WO2020151500A1 - Composé organique électroluminescent, matériau électroluminescent et dispositif organique électroluminescent associés - Google Patents

Composé organique électroluminescent, matériau électroluminescent et dispositif organique électroluminescent associés Download PDF

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WO2020151500A1
WO2020151500A1 PCT/CN2020/071186 CN2020071186W WO2020151500A1 WO 2020151500 A1 WO2020151500 A1 WO 2020151500A1 CN 2020071186 W CN2020071186 W CN 2020071186W WO 2020151500 A1 WO2020151500 A1 WO 2020151500A1
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organic electroluminescent
substituted
layer
carbon atoms
organic
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PCT/CN2020/071186
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Chinese (zh)
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崔林松
张业欣
林久栋
陈华
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苏州久显新材料有限公司
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Definitions

  • the present disclosure relates to an organic electroluminescent compound, a light emitting material containing the organic electroluminescent compound, and an organic electroluminescent device containing the organic electroluminescent compound.
  • Organic electroluminescence devices generally consist of an anode, a metal cathode and an organic layer sandwiched between them.
  • the organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the basic mechanism of organic electroluminescent devices involves the injection, transport, and recombination of charges, and the formation of excitons to emit light.
  • fluorescent light-emitting materials include DPVBi, DSA-ph, dinaphthalene anthracene and so on. Due to the poor thermal stability of the above-mentioned materials, long-term driving will cause the color purity to decrease, resulting in problems such as color difference when the panel is applied. Therefore, it is urgent to develop a batch of new materials that can meet the requirements in terms of color purity, efficiency and thermal stability.
  • the purpose of the present disclosure is to solve the problems of the prior art and provide an organic electroluminescent device with thermal stability, high luminous efficiency, high brightness, and long life.
  • the present disclosure provides an organic electroluminescent compound, which is represented by the following formula (1):
  • M means C(R 1 ) 2 or
  • the dotted line represents the bond from M
  • Z is the same or different every time it appears, which means C, CR 1 or N;
  • A represents a substituted or unsubstituted condensed aromatic ring unit having 2 to 5 rings.
  • Ar 1 and Ar 2 are the same or different each time they have 5 to 30 aromatic ring atoms and may be substituted by one or more A R 1 substituted aromatic or heteroaromatic ring system;
  • two adjacent R 1 or two adjacent R 2 optionally form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, and the ring system may be composed of one or more R 2 is substituted; and two or more R 1 may be connected to each other and form a ring;
  • R 2 is the same or different in each case and is selected from H, D, F, CN, aliphatic groups having 1 to 20 carbon atoms, aromatic or heteroaromatic groups having 5 to 30 aromatic ring atoms A ring system, or an aliphatic ring system with multiple rings, in which one or more hydrogen atoms can be substituted by D, F, or CN.
  • a in the formula (1) has a structure selected from the group consisting of the following formulas:
  • R 2 to R 15 are independently selected from hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and groups having 3 to 30 carbon atoms.
  • organic electroluminescent compound according to the present disclosure is represented by any one of the following formulas (1-1) to (1-4):
  • Ar 1 , Ar 2 , M, Z, and A are the same as defined in formula (1).
  • organic electroluminescent compound according to the present disclosure wherein the compound represented by the formula (1) is selected from the following compounds:
  • the present disclosure also provides a luminescent material, which includes the organic electroluminescent compound according to the present disclosure.
  • the light-emitting material according to the present disclosure is a fluorescent light-emitting guest material.
  • the present disclosure also provides an organic electroluminescent device, which includes: a first electrode, a second electrode provided opposite to the first electrode, and sandwiched between the first electrode and the second electrode At least one organic layer,
  • the organic layer includes the organic electroluminescent compound according to the present disclosure.
  • organic electroluminescent device wherein the organic layer containing the organic electroluminescent compound is a light emitting layer.
  • the spirobifluorene molecule has a non-planar space structure. Two fluorene monomers are bridged together with sp 3 hybridized carbon atoms as the center to obtain an orthogonal three-dimensional structure with excellent thermal stability and film-forming properties. More importantly, the steric hindrance between molecules is large, which can effectively reduce the output of unfavorable factors such as excimer and concentration quenching. Therefore, introducing it into molecules with electroluminescent properties is beneficial to improve Molecular stability, color purity and luminous efficiency, etc.
  • the beneficial effect of the present disclosure is that the luminescent material prepared by the present disclosure has a higher glass transition temperature, fluorescence quantum yield, and charge mobility, which can increase the efficiency and lifetime of the organic electroluminescent device and reduce the driving voltage and power consumption.
  • the compound of formula (1) of the present disclosure as a light-emitting material (doping compound) of an organic electroluminescent device, can stabilize the film state and has excellent heat resistance. By using the compound, organic electroluminescent devices with high efficiency, high brightness, long life, and low driving voltage can be prepared.
  • Figure 1 shows the ultraviolet absorption spectrum (UV-Vis) and room temperature fluorescence spectrum (PL) of the luminescent material compound 83 in OLED3 in the embodiment; the ultraviolet absorption spectrum and room temperature fluorescence spectrum in a dilute solution of dichloromethane (1 ⁇ 10 -5) mol/L).
  • Figure 2 shows the organic electroluminescence spectra of OLED2 and OLED3 in the embodiment.
  • Fig. 3 is a diagram showing the configuration of organic electroluminescent devices of Examples and Comparative Examples.
  • references to “one embodiment” or “embodiment” or “in another embodiment” or “in certain embodiments” or “in some embodiments of this application” throughout this specification mean that At least one embodiment includes specific reference elements, structures, or features related to the embodiment. Therefore, the phrases “in one embodiment” or “in an embodiment” or “in another embodiment” or “in certain embodiments” or “in part of this application” appearing in various places throughout the specification In the embodiments, “not all refer to the same embodiment. In addition, specific elements, structures, or features may be combined in one or more embodiments in any suitable manner.
  • the organic electroluminescent compound of the present disclosure is represented by the following formula (1):
  • M means C(R 1 ) 2 or
  • the dotted line represents the bond from M
  • Z is the same or different every time it appears, which means C, CR 1 or N;
  • A represents a substituted or unsubstituted condensed aromatic ring unit having 2 to 5 rings.
  • Ar 1 and Ar 2 are the same or different each time they have 5 to 30 aromatic ring atoms and may be substituted by one or more A R 1 substituted aromatic or heteroaromatic ring system;
  • two adjacent R 1 or two adjacent R 2 optionally form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, and the ring system may be composed of one or more R 2 is substituted; and two or more R 1 may be connected to each other and form a ring;
  • R 2 is the same or different in each case and is selected from H, D, F, CN, aliphatic groups having 1 to 20 carbon atoms, aromatic or heteroaromatic groups having 5 to 30 aromatic ring atoms A ring system, or an aliphatic ring system with multiple rings, in which one or more hydrogen atoms can be substituted by D, F, or CN.
  • condensed aromatic ring unit having 2 to 5 rings in the formula (1) specific examples include biphenyl, terphenyl, tetraphenyl, naphthalene, anthracene, acenaphthylene, fluorene, phenanthrene, indene , Pyrene, perylene, fluoranthene, benzanthracene, triphenylene, etc.
  • Halogen atom such as fluorine atom, chlorine atom, bromine atom or iodine atom
  • alkyl group having 1 to 6 carbon atoms for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl Or n-hexyl;
  • alkoxy group having 1 to 6 carbon atoms such as methoxy, ethoxy or propoxy
  • Alkenyl such as vinyl or allyl
  • Aryloxy such as phenoxy or tolyloxy
  • Arylalkoxy such as benzyloxy or phenethoxy
  • Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, pyrenyl, perylene, fluoranthene, benzene And [9,10] phenanthryl or spirobifluorenyl;
  • Aromatic heterocyclic groups such as pyridyl, thienyl, furyl, pyrrolyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazole Group, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, azafluorenyl, diazafluorenyl, carboline, aza Spirobifluorenyl or diazaspirobifluorenyl;
  • Aryl vinyl groups such as styryl or naphthalene vinyl groups
  • Acyl for example acetyl or benzoyl.
  • the aromatic ring system represented by Ar 1 and Ar 2 can be exemplified by benzene, biphenyl, terphenyl, tetraphenyl, styrene, naphthalene, anthracene, acenaphthene, phenanthrene, fluorene, indene, pyrene, perylene, fluoranthene, benzene And [9,10] phenanthrene, snail difluorene and so on.
  • the heteroaromatic ring system represented by Ar 1 and Ar 2 can exemplify pyridine, bipyridine, terpyridine, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole, imidazole, triazole, oxazole, isooxazole Azole, thiazole, isothiazole, oxadiazole, thiadiazole, furan, thiophene, quinoline, isoquinoline, quinoxaline, quinazoline, naphthyridine, indole, isoindole, benzimidazole, benzo Triazole, benzofuran, benzothiophene, benzoxazole, benzoxadiazole, benzothiazole, benzothiadiazole, pyridopyrrole, pyridoimidazole, pyridotriazole, pteridine, acridine , Ph
  • Examples of the linear or branched alkyl group having 1 to 20 carbon atoms in R 1 of the formula (1) include methyl, ethyl, n-propyl, isopropyl, n-butyl, iso Butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n Decyl, isodecyl, n-undecyl, isoundecyl, n-dodecyl, isododecyl, n-tridecyl, isotridecyl, n-tetradecyl, iso Myristyl, n-pentadecyl, isopentade
  • cyclic alkyl group having 3 to 20 carbon atoms in R 1 of the formula (1) cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclo Decyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentadecyl, cyclohexadecyl, cycloheptadecanyl, cyclooctadecyl , Cyclononadecyl, cycloeicosyl, 1-adamantyl, 2-adamantyl, etc.
  • alkenyl or alkynyl group having 2 to 20 carbon atoms in R 1 of the formula (1) vinyl, allyl, isopropenyl, 2-butenyl, 1-pentenyl, 2 -Hexenyl, 1-heptenyl, 1-octenyl, 1-nonenyl, 1-decenyl, 1-undecenyl, 1-dodecenyl, 1-tridecenyl, 1-tetradecenyl, 1-pentadecenyl, 1-hexadecenyl, 1-heptadecenyl, 1-octadecenyl, 1-nonadecanyl, 1-eicosenyl, 2 -Heptenyl, 2-methyl-2-hexenyl, 2-octenyl, 2-ethylhexenyl, 3-methyl-2-heptenyl, 2-nonenyl, 2-decenyl Alkenyl, 2-hexadecen
  • aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms in R 1 of formula (1) As an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms in R 1 of formula (1), the same as the above-mentioned aromatic or heteroaromatic ring system represented by Ar 1 and Ar 2 can be exemplified example of.
  • an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in R 2 of formula (1) As an aliphatic group having 1 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in R 2 of formula (1), the same as those in the above R 1 The same example.
  • an aliphatic epoxy compound and the like can be exemplified.
  • a in the formula (1) has a structure selected from the group consisting of the following formulas:
  • R 2 to R 15 are independently selected from hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and groups having 3 to 30 carbon atoms.
  • alkyl group As the alkyl group, the aryl group, and the heteroaromatic group here, the same examples as in the above-mentioned Ar 1 , Ar 2 , R 1 , and R 2 can be illustrated.
  • the organic electroluminescent compound of the present disclosure is represented by any one of the following formulas (1-1) to (1-4):
  • Ar 1 , Ar 2 , M, Z, and A are the same as defined in formula (1).
  • the organic electroluminescent compound of the present disclosure is selected from the following compounds, but the present disclosure is not limited to these compounds.
  • the purification of the organic electroluminescent compound of the present disclosure is performed by purification using column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization using a solvent, crystallization method, sublimation purification method, and the like.
  • the identification of organic electroluminescent compounds is performed by mass spectrometry and elemental analysis.
  • the light-emitting material of the present disclosure includes the above-mentioned organic electroluminescent compound.
  • the luminescent material of the present disclosure can be used in organic electroluminescent devices, especially as a fluorescent light-emitting guest material of organic electroluminescent devices.
  • the organic electroluminescence device of the present disclosure includes: a first electrode, a second electrode provided opposite to the first electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, wherein the organic layer contains the present Disclosed organic electroluminescent compound.
  • FIG. 3 is a diagram showing the configuration of the organic electroluminescent device of the present disclosure.
  • the organic electroluminescent device of the present disclosure for example, the anode 2, the hole injection layer 3, the hole transport layer I4, the hole transport layer II5, the electron blocking layer 6, the light emitting layer 7, the air
  • the hole blocking layer 8, the electron transport layer 9, the electron injection layer 10 and the cathode 11 are arranged on the substrate 1 in this order.
  • the organic electroluminescent device of the present disclosure is not limited to such a structure, for example, in the multilayer structure, some organic layers may be omitted.
  • it can be the hole injection layer 3 between the anode 2 and the hole transport layer I4, the hole blocking layer 8 between the light-emitting layer 7 and the electron transport layer 9, and the electrons between the electron transport layer 9 and the cathode 11.
  • the injection layer 10 is omitted, and the configuration of the anode 2, the hole transport layer I4, the light emitting layer 7, the electron transport layer 9 and the cathode 11 are sequentially arranged on the substrate 1.
  • the organic electroluminescent device according to the present disclosure can be manufactured by materials and methods known in the art, except that the above-mentioned organic layer contains the compound represented by the above-mentioned formula (1).
  • the organic electroluminescence device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
  • the organic electroluminescent device may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, a metal or a conductive metal oxide or their alloy is vapor-deposited on a substrate to form an anode, Then, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer.
  • PVD physical vapor deposition
  • the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
  • the anode of the organic electroluminescent device of the present disclosure may be composed of a known electrode material.
  • electrode materials with large work functions such as vanadium, chromium, copper, zinc, gold and other metals or their alloys; such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) and other metals Oxide; such as ZnO: Al or SNO 2 : Sb and other metal and oxide combinations; poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene]( PEDOT), conductive polymers such as polypyrrole and polyaniline.
  • ITO is preferable.
  • a known material having hole injection properties can be used as the hole injection layer of the organic electroluminescence device of the present disclosure.
  • Examples include: porphyrin compounds represented by copper phthalocyanine, naphthalenediamine derivatives, star-shaped triphenylamine derivatives, and divalent groups with three or more triphenylamine structures in the molecule through single bonds or no heteroatoms Triphenylamine trimers and tetramers such as arylamine compounds with a group-linked structure, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials. These materials can be formed into thin films by well-known methods such as vapor deposition, spin coating, and inkjet.
  • hole transport layers I and II of the organic electroluminescent device of the present disclosure well-known materials having hole transport properties can be used.
  • examples include: compounds containing m-carbazolyl phenyl; such as N,N'-diphenyl-N,N'-bis(m-tolyl)benzidine (TPD), N,N'-diphenyl- N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N,N',N'-tetraphenylbenzidine and other benzidines Derivatives; 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC); various triphenylamine trimers and tetramers; 9,9',9”-triphenyl Base-9H,9'H,9"H-3,3':6',3"-Tris-PCz, etc.
  • They can be formed into a film alone or mixed with other materials to form a film It can be used in the form of a single layer, and it can also be made into a laminated structure of layers formed by separate films, a laminated structure of layers formed by mixed films, or layers formed by separate films and mixed films The laminated structure of the resulting layer.
  • These materials can be formed into thin films by well-known methods such as vapor deposition, spin coating, and inkjet.
  • the hole injection layer or the hole transport layer it is also possible to use a material obtained by P-doping tribromoaniline antimony hexachloride, axene derivatives, etc., for the materials commonly used in the layer, and its partial structure Polymer compounds having the structure of benzidine derivatives such as TPD.
  • the electron blocking layer of the organic electroluminescent device of the present disclosure can be formed using a known compound having an electron blocking effect.
  • a known compound having an electron blocking effect for example, 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), 4,4',4"-tris(N-carbazolyl) triphenylamine (TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (mCP), 2,2-bis(4- Carbazole derivatives such as carbazole-9-ylphenyl)adamantane (Ad-Cz); 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilane) (Yl)phenyl]-9H-fluorene represented by compounds having triphenylsilyl and triarylamine structures; monoamine compounds with high electron blocking properties
  • They can be formed into a film individually, or they can be used in the form of a single layer formed by mixing with other materials, and can also be formed into a laminated structure of layers formed by separate films, or layers formed by mixing and forming films.
  • These materials can be formed into thin films by well-known methods such as vapor deposition, spin coating, and inkjet.
  • a light-emitting material containing the organic electroluminescent compound represented by formula (1) is preferably used.
  • various metal complexes such as metal complexes of quinoline derivatives such as Alq 3 , compounds having a pyrimidine ring structure, anthracene derivatives, bisstyrylbenzene derivatives, Pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, etc.
  • the light-emitting layer may be composed of a host material and a dopant material.
  • a host material for example, mCBP, mCP, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, heterocyclic compounds having an indole ring as a partial structure of a condensed ring, and the like can be used.
  • a light-emitting material containing an organic electroluminescent compound represented by formula (1) is preferably used as the dopant material.
  • the doping weight ratio of the organic electroluminescent compound of the present disclosure is preferably 0.1-50%, more preferably 0.5-20%, and particularly preferably 0.5-8%.
  • the dopant materials can also use pyrene derivatives, anthracene derivatives, quinacridones, coumarins, rubrene, perylene and their derivatives, benzopyrene Pyran derivatives, rhodamine derivatives, aminostyryl derivatives, spirocyclic bifluorene derivatives, etc. They can be formed into a film individually, or they can be used in the form of a single layer formed by mixing with other materials, and can also be formed into a laminated structure of layers formed by separate films, or layers formed by mixing and forming films. The laminated structure of, or the laminated structure of the layer formed by separate film formation and the layer formed by mixing film. These materials can be formed into thin films by well-known methods such as vapor deposition, spin coating, and inkjet.
  • the hole blocking layer of the organic electroluminescent device of the present disclosure can be formed using a known compound having hole blocking properties.
  • a known compound having hole blocking properties for example, 2,4,6-tris(3-phenyl)-1,3,5-triazine (T2T), 1,3,5-tris(1-phenyl-1H-benzimidazole-2- Phenanthroline derivatives such as benzene (TPBi) and bath copper spirit (BCP), and quinolines such as aluminum (III) bis(2-methyl-8-hydroxyquinoline)-4-phenylphenolate (BAlq) Metal complexes of alcohol derivatives, and various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and other compounds having hole blocking effects.
  • T2T 2,4,6-tris(3-phenyl)-1,3,5-triazine
  • 1,3,5-tris(1-phenyl-1H-benzimidazole-2- Phenanthroline derivatives such
  • They can be formed into a film alone, or they can be used in the form of a single layer formed by mixing with other materials, or they can be formed into a laminated structure of layers formed separately, or a layer formed by mixing.
  • These materials can be formed into thin films by well-known methods such as vapor deposition, spin coating, and inkjet.
  • the material having hole blocking properties described above can also be used for the formation of the electron transport layer described below. That is, by using the above-mentioned well-known material having hole blocking properties, it is possible to form a layer that serves as both a hole blocking layer and an electron transport layer.
  • a known compound having electron transport properties is used.
  • ZADN 1H-benzimidazole
  • thiadiazole derivatives anthracene derivatives
  • carbodiimide derivatives
  • They can be formed into a film alone, or they can be used in the form of a single layer formed by mixing with other materials, or they can be formed into a laminated structure of layers formed separately, or a layer formed by mixing.
  • These materials can be formed into thin films by well-known methods such as vapor deposition, spin coating, and inkjet.
  • the electron injection layer of the organic electroluminescence device of the present disclosure can be formed using a material known per se.
  • alkali metal salts such as lithium fluoride and cesium fluoride
  • alkaline earth metal salts such as magnesium fluoride
  • metal complexes of quinolinol derivatives such as lithium quinolate
  • metal oxides such as alumina.
  • the electron injection layer or the electron transport layer as the material generally used in the layer, a material obtained by further N-doping metals such as cesium, triarylphosphine oxide derivatives, and the like can be used.
  • an electrode material having a low work function such as aluminum and magnesium, or an alloy having a low work function such as magnesium silver alloy, magnesium indium alloy, and aluminum magnesium alloy as the electrode material.
  • a substrate in a conventional organic light emitting device such as glass or plastic
  • a glass substrate is selected.
  • intermediate 44A 5.00g (12.27mmol), 9,10-dibromoanthracene 1.65g (4.91mmol), tris(dibenzylideneacetone)dipalladium 0.22g (0.25mmol), tert 0.14 g (0.49 mmol) of butylphosphine tetrafluoroborate, 2.36 g (24.54 mmol) of sodium tert-butoxide, 150 mL of toluene, under the protection of argon, reflux and stir for 12 hours, and the reaction is complete.
  • intermediate 74A 5.00g (17.52mmol), 1,6-diisopropyl-3,8-dibromopyrene 3.11g (7.01mmol), tris(dibenzylideneacetone)dipalladium 0.32g (0.35mmol), 0.20g (0.70mmol) of tri-tert-butylphosphine tetrafluoroborate, 3.37g (35.04mmol) of sodium tert-butoxide, 150mL of toluene, under the protection of argon, reflux and stir for 12 hours. The reaction is complete.
  • the hole injection layer 3, the hole transport layer I 4, the hole transport layer II 5, the electron blocking layer 6, the light emitting layer 7, the hole blocking layer 8, the electron transport layer 9, the electron injection layer 10, and the cathode 11 are sequentially formed On the transparent anode 2 previously formed on the glass substrate 1 to prepare an organic electroluminescent device as shown in FIG. 3.
  • the glass substrate coated with a transparent conductive layer of ITO with a thickness of 100nm was ultrasonically processed in Decon 90 alkaline cleaning solution, rinsed in deionized water, rinsed in acetone and ethanol three times each, and baked in a clean environment To completely remove the water, clean with ultraviolet light and ozone, and bombard the surface with a low-energy cation beam.
  • the glass substrate with the ITO electrode is placed in the vacuum chamber and evacuated to 4 ⁇ 10 -5 to 2 ⁇ 10 -5 Pa.
  • HAT-CN Hexaazatriphenylene
  • N, N' is deposited at an evaporation rate of 2.0nm/s -Diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB) to form a layer with a thickness of 40nm as the hole transport layer I ( HTL I), and then on the hole transport layer I (HTL I), 9,9',9”-triphenyl-9H,9'H,9”H- is evaporated at an evaporation rate of 2.0nm/s 3,3':6',3”-tricarbazole (Tris-PCz) is formed with a thickness of 20nm as the hole transport layer II (HTL II).
  • the thickness is 2.0nm/ s evaporation rate 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP) is evaporated to form a layer with a film thickness of 15nm as the electron blocking layer (EBL).
  • EBL electron blocking layer
  • the evaporation rate of 9-(4-(1-naphthyl)-10-(2-naphthyl)anthracene (NNPA) is 2.0nm/s and that of Preparation Examples 1, 2, 3, 4, 5
  • the vapor deposition rate of the compounds (compounds 44, 74, 83, 87, and 98) was 0.16nm/s.
  • the vapor deposition rate was 0.16nm/s.
  • Dual source co-evaporation was performed to form a layer with a thickness of 20nm as the light-emitting layer.
  • Preparation Examples 1, 2, 3 The doping mass ratio of the compounds of, 4, and 5 (compounds 44, 74, 83, 87, and 98) is 8wt%.
  • 2,4,6-three are evaporated at an evaporation rate of 2.0nm/s.
  • (3-Phenyl)-1,3,5-triazine (T2T) is formed with a thickness of 10nm as the hole blocking layer (HBL).
  • vapor deposition is performed at 2.0nm/s Rate deposition of 2-[4-(9,10-dinaphthalene-2-anthracene-2-yl)phenyl]-1-phenyl-1H-benzimidazole (ZADN) to form a layer with a thickness of 40nm as Electron transport layer (ETL).
  • ETL Electron transport layer
  • 8-hydroxyquinoline-lithium (Liq) is vapor-deposited at a vapor deposition rate of 0.2 nm/s to form a layer with a thickness of 2 nm as the electron injection layer.
  • use Aluminum is vapor deposited at a vapor deposition rate of 3.0 nm/s or more to form a cathode with a film thickness of 100 nm.
  • the current-brightness-voltage characteristics of the device are completed by the Keithley source measurement system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) with a calibrated silicon photodiode, and the electroluminescence spectrum is performed by the Photoresearch company PR655 spectrometer Measured, the external quantum efficiency of the device can be calculated by the method of Adv. Mater., 2003, 15, 1043-1048.
  • the lifetime of the device refers to the time for the brightness to decay to 9,000 canter per square meter (90%) starting with 10,000 canter per square meter. All devices are packaged in a nitrogen environment.
  • OLED1-5) The structure of the organic electroluminescent device (OLED1-5) prepared in the example and the film thickness of each layer are as follows:
  • Comparative Examples 1 and 2 are the same as the Examples, except that the fluorescent light-emitting compound is changed.
  • the device structure of Comparative Example 1 is as follows:
  • the device structure of Comparative Example 2 is as follows:
  • the organic electroluminescent compound of the present disclosure has excellent luminous efficiency, excellent material color purity and lifetime characteristics. Therefore, organic electroluminescent devices with excellent service life can be prepared from the compound.

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Abstract

L'invention concerne un composé organique électroluminescent, matériau électroluminescent et dispositif organique électroluminescent associés, lequel composé électroluminescent de formule (1) peut être un matériau fluorescent possédant de bonnes propriétés. Le dispositif électroluminescent fait d'un matériau fluorescent possède les avantages suivants, sans s'y limiter : faible tension d'attaque, forte efficacité lumineuse, une longue vie utile et une chromatographie optique très pure.
PCT/CN2020/071186 2019-01-23 2020-01-09 Composé organique électroluminescent, matériau électroluminescent et dispositif organique électroluminescent associés WO2020151500A1 (fr)

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CN111875505B (zh) 2019-12-20 2021-10-08 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和电子装置
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CN115894417A (zh) * 2021-09-30 2023-04-04 广州华睿光电材料有限公司 芘类化合物及其混合物、组合物、有机电子器件

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