WO2014042322A1 - Composé organique électroluminescent et dispositif organique électroluminescent l'utilisant - Google Patents

Composé organique électroluminescent et dispositif organique électroluminescent l'utilisant Download PDF

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WO2014042322A1
WO2014042322A1 PCT/KR2013/001031 KR2013001031W WO2014042322A1 WO 2014042322 A1 WO2014042322 A1 WO 2014042322A1 KR 2013001031 W KR2013001031 W KR 2013001031W WO 2014042322 A1 WO2014042322 A1 WO 2014042322A1
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최태진
연규만
김동연
김충한
송보경
김지이
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주식회사 두산
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Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel organic light emitting compound having excellent light emitting ability, hole transporting ability, electron transporting ability, and the like, to the at least one organic material layer.
  • the present invention relates to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime.
  • An organic electroluminescent device (hereinafter referred to as an organic EL device) generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic EL device, for example, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) ), An electron injection layer (EIL), and the like.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML light emitting layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors.
  • yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
  • a host / dopant system may be used as the 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 give high efficiency light. At this time, since 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 to be used.
  • carbazole compounds such as CBP (4,4-dicarbazolybiphenyl) are used as the phosphorescent host material, and metal complex compounds containing heavy atoms such as Ir and Pt are widely used as the phosphorescent dopant material. It is used.
  • CBP which is currently used phosphorescent host material, has a low glass transition temperature (Tg) of about 110 ° C., and crystallization in the device is easy, resulting in a very short lifespan of about 150 hours.
  • the present invention has been made to solve the above object, and an object of the present invention is to provide an organic light emitting compound and an organic EL device using the same that can improve the characteristics such as luminous efficiency, driving voltage, thermal stability, life.
  • the present invention provides a compound represented by the following formula (1).
  • R a and R b are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 alkynyl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 aryl An oxy group, a substituted or unsubstituted C 1 -C 40 alkyloxy group, and a substituted or unsubstituted C 3 -C 40 cycloalkyl group, or a condensed aliphatic ring, a condensed aromatic ring with adjacent groups , A group forming a condensed heteroaliphatic ring or a condensed heteroaromatic ring.
  • the present invention is an organic EL device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the organic layer comprises a compound represented by the formula (1) of the present invention
  • An organic EL device is provided.
  • the compound represented by the formula (1) of the present invention has excellent luminous ability, electron transport ability and hole transport ability. Therefore, the organic EL device including the same may greatly improve characteristics such as light emission performance, driving voltage, and lifetime, and thus may be effectively applied to a full color display panel.
  • the novel organic light emitting compound according to the present invention has a structure represented by the formula (1) in which various substituents, in particular, N-containing heterocycles, aromatic rings, etc., are connected to the parent base of the dihydroferransene system.
  • R a and R b are to each other the same or different and each independently represents C of 6 ⁇ C 40 aryl group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl Or an alkyl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C 6 to C 40 , an alkyloxy group of C 1 to C 40 , and a cycloalkyl group of C 3 to C 40 , or And a group forming a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group.
  • R 1 and R 2 are the same as or different from each other, each independently C 6 ⁇ C 40 An aryl group, the number of nuclear atoms 5 Or a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring formed with an adjacent group.
  • the C 6 ⁇ C 40 aryl group, the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of, C 6 ⁇ C 40 aryl amine group, C 6 ⁇ C 40 aryl group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 of the heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, and a C 6 ⁇ of It may be substituted with one or more substituents selected from the group consisting of C 40 arylsilyl groups.
  • the compound of Chemical Formula 1 may be more embodied as any one of the compounds represented by the following Chemical Formula 2 or Chemical Formula 3.
  • X 1 to X 10 are the same as or different from each other, and each independently C or N,
  • R 3 to R 16 are to each other the same or different and each independently represent hydrogen, deuterium, halogen, C 1 ⁇ C 10 alkyl group, C 2 ⁇ alkynyl, C 6 of the C 10 alkenyl group, C 2 ⁇ C 10 of the It is selected from the group consisting of an aryl group of ⁇ C 8 , a heteroaryl group of 5 to 8 nuclear atoms, a cycloalkyl group of C 3 ⁇ C 10 and a heterocycloalkyl group of 3 to 10 nuclear atoms.
  • the C 1 ⁇ C 10 Alkyl group, C 2 ⁇ C 10 Alkenyl group, C 2 ⁇ C 10 Alkynyl group, C 6 ⁇ C 8 Aryl group, Nuclear atoms of 5 to 8 heteroaryl group, C of 3 ⁇ C 10 cycloalkyl group, and the number of nuclear atoms 3 heterocycloalkyl group of to 10 are each independently selected from deuterium, halogen, cyano, C alkyl group of 1 ⁇ C 40, C 2 ⁇ C 40 alkenyl group, C 2 C 40 alkynyl group, C 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 -aryl group, C 6 -C 40 arylalkyl group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 1 -C
  • unsubstituted alkyl is a straight or branched chain saturated hydrocarbon of 1 to 40 (10) carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, Hexyl and the like.
  • Unsubstituted aryl means an aromatic moiety having 6 to 40 (8) carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached in a simple or condensed form with one another.
  • Unsubstituted heteroaryl means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 40 (8) nucleoatoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, Substituted by heteroatoms such as O and S. It is understood that two or more rings may be attached in a simple attached or condensed form with each other, and further include condensed forms with aliphatic rings or aromatic rings.
  • Condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
  • the compound represented by the formula (1) of the present invention described above may be further embodied by the formulas illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
  • the compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device includes an anode; Cathode; And one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 may include one kind or two or more kinds.
  • the organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer, preferably a light emitting layer, a hole transport layer and / or an electron transport layer. Can be.
  • the light emitting layer of the organic electroluminescent device according to the present invention may contain a host material, wherein any one of the compounds represented by Formula 1 may be used as the host material.
  • a host material such as any one of the compounds represented by Chemical Formula 1
  • organic electroluminescence having excellent efficiency (light emitting efficiency and power efficiency), lifetime, luminance, driving voltage, etc., because the bonding force between holes and electrons in the light emitting layer is increased.
  • An element can be provided.
  • the compound represented by Chemical Formula 1 may be included in the organic light emitting device as a blue, green and / or red phosphorescent host, a fluorescent host, or a dopant material. It can also be used as a dopant material.
  • the structure of the organic electroluminescent element of this invention is not specifically limited, It may be a structure which laminated
  • Non-limiting examples thereof include (i) an anode, a light emitting layer, a cathode; (ii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode; Or (iii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, or a cathode.
  • the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between an electrode and an organic material layer.
  • the organic material layer including the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the organic EL device according to the present invention forms an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Formula 1 of the present invention. It can be manufactured by.
  • a silicon wafer, quartz or 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); Combinations of metals and oxides such as ZnO: Al or SnO 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 is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
  • 2,7-dibromo-9,10-dihydrophenanthrene (10g, 29.58mmol) and carbazole (12.4g, 73.95mmol) are dissolved in 300 ml of toluene and Pd 2 (dba) 3 (1.4g, 1.48mmol) is added under nitrogen. It was. Then, NaOBu-t (17.0 g, 176.88 mmol) was added, (t-Bu) 3 P (1.48 mL, 1.48 mmol) was added to the reaction solution, and the mixture was stirred under reflux for 5 hours.
  • 2,7-dibromo-9,10-dihydrophenanthrene (10g, 29.58mmol), dibenzothiophenyl boronic acid (16.9g, 73.95mmol) and Pd (PPh 3 ) 4 (3.4g, 3.0mmol) were added to the flask and 2N Na 2 CO after 3 was dissolved into a saturated aqueous solution 177.5ml and Toluene 240 ml, EtOH 60 ml was stirred under heating for 13 hours.
  • 2,7-dibromo-9,10-dihydrophenanthrene (10g, 29.58mmol), dibenzothiophenyl boronic acid (6.7g, 29.58mmol) and Pd (PPh 3 ) 4 (1.7g, 1.47mmol) were added to the flask and 2N Na 2 CO 3, 88.7 ml of saturated aqueous solution, 240 ml of Toluene, and 60 ml of EtOH were dissolved and heated and stirred for 13 hours.
  • 2,7-dibromo-9,10-dihydrophenanthrene (10 g, 29.58 mmol) and carbazole (4.94 g, 29.58 mmol) were dissolved in 300 ml of toluene and Pd (OAc) 2 (0.33 g, 1.48 mmol) was added under nitrogen. . Then, Cs 2 CO 3 (19.3g, 59.23mmol) was added, BINAP (0.92g, 1.48mmol) was added to the reaction solution, and the mixture was stirred under reflux for 5 hours.
  • 2,7-dibromo-9,10-dihydrophenanthrene (10g, 29.58mmol), dibenzothiophenyl boronic acid (6.7g, 29.58mmol) and Pd (PPh 3 ) 4 (1.7g, 1.47mmol) were added to the flask and 2N Na 2 CO 3, 88.7 ml of saturated aqueous solution, 240 ml of Toluene, and 60 ml of EtOH were dissolved and heated and stirred for 13 hours.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / cpd (1, 4, 7-8, 11-18, 22, 27-30) compound (respectively) + 10% Ir (ppy) on the thus prepared ITO transparent electrode ) was fabricated in order of 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
  • the green organic EL in the same manner as in Examples 1 to 17 The device was produced.
  • Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 One 6.78 515 42.4 Example 2 4 6.81 518 41.1 Example 3 7 6.79 517 40.8 Example 4 8 6.81 518 41.1 Example 5 11 6.79 517 40.8 Example 6 12 6.78 515 42.4 Example 7 13 6.81 518 41.1 Example 8 14 6.79 517 40.8 Example 9 15 6.81 518 41.1 Example 10 16 6.79 517 40.8 Example 11 17 6.79 517 40.8 Example 12 18 6.81 518 41.1 Example 13 22 6.78 515 42.4 Example 14 27 6.81 518 41.1 Example 15 28 6.79 517 40.8 Example 16 29 6.81 518 41.1 Example 17 30 6.79 517 40.8 Comparative Example 1 CBP 6.93 516 38.2
  • the organic EL device of Examples 1 to 17 using the compound according to the present invention as a light emitting layer of the green organic EL device is compared with the green organic EL device of Comparative Example 1 using the conventional CBP. It can be seen that the better performance in terms of efficiency and driving voltage.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • Example 18 One 7.22 471 5.99
  • Example 19 4 7.12 472 5.85
  • Example 20 7 7.00 472 6.34
  • Example 21 8 7.29 473 6.90
  • Example 22 11 7.30 474 6.34
  • Example 23 12 7.24 475 6.55
  • Example 25 14 7.23 472 6.25
  • Example 26 15 7.00 472 6.34
  • Example 27 16 7.29 473 6.90
  • Example 28 17 7.30 474 6.34
  • Example 29 18 7.24 475 6.55
  • Example 30 22 7.15 471 6.94
  • Example 31 27 7.23 472 6.25
  • Example 32 28 7.22 471 5.99
  • Example 34 30 7.00 472 6.34 Comparative Example 2 CBP 7.80 474 5.80
  • the organic EL device of Examples 18 to 34 using the compound according to the present invention as the light emitting layer of the blue organic EL device compared with the blue organic EL device of Comparative Example 2 using the conventional CBP It can be seen that the better performance in terms of efficiency and driving voltage.

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Abstract

L'invention concerne un nouveau composé organique électroluminescent ayant d'excellentes capacités d'émission de lumière, de transport de trous, de transport d'électrons, etc. L'invention concerne également un dispositif organique électroluminescent comprenant une ou plusieurs couches de matériau organique qui contiennent ledit composé, améliorant ainsi les caractéristiques de l'appareil comme son efficacité d'émission de lumière, sa tension de commande et sa durée de vie.
PCT/KR2013/001031 2012-09-11 2013-02-08 Composé organique électroluminescent et dispositif organique électroluminescent l'utilisant WO2014042322A1 (fr)

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EP3421461A1 (fr) * 2017-06-28 2019-01-02 Cynora Gmbh Dérivés du triazine, en particulier pour l'utilisation dans les dispositifs optoélectroniques
WO2019002355A1 (fr) * 2017-06-28 2019-01-03 Cynora Gmbh Molécules organiques destinées en particulier à être utilisées dans des dispositifs optoélectroniques
CN114685288A (zh) * 2020-12-25 2022-07-01 广州华睿光电材料有限公司 多环芳胺类有机化合物及其用途

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EP3421461A1 (fr) * 2017-06-28 2019-01-02 Cynora Gmbh Dérivés du triazine, en particulier pour l'utilisation dans les dispositifs optoélectroniques
WO2019002355A1 (fr) * 2017-06-28 2019-01-03 Cynora Gmbh Molécules organiques destinées en particulier à être utilisées dans des dispositifs optoélectroniques
KR20200011980A (ko) * 2017-06-28 2020-02-04 시노라 게엠베하 유기 분자, 특히 광전자 장치에 사용하기 위한 유기 분자
CN110914255A (zh) * 2017-06-28 2020-03-24 辛诺拉有限公司 有机分子，特别是用于光电装置的有机分子
KR102328890B1 (ko) 2017-06-28 2021-11-18 시노라 게엠베하 유기 분자, 특히 광전자 장치에 사용하기 위한 유기 분자
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CN110914255B (zh) * 2017-06-28 2023-03-31 三星显示有限公司 有机分子，特别是用于光电装置的有机分子
CN114685288A (zh) * 2020-12-25 2022-07-01 广州华睿光电材料有限公司 多环芳胺类有机化合物及其用途
CN114685288B (zh) * 2020-12-25 2024-02-02 广州华睿光电材料有限公司 多环芳胺类有机化合物及其用途

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