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WO2014185655A1 - Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique associé - Google Patents

Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique associé Download PDF

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WO2014185655A1
WO2014185655A1 PCT/KR2014/004061 KR2014004061W WO2014185655A1 WO 2014185655 A1 WO2014185655 A1 WO 2014185655A1 KR 2014004061 W KR2014004061 W KR 2014004061W WO 2014185655 A1 WO2014185655 A1 WO 2014185655A1
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group
compound
organic
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layer
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Korean (ko)
Inventor
박남진
이선희
정화순
박보람
박정환
박성제
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Duksan Hi Metal Co Ltd
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Duksan Hi Metal Co Ltd
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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 layer is often made of a multi-layer 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 element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
  • a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • 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.
  • 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.
  • 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.
  • saturated or unsaturated ring as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
  • 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
  • Substituent R 1 is absent when a is an integer of 0; when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, respectively R 1 may be the same or different from each other, and when a is an integer of 4 to 6, 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. do.
  • 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 is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound of the present invention may be used as the light emitting layer 150, hole transport layer 140 and / or light emitting auxiliary layer 151.
  • a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each light emitting layer (R, G, B) It is time to develop different light emitting auxiliary layers.
  • the light emitting auxiliary layer it is very difficult to infer the characteristics if the organic material layer used is different even if a parent compound uses a compound similar to the hole transport layer and the light emitting layer (host).
  • the hole transport layer, the light emitting layer, or the light emitting auxiliary layer is formed by using the compound represented by the formula (1), the energy level and T1 value between the organic material layers, the intrinsic properties (mobility, interface properties, etc.) ), Etc., can improve the life and efficiency of the organic electric device at the same time.
  • 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 using a variety of polymer materials is less by a solution process or solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition It can be prepared in a number of layers. 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
  • WOLED has the advantage that can be manufactured using the color filter technology of the existing LCD while being easy to realize high resolution and excellent processability.
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented.
  • a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are arranged in a plane, and a stack in which R, G, and B light emitting layers are stacked up and down ( stacking), and a color conversion material (CCM) method using electroluminescence by a blue (B) organic light emitting layer and photo-luminescence of inorganic phosphors using light therefrom.
  • CCM color conversion material
  • the present invention may also be applied to such WOLEDs.
  • 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.
  • X and Y are each independently CRR, SiRR, NR ', O or S,
  • R is hydrogen, an alkyl group of C 1 ⁇ C 50 ; C 6 ⁇ C 60 Aryl group; C 3 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, P; or, in the case of neighboring R, they combine with each other to form a spiro compound,
  • R ' is hydrogen, an alkyl group of C 1 ⁇ C 50 ; C 6 ⁇ C 60 Aryl group; C 3 ⁇ C 60 Heterocyclic group containing at least one hetero atom of O, N, S, Si, P;
  • n 0 or 1
  • Ar 1 to Ar 4 are each independently of the other C 6 ⁇ C 60 An aryl group; C 3 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, P; C 1 ⁇ C 50 Alkyl group; Or a fluorene group;
  • p, q, r and s are integers from 0 to 3
  • R 1 to R 4 are the same as or different from each other as plural when p, q, r and s are 2 or more, and each independently deuterium; C 6 ⁇ C 60 Aryl group; Fluorenyl groups; 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 It is selected from the group consisting of an aryloxy group, or they are combined with each other to form a ring,
  • R 5 and R 6 are each independently hydrogen; heavy hydrogen; C 6 ⁇ C 60 Aryl group; Fluorenyl groups; 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 it is selected from the group consisting of C 6 ⁇ C 30 aryloxy group,
  • the present invention provides a compound represented by the following formula (2) or formula (3).
  • the present invention provides a compound represented by the following formulas (4) to (6).
  • the compounds represented by the formulas (4) to (6) are exemplarily described as Ar 3 and Ar 4 are the same as Ar 1 and Ar 2 in the compounds represented by the formulas (1) to (3).
  • the present invention provides a compound represented by any one of the following formulas (1-1) to (2-33), but is not limited thereto.
  • the invention comprises a first electrode, a second electrode, and an organic layer located between the first and second electrodes, the organic layer according to an embodiment of the invention
  • An organic electric device containing a compound is provided.
  • the present invention provides an organic electroluminescent device further comprising a light efficiency improving layer on at least one of a lower portion of the first electrode or an upper portion of the second electrode.
  • the present invention provides an organic electric device, characterized in that to form the compound according to an embodiment of the present invention to the organic material layer by a soluble process (soluble process).
  • the present invention provides an organic electroluminescent device comprising a compound according to an embodiment of the present invention as a dopant material of a light emitting layer.
  • the present invention provides an electronic device including a display device including the above-described organic electroluminescent element and a control unit for driving the display device.
  • the organic electroluminescent device described above is 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 provides an electronic device characterized in that at least one of.
  • Final products according to the present invention is prepared by reacting with ⁇ Reaction Scheme 1>, but is not limited thereto.
  • the sub 1 compound of Scheme 1 may be synthesized by the reaction pathways of ⁇ Scheme 2> to ⁇ Scheme 11>.
  • Sub 1-1 compound (8.2g, 20mmol) was dissolved in DMF in a round bottom flask, Bis (pinacolato) diboron (11.2g, 44mmol), Pd (dppf) Cl 2 (0.44g, 0.6mmol), KOAc (5.89) g, 60 mmol) was added and stirred at 90 ° C. After the reaction was completed, DMF was removed by distillation and extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 , concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain 7.6g of Sub 1-2 compound. (Yield 75%)
  • Sub 1-2 compound (7.6g, 15mmol), 1-bromo-4-iodobenzene (4.2g, 15mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), K 2 CO 3 (6.2g, 45mmol) ) was dissolved in anhydrous THF and a small amount of water and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. A small amount of water was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated using column chromatography to obtain 5.1 g of the desired Sub 1-3 compound. (Yield 64%)
  • Sub 1-5 compound (1 equiv) and Sub 1-6 compound (1.1 equiv) were added to toluene and Pd 2 (dba) 3 (0.05 equiv), PPh 3 (0.1 equiv), NaO t -Bu (3 equiv) After each addition, the mixture was refluxed with stirring at 100 ° C for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO 4 and concentrated and the resulting organic material was silicagel column and recrystallized to obtain Sub 1 (A).
  • Sub 1-9 compound (1 equivalent) obtained in the above synthesis was added to Acetic acid, and the temperature of the reaction was lowered to 0 ° C. and stirred for 10 minutes. After adding phosphoric acid, it is stirred at 20 ° C for 1 hour. Finally add Sudium hydroxide to terminate the reaction. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1 (B).
  • Sub 1-12 compound (1 equiv) and Sub 1-6 compound (2.2 equiv) were added to toluene and Pd 2 (dba) 3 (0.05 equiv), PPh 3 (0.1 equiv), NaO t -Bu (3 equiv) After each addition, the mixture was refluxed with stirring at 100 ° C for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO 4 , concentrated and the resulting organic material was silicagel column and recrystallized to obtain Sub 1 (D).
  • Sub 1-14 compound (1 equivalent) obtained in the above synthesis was added to Acetic acid, and the reaction temperature was lowered to 0 ° C. and stirred for 10 minutes. After adding phosphoric acid, it is stirred at 20 ° C for 1 hour. Finally, Sudium hydroxide was added to terminate the reaction. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1 (E).
  • Sub 1 compounds include, but are not limited to the following compounds.
  • Sub 2 compounds used in one embodiment of the present invention include, but are not limited to the following compounds.
  • Sub 1 compound (1 equivalent) and Sub 2 compound (2 equivalents) were added to toluene, followed by addition of Pd 2 (dba) 3 (0.05 equivalents), PPh 3 (0.1 equivalents) and NaO t -Bu (3 equivalents), respectively. It refluxed under stirring at 100 ° C for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain a final product.
  • An organic light emitting diode was manufactured according to a conventional method using the compound according to the present invention obtained through synthesis as a dopant material for a light emitting layer.
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl as a hole injection layer ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) membrane was vacuum deposited to form a thickness of 60 nm.
  • -NPD 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq electron transport layer Tris (8-quinolinol) aluminum
  • Alq 3 the electron transport layer Tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to prepare an organic EL device by using the Al / LiF as a cathode.
  • the electroluminescent (EL) characteristics of the organic electroluminescent devices prepared according to the experimental and comparative examples thus prepared were measured by applying a forward bias DC voltage to the photoresearch company PR-650, and the measurement result was 500 cd /
  • the T95 lifetime was measured using a life measurement instrument manufactured by McScience Inc. at m2 reference luminance.
  • the device fabrication and evaluation results are shown in Table 4 below.
  • the organic electroluminescent device using the compound according to the present invention as an organic electroluminescent device material can be used as a light emitting layer material can significantly improve the high luminous efficiency, low driving voltage and lifespan.
  • a compound according to the present invention in which a heterocyclic ring and a carbon ring are condensed in a perylene in a comparative compound (1) having an anthracene core, a comparative compound (2) having a perylene core, and a comparative compound (3) This gave a better result. This is due to the condensation of hetero rings and carbon rings in perylene, which is different from the energy of the original perylene, which can be explained by the improved energy balance between neighboring layers.
  • the same effect may be obtained even when used in the auxiliary layer, the electron injection layer, the electron transport layer, and the hole injection layer.

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Abstract

La présente invention porte sur un nouveau composé qui permet d'améliorer le rendement d'émission de lumière, la stabilité et la durée de vie d'un élément, sur un élément électrique organique l'utilisant et sur un dispositif électronique associé.
PCT/KR2014/004061 2013-05-13 2014-05-08 Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique associé Ceased WO2014185655A1 (fr)

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WO2018186462A1 (fr) * 2017-04-07 2018-10-11 コニカミノルタ株式会社 Composé fluorescent, composition de matériau organique, film électroluminescent, matériau d'élément électroluminescent organique et élément électroluminescent organique
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CN112824367A (zh) * 2019-11-21 2021-05-21 乐金显示有限公司 有机化合物、以及包含其的有机发光二极管和有机发光显示装置
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CN113024444A (zh) * 2021-03-29 2021-06-25 北京八亿时空液晶科技股份有限公司 一种化合物以及含有该化合物的有机电致发光元件用材料、有机电致发光装置和电子设备

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