WO2015083948A1 - Composé pour élément électrique organique, élément électrique organique utilisant celui-ci, et dispositif électronique correspondant - Google Patents

Composé pour élément électrique organique, élément électrique organique utilisant celui-ci, et dispositif électronique correspondant Download PDF

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WO2015083948A1
WO2015083948A1 PCT/KR2014/010755 KR2014010755W WO2015083948A1 WO 2015083948 A1 WO2015083948 A1 WO 2015083948A1 KR 2014010755 W KR2014010755 W KR 2014010755W WO 2015083948 A1 WO2015083948 A1 WO 2015083948A1
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박형근
최연희
박정근
조혜민
이대원
김석현
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덕산네오룩스 주식회사
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Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the material used as the organic material layer in the organic electric device may be classified into a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material and the like according to a function.
  • Efficiency, lifespan, and driving voltage are related to each other.As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Jouleheating generated during driving decreases, resulting in a lifetime. This tends to be higher. However, simply improving the organic layer may not maximize the efficiency. Because of the optimal combination of energy level, T 1 value, and intrinsic properties (mobility, interfacial properties, etc.) between organic layers, long life and high efficiency can be achieved simultaneously. Because.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • the present invention provides a compound having high electron mobility and high temperature stability and having a more efficient electron transport ability with a high T 1 value, and using the compound, an organic electric device having improved efficiency, lifetime and color purity, and an electron including the same. It is an object to provide a device.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • the present invention it is possible to provide a compound having high electron mobility and high temperature stability and more efficient electron transport ability with a high T 1 value, and by using such a compound, it is possible to improve the efficiency, lifespan and color purity of the device.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a hetero ring having 2 to 60 carbon atoms, or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consist
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • a protective layer or a light efficiency improving layer Capping layer
  • the compound according to the present invention applied to the organic material layer of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host of the dopant or light efficiency improvement layer of the light emitting layer 150 Can be used as a material.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • R 1 and R 2 independently of each other deuterium; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; And C 6 ⁇ C 30 An aryloxy group; It is selected from the group consisting of, m is an integer of 0 to 4, n is an integer of 0 to 6.
  • a plurality of R 1 may be the same or different from each other, and a plurality of R 2 may also be the same or different from each other.
  • R 1 and R 2 are an aryl group
  • C 6 ⁇ C 60 It may be an aryl group, preferably C 6 ⁇ C 30 It may be an aryl group, more preferably C 6 ⁇ C 15 It may be an aryl group.
  • R 1 and R 2 are heterocycles, C 2 ⁇ C 60 heterocyclic group, preferably C 2 ⁇ C 30 heterocyclic group, more preferably C 2 ⁇ C 20 heterocyclic group, more Preferably it may be a C 3 ⁇ C 15 heterocyclic group.
  • R 1 and R 2 are independently of each other aryl such as phenyl, biphenyl, anthracene, phenanthrene, or the like, or hetero, such as pyridine, quinoline, phenanthroline, dibenzothiophene, dibenzofuran, triazine, quinazoline, or the like. It may be a ring.
  • L 1 and L 2 are each independently a single bond; C 6 ⁇ C 60 aromatic ring; Fluorene; C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60 fused ring of an aromatic ring; And C 2 ⁇ C 60 heterocycle including at least one heteroatom of O, N, S, Si, and P, each of which may be selected from deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C 1 ⁇ C 20 of the import alkylthio; C 1 -C 20 alkoxyl group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 6 -C 20 aryl group; C 6 ⁇ C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P;
  • L 1 is a single bond
  • L 2 is bonded to L 1 , which is a single bond
  • L 2 is the same as that directly bonded to the benzoacridin skeleton.
  • L 2 is a single bond
  • the same as the Ar 1 are the same as those that are directly coupled to L 1, the case that L 1 and L 2 are both a single bond the Ar 1 that is directly coupled to Ben Joa acridine skeleton Done.
  • L 2 may vary in valence depending on x.
  • L 2 may be bivalent, x is 2, trivalent, and x may be tetravalent.
  • L 1 may also have a different valence depending on x.
  • L 1 may be bivalent, x is 2, trivalent, and x may be tetravalent. will be.
  • L 1 when L 2 is not a single bond, L 1 may be a single bond or a divalent group.
  • L 1 and L 2 may be an aromatic ring of C 6 ⁇ C 60 , preferably an aromatic ring of C 6 ⁇ C 30 , more preferably may be an aromatic ring of C 6 ⁇ C 20 .
  • L 1 and L 2 may be a C 2 ⁇ C 60 heterocyclic group, preferably a C 2 ⁇ C 30 heterocyclic group, more preferably a C 2 ⁇ C 20 heterocyclic group, more preferably May be a heterocyclic group of C 3 ⁇ C 15 .
  • L 1 is, for example, a divalent benzene ring, naphthylene, anthracene, phenanthrene, perylene, triphenylene, pyrene, benzophenanthrene, fluorene, pyridine, pyrimidine, pyridazine, triazine, benzoacridine , Quinazoline, quinoline, isoquinoline, quinoxaline, 2,6-naphthyridine, pyrido [2,3- d ] pyrimidine, pyrido [3,4- d ] pyrimidine, phenanthridine, benzo [ h ] Quinazolin, pyrrole, imidazole, triazole, thiophene, isoxazole, 1,3,4-thiadiazole, 1 H -benzo [ d ] imidazole, benzo [ d ] oxazole, benzo [ d ] thiazol or derivative
  • Ar 1 is a C 6 ⁇ C 60 An aryl group; Fluorenyl group; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P.
  • C 6 ⁇ C 60 It may be an aryl group, preferably C 6 ⁇ C 30 It may be an aryl group, more preferably C 6 ⁇ C 15 aryl group, more preferably C It may be an aryl group of 6 ⁇ C 10 .
  • a C 2 ⁇ C 60 heterocyclic group preferably a C 2 ⁇ C 30 heterocyclic group, more preferably a C 2 ⁇ C 20 heterocyclic group, more preferably C 3 ⁇ C 15 It may be a heterocyclic group.
  • X which is an index of Ar 1 , is an integer of 1 to 3.
  • x is an integer of 1.
  • Ar 1 may be bonded to L 2 .
  • L 2 is the case of a single bond
  • the Ar 1 is the same as directly bonded to L 1
  • the case that L 1 and L 2 are both a single bond the Ar 1 is the same as directly bonded to Ben Joa acridine skeleton .
  • the aryl group, fluorenyl group, heterocyclic group and fused ring group of R 1 , R 2 and Ar 1 , and the alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group of R 1 and R 2 are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C 1 ⁇ C 20 of the import alkylthio; C 1 -C 20 alkoxyl group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; A C 6 -C 20 aryl group unsubstituted or substituted with a C 2 -C 20 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; C 6 ⁇ C 20 aryl group substituted with deuterium; Fluorenyl group; A heterocyclic group substituted
  • Ar 1 of Formula 1 may be one of those represented by A1 to A52 of Formula 2 below.
  • a is an integer of 0-5, b is an integer of 0-7, c is an integer of 0-9, d is an integer of 0-6, e is an integer of 0-5, f is 0- An integer of 8, g is an integer of 0-4, h is an integer of 0-3, i is an integer of 0-2, j is an integer of 0 or 1.
  • a plurality of R 3 are the same as or different from each other, and independently from each other deuterium; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; And C 6 ⁇ C 30 An aryloxy group; may be selected from one or more groups.
  • Q 1 is N (R 4 ), S or O
  • Q 2 is N (R 4 ), C (R 5 ) (R 6 ), S or O
  • R 4 and R 5 are each independently, a C 6 ⁇ C 60 An aryl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; C 1 ⁇ C 30 Alkoxy group; And fluorenyl group; It is selected from the group consisting of, R 5 and R 6 Also C 6 ⁇ C 60 An aryl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; C 1 ⁇ C 30 Alkoxy group; And a fluorenyl group; or R 5 and R 6 may be bonded to each other to form a spiro
  • the compound represented by the formula may be one of the compounds of the formula (3).
  • the present invention provides a compound for an organic electric device represented by Chemical Formula 1.
  • the present invention provides an organic electric device containing the compound represented by the formula (1).
  • the organic electric element includes a first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode.
  • the organic material layer may include a compound represented by Chemical Formula 1, and Chemical Formula 1 may be included in the electron transport layer of the organic material layer. That is, the compound represented by Formula 1 may be used as the electron transport layer material.
  • it provides an organic electroluminescent device comprising one of the compounds represented by Formula 2 and Formula 3 in the organic material layer, and more specifically, the present invention is an organic electroluminescent device comprising a compound represented by the individual formula in the organic material layer To provide.
  • the present invention may include at least a light emitting auxiliary layer in the organic material layer.
  • the present invention provides a light efficiency improving layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric element further comprising.
  • the present invention provides a light efficiency improving layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric element further comprising.
  • the present invention provides an organic electroluminescent device is formed by any one of the organic coating layer, spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process and roll-to-roll process do.
  • the present invention provides a display device including an organic electric element including the organic material layer; And a controller for driving the display device.
  • the organic electroluminescent device according to the present invention is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochrome or white illumination It can be one.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • a device for monochrome or white illumination It can be one.
  • the compound represented by Chemical Formula 3 according to the present invention (Final Product: P-1 to P-120) may be synthesized by reacting Sub 1 with (Ar 1 ) x -L 2 -Hal 3 as in Scheme 1 below. Can be.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Compound belonging to Sub 1 may be a compound as follows, but is not limited thereto.
  • Table 1 shows the FD-MS values of the compounds belonging to Sub 1.
  • Sub 1-III-1 (8.92 g, 25.1 mmol) obtained in the synthesis of 2-bromo-7-iodo-9,9-diphenyl-9 H- fluorene (19.71 g, 37.7 mmol), Pd (PPh 3 ) 4 (1.45 g, 1.3 mmol), K 2 CO 3 (10.41 g, 75.3 mmol), THF, and water were obtained using the Sub 1-IV-1 synthesis method to obtain 10.82 g (yield: 69%) of the product.
  • Sub 1-1 (4.21 g, 9.8 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, followed by 3,3 '-(5'-chloro- [1,1': 3 ', 1''-terphenyl ] -3,3 ''-diyl) dipyridine (4.5 g, 10.7 mmol), Pd (PPh 3 ) 4 (0.56 g, 0.5 mmol), K 2 CO 3 (4.05 g, 29.3 mmol), add water and add 95 Stir at ° C.
  • the starting material-> Sub 1-I reaction in Scheme 2 is based on the Copper-Catalyzed Amination of Bromobenzoic Acids reaction, and the Sub 1-I-> Sub 1-II reaction in Scheme 2 is Cyclization by POCl 3.
  • the reaction is based on the reaction, and the reaction of Sub 1-II-> Sub 1-III, Sub 1-IV-> Sub 1 in Scheme 2 is based on Miyaura boration reaction.
  • Sub 1-III-> Sub 1-IV and ⁇ Scheme 7> to ⁇ Scheme 14> in Scheme 2 are based on the Suzuki cross-coupling reaction. It is clear that the reactions can proceed even if substituents not specifically specified in these are attached.
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as an electron transport layer material.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium
  • BAlq (1,1'bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • a layer was formed, and the electron transport layer was formed by vacuum depositing the compound P-1 of the present invention on the hole blocking layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • LiF which is an alkali metal halide
  • An organic electroluminescent device was manufactured according to the same method as Example 1 except for using the compounds P-2 to P-120 of the present invention shown in Table 3 below instead of the compound P-1 of the present invention as the electron transporting material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used instead of Compound P-1 of the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used instead of Compound P-1 of the present invention as an electron transport layer material.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared by Examples 1 to 120, Comparative Examples 1 and 2 of the present invention The T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at 5000 cd / m 2 reference luminance. The measurement results are shown in Table 3 below.
  • the organic electroluminescent device using the compound of the present invention as the material of the electron transport layer has a driving voltage compared to the organic electroluminescent device using the comparative compound 1 and the comparative compound 2 as the material of the electron transport layer. It was low, and not only the luminous efficiency was improved but also the life and the like markedly improved.
  • the materials used as the electron transport layer are generally organic electron, such as the electron injection layer, hole injection layer, hole transport layer, light emitting auxiliary layer, light emitting layer, etc.
  • the organic layer of the device can be used in combination with a single or other material. Therefore, the compounds of the present invention may be used in combination with a single or other materials in addition to the electron transport layer, for example, other organic material layers, for example, an electron injection layer, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer.

Abstract

La présente invention concerne un nouveau composé apte à améliorer l'efficacité lumineuse, la stabilité, et la durée de vie d'un élément ; un élément électrique organique utilisant ledit composé ; et un dispositif électronique associé.
PCT/KR2014/010755 2013-12-03 2014-11-10 Composé pour élément électrique organique, élément électrique organique utilisant celui-ci, et dispositif électronique correspondant WO2015083948A1 (fr)

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EP3182478A1 (fr) 2015-12-18 2017-06-21 Novaled GmbH Couche d'injection d'électrons pour une diode électroluminescente organique (oled)
EP3208861A1 (fr) 2016-02-19 2017-08-23 Novaled GmbH Couche de transport d'électrons comprenant un mélange composé de matrice pour une diode électroluminescente organique (oled)
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CN110845496A (zh) * 2019-11-21 2020-02-28 吉林奥来德光电材料股份有限公司 一种电子传输材料及其合成方法与应用
CN114929687A (zh) * 2019-12-10 2022-08-19 诺瓦尔德股份有限公司 吖啶化合物以及包含它的有机半导体层、有机电子器件和显示装置
WO2021116225A1 (fr) * 2019-12-10 2021-06-17 Novaled Gmbh Composé d'acridine et couche semiconductrice organique, dispositif électronique organique et dispositif d'affichage le comprenant
EP3835295A1 (fr) * 2019-12-10 2021-06-16 Novaled GmbH Composé acridine et couche semiconductrice organique, dispositif électronique organique et dispositif d'affichage le comprenant
CN116924986A (zh) * 2023-09-18 2023-10-24 山东千铄新材料有限公司 一种含氮杂环的功能层材料、制备方法及应用
CN116924986B (zh) * 2023-09-18 2024-04-09 山东千铄新材料有限公司 一种含氮杂环的功能层材料、制备方法及应用

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