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WO2013191404A1 - Composé, élément électronique organique l'utilisant, et dispositif électronique à base de celui-ci - Google Patents

Composé, élément électronique organique l'utilisant, et dispositif électronique à base de celui-ci Download PDF

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WO2013191404A1
WO2013191404A1 PCT/KR2013/005098 KR2013005098W WO2013191404A1 WO 2013191404 A1 WO2013191404 A1 WO 2013191404A1 KR 2013005098 W KR2013005098 W KR 2013005098W WO 2013191404 A1 WO2013191404 A1 WO 2013191404A1
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substituted
aryl
unsubstituted
deuterium
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Korean (ko)
Inventor
박정철
문성윤
이범성
김기원
박정근
지희선
김혜령
강문성
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Duksan Hi Metal Co Ltd
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Duksan Hi Metal Co Ltd
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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 in which electrical energy is converted 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 electrical 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.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • 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 device has not been made sufficiently, and therefore, the development of new materials is still 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 (1).
  • the present invention provides an organic electronic device using the compound represented by Formula 1 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 includes 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
  • 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
  • the organic material layer according to the present invention can be formed by various methods, and the scope of the present invention is not limited by the method of forming the same.
  • 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).
  • Ar One And Ar 2 are each independently hydrogen, deuterium, tritium, halogen, amino, nitrile, nitro, C One ⁇ C 20 Alkyl group, C One ⁇ C 20 Alkoxy group, C One ⁇ C 20 Alkylamine groups, C 6 ⁇ C 60 Arylamine group, C One ⁇ C 20 Alkylthiophene groups, C 6 ⁇ C 20 Arylthiophene group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 3 ⁇ C 20 Cycloalkyl group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 60 Aryl group, C 8 ⁇ C 20 Aryl alkenyl group, silane group, boron group, germanium group and C 2 ⁇ C 60 C unsubstituted or substituted with a substituent selected from the group consisting of heterocyclic groups 6 ⁇ C 60 Aryl group; Hydrogen, deuterium, tritium, halogen, C One
  • R One To R 12 Each independently of one another is hydrogen; heavy hydrogen; Tritium; Hydrogen, deuterium, tritium, halogen, C One ⁇ C 60 Alkyl group, C One ⁇ C 60 Alkoxy group, C One ⁇ C 60 Alkylamine groups, C 5 ⁇ C 60 Arylamine group, C One ⁇ C 60 Alkylthiophene groups, C 6 ⁇ C 60 Aryl thiophene group, C 2 ⁇ C 60 Alkenyl, C 2 ⁇ C 60 Alkynyl, C 3 ⁇ C 60 Cycloalkyl group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 60 Aryl group, C 8 ⁇ C 60 Aryl alkenyl group, substituted or unsubstituted silane group, substituted or unsubstituted boron group, substituted or unsubstituted germanium group and substituted or unsubstituted C 2 ⁇ C 60 Unsubstituted or substituted with a
  • R 6 and R 7 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 may each combine with neighboring groups to form a saturated or unsaturated ring.
  • the compound represented by Chemical Formula 1 may be one of the following Chemical Formulas (2) to (6).
  • the compound represented by Formula 1 may be one of the following compounds P1-1 to P6-46.
  • Sub C can be prepared by the following scheme.
  • Sub C compounds synthesized using the synthesis examples are as follows, but are not limited thereto, and their FD-MS are shown in Table 1 below.
  • Compound S 1 can be synthesized by the reaction route of Scheme 6 below.
  • Compound S 2 can be synthesized by the reaction route of Scheme 7 below.
  • Compound S 3 may be synthesized by the reaction pathway of Scheme 8 below.
  • Compound S 4 may be synthesized by the reaction pathway of Scheme 9 below.
  • Compound S 5 may be synthesized by the reaction pathway of Scheme 10 below.
  • the compounds synthesized using the synthesis method of S 1 to S 5 are as follows, which is illustrative but not limited thereto.
  • B (pin) is to be.
  • the S-2-1 generation step in Scheme 7 and the S-3-1 generation step in Scheme 8 are based on the Suzuki cross-coupilng reaction, the C-1 generation step in Scheme 2, and the C-2 generation step in Scheme 3 , C3 generation step in Scheme 4, C4 generation step in Scheme 5, S-1-2 generation step in Scheme 6, S-2-3 generation step in Scheme 7, S-3-3 generation step in Scheme 8, Scheme 9
  • S-4-3 generation step, S-5-2 generation step in Scheme 10, etc. are all based on the Buchwald-Hartwig cross coupling reaction
  • the S 3 generation step, the S 4 generation step in Scheme 9, and the S 5 generation step in Scheme 10 are all based on the Miyaura boration reaction. Therefore, it will be appreciated by those skilled in the art that the reaction will proceed with the same mechanism with respect to the compound to which other substituents are attached in addition to the substituents exemplified.
  • the hole transport layer by vacuum depositing 2-TNATA on the ITO layer (anode) formed on the organic substrate to form a hole injection layer with a thickness of 60nm, the hole transport layer by vacuum depositing the compound according to the present invention to a thickness of 20nm on the hole injection layer Formed.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium] as the dopant material were 9:
  • the light emitting layer was deposited by doping to a thickness of 30nm with a weight ratio of 1.
  • An organic light emitting display device was manufactured in the same manner as in [Example 8], except that Comparative Compound 1 was used instead of the compound of the present invention when forming the hole transport layer.
  • An organic light emitting display device was manufactured in the same manner as in [Example 8], except that Comparative Compound 2 was used instead of the compound of the present invention when forming the hole transport layer.
  • An organic light emitting display device was manufactured in the same manner as in [Example 8], except that Comparative Compound 3 was used instead of the compound of the present invention when forming the hole transport layer.
  • Example 8 (Example (1) to Example 272) and [Comparative Example 1] to [Comparative Example 3] (Comparative Example (1) to Comparative Example (3) of the present invention prepared as described above
  • the electroluminescent (EL) characteristics were measured with a PR-650 photoresearch company by applying a forward bias DC voltage to the organic electroluminescent device of The instrument was measured for T90 life.
  • EL electroluminescent
  • Example 8 Examples (1) to (272)
  • Example 1 to [Comparative Example 3] (Comparative Example (1) to Comparative Example (3)) of the present invention.
  • the driving voltage, current density, luminance, luminous efficiency, and lifetime of the organic light emitting diodes were measured, as shown in Table 4 below.
  • a copper phthalocyanine (hereinafter abbreviated as CuPc) is vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 40 nm, and then the compound P3 of the present invention on the hole injection layer.
  • -27 was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • the compound of the present invention was vacuum deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) iridium
  • the light emitting layer was doped to a thickness of 30 nm with a weight ratio of 95: 5.
  • the reason why the compound P3-27 of the present invention is used as the hole transport layer material is because, as shown in Table 4, the driving voltage of the organic electric element to which the compound P3-27 is applied is low, the luminous efficiency is high, and the lifetime is also high. to be.
  • An organic light emitting display device was manufactured in the same manner as in [Example 9], except that the light emitting auxiliary layer was omitted. That is, an organic light emitting display device was manufactured in the same manner as in [Example 9], except that the light emitting auxiliary layer was not formed.
  • An organic light emitting display device was manufactured in the same manner as in [Example 9], except that the Comparative Compound 3 was used to form the emission auxiliary layer instead of the compound of the present invention.
  • Example 9 (Examples 273 to 544), [Comparative Example 4] (Comparative Example (4)), and [Comparative Example 5] (Comparative Example (5) of the present invention prepared as described above.
  • the electroluminescence (EL) characteristics of the organic electroluminescent elements of)) were applied to the PR-650 photoresearch company by applying a forward bias DC voltage.
  • the T95 life was measured with a life measuring instrument.
  • the driving voltage, current density, luminance, light emission efficiency, and lifetime of the organic light emitting diodes were measured as shown in Table 5 below.
  • 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 lighting element, etc. 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)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/KR2013/005098 2012-06-22 2013-06-11 Composé, élément électronique organique l'utilisant, et dispositif électronique à base de celui-ci Ceased WO2013191404A1 (fr)

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