WO2014010910A1 - Composé, élément électronique organique l'utilisant et dispositif électronique associé - Google Patents

Composé, élément électronique organique l'utilisant et dispositif électronique associé Download PDF

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WO2014010910A1
WO2014010910A1 PCT/KR2013/006087 KR2013006087W WO2014010910A1 WO 2014010910 A1 WO2014010910 A1 WO 2014010910A1 KR 2013006087 W KR2013006087 W KR 2013006087W WO 2014010910 A1 WO2014010910 A1 WO 2014010910A1
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aryl
substituted
deuterium
organic
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정화순
장재완
이선희
박남진
김혜령
황선필
박정환
이범성
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덕산하이메탈(주)
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound, an organic electric element comprising 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 include fluorine, chlorine, bromine, and iodine unless otherwise stated.
  • alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it 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 a monocyclic or polycyclic aromatic, 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.
  • 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 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only single ring but also multiple rings, and adjacent groups may be formed by combining.
  • heterocycloalkyl includes one or more heteroatoms, unless otherwise indicated, having from 2 to 60 carbon atoms, including single rings as well as multicycles. Adjacent groups may be formed in combination.
  • heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
  • heteroatom refers to N, O, S, P, and Si unless otherwise indicated.
  • 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.
  • 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 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Group, germanium group, and C 5 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
  • 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.
  • An organic material layer containing a compound represented by the formula (1) between) is provided.
  • 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 electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material 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
  • 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.
  • 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).
  • B represents a benzene ring condensed by sharing one side with two adjacent rings (D and E), respectively, and may be represented by Formula 1a.
  • D is a pentagonal ring condensed by sharing one side with two adjacent rings (A and B), respectively, and may be represented by Formula 1b.
  • a and B adjacent rings
  • the side connecting the * and * of Formula 1b condensed by sharing with any one of the A ring and the B ring, and condensed by sharing the side connecting the ** and ** with the other.
  • E is a pentagonal ring condensed by sharing two sides with two adjacent rings (B and a benzene ring substituted with R 7 to R 10 ), respectively, which may include Y, and may be represented by the following Formula 1c: have.
  • the side connecting the * and * in Formula 1c condensed by sharing with any one of the ring B and the benzene ring substituted with R 7 to R 10 by sharing the side connecting ** and ** with the other To condense.
  • X and Y are each independently NR ', SiR'R ", CR'R” or S.
  • R ′, R ′′ may be each independently represented by one of the following chemical formulas, and in the following chemical formulas, Z 1 to Z 23 may be each independently C or N.
  • Ar 1 is hydrogen, deuterium, tritium, halogen group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkyl Thiophene group, C 6 -C 20 arylamine group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 3 -C 20 cyclo alkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted with a heavy hydrogen aryl, C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron group, a heteroaryl of germanium group, a C 2 ⁇ C 20 C 6 ⁇ C 60 aryl group unsubstituted or substituted with a substituent selected from the group consisting of a cyclic group; Hydrogen, deuterium
  • R One , R 2 are each independently hydrogen, deuterium, tritium, halogen, C 2 ⁇ C 20 Alkenyl, C One ⁇ C 20 Alkoxy group, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 7 ⁇ C 20 Arylalkyl group, C 8 ⁇ C 20 Aryl alkenyl group, C 2 ⁇ C 20 C unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group One ⁇ C 50 Alkyl groups; or Hydrogen, deuterium, tritium, halogen, C One ⁇ C 20 Alkyl group, C One ⁇ C 20 Alkoxy group, C One ⁇ C 20 Alkylamine groups, C One ⁇ C 20 Alkylthiophene groups, C 6 ⁇ C 20 Arylamine group, C 6 ⁇ C 20 Arylthiophene group, C 2 ⁇
  • R 3 to R 11 are each independently hydrogen; heavy hydrogen; Tritium; Halogen group;
  • n is an integer of 1 or 2
  • m is an integer of 0-5.
  • the compound represented by Chemical Formula 1 may be one of the following Chemical Formulas 2 to 8.
  • A, B, R ′, R ′′, R 1 to R 11 , n, m are the same as A, B, R ′, R ′′, R 1 to R 11 , n, m defined in Chemical Formula 1.
  • the compound represented by Formula 1 may be one of the following compounds 1-1 to 7-20.
  • Sub 1-1 examples are as follows, but are not limited thereto, and their FD-MS are shown in Table 1 below.
  • Sub 1-2, Sub 1-3, Pd (PPh 3 ) 4 and K 2 CO 3 obtained were dissolved in toluene 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 and filtered under reduced pressure, and then the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired product.
  • Sub 6 examples are as follows, but are not limited thereto, and FD-MS of Sub 6-5 to Sub 6-14 is shown in Table 3 below.
  • Sub 2-5, Sub 2-6, Pd (PPh 3 ) 4 and K 2 CO 3 obtained were dissolved in toluene 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 and filtered under reduced pressure, and then the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired product.
  • Sub 3-2 examples are as follows, but are not limited thereto, and their FD-MS are shown in Table 5 below.
  • Sub 4-4, Sub 2-6, Pd (PPh 3 ) 4 , and K 2 CO 3 obtained were dissolved in toluene 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 and filtered under reduced pressure, and then the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired product.
  • Sub 5-1 is dissolved in acetic acid, and hydrogen peroxide dissolved in acetic acid is dropped dropwise and stirred at room temperature for 6 hours. Upon completion of the reaction, acetic acid was removed using a decompression device and separated using column chromatography to obtain the desired Sub 5-2.
  • Sub 5-2 examples are as follows, but are not limited thereto, and their FD-MSs are shown in Table 7 below.
  • An organic electroluminescent device was manufactured according to a conventional method using a compound obtained through synthesis as a light emitting host material or a light emitting auxiliary layer material of the light emitting layer.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) film was first vacuum deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm. Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 30 nm as a hole transport compound on the film by a hole transport layer. Formed.
  • CuPc copper phthalocyanine
  • the compounds of the present invention are deposited as a phosphorescent host material to form a light emitting layer, and then tris (2-phenylpyridine) iridium as a phosphorescent Ir metal complex dopant. (Hereinafter abbreviated as Ir (ppy) 3 ) was added. At this time, the concentration of Ir (ppy) 3 in the light emitting layer was added at 5% by weight to form a light emitting layer by vacuum deposition at a thickness of 30 nm.
  • BAlq (1,1′-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq Tris (8-quinolinol) aluminum
  • Alq 3 Tris (8-quinolinol) aluminum
  • LiF which is an alkali metal halide
  • Al was deposited to a thickness of 150 nm to prepare an organic electroluminescent device by using the Al / LiF as a cathode.
  • An organic electroluminescent device was manufactured in the same manner as Experimental Example I, except that Comparative Compound 1 (CBP) was used instead of the compound of the present invention as a light emitting host material.
  • CBP Comparative Compound 1
  • An organic electroluminescent device was manufactured in the same manner as Experimental Example I, except that Comparative Compound 2 was used instead of the compound of the present invention as a light emitting host material.
  • An organic electroluminescent device was manufactured in the same manner as Experimental Example I, except that Comparative Compound 3 was used instead of the compound of the present invention as a light emitting host material.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention is used as a light emitting layer material and the driving voltage is higher than that of Comparative Example 1 (CPB), Comparative Example 2 and Comparative Example 3. It is low, the luminous efficiency is not only improved, but also the color purity and life are remarkably improved. In other words, it can be seen that the compounds of the present invention significantly improve efficiency and lifespan than Comparative Compounds 1, 2, and 3 having CBP, carbazole, or five-membered heterocycle as a core.
  • the compound according to the present invention is not only an organic electroluminescent device (OLED) but also a display device, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device, and the like. May also be used.
  • OPC organic photoconductor
  • organic TFT organic transistor
  • a monochromatic or white illumination device and the like. May also be used.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a hole injection layer, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, the same effect can be obtained.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) film was first vacuum deposited as a hole injection layer to form a 40 nm thick. Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to a thickness of 20 nm as a hole transport compound on the membrane to form a hole transport layer. Formed.
  • CuPc copper phthalocyanine
  • the compounds of the present invention as luminescent auxiliary layer materials (compounds 1-71, 1-73, 1-75, 2-31, 3-6, 3-27, 4-31, 5-13, 6-15 and 7).
  • One of -20) was vacuum deposited to a thickness of 20 nm to form a light emission auxiliary layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium] as a host.
  • the light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer by doping at 95: 5 weight.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • BAlq the electron transport layer Tris (8-quinolinol) aluminum
  • Alq3 the electron transport layer Tris (8-quinolinol) aluminum
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, but the emission auxiliary layer was omitted. That is, the organic electroluminescent device was manufactured by the same method as Experimental Example II except that the light emitting auxiliary layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound 3 was used to form a light-emitting auxiliary layer instead of the compound of the present invention.
  • Example II to the organic electroluminescent elements of Example (368) to Example (377), Comparative Example 4 and Comparative Example 5 prepared as described above by applying a forward bias DC voltage PR- Photoresearch (PR)
  • PR PR- Photoresearch
  • the electroluminescence (EL) characteristics were measured at 650, and the T90 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 300 cd / m2.
  • Example II The driving voltage, current density, luminance, luminous efficiency, lifetime and color purity of the organic electroluminescent device manufactured according to Example (368) to Example (377), Comparative Example 4 and Comparative Example 5 of the present invention. The measurement results are shown in Table 10 below.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention is used as a light emitting auxiliary layer material, Comparative Example 4, Comparative Compound 3, the light emitting auxiliary layer is not used, Compared with Comparative Example 5 used as the layer material, the driving voltage was lower, the luminous efficiency was improved, and the color purity and life were significantly improved. This is because, when the compound of the present invention is used alone as a light emitting auxiliary layer, it has a high T1 energy level and improves the low voltage, high luminous efficiency and device life of the organic electroluminescent device due to the deep HOMO energy level.
  • the compound according to the present invention is not only an organic electroluminescent device (OLED) but also a display device, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochrome or white lighting device May also be used.
  • OPC organic photoconductor
  • organic TFT organic transistor
  • a monochrome or white lighting device May also be used.
  • the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a hole injection layer, a light emitting layer, an electron injection layer, an electron transport layer, the same effect can be obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Photovoltaic Devices (AREA)

Abstract

La présente invention concerne un nouveau composé, un élément électronique organique l'utilisant, et un dispositif électronique associé. Selon la présente invention, l'efficacité lumineuse, la pureté de la couleur, et la durée de vie de l'élément peuvent être améliorées, et la tension nécessaire pour activer l'élément peut être abaissée.
PCT/KR2013/006087 2012-07-13 2013-07-09 Composé, élément électronique organique l'utilisant et dispositif électronique associé WO2014010910A1 (fr)

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WO2018097937A1 (fr) * 2016-11-23 2018-05-31 E. I. Du Pont De Nemours And Company Composés électroactifs
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