WO2014129764A1 - Composé pour élément électronique organique, élément électronique organique employant le composé et dispositif électronique avec celui-ci - Google Patents

Composé pour élément électronique organique, élément électronique organique employant le composé et dispositif électronique avec celui-ci Download PDF

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WO2014129764A1
WO2014129764A1 PCT/KR2014/001096 KR2014001096W WO2014129764A1 WO 2014129764 A1 WO2014129764 A1 WO 2014129764A1 KR 2014001096 W KR2014001096 W KR 2014001096W WO 2014129764 A1 WO2014129764 A1 WO 2014129764A1
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박용욱
최연희
이범성
박정철
지희선
강문선
김석현
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덕산하이메탈(주)
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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.
  • Materials used as the organic material layer in the organic electric device 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.
  • Efficiency, lifespan, and driving voltage are related to each other, and as efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases. It shows a tendency to increase lifespan.
  • a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission assist according to each light emitting layer (R, G, B) It is time to develop the floor.
  • 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 OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.
  • the materials 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, a light emitting auxiliary layer material, etc. Supported by the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials continues to be required, and in particular, the development of material combinations of the light emitting auxiliary layer and the hole transport layer is urgently 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 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, a spirobifluorene 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. And not only a single ring, but also multiple rings, and adjacent groups may be formed by bonding.
  • heterocycloalkyl include one or more heteroatoms, unless otherwise indicated, have a carbon number from 2 to 60, include not only a single ring but also multiple rings; 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.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or 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.
  • 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 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ arylalkenyl group, a silane group, a boron of C 20 of Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of,
  • 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 electric 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 Preferably, the compound of the present invention may be used as at least one of the host material, the hole transport layer material and the light emitting auxiliary layer material of the light emitting layer.
  • the band gap, electrical characteristics, interface characteristics, etc. may vary depending on which substituents are bonded at which positions, so the selection of the cores and the combination of sub-substituents bound thereto are very good.
  • long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.
  • a light emitting auxiliary layer be formed between the hole transport layer and the light emitting layer, and the light emitting layer R, G, and B may be formed according to each other. It is time to develop another light emitting auxiliary layer. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.
  • the compound represented by the formula (1) as a hole transport layer material and the light emitting auxiliary layer material, the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interfacial properties, etc.) between the organic layer By optimizing it 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 conductive metal oxide or an alloy thereof on the substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer (on the substrate) 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 may be formed by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. 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, an organic solar cell, an organic photoconductor, an organic transistor, a monochromatic or white illumination device.
  • Another embodiment of the present invention may include an electronic device including a display device including the organic electric element of the present invention described above, and 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.
  • Ar 1 and Ar 2 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl groups; C 1 ⁇ C 50 Alkyl group; And C 6 ⁇ C 30 An aryloxy group; may be selected from the group consisting of.
  • n and n are each an integer of 1-4.
  • n is 2 or more
  • a plurality of R 1 may be the same as or different from each other
  • m is 2 or more
  • a plurality of R 2 may be the same or different from each other.
  • R 1 and R 2 are, independently from each other, hydrogen; heavy hydrogen; Tritium; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl groups; C 2 -C 60 heterocyclic group containing at least one hetero atom of O, N, S, Si and P; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; -LN (Ar 4 ) (Ar 5 ); C 1 -C 30 alkoxyl group; And C 6 ⁇ C 30 An aryloxy group; may be selected from the group consisting of.
  • R 1 and R 2 may combine with each other to form at least one ring.
  • the group that does not form a ring may be as defined above.
  • the scope of the present invention is not limited by the substituents and which reactions form the ring.
  • the ring is a known reaction (Heck reaction or Chem. Eur. J. 2009, 15, 742, Molecules. 2008, 13, 3236-3245, J. Am. Chem. Soc. 2008, 130, 472-480, Tetrahedron Letters. 1997, 38, 4761-4764 and the like).
  • the ring formed by adjoining adjacent groups to each other may be a single ring or a heterocyclic ring containing at least one heterocyclic ring or multiple rings, as well as a fused form of an aromatic ring and an aliphatic ring, or an aromatic formed
  • the nuclear carbon number of the ring may be 6 to 60.
  • adjacent groups may combine with each other to form a hetero ring such as thiophene, furan, pyridine, indole, quinoline, etc., wherein the carbon number may be 2 to 60.
  • the ring may be fused to each other, a plurality of rings may not be fused to each other, or a ring in which the fused and non-fused forms are mixed.
  • compounds 1-152 to 1-204 of the present invention are examples of the case where R 1 and / or R 2 form a ring.
  • L in -LN (Ar 4 ) (Ar 5 ) is a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And divalent aliphatic hydrocarbon group; may be selected from the group consisting of.
  • the arylene group, fluorenylene group, heterocyclic group and aliphatic hydrocarbon group are each nitro group, cyano group, halogen group, C 1 ⁇ C 20 alkyl group, C 6 ⁇ C 20 aryl group, C 2 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group, a C 1 ⁇ C 20 alkoxyl group and an amino group.
  • Ar 4 And Ar 5 It is a C 2 ⁇ C 60 heterocyclic group containing at least one hetero atom of O, N, S, Si and P independently of each other; C 6 ⁇ C 60 Aryl group; C 2 ⁇ C 20 Alkenyl group; C 1 ⁇ C 50 Alkyl group; And fluorenyl group; may be selected from the group consisting of.
  • R 1 , R 2 , Ar 1 , Ar 2 , Ar 4, and Ar 5 may be further substituted with other substituents.
  • R 1 , R 2 , Ar 1 , Ar 2 , Ar 4, and Ar 5 are aryl groups, this is deuterium, halogen, silane group, boron group, germanium group, cyano group, nitro group, C 1 ⁇ C 20 alkyl Cthio, C 1 ⁇ C 20 Alkoxyl, C 1 ⁇ C 20 Alkyl, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 6 ⁇ C 20 Aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 2 ⁇ C 20 heterocyclic group, C 3 ⁇ C 20 cycloalkyl group, C 7 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C 8 to C 20 .
  • R 1 , R 2 , Ar 4 and Ar 5 are heterocyclic groups, it is deuterium, halogen, silane group, cyano group, nitro group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkyl group, C of 2 ⁇ C 20 alkenyl group (alkenyl), C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 2 ⁇ C heterocyclic group of 20, cycloalkyl of C 3 ⁇ C 20 Alkyl group, C 7 ⁇ C 20 It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C 8 to C 20 .
  • R 1 , R 2 , Ar 1 , Ar 2 , Ar 4, and Ar 5 are fluorenyl groups, this is deuterium, halogen, silane group, cyano group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 alkenyl group (alkenyl), C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, from the group consisting of a cycloalkyl group of C 2 ⁇ C 20 heterocyclic group and C 3 ⁇ C 20 of It may be substituted with one or more substituents selected.
  • R 1 , R 2 , Ar 1 , Ar 2 , Ar 4, and Ar 5 are alkyl groups
  • this is halogen, silane group, boron group, cyano group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20 of alkenyl groups (alkenyl), C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a heterocyclic group of C 2 ⁇ C 20, C 7 ⁇ C 20 of It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C 8 to C 20 .
  • R 1 , R 2 , Ar 4 and Ar 5 are alkenyl groups, it is deuterium, halogen, silane group, cyano group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkyl group, C 2 ⁇ C 20, an alkenyl group (alkenyl), a heterocyclic group of C 6 ⁇ C 20 aryl group, a C 6 ⁇ C 20 aryl group, C 2 ⁇ C 20 substituted by deuterium, C 3 ⁇ C 20 cycloalkyl group, C 7 to C 20 It may be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C 8 to C 20 .
  • R 1 and R 2 is an alkoxy group, which is heavy hydrogen, a halogen, a silane group, a C 1 ⁇ C 20 alkyl group, C 6 ⁇ C 20 aryl group, a C 6 ⁇ C 20 substituted with a heavy hydrogen of the aryl group, It may be substituted with one or more substituents selected from the group consisting of C 2 ⁇ C 20 heterocyclic group and C 3 ⁇ C 20 cycloalkyl group.
  • R 1 , R 2 , Ar 1, and Ar 2 are aryloxy groups, they are deuterium, silane groups, cyano groups, C 1 ⁇ C 20 alkyl groups, C 6 ⁇ C 20 aryl groups, C 6 substituted with deuterium It may be substituted with one or more substituents selected from the group consisting of an aryl group of ⁇ C 20 , a heterocyclic group of C 2 ⁇ C 20 and a cycloalkyl group of C 3 ⁇ C 20 .
  • the carbon number may be 6 to 60, preferably 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms,
  • heterocyclic group has 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably a hetero ring having 2 to 20 carbon atoms,
  • the carbon number may be 6 to 60, preferably 6 to 30 carbon atoms, more preferably an arylene group having 6 to 20 carbon atoms,
  • the carbon number is 1 to 50, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably an alkyl group having 1 to 10 carbon atoms.
  • Ar 1 and Ar 2 may be any one of the following groups independently of each other.
  • the compound represented by Formula 1 may be represented by one of the following formula.
  • Ar 1 and Ar 2 may be defined the same as defined in Formula 1
  • R 3 and R 4 may be defined the same as the definition of R 1 and R 2 in Formula 1. .
  • Formula 9 and Formula 10 are integers of 1 to 4
  • p in Formulas 2 to 4 and 6 to 8 is an integer of 1 to 6
  • q in Formulas 6 to 8 Is an integer of 1 to 6.
  • formula represented by Formula 1 may be one of the following compounds.
  • the compound according to the present invention (Final Products) is prepared by reacting Sub 2 and Sub 3 as in Scheme 1, but is not limited thereto.
  • Sub 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Sub 1-I-1 (101.07 g, 319.5 mmol) obtained in the above synthesis was dissolved in MeOH in a round bottom flask, and the temperature of the reactant was lowered to 0 ° C., and conc. hydrochloric acid was slowly added dropwise for 15 minutes.
  • Sodium nitrite (22.04 g, 319.5 mmol) solution was slowly added dropwise at 0 ° C. and stirred for 10 minutes, followed by potassium thiocyanate (99.34 g, 1022.3 mmol) and iron (III) chloride (36.27 g, 223.6 mmol) An aqueous solution was added and stirred at room temperature.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 7, but is not limited thereto.
  • Sub 2-II-8 (7.53 g, 45 mmol) in Sub 1-7 (17.42 g, 58.5 mmol), Na 2 SO 4 (6.4 g, 45 mmol), K 2 CO 3 (6.22 g, 45 mmol), Cu (0.86 g, 13.5 mmol) and nitrobenzene were obtained using the Sub 2-4 synthesis method to give 11.06 g (yield: 64%) of the product.
  • Sub 2-II-13 (9.27 g, 38.1 mmol) in Sub 1-1 (14.74 g, 49.5 mmol), Na 2 SO 4 (5.41 g, 38.1 mmol), K 2 CO 3 (5.27 g, 38.1 mmol), Cu (0.73 g, 11.4 mmol) and nitrobenzene were obtained using the Sub 2-4 synthesis method to obtain 10.87 g (yield: 62%) of the product.
  • Sub 2-II-25 (15.36 g, 48.1 mmol) in Sub 1-1 (18.61 g, 62.5 mmol), Na 2 SO 4 (6.83 g, 48.1 mmol), K 2 CO 3 (6.65 g, 48.1 mmol), Cu (0.92 g, 14.4 mmol) and nitrobenzene were obtained using the Sub 2-4 synthesis method to give 15.21 g (yield: 59%) of the product.
  • Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 16 below.
  • Sub 3-17 (7.49 g, 23.3 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, and then Sub 2-4 (10.74 g, 28 mmol), Pd 2 (dba) 3 (0.64 g, 0.7 mmol) , 50% P ( t -Bu) 3 (0.9 ml, 1.9 mmol), NaO t -Bu (6.72 g, 69.9 mmol) was added and stirred at 100 ° C.
  • reaction with starting material-> Sub 1-I in Scheme 2 and the reaction with starting material-> Sub 2-I in Scheme 7 are all based on the Suzuki cross-coupling reaction
  • Sub 1-I in Scheme 2 -> Sub 1-II reaction is based on Diazotization-Thiocyanation reaction
  • Sub 1-II-> Sub 1-III reaction in Scheme 2 is based on Reduction reaction
  • Sub 1-III-> Sub 1 reaction in Scheme 2 It is based on the MW (Microwave) -assisted cyclization reaction.
  • Sub-I-> Sub 2-II reaction in Scheme 7 is then based on PPh 3 -mediated reductive cyclization reaction, and Sub 2-II-> Sub 2 reaction in Scheme 7 is based on Ullmann reaction, starting from Scheme 16 Substance-> Sub 3,
  • Product Synthesis Schemes (Scheme 22-29) are based on the Buchwald-Hartwig cross coupling reaction, which will proceed even if the substituents are not specified.
  • 2-TNATA 4,4 ', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 2,4'-N, N'-dicarbazole-biphenyl
  • the light emitting layer was deposited to a thickness of 30 nm with a weight ratio of 95: 5.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • LiF which is an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of Compounds 1-2 to 1-204 of the present invention shown in Table 4 was used instead of Compound 1-1 of the present invention as a hole transport layer material. Prepared.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used instead of Compound 1-1 of the present invention as a hole 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 1-1 of the present invention as a hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 was used instead of Compound 1-1 of the present invention as a hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 4 was used instead of Compound 1-1 of the present invention as a hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 5 was used instead of Compound 1-1 of the present invention as a hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 6 was used instead of Compound 1-1 of the present invention as a hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 7 was used instead of Compound 1-1 of the present invention as a hole 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 204 and Comparative Examples 1 to 7 of the present invention The T90 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at a luminance of 300 cd / m 2. The measurement results are shown in Table 4 below.
  • Comparative Examples 1 to 7 using Example 1 to Example 204 and Comparative Compound 1 to Comparative Compound 7 using the compound according to the present invention as the hole transport layer material were used as the hole transport layer material.
  • the driving voltage is relatively low, the luminous efficiency is improved, and the life is significantly improved as compared with Comparative Examples 1 to 7.
  • Comparative Examples 2 to 7 in which the compound of the present invention and the linking group were different showed a tendency to show higher driving voltage, lower efficiency, and lower lifetime than the compound of the present invention.
  • the compound of the present invention wherein the linking group is dibenzothiophene has a relatively shorter conjugation length than Comparative Examples 2 to 7 in which one more phenyl group is connected to the dibenzothiophene. It has a band gap and a high T1 value, which makes it easier to block electrons from the light emitting layer.
  • the packing density of the compound of the present invention is better than Comparative Examples 2 to 7 has a fast hole mobility (hole mobility) is lowered the driving voltage, the thermal damage is reduced due to the low driving voltage Efficiency and lifetime are improved.
  • the band gap, electrical characteristics, and interfacial characteristics can be greatly changed depending on the type of linking group between carbazole and diarylamine. It can be seen that this can be a major factor in improving device performance.
  • Example 205 Green organic electroluminescent element (light emitting auxiliary layer)
  • the compound 1-52 of the present invention was vacuum deposited on the hole injection layer to a thickness of 20 nm to form a hole transport layer. Formed.
  • Compound 1-49 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer.
  • a light emitting layer was deposited on the light emitting auxiliary layer by doping CBP as a host material and Ir (ppy) 3 as a dopant material in a 95: 5 weight ratio.
  • BAlq was vacuum-deposited on the light emitting layer to a thickness of 10 nm to form a holdoff layer, and an electron transport layer was formed on the holdoff layer to form 40 nm thick of Alq 3 .
  • LiF which is an alkali metal halide
  • LiF was deposited to a thickness of 0.2 nm to form an electron injection layer
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • An organic electroluminescent device was manufactured in the same manner as in Example 205, except that the light emitting auxiliary layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 205, except that Comparative Compound 2 was used instead of Compound 1-49 of the present invention as a light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 205, except that Comparative Compound 3 was used instead of Compound 1-49 of the present invention as a light-emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 205, except that Comparative Compound 4 was used instead of Compound 1-49 of the present invention as a light-emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 205, except that Comparative Compound 5 was used instead of Compound 1-49 of the present invention.
  • An organic electroluminescent device was manufactured in the same manner as in Example 205, except that Comparative Compound 6 was used instead of Compound 1-49 of the present invention as a light-emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 205, except that Comparative Compound 7 was used instead of Compound 1-49 of the present invention as a light-emitting auxiliary layer material.
  • Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples 205 to 299 and Comparative Examples 8 to 14 of the present invention The T90 lifetime was measured using a life-time measuring instrument manufactured by McScience Inc. at 300 cd / m 2 reference luminance. The measurement results are shown in Table 5 below.

Abstract

La présente invention concerne un nouveau composé qui améliore l'efficacité d'émission lumineuse, la stabilité et la durée de vie d'un élément, un élément électronique organique l'employant et un dispositif électronique avec celui-ci.
PCT/KR2014/001096 2013-02-19 2014-02-10 Composé pour élément électronique organique, élément électronique organique employant le composé et dispositif électronique avec celui-ci WO2014129764A1 (fr)

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WO2019101719A1 (fr) * 2017-11-23 2019-05-31 Merck Patent Gmbh Matériaux pour dispositifs électroniques
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KR102557030B1 (ko) * 2020-08-25 2023-07-19 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
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TWI815831B (zh) * 2017-11-23 2023-09-21 德商麥克專利有限公司 用於電子裝置之材料
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US11832513B2 (en) 2017-11-23 2023-11-28 Merck Patent Gmbh Materials for electronic devices
CN113135903A (zh) * 2020-01-17 2021-07-20 江苏三月科技股份有限公司 一种芳香族二苯并呋喃类衍生物及其应用
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