WO2016060463A2 - Nouveau composé et élément électroluminescent organique comprenant le nouveau composé - Google Patents

Nouveau composé et élément électroluminescent organique comprenant le nouveau composé Download PDF

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WO2016060463A2
WO2016060463A2 PCT/KR2015/010829 KR2015010829W WO2016060463A2 WO 2016060463 A2 WO2016060463 A2 WO 2016060463A2 KR 2015010829 W KR2015010829 W KR 2015010829W WO 2016060463 A2 WO2016060463 A2 WO 2016060463A2
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group
halogen
nitrile
deuterium
substituted
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PCT/KR2015/010829
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WO2016060463A3 (fr
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함호완
김봉기
김성훈
안현철
배유진
김동준
민병철
조지은
박민수
이형진
임동환
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주식회사 동진쎄미켐
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Priority claimed from KR1020150143227A external-priority patent/KR20160045019A/ko
Publication of WO2016060463A2 publication Critical patent/WO2016060463A2/fr
Publication of WO2016060463A3 publication Critical patent/WO2016060463A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

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  • the present invention relates to a novel compound and an organic light emitting device comprising the same, in particular, when applied to the organic light emitting device for fluorescence and phosphorescence excellent hole injection and hole transfer characteristics, at the same time excellent electron blocking characteristics, high triplet energy And a novel compound capable of realizing high Tg and having low driving voltage, low power consumption, high efficiency and long life.
  • an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices.
  • LCD liquid crystal display
  • the material used as the organic material layer in the organic light emitting device can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function.
  • the light emitting material may be classified into a polymer and a low molecule according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. According to the emission color can be divided into blue, green, red light emitting material and yellow and orange light emitting material required to implement a better natural color.
  • a host / dopant system may be used as a light emitting material.
  • the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light.
  • the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.
  • the present invention is excellent in the hole injection and hole transfer characteristics when applied to the organic light emitting device, and at the same time excellent in the electron blocking characteristics, high triplet energy and high Tg can be realized, low driving
  • An object of the present invention is to provide a novel compound which can have a voltage, low power consumption, high efficiency and long life, and is particularly suitable for an organic light emitting device for blue and phosphorescence.
  • the present invention also includes the novel compound, which has excellent hole injection and hole transport characteristics, and at the same time, excellent electron blocking characteristics, and at the same time, can realize high triplet energy and high Tg, and low driving voltage, low power consumption, and high efficiency. And it is an object to provide an organic light emitting device that can have a long life.
  • Ar is each independently a C 6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, nitro group; Or a C 2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group,
  • R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-50 aryl group which is optionally substitute
  • the present invention also provides an organic light emitting device including one or more organic material layers containing a compound represented by Chemical Formula 1 between a first electrode, a second electrode, and two electrodes.
  • the compound of the present invention has excellent hole injection and hole transport characteristics when applied to the organic light emitting device for blue and phosphorescence, at the same time excellent in the electron blocking characteristics, high triplet energy and high Tg, low drive voltage, low consumption It can have power, high efficiency and long life.
  • FIG. 1 schematically illustrates a cross section of an OLED according to an embodiment of the invention.
  • the compound of the present invention is characterized by represented by the following formula (1).
  • Ar is each independently a C 6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, nitro group; Or a C 2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group,
  • R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-50 aryl group which is optionally substitute
  • the compound represented by Chemical Formula 1 may be one of the compounds represented by the following Chemical Formulas 1-1 to 1-7.
  • N, p, q and r in the formulas are each independently an integer selected from 1 to 3,
  • Ar 1 and Ar 2 are each independently a C 6-50 aryl group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile, or nitro groups; Or a C 2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group,
  • R 1 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , Ar 1 , Ar 2 may form an adjacent group or a ring with each other.
  • the compound of formula 1 according to the present invention has excellent hole injection and hole transport characteristics when applied to an organic light emitting device, and at the same time excellent in electron blocking characteristics, high triplet energy and high Tg, low driving voltage, low consumption It can have power, high efficiency and long life.
  • the compounds represented by Chemical Formulas 1-1 and 1-2 may exhibit more excellent device characteristics in fluorescent and red phosphorescent organic light emitting diodes, and the compounds represented by Chemical Formula 1-7 may be further represented in green phosphorescent organic light emitting diodes It can exhibit excellent device characteristics.
  • the present invention also provides an organic light emitting device comprising the compound represented by Chemical Formula 1 in an organic material layer. Specifically, it will be included as a hole injection material, a hole transport material, a light emitting auxiliary material, wherein the compound of the present invention may be used alone or in combination with a known organic light emitting compound. More specifically, the organic light emitting device is preferably a fluorescent, red phosphorescent, green phosphorescent organic light emitting device.
  • the organic light emitting device of the present invention includes one or more organic material layers including the compound represented by Chemical Formula 1, and the method of manufacturing the organic light emitting device is as follows.
  • the organic light emitting diode includes a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, an emission layer (EML), and an electron transport layer between a first electrode (anode) and a second electrode (cathod).
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emission auxiliary layer
  • ETL electron injection layer
  • EIL electron injection layer
  • an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
  • the substrate may be a substrate used in a conventional organic light emitting device, it is particularly preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
  • the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
  • the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
  • the hole injection layer material may be formed on the anode electrode by a method such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB).
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and generally, a deposition temperature of 50-500 ° C., It can be suitably selected from a vacuum degree of 10 ⁇ 8 to 10 ⁇ 3 torr, a deposition rate of 0.01 to 100 kPa / sec, and a layer thickness of 10 kPa to 5 ⁇ m.
  • the hole injection layer material may be a compound represented by Formula 1 of the present invention, it may be used with a known material.
  • the known material is not particularly limited, and TCTA (4,4 ′, 4 ′′ -tri (N-carbazolyl) triphenyl, which is a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Pat. No.
  • the hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, or the like.
  • the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in the same condition range as the formation of the hole injection layer.
  • the hole transport material may be a compound represented by the formula (1) of the present invention, it may be used with a known material.
  • the known material is not particularly limited, and may be arbitrarily selected and used from conventional known materials used in the hole transport layer.
  • the hole transport layer material is carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Derivatives and the like can be used.
  • an auxiliary layer may be further included on the hole transport layer.
  • the auxiliary layer may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, cast, LB, or the like.
  • the auxiliary layer may be a compound represented by the formula (1) of the present invention, in this case, the hole transport layer is preferably used a compound represented by the formula (2).
  • Ar is each independently a C 6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, nitro group; Or a C 2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group,
  • R 1 , R 2 , R 3 , R 4 , and R 5 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-50 aryl group which is optionally substituted with deuter
  • the light emitting layer material may be formed on the hole transport layer or the auxiliary layer by a method such as vacuum deposition, spin coating, cast, LB, or the like.
  • a method such as vacuum deposition, spin coating, cast, LB, or the like.
  • the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition range as the formation of the hole injection layer.
  • the light emitting layer material may use a known compound as a host or dopant.
  • a fluorescent dopant may be IDE102 or IDE105 available from Idemitsu, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethycrylicene- 6,12-diamine) can be used as green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6- Difluorophenyl) -pyridinato-N, C2 '] picolinate), a red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).
  • Ir ppy
  • F2Irpic iridium (III) bis [4,6- Difluorophenyl) -pyridinato-N, C2 '] picolinate
  • the hole suppressing material when used with a phosphorescent dopant in the light emitting layer, to prevent the triplet exciton or hole from being diffused into the electron transport layer, the hole suppressing material (HBL) may be further laminated by vacuum deposition or spin coating.
  • the hole-suppressing material that can be used at this time is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used.
  • an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1) can be cited.
  • Oxy-2-methylquinolinolato) -aluminum biphenoxide), a phenanthrolines-based compound e.g., BCP (vasocuproin) from UDC
  • BCP vasocuproin
  • An electron transport layer is formed on the light emitting layer formed as described above, wherein the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like.
  • the electron transport layer material functions to stably transport electrons injected from the electron injection electrode, and the type thereof is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3). ), Or ET4 (6,6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine).
  • an electron injection layer (EIL) which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer material may be LiF, NaCl, CsF, Li 2 O, BaO, or the like. The substance of can be used.
  • the deposition conditions of the electron transport layer is different depending on the compound used, but can be generally selected in the same condition range as the formation of the hole injection layer.
  • an electron injection layer material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is good to form.
  • a cathode forming metal is formed on the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode.
  • the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
  • a transmissive cathode using ITO or IZO may be used to obtain the front light emitting device.
  • the organic light emitting device of the present invention is capable of not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device having a cathode structure, but also an organic light emitting device having various structures, and emits light as necessary. It is also possible to form one or two intermediate layers such as an auxiliary layer.
  • each organic material layer formed according to the present invention as described above can be adjusted according to the required degree, specifically 1 to 1,000 nm, more preferably 5 to 200 nm. Within this range, the effect of high efficiency, long life and high color purity is more excellent.
  • the present invention has an advantage that the organic material layer including the compound represented by Formula 1 has a uniform surface and excellent shape stability because the thickness of the organic material layer can be adjusted in molecular units.
  • the organic light emitting device of the present invention includes the compound represented by Chemical Formula 1, and has excellent hole injection and hole transport characteristics, and at the same time, excellent electron blocking characteristics, high triplet energy and high Tg, and low driving voltage. It has low power consumption, high efficiency and long life.
  • An organic light emitting device was manufactured according to the structure of FIG. 1.
  • the organic light emitting element is formed from the bottom of the anode (hole injection electrode 11) / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transfer layer 15 / cathode (electron injection electrode 16) It is laminated in order.
  • the substrate 10 may be a transparent glass substrate or a flexible plastic substrate when the organic light emitting diode is manufactured.
  • the hole injection electrode 11 is used as an anode for hole injection of the organic light emitting device.
  • a material having a low work function may be used to inject holes, and may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.
  • the hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of Examples and Comparative Examples used the following materials.
  • the cathode 16 for electron injection is formed on the electron injection layer 15.
  • Various metals may be used as the cathode. Specific examples include materials such as aluminum, gold, and silver.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After the distilled water is washed, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes using an oxygen plasma. Using an evaporator, a film was deposited with a hole injection layer HT01 600 ⁇ and a compound transport 1 with 250 ⁇ as the hole transport layer. Next, the light emitting layer was doped with BH01: BD01 5% to form 250 ⁇ . Next, ET01: Liq (1: 1) 300 ⁇ was formed into an electron transport layer, followed by LiF 10 ⁇ and aluminum (Al) 1000 ⁇ , which were encapsulated in a glove box to produce an organic light emitting device.
  • ITO indium tin oxide
  • a device was manufactured in the same manner as in Example 1, except that Compound 1 was used as the NPB as the hole transport layer.
  • a device was manufactured in the same manner as in Example 1, except that Compound 1 was used as Ref. 1 as the hole transport layer.
  • a device was manufactured in the same manner as in Example 1, except that Compound 1 was used as Ref. 2 as the hole transport layer.
  • Example 1 4.441 10 5.85 4.79 0.141 0.120 22
  • Example 2 4.352 10 5.85 4.71 0.141 0.117 27
  • Example 3 4.343 10 5.88 4.76 0.142 0.115 30
  • Example 4 4.221 10 5.97 4.94 0.139 0.112 32
  • Example 5 4.212 10 6.00 4.92 0.138 0.113 35
  • Example 6 4.203 10 6.04 4.94 0.140 0.113 35
  • Example 7 4.295 10 6.07 4.99 0.140 0.113 37
  • Example 8 4.157 10 6.70 5.69 0.140 0.111 50
  • Example 9 4.130 10 6.63 5.64 0.139 0.112 47
  • Example 10 4.104 10 6.70 5.64 0.141 0.112 49
  • Example 11 4.100 10 6.59 5.67 0.142 0.112 49
  • Example 12 4.110 10 6.60 5.69 0.141 0.113 48
  • Example 13 4.109 10 6.63 5.65 0.142 0.113 50
  • Example 14 4.241 10 6.11 4.97 0.141 0.114 32
  • Example 15 4.214 10 6.19 4.80 0.141 0.113 35
  • Example 16 4.4
  • the Examples evaluated by the hole transport layer of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Examples 1 to 3.
  • the structure in which the aryl group is substituted at the position of indole 3 as shown in Chemical Formulas 1-1 and 1-2 has better planarity of molecules than simultaneous substitution of indole 2 and indole 2,3, and excellent mobility of molecules in the thin film. It can be seen that the efficiency and device life are significantly improved due to the excellent increase and chemical stability.
  • the linking group of Formula 1-6, indole, and arylamine is a phenyl moiety
  • the planarity of the fluorene groups improves the arrangement of the thin films, increases mobility, and significantly improves efficiency and lifetime. Able to know.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After the distilled water is washed, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes using an oxygen plasma.
  • 600 cc of the hole injection layer HT01 and 400 cc of the compound 31 were formed into a first hole transport layer using an evaporator.
  • 150 ⁇ of the compound 8 was formed as an auxiliary layer, and then 250 ⁇ was formed by doping with 5% of BH01: BD01.
  • An organic light-emitting device was manufactured in the same manner as in Example 26, using Compound 32 as an auxiliary layer and Compound 8 as an auxiliary layer.
  • Example 26 In the same manner as in Example 26, an organic light emitting device was manufactured by using the compound 33 as an auxiliary layer and the compound 8 as a hole transport layer.
  • Example 26 In the same manner as in Example 26, an organic light emitting device was manufactured by using the compound 34 as a hole transport layer and the compound 8 as an auxiliary layer.
  • An organic light-emitting device was manufactured in the same manner as in Example 26, using Compound 35 as an auxiliary layer and Compound 8 as an auxiliary layer.
  • Example 26 In the same manner as in Example 26, an organic light emitting diode was manufactured by using Compound 36 as an auxiliary layer and Compound 8 as an auxiliary layer.
  • Example 26 In the same manner as in Example 26, an organic light emitting device was manufactured by using the compound 37 as a hole transport layer and the compound 8 as an auxiliary layer.
  • An organic light-emitting device was manufactured in the same manner as in Example 26, using Compound 38 as an auxiliary layer and Compound 8 as an auxiliary layer.
  • a device was manufactured in the same manner as in Example 26, except that Compound 24 was used as the NPB as the hole transport layer.
  • a device was manufactured in the same manner as in Example 26, except that Compound 24 was used as Ref. 3 as the hole transport layer.
  • a device was manufactured in the same manner as in Example 26, except that Compound 24 was used as Ref. 4 as the hole transport layer.
  • the embodiments of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Examples 4 to 6.
  • the driving voltage was significantly lowered, and the efficiency and lifespan were increased.
  • It can have easy homo and fast hole mobility in the hole transport layer in accordance with the 2,3 arylamine substitution of indole, and in the case of indole N substitution, it can form a deep homogeneous easily in the auxiliary layer. It can be seen that greatly improved.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After the distilled water is washed, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes using an oxygen plasma.
  • a film injection layer HT01 600 ⁇ a hole transport layer to the film 37 to 400 ⁇ was formed into a film.
  • 250 ⁇ of Compound 8 was formed as an auxiliary layer, and then 300 ⁇ was formed by doping with 10% CzT: Ir (ppy) 3 .
  • An organic light-emitting device was manufactured in the same manner as in Example 34, using the auxiliary layer as a compound 26 to form a film.
  • Example 34 In the same manner as in Example 34, an organic light emitting device was manufactured by using the auxiliary layer as a compound 27.
  • Example 34 In the same manner as in Example 34, an organic light-emitting device was manufactured by using the auxiliary layer as a compound 28.
  • Example 34 In the same manner as in Example 34, an organic light-emitting device was manufactured by using the auxiliary layer as a compound 29.
  • An organic light-emitting device was manufactured in the same manner as in Example 34, using the auxiliary layer as a compound 30.
  • an organic light emitting diode was manufactured by using the hole transport layer as an NPB and the auxiliary layer as a compound 30.
  • a device was fabricated in the same manner as in Example 34, except that Ref. 1 was used as the hole transport layer and NPB.
  • a device was fabricated in the same manner as in Example 34, except that the hole transport layer was NPB, and the auxiliary layer was Ref.2.
  • the embodiments of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Example 7 and Comparative Example 8.
  • the compound in which the linking group between indole N and arylamine is substituted with phenyl moiety and meta, ortho as an auxiliary layer of the phosphor it may have a wide band gap capable of forming a deep homo with short conjugation length. It can be seen that the triplet energy is easy to block excitons from phosphorescent light emission, thereby improving efficiency and improving lifespan.
  • the compound of the present invention has excellent hole injection and hole transport characteristics when applied to the organic light emitting device for blue and phosphorescence, at the same time excellent in the electron blocking characteristics, high triplet energy and high Tg, low drive voltage, low consumption It can have power, high efficiency and long life.

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Abstract

La présente invention concerne un nouveau composé et, en particulier, lorsqu'il est appliqué à un élément électroluminescent organique fluorescent et phosphorescent, le nouveau composé présente de très bonnes caractéristiques d'injection de trous et de transmission de trous ainsi qu'une excellente caractéristique de blocage d'électrons, il peut montrer une grande énergie de triplet et une Tg élevée, et peut procurer une faible tension de commande, une faible consommation d'énergie, un très bon rendement et une longue durée de vie.
PCT/KR2015/010829 2014-10-14 2015-10-14 Nouveau composé et élément électroluminescent organique comprenant le nouveau composé WO2016060463A2 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
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WO2018058497A1 (fr) * 2016-09-30 2018-04-05 Dow Global Technologies Llc Composé organique et dispositif électronique comprenant une couche organique comprenant le composé organique
WO2018119729A1 (fr) * 2016-12-28 2018-07-05 Dow Global Technologies Llc Composé organique et dispositif électronique comprenant une couche organique contenant le composé organique
US10283716B2 (en) * 2015-02-09 2019-05-07 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using the same, and electronic device comprising same
CN110799499A (zh) * 2017-06-30 2020-02-14 株式会社斗山 有机化合物及包含其的有机电致发光元件

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