份有限公司 一种有机电致发光器件
CN114315742B (zh) * 2021-12-21 2024-06-28 湖北尚赛光电材料有限公司 一种含芴的化合物及其应用
CN114478499A (zh) * 2022-01-29 2022-05-13 阜阳欣奕华材料科技有限公司 一种螺芴杂蒽类化合物及其应用
CN114426530A (zh) * 2022-02-10 2022-05-03 阜阳欣奕华材料科技有限公司 一种螺芴杂蒽类化合物及其在发光层掺杂材料中的应用
WO2024057958A1 (fr) * 2022-09-14 2024-03-21 日鉄ケミカル＆マテリアル株式会社 Matériau pour élément de conversion photoélectrique, et élément de conversion photoélectrique
WO2024186095A1 (fr) * 2023-03-08 2024-09-12 삼성에스디아이 주식회사 Diode optoélectronique organique et dispositif d'affichage

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104966786A (zh) * 2015-07-03 2015-10-07 北京鼎材科技有限公司 一种有机电致发光器件

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016076384A1 (fr) * 2014-11-14 2016-05-19 保土谷化学工業株式会社 Élément électroluminescent organique
CN105576146B (zh) * 2016-03-23 2017-09-26 京东方科技集团股份有限公司 发光器件及其制造方法和显示装置
TWI625326B (zh) * 2016-09-09 2018-06-01 昱鐳光電科技股份有限公司 有機電激發光元件

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104966786A (zh) * 2015-07-03 2015-10-07 北京鼎材科技有限公司 一种有机电致发光器件

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11548877B2 (en) 2018-11-30 2023-01-10 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device
US12048242B2 (en) 2019-05-31 2024-07-23 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US11744149B2 (en) 2019-05-31 2023-08-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
WO2021112403A1 (fr) * 2019-12-06 2021-06-10 덕산네오룩스 주식회사 Élément électronique organique comprenant un composé organique, et dispositif électronique le comprenant
KR20210086504A (ko) * 2019-12-31 2021-07-08 난징고광반도체재료유한회사 신규한 유기 전계 발광 화합물 및 유기 전계 발광 소자
KR102279004B1 (ko) * 2019-12-31 2021-07-19 난징고광반도체재료유한회사 신규한 유기 전계 발광 화합물 및 유기 전계 발광 소자
US11678569B2 (en) 2020-03-31 2023-06-13 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
KR20220162113A (ko) 2020-03-31 2022-12-07 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기
WO2022003491A1 (fr) * 2020-07-03 2022-01-06 株式会社半導体エネルギー研究所 Composé organique, dispositif électroluminescent, appareil électroluminescent, machine électronique et dispositif d'éclairage
US11527722B2 (en) * 2020-08-20 2022-12-13 Samsung Display Co., Ltd. Light-emitting device and electronic apparatus including the same
US12035621B2 (en) 2020-08-20 2024-07-09 Samsung Display Co., Ltd. Light-emitting device and electronic apparatus including the same
WO2022139445A1 (fr) * 2020-12-22 2022-06-30 덕산네오룩스 주식회사 Élément électrique organique comprenant un composé pour élément électrique organique, et dispositif électronique associé
WO2022173203A1 (fr) * 2021-02-09 2022-08-18 주식회사 엘지화학 Composé et dispositif électronique organique le comprenant
CN114242907A (zh) * 2021-11-03 2022-03-25 阜阳欣奕华材料科技有限公司 一种有机电致发光器件、显示装置

Also Published As

Publication number Publication date
WO2019206292A9 (fr) 2019-11-28
CN110416422B (zh) 2021-06-15
CN110416422A (zh) 2019-11-05

Similar Documents

Publication Publication Date Title
WO2019206292A1 (fr) Dispositif électroluminescent organique et afficheur le comprenant
WO2019206291A1 (fr) Dispositif électroluminescent organique et dispositif le comprenant
TWI468494B (zh) Organic electroluminescent elements
WO2017010489A1 (fr) Élément électroluminescent organique et dispositif électronique
JP7037543B2 (ja) 有機電界発光素子
TWI658117B (zh) 有機電致發光裝置之發光材料
TW201434828A (zh) 具有二氮雜聯三伸苯環結構之化合物及有機電致發光元件
KR20100131745A (ko) 유기광전소자용 조성물 및 이를 이용한 유기광전소자
CN103314463B (zh) 有机电致发光元件、组合物以及有机电致发光装置
TW201130843A (en) Organic electroluminescent element
KR20190065277A (ko) 유기 발광 소자와, 그에 이용하는 발광 재료 및 화합물
CN110416256B (zh) 有机电致发光器件及包括其的显示器
KR101297162B1 (ko) 유기광전소자용 조성물 및 이를 이용한 유기광전소자
TWI542586B (zh) 具有經取代之聯吡啶基與吡啶并吲哚環結構之化合物及有機電致發光元件
JP2015106661A (ja) 有機エレクトロルミネッセンス素子および電子機器
CN116761868A (zh) 有机电致发光元件、有机电致发光显示装置和电子设备
CN102696127A (zh) 有机el 元件及有机发光器件
JP5252880B2 (ja) オリゴフルオレン化合物及びそれを用いた有機ｅｌ素子
CN110504374A (zh) 一种复合空穴传输/电子阻挡层及其oled器件
TW201622203A (zh) 新穎化合物及包含該化合物之有機發光元件
JP6860765B1 (ja) 化合物及びこれを含む有機発光素子
CN110504375A (zh) 一种复合空穴传输材料及其oled器件
US20130306961A1 (en) Organic light emitting device and materials for use in same
JP7094215B2 (ja) 熱活性化遅延蛍光発光材料、及び有機電界発光素子
WO2020119503A1 (fr) Dispositif électroluminescent organique comprenant une couche d&#39;extraction de lumière, composé cyclique polyaromatique d&#39;hétéroatome et composition

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: 19793943

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: 19793943

Country of ref document: EP

Kind code of ref document: A1