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WO2013009095A1 - Composé à base de triphénylène et diode électroluminescente organique l'utilisant - Google Patents

Composé à base de triphénylène et diode électroluminescente organique l'utilisant Download PDF

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WO2013009095A1
WO2013009095A1 PCT/KR2012/005502 KR2012005502W WO2013009095A1 WO 2013009095 A1 WO2013009095 A1 WO 2013009095A1 KR 2012005502 W KR2012005502 W KR 2012005502W WO 2013009095 A1 WO2013009095 A1 WO 2013009095A1
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Korean (ko)
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배형찬
김성무
손효석
김태형
라종규
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Doosan Corp
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Doosan Corp
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Priority claimed from KR1020110078484A external-priority patent/KR20130007951A/ko
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Definitions

  • the present invention relates to a triphenylene-based organic electroluminescent device material having a specific structure and to the organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifetime by including the material in at least one organic material layer It is about. Background Art
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
  • a host / dopant system may be used as a light emitting material.
  • Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Since the luminous efficiency can be improved up to 4 times compared to the phosphorescent dopant, a lot of research on phosphorescent host materials has been conducted.
  • the hole injection layer, the hole transport layer, NPB, BCP, Alq 3, etc. are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives are used as the fluorescent material.
  • phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 .
  • CBP has shown high characteristics as a phosphorescent host material, but existing materials have advantages in terms of luminescence properties, but have low glass transition temperature and thermal stability. It is not so good that it is not satisfactory in terms of lifespan in OLED devices, and therefore, development of more excellent materials is required.
  • the present invention has been made to solve the above problems, and an object thereof is to provide a novel organic compound having an improved glass transition temperature and excellent thermal stability.
  • an object of the present invention is to provide an organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, power efficiency, thermal stability, driving voltage, device life, including the novel organic compound.
  • the present invention provides a compound represented by the following formula (1) or (2), preferably a triphenylene-based organic electroluminescent device material.
  • X and Y are the same as or different from each other, and are each independently NR I5 or a directly linked single bond, wherein one of X and Y is NR 15 (one of m and n is 1), and the other is a single bond ( one of m and n is 0),
  • R, to R 15 are the same or different and are each independently a hydrogen, a deuterium, a halogen, an amino group, a nitro group, a nitrile group, a C ⁇ o alkyl, C 2 ⁇ C 40 alkenyl nilga C 2 ⁇ C 40 of Alkynyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, ⁇ 0 alkoxy group, C 6 ⁇ C 40 aryloxy group, ⁇ C 40 alkylamino group, C 6 ⁇ C 40 Arylamino group, C 6 ⁇ C 40 diarylamino group, C 5 ⁇ C 40 heteroarylamino group, C 5 ⁇ C 40 diheteroarylamino group, C 6 ⁇ C 40 arylalkyl group, C 5 ⁇ C 40 a heteroaryl group, c 3 ⁇ c 40 cycloalkyl group, do a halogen group, a c 2 ⁇
  • R 15 may be condensed with substituents adjacent to each other to form a ring
  • n 0 or 1.
  • the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode.
  • an organic electroluminescent device comprising at least one compound selected from the group consisting of compounds represented.
  • the organic material layer including the compound represented by Chemical Formula 1 or Chemical Formula 2 is preferably at least one selected from the group consisting of a light emitting layer, a hole injection layer, and a hole transporting layer, more preferably, a phosphorescent or fluorescent host material of the light emitting layer. .
  • Compound represented by the formula (1) of the present invention is excellent in brightness, power efficiency, heat resistance, hole or electron transport, injection performance, and can exhibit an increase in color purity and luminous efficiency to the light emitting layer, it is a hole and charge injection of the organic EL device It can be applied to one or more of the phosphorescent and fluorescence host, dopant of the layer, the transport layer and the light emitting layer.
  • OLED organic electroluminescent device
  • FIG. 1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention. ⁇ Description of Drawing Symbols>
  • organic electroluminescent device 101 substrate
  • conventional organic light emitting device materials eg, N4, N4'-di (naphthalene-l-yl) -N4, N4'-diphenylbiphenyl-4,4'-diamine (hereinafter referred to as NPB) and 4,4- dicarbazolybiphenyl (hereinafter referred to as CBP)
  • NPB N4, N4'-di (naphthalene-l-yl) -N4, N4'-diphenylbiphenyl-4,4'-diamine
  • CBP 4,4- dicarbazolybiphenyl
  • the compound represented by Formula 1 or Formula 2 has an effect of stably forming triplet energy levels through orbital mixing by condensed heterocyclic moieties connected to a triphenylene base skeleton.
  • the energy level is controlled by a variety of substituents to have a wide bandgap (sky blue ⁇ red).
  • the phosphorescence property of the device may be improved, and the electron and / or hole transport ability, the luminous efficiency, the driving voltage, and the lifespan characteristics may be improved. Therefore, it can be used as a hole transporting layer, an electron transporting layer, a host, etc. by introducing various substituents as well as the light emitting layer.
  • the broad band 3 ⁇ 4 derived from the triphenylene-based skeleton may exhibit excellent properties as a host material, and due to introduction of substituents such as tertiary amines, it may exhibit excellent properties as a hole transport layer (HTL) material. have.
  • HTL hole transport layer
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the triphenylene-based skeleton, so that the glass transition temperature is improved, which may have higher thermal stability than conventional NPB or CBP. have. Therefore, the device containing the triphenylene-based compound of the present invention can exhibit durability and lifespan improvement.
  • the compound represented by Formula 1 or Formula 2 may greatly contribute to the improvement and lifespan of the organic light emitting device. It is also effective in maximizing performance in full color organic light emitting panels.
  • L is a direct link; C 40 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group,
  • R, 6 and R 17 are to each other the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, 'a nitro group, a nitrile group, do alkyl group, C 2 ⁇ alkenyl group of C 40, C 2 ⁇ C 40 Alkynyl group ', C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C aloe C 40 alkoxy group, C 6 ⁇ C 40 aryloxy group, ⁇ C 4 o alkylamino group, C 6 ⁇ C 40 arylamino group, C 6 ⁇ C 40 diarylamino group, C 5 ⁇ C 40 heteroarylamino group, c 5 ⁇ c 40 diheteroarylamino group, C 6 ⁇ C 40 arylalkyl group, C 5 to C 40 heteroarylalkyl group, C 3 to C 40 cycloalkyl group, C 40 to halogen group, C 2 to C 40 heterocycloal
  • Ar, R 18 to R 21 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, alkyl group of, alkenyl group of C 2 to C 40 ,
  • C 2 ⁇ C 40 alkynyl group C 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, Co alkoxy group, C 6 ⁇ C 40 aryloxy group, Cr o alkylamino group, C 6 ⁇ C 40 arylamino group, C 6 ⁇ C 40 diarylamino group, C 5 ⁇ C 40 heteroarylamino group, C 5 ⁇ C 40 Diheteroarylamino group, c 6 to c 40 arylalkyl group, c 5 to c 40 heteroarylalkyl group, c 3 to c 40 cycloalkyl group, C ⁇ Gto halogen alkyl group, C 2 to C 40 heterocycloalkyl group, It is selected from the group consisting of an alkylsilyl group of d Co, an arylsilyl group of C 6 ⁇ C 40 , and a heteroarylsilyl group of C 5 ⁇ C 40 , except that it is Ar hydrogen,
  • R, to R 15 are the same as defined in Formula 1 or Formula 2.
  • L is a direct connection, it means that the direct connection due to nonbond (nonbond).
  • A from the L, d ⁇ C 4 o alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C of the 40 aryl group, C 5 ⁇ C 40 heteroaryl group, CH ⁇ o alkoxy group, C 6 ⁇ C 40 aryloxy group, Cro alkylamino group, C 6 ⁇ C 40 arylamino group, C 6 ⁇ C 40 diarylamino group, C 5 to C 40 heteroarylamino group, C 5 to C 40 diheteroarylamino group, C 6 to C 40 arylalkyl group, C 5 to C 40 heteroarylalkyl group, C 3 to C A 40 cycloalkyl group, a C 40 halogen alkyl group, a C 2 -C 40 heterocycloalkyl group, a d Cuj alkylsilyl group, a C 6 cycloalkyl group, a C 40 halogen alkyl group
  • C 6 ⁇ C 40 aryl group nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, CH ⁇ o alkyloxy group, C 6 ⁇ C 40 arylamine group, C 6 ⁇ C 40 aryl group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 of the heterocycloalkyl group, do the alkylsilyl group, and a C 6 ⁇ C at least one selected from 40 arylsilyl group consisting of substituents It may be substituted by.
  • the compound of formula 1 containing N as X may be more embodied by the formulas illustrated below.
  • the compound represented by Formula 1 of the present invention is not limited to those illustrated below.
  • the compound of formula ( 2) containing N as X can be more specified by the formulas illustrated below.
  • the compound represented by the formula (2) of the present invention is not limited to those illustrated below.
  • the compound represented by Formula 1 or Formula 2 of the present invention may be synthesized according to a general synthesis method. (see chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995)) A detailed synthesis procedure for the compounds of the present invention is described in This is also described in detail.
  • Another aspect of the present invention relates to an organic electroluminescent device comprising the compound represented by Chemical Formula 1 or Chemical Formula 2, preferably Chemical Formulas 3 to 8.
  • the present invention is an anode (anode); Cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer is represented by Chemical Formula 1 or Chemical Formula 2, preferably Chemical Formulas 3 to 8. It is characterized by including a compound represented by. At this time, the compound of Formula 1 to Formula 8 may be included alone or in plurality.
  • the organic layer including the compound represented by Chemical Formula 1 or Chemical Formula 2, preferably Chemical Formulas 3 to 8 may be any one or more of a hole injection layer, a hole transport layer, and a light emitting layer.
  • it can be included in the organic EL element as a hole injection layer and a hole transport layer material.
  • the organic EL element can maximize the hole injection / transport capability.
  • the organic EL element can be used as a light emitting layer material of the organic EL element, thereby providing improved efficiency and lifetime.
  • the light emitting layer may include a phosphorescent guest material or a fluorescent guest material.
  • the compound represented by Formula 1 to Formula 8 is a blue, green and / or red phosphorescent host, fluorescent host, hole transport material and / or hole transport It may be included in the organic light emitting device as a material.
  • a host material including a compound of Formula 1 or Formula 2, wherein X is N is preferable, and may be a compound represented by any one of Formulas 3 to 8.
  • a hole transport layer (HTL) material comprising a compound of formula (1) in which a substituent such as a tertiary amine is introduced, for example a compound of formulas (4) to (7).
  • HTL hole transport layer
  • compounds of the Invl and Inv5 groups may be used as phosphorescent host materials, and compounds of the Inv2 and Inv6 groups may be used as host materials having side substituents.
  • Inv3 to Inv4 and Inv7 to Inv8 compounds may be used as the hole transport layer material. But it is not limited to this.
  • the compound represented by Formula 1 or Formula 2, preferably Formula 3 to Formula 8 according to the present invention has a high glass transition temperature of 150 ° C or more. Therefore, when the compound is used as an organic layer of the organic light emitting device, since crystallization in the organic light emitting device is minimized, the driving voltage of the device can be lowered, and the luminous efficiency, thermal stability, and lifetime characteristics can be improved. have.
  • Non-limiting examples of the organic EL device structure 100 include the substrate 101, the anode 102, the hole injection layer, the hole transport layer 103, the light emitting layer 104, the electron transport layer 106 and The cathodes 108 may be sequentially stacked.
  • at least one of the light emitting layer, the hole injection layer, and the hole transport layer may include the compound represented by Formula 1 or Formula 2.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic light emitting device may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic layer.
  • the organic layer including the compound of Formula 1 to Formula 8 may be formed by a vacuum deposition method or a solution coating method.
  • the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
  • the organic electroluminescent device according to the invention is, an organic material layer and using conventional materials and methods known in the art, except that the form to include the compound represented by the "one layer or more of the organic material layer by the above formula (1) It can be manufactured by forming an electrode.
  • a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ⁇ : ⁇ 1 or Sn0 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are limited to these 89
  • Synthesis Example 4 was prepared using 0.95 g (39.55 mmol) of NaH, 5.02 g (15.82 mmol) of 10H-phenanthro [9, 10-b] carbazole, 6 g (31.64 mmol) of 2-chloro-3-phenylpyridine, and 200 ml of DMF. In the same manner, 3.28 g (yield 44%) of the desired compound, Invl-131, was obtained.
  • 6-bromo-15H-phenanthro [9, 10-a] carbazole 12.95 g (32.68 mmol), iodobenzene 10 g (49.02 mmol), Cu powder 0.21 g (3.27 mmol), K 2 C0 3 4.52 g (32.68 mmol), 4.64 g (32.68 mmol) of Na 2 S0 4 and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85, and 9.11 g of lS-phenyl-lSH-phenanthro ⁇ l-aJcarbazole as a target compound was obtained. 59%) was obtained.
  • 6-bromo-15H-phenant ro [9, 10-a] carbazole 9.43 g (23.80 mmol), 4-iodobiphenyl 10 g (35.70 mmol), Cu powder 0.15 g (2.38 mmol), K 2 C0 3 3.29 g (23.80 mmol), Na 2 S0 4 3.38 g (23.80 mmol), and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85, and the target compound l 5- (biphenyl- 4 -yl) -6-bromo-l 6.66 g (51% yield) of 5 H-phenanthro [9, U) -a] carbazole was obtained.
  • An organic EL device was manufactured in the following manner. Glass substrates coated with ITO (Indium tin oxide) to a thickness of 1500 A were washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • NPB, CBP, Ir (ppy) 3 and BCP are as follows.
  • An organic EL device was manufactured in the following manner.
  • Example 58 to 65 , 102-109 Compound / CBP + 10% Ir (ppy) 3 (20nm) / BCP (lOnm) / Alq 3 using the compounds of the present invention as a hole transporting layer on the ⁇ (anode) prepared as above (40 nm) / LiF (lnm) / Al in order to configure the light emitting device and their light emission characteristics were evaluated, the results are shown in Table 2 below.
  • the compound applied as the hole transport layer is shown in Table 2 below.

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Abstract

Cette invention concerne un nouveau composé électroluminescent organique et une diode électroluminescente organique le contenant, et plus particulièrement, un nouveau composé électroluminescent organique qui est utilisé à titre de matériau pour injecter et transférer des trous ou des électrons et émettre une lumière, et une diode électroluminescente organique l'utilisant.
PCT/KR2012/005502 2011-07-11 2012-07-11 Composé à base de triphénylène et diode électroluminescente organique l'utilisant Ceased WO2013009095A1 (fr)

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EP3093288A1 (fr) * 2015-05-12 2016-11-16 Novaled GmbH Diode électroluminescente organique comprenant différents composés matriciels dans la première et la seconde couche de transport d'électrons
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EP3795569A4 (fr) * 2018-07-13 2021-06-30 Lg Chem, Ltd. Composé hétérocyclique et diode électroluminescente organique le comprenant
TWI792166B (zh) * 2021-01-29 2023-02-11 機光科技股份有限公司 有機化合物和以其作為材料的紅光有機發光裝置
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WO2015099450A1 (fr) * 2013-12-27 2015-07-02 주식회사 두산 Composé organique et élément électroluminescent organique le contenant
CN106083610A (zh) * 2015-04-29 2016-11-09 机光科技股份有限公司 有机材料及使用其的有机电激发光装置
CN106083610B (zh) * 2015-04-29 2017-10-27 机光科技股份有限公司 有机材料及使用其的有机电激发光装置
KR20180005199A (ko) * 2015-05-12 2018-01-15 노발레드 게엠베하 제1 전자 수송층 및 제2 전자 수송층에 상이한 매트릭스 화합물들을 포함하는 유기 발광 다이오드
WO2016180891A1 (fr) * 2015-05-12 2016-11-17 Novaled Gmbh Diode électroluminescente organique comprenant des composés de matrice différents dans les première et deuxième couches de transport d'électrons
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EP3093288A1 (fr) * 2015-05-12 2016-11-16 Novaled GmbH Diode électroluminescente organique comprenant différents composés matriciels dans la première et la seconde couche de transport d'électrons
EP3872074A1 (fr) 2015-05-12 2021-09-01 Novaled GmbH Diode électroluminescente organique comprenant différents composés matriciels dans la première et la seconde couche de transport d'électrons
US11081652B2 (en) 2015-05-12 2021-08-03 Novaled Gmbh Organic light-emitting diode comprising different matrix compounds in the first and second electron transport layer
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US11858947B2 (en) 2018-07-13 2024-01-02 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device including the same
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CN111320607A (zh) * 2018-12-17 2020-06-23 机光科技股份有限公司 以含有三亚苯的多环杂芳族基团为核心的有机化合物及其应用
TWI792166B (zh) * 2021-01-29 2023-02-11 機光科技股份有限公司 有機化合物和以其作為材料的紅光有機發光裝置
CN116063240A (zh) * 2023-01-20 2023-05-05 宁波卢米蓝新材料有限公司 一种有机电致发光多种主体材料、发光器件和应用
CN116063240B (zh) * 2023-01-20 2025-05-27 宁波卢米蓝新材料有限公司 一种有机电致发光多种主体材料、发光器件和应用

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