KR20160123831A - Hole transporting material and organic light emitting diodes using the same - Google Patents
Hole transporting material and organic light emitting diodes using the same Download PDFInfo
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- C07D209/56—Ring systems containing three or more rings
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Abstract
Description
The present invention relates to a novel hole transport material for organic electroluminescent devices and an organic electroluminescent device using the same. More particularly, the present invention relates to a spirobifluorene derivative, a carbazole derivative or a triphenylamine derivative by a Suzuki coupling reaction A hole transporting material for an organic electroluminescence device and an organic electroluminescence device using the same.
OLEDs have emerged as one of the most promising new technologies in flat panel displays and solid state lihgting.
The main cause of the decrease in the performance of the organic electroluminescent device is the morphological change of the amorphous organic layer, especially the transport layer. This change is caused by Joule heating during operation of the organic electroluminescent device. Therefore, the need for an amorphous material having a high resistance to heat and a high glass transition temperature (Tg) is increasingly urgent. Therefore, in order to produce an organic electroluminescent device having thermal stability, it is necessary to develop various methods for synthesizing a hole transporting material (HTMs) having a high glass transition temperature.
It has been demonstrated that a major carrier material with a planar core, such as spirobifluorene, can increase the glass transition temperature. Therefore, there is a further need for studies on the synthesis of spirobifluorene core based carrier transport materials because of their advantages such as thermal stability, shape stability, chemical stability, chemical diversity and high triplet energy.
On the other hand, it is known that triphenylamine and carbazole having a strong electron cycle have an excellent water-base property and act as an important part of a major transportation material. The weak thermal stability of triphenylamine has a lower electron cycle than the diphenylamine moiety, but thermal stability can be greatly improved when a stable and stable carbazole moiety is bonded to such triphenylamine. Therefore, bonding of triphenylamine and carbazole can improve the thermal stability and the transportation characteristics of the majors.
In order to solve the problems of the prior art as described above, the present invention provides a hole transport material for an organic electroluminescent device having a high glass transition temperature, excellent thermal and morphological stability, and excellent hole transporting property, and an organic electroluminescent device And to provide the above-mentioned objects.
It is another object of the present invention to provide a novel hole transport material for organic electroluminescent devices suitable for application to organic electroluminescent devices requiring high temperature and long life, and an organic electroluminescent device using the same.
In order to achieve the above object, the present invention provides a spirobifluorene derivative for a hole transport material of an organic electroluminescent device represented by the following general formula (1).
[Chemical Formula 1]
In Formula 1,
R and R 'are each independently H,
R and R 'can not be hydrogen at the same time.
In particular, the spirobifluorene derivative is preferably a compound represented by the following formula (1a) or (1b).
[Formula 1a]
[Chemical Formula 1b]
The present invention also provides a process for producing a hole transporting material for an organic electroluminescence device, wherein the spirobifluorene derivative and the carbazole derivative or the triphenylamine derivative are subjected to a Suzuki coupling reaction. do.
The spirobifluorene derivative may be 9,9'-spirobi (9H-fluorene) -2-yl-boronic acid or 9,9'- 7-dibromo-9,9'-spirobi (9H-fluorene) (2,7-dibromo-9,9'-spirobi (9H-fluoren)) can be used.
The carbazole derivative can be prepared by reacting 9- (3-bromo-5- (9H-carbazol-9-yl) phenyl) -9H- ) phenyl) -9H-carbazole), and it may be used, wherein the triphenylamine derivative is 4- (N- (naphthalen-1-yl) -N- (naphthalen-3-yl) amino) phenyl (4- (N - (naphthalen-1-yl) - N - (naphthalene-3-yl) may be used amino) pheny).
The present invention also provides an organic electroluminescent device including the hole transporting material represented by Formula 1 in a hole transporting layer.
According to the present invention, it is possible to provide a hole transporting material for an organic electroluminescence device having a high glass transition temperature, excellent thermal and morphological stability, and excellent hole transporting properties. Such a hole transporting material has a high temperature and long lifetime It is possible to improve current efficiency, power efficiency and lifetime characteristics as compared with conventional organic electroluminescent devices.
Hereinafter, the present invention will be described in detail.
Unless defined otherwise, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Repeated descriptions of the same technical constitution and operation as those of the conventional art will be omitted.
In the present invention, spirobifluorene derivatives were prepared by reacting triarylamine and carbazole, and their thermal and optical physical properties were confirmed, confirming that they were suitable for use as an electron transporting material for an organic electroluminescence device.
The present invention provides a spirobifluorene derivative for a hole transport material of an organic electroluminescent device represented by the following general formula (1).
[Chemical Formula 1]
In Formula 1,
R and R 'are each independently H,
R and R 'can not be hydrogen at the same time.
Specifically, the hole transporting material for an organic electroluminescence device represented by Formula 1 may be a spirobifluorene derivative represented by the following Formula 1a or 1b.
[Formula 1a]
[Chemical Formula 1b]
The hole transporting material for an organic electroluminescence device represented by Formula 1 is based on a spirobifluorene derivative, and a triarylamine or carbazole is bonded to the spirobifluorene derivative to increase a glass transition temperature (Tg) value And can improve thermal, morphological, and chemical stability.
The method for preparing a spirobifluorene derivative for a hole transport material according to the present invention represented by the general formula (1) of the present invention can be represented by the following reaction formula (1) or (2). The production method of the present invention is not limited to the following Reaction Scheme 1 or Reaction Scheme 2, and it is a matter of course that various organic synthesis methods can be used to produce the product.
[Reaction Scheme 1]
[Reaction Scheme 2]
(9H-fluorene) -2-yl) -5- (9H, 9H-fluorene) -2-pyridylcarbamate, which is a hole transporting material for organic EL devices, (9H-fluoren) -2-yl) -5- (9H-carbazol-9-yl) phenyl) -9H- 9H-carbazole) can be prepared by a Suzuki coupling reaction of a spirobifluorene derivative and a carbazole derivative.
According to Reaction Scheme 2, the hole transporting material for organic electroluminescent devices represented by Formula 1b of the present invention, 2,7-di [4- (N- (naphthalen-1-yl) -N- (naphthalene- (Naphthalene-3-yl) amino) phenyl] -9,9'-spiro phenyl] -9,9'-spirobi (9H-fluorene) can be prepared by a Suzuki coupling reaction of a spirobifluorene derivative and a triphenylamine derivative.
The spirobifluorene derivative may be 9,9'-spirobi (9H-fluorene) -2-yl-boronic acid or 9 , 7-dibromo-9,9'-spirobi (9H-fluorene) (2,7-dibromo-9,9'-spirobi (9H-fluoren)) can be used.
The carbazole derivatives include 9- (3-bromo-5- (9H-carbazol-9-yl) phenyl) -9H- yl) phenyl) -9H-carbazole) can be used as the triphenylamine derivative, and 4- (N- (naphthalen-1-yl) -N- N - (naphthalen-1-yl ) - N - (naphthalene-3-yl) may be used amino) pheny).
It is needless to say that the Suzuki coupling reaction can be carried out according to a conventional method in the art. Specifically, the 4- (9H-carbazol-9-yl) triphenylamine derivative and the bromoaryl derivative are dissolved in an organic solvent, and Pd (PPh 3 ) 2 Cl 3 , K 2 CO 3 and Water is added and reacted in an Ar atmosphere at 50 to 70 ° C for 10 to 14 hours, preferably at 60 ° C for 12 hours. Next, the reaction product is extracted with dichloromethane, and the organic layer is separated, dried with MgSO 4 , filtered and concentrated to obtain a hole transport material for an organic electroluminescence device represented by Formula 1 of the present invention.
The solvent used in the Suzuki coupling reaction may be water, chloroform, toluene, tetrahydrofuran, dioxalic acid, and the like, but is not limited thereto.
The present invention also provides an organic electroluminescent device including the hole transporting material represented by Formula 1 of the present invention as described above as a hole transporting layer. The hole transport material represented by Formula 1 may be used in a hole transport layer of an organic electroluminescent device to improve current efficiency, power efficiency, and lifetime characteristics.
The organic electroluminescent device includes a first electrode, a second electrode, and at least one organic material layer interposed between the first electrode and the second electrode. The organic material layer includes the electron transporting material represented by Formula 1 of the present invention Lt; / RTI > electron transport layer.
The organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection layer.
Specifically, the organic electroluminescent device is formed by coating an anode material as a first electrode on an upper portion of a lower substrate.
The substrate may be a glass, an organic substrate, or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness, which is used in a conventional organic electroluminescent device.
The anode material used as the first electrode is a metal film that is a reflective film in the case of a top emission structure, and a transparent and highly conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide 2 ), zinc oxide (ZnO) or the like is used. Thereafter, an insulating film (PDL) defining a pixel region is formed.
After forming an insulating film, a hole injecting layer and / or a hole transporting layer are stacked over the entire substrate with an organic film.
The hole injection layer material may be selectively deposited on the anode by vacuum thermal deposition or spin coating to form a hole injection layer (HIL). The hole injection layer material is not particularly limited, and copper phthalocyanine (CuPc) or Starburst type amines such as TCTA, m-MTDATA, and IDE406 (Idemitsu Materials) can be used.
A hole transport layer (HTL) is formed on the hole injection layer by vacuum thermal deposition or spin coating to form a hole transport layer (HTL). At this time, it is more preferable that the hole transporting layer is formed to have a thickness of about 50 to 1,500 angstroms in terms of hole transporting characteristics and driving voltage characteristics.
Then, a red light emitting material, a green light emitting material, and a blue light emitting material are patterned in the R and G regions of the pixel region to form a light emitting layer (EML) as a pixel region. The light emitting layer forming method is not particularly limited, but a vacuum deposition method, an ink jet printing method, a laser transfer method, and a photolithography method may be used.
An electron injection layer (EIL) may be selectively deposited on the electron transport layer. The electron injection layer material is not particularly limited, and materials such as LiF, NaCl, CsF, Li2O, BaO, and Liq can be used.
Subsequently, a metal for a cathode, which is a second electrode, is deposited on the electron injection layer by vacuum thermal deposition, and the cathode, which is the second electrode, is coated over the entire surface of the substrate and sealed to complete the organic electroluminescent device. The cathode metal may be Li, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ) May be used.
Hereinafter, the present invention will be described in more detail with reference to examples. These embodiments are for purposes of illustration only and are not intended to limit the scope of protection of the present invention.
The reagents and solvents used in the following examples were purchased from Aldrich and TCI Chemicals, Inc., and used without purification.
1 H and 13 C NMR spectra were measured using JEON JNM-ECP FT-NMR spectra operating at 500 MHz and 125 MHz, and infrared spectra were measured using Shimadzu Prestige-21 FT-IR spectra. Samples were measured by KBr pellet method and scanned in the range of 4000-400 cm -1 . The UV-vis absorption spectrum was measured using a Scinco S-3100 spectrophotometer, and the photoluminescence (PL) spectra were measured using a CARY Eclipse Varian fluorescence spectrophotometer. The HOMO value was calculated from the oxidation potential and the LUMO value was calculated based on the lowest energy absorption edge of the HOMO value and the UV-vis absorption spectrum. Thermogravimetric analysis (TGA) was also measured using a TG 209F1 (NET-ZSCH) thermal analysis system at a heating rate of 20 ° C min -1 .
Example 1. (9H-carbazol-9-yl) phenyl) -9H-carbazole < (Formula 1a) Preparation
1.2 g (3.33 mmol) of 9,9'-spirobi (9H-fluorene) -2-yl-boronic acid (9,9- 9- (9H-carbazol-9-yl) phenyl) -9H-carbazole (9- (3-bromo-5- 0.24 g (0.21 mmol) of Pd (Pd 3 P) 4 and 0.85 g (6.15 mmol) of K 2 CO 3 were placed in 20 mL of toluene, 20 mL of THF and 10 mL of distilled water, At 60 < 0 > C for 2 days. After the reaction was completed, the mixture was extracted with dichloromethane. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using n-hexane: dichloromethane as eluent to obtain (3- (9,9'-spirobi (9H-fluorene) -2-yl) -5- - carbazol-9-yl) phenyl) -9H- carbazole (3- (9,9'-spirobi (9H -fluoren) -2-yl) -5- (9H-carbazol-9-yl) phenyl) - 9H-carbazole , formula 1a).
Yield: 94%; white solid; FT-IR (KBr pellet): υ max cm -1 ; 1 H NMR (500MHz, CDCl 3 ) δ8.15 (d, J = 7.5 Hz, 4H), 7.98 (d, J = 8.0 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.83 (d , J = 7.5 Hz, 2H) , 7.76 (m, 3H), 7.68 (m, 1H), 7.49 (d, J = 8.0 Hz, 4H), 7.42 (m, 4H), 7.31 (m, 7H), 7.12 (m, 3H), 7.02 (s, IH), 6.80 (d, J = 7.5 Hz, 2H), 6.75 (d, J = 7.5 Hz, 1H); 13 C NMR (125MHz, CDCl 3 ) δ 149.9, 149.3, 148.2, 144.8, 142.2, 141.8, 140.9, 140.6, 139.5, 138.9,128.2, 127.9, 127.8, 127.1, 126.1, 124.7, 124.1, 124.0, 123.5, 122.8, 120.6, 120.4, 120.2, 120.1, 109.7.
Example 2. Di [4- (N- (naphthalen-1-yl) -N- (naphthalen-3-yl) amino) phenyl] -9,9'-spiro (Formula 1b) Preparation
(2.11 mmol) of 2,7-dibromo-9,9'-spirobi (9H-fluorene) (2,7-dibromo-9,9'-spirobi - (N- (naphthalen-1-yl) -N- (naphthalen-3-yl) amino) phenyl-4- (N - (naphthalen-1 -yl) - N - (naphthalene-3-yl) amino) phenyl 2.87 0.48 g (0.42 mmol) of Pd (Pd 3 P) 4 , 0.4 mL (0.85 mmol) of 50% t-Bu 3 P (50% in toluene) and 0.85 g (6.15 mmol) of K 2 CO 3 , Were placed in 50 mL of toluene and 25 mL of distilled water and stirred in an argon atmosphere at 100 DEG C for 3 days. After the reaction was completed, the mixture was extracted with dichloromethane. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using n-hexane: dichloromethane as eluent to obtain 2,7-di [4- (N- (naphthalen-1-yl) -N- ) Amino) phenyl] -9,9'-spiro (9H-fluorene) ( 2,7-di [4- (N- (naphthalen- ] -9,9'-spirobi (9H-fluorene) , formula (1b).
Yield: 65%; white solid; FT-IR (KBr pellet): υ max cm -1 ; 1 H NMR (500MHz, CDCl 3 ) δ7.88 (m, 8H), 7.78 (d, J = 8.5 Hz, 2H), 7.72 (d, J = 8.5 Hz, 2H), 7.66 (d, J = 8.5 Hz , 2H), 7.59 (d, J = 8.5 Hz, 2H), 7.46 (m, 6H), 7.32 (m, 18H), 7.11 (t, J = 7.5 Hz, 2H), 6.99 (d, J = 8.5 Hz , 4H), 6.90 (s, 2H), 6.81 (d, J = 7.5 Hz, 2H); 13 C NMR (125MHz, CDCl 3 ) δ149.7, 148.8, 147.6, 145.8, 143.3, 141.8, 140.2, 140.1, 135.2, 134.3, 134.2, 131.0, 130.0, 128.8, 128.4, 127.8, 127.7, 127.6, 127.5, 127.2 , 126.8, 126.6, 126.5, 126.3, 126.2, 126.1, 124.2, 124.1, 122.9, 122.1, 122.0, 120.2, 120.0, 117.8.
NMR, IR, UV-vis, PL spectroscopies and HOMO-LUMO energy levels were measured using the compounds represented by the general formula (1a) or (1b) prepared in Examples 1 and 2, Respectively.
As shown in Table 1, the Examples 1 and 2 spiro one for the hole transporting material of Formula 1a or 1b manufactured by fluorene derivative is T d (℃) values> than 400 ℃ (approximately 425, 500 ℃) And the HOMO and LUMO values are suitable for use as the hole transport layer, and the Tg values are 110 DEG C and 120 DEG C in the formula (1a) or (1b), respectively.
As described above, the spirobifluorene derivatives for the hole transporting material of Formula 1a or 1b prepared in Examples 1 and 2 prepared according to the present invention can be produced with high yield by an economical production method, Lt; / RTI > as a hole transport layer material of the < RTI ID = 0.0 >
Although the present invention has been described in terms of the preferred embodiments mentioned above, it is possible to make various modifications and variations without departing from the spirit and scope of the invention. It is also to be understood that the appended claims are intended to cover such modifications and changes as fall within the scope of the invention.
Claims (8)
[Chemical Formula 1]
In Formula 1,
R and R 'are each independently H,
R and R 'can not be hydrogen at the same time.
Wherein the spirobifluorene derivative is a compound represented by the following formula (1a) or (1b): < EMI ID =
[Formula 1a]
[Chemical Formula 1b]
[Chemical Formula 1]
In Formula 1,
R and R 'are each independently H,
R and R 'can not be hydrogen at the same time.
The spirobifluorene derivative may be 9,9'-spirobi (9H-fluorene) -2-yl-boronic acid or 9,9'- (9H-fluoren)), characterized in that the hole transporting material for organic electroluminescent devices is a material selected from the group consisting of 7-dibromo-9,9'-spirobi (9H-fluorene) ≪ / RTI >
The carbazole derivative can be prepared by reacting 9- (3-bromo-5- (9H-carbazol-9-yl) phenyl) -9H- ) phenyl) -9H-carbazole). < / RTI >
The triphenylamine derivative is 4- (N- (naphthalen-1-yl) -N- (naphthalen-3-yl) amino) phenyl (4- (N - (naphthalen- 1-yl) - N - (naphthalene- 3-yl) amino) pheny). ≪ / RTI >
[Chemical Formula 1]
In Formula 1,
R and R 'are each independently H,
R and R 'can not be hydrogen at the same time.
Wherein the hole transporting material is a compound represented by the following formula (1a), (1b) or (1c):
[Formula 1a]
[Chemical Formula 1b]
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| KR20180060277A (en) * | 2016-11-28 | 2018-06-07 | 원광대학교산학협력단 | Compound for hole transporting material and preparing method thereof |
| CN111607069A (en) * | 2020-06-09 | 2020-09-01 | 太原理工大学 | Conjugated microporous organic polymer based on spiro [3.3] heptane-2, 6-spirofluorene and preparation thereof |
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| US11233200B2 (en) | 2018-01-16 | 2022-01-25 | Samsung Electronics Co., Ltd. | Condensed cyclic compound, composition including the same, and organic light-emitting device including the condensed cyclic compound |
| KR102350041B1 (en) | 2020-02-24 | 2022-01-11 | 한국교통대학교 산학협력단 | Indenocabazole derivative compound for organic electroluminescent device and organic electroluminescent device comprising the same |
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| KR101002733B1 (en) | 2007-09-14 | 2010-12-21 | 제일모직주식회사 | Organic compound, and organic photoelectric device comprising the same |
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| US6822094B2 (en) * | 1997-03-20 | 2004-11-23 | Aventis Research & Technologies, Gmbh & Co. Kg | Spiro compounds and their use |
| CN103187537B (en) * | 2011-12-31 | 2016-09-07 | 固安翌光科技有限公司 | A kind of High-efficient white-light organic electroluminescence device |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180060277A (en) * | 2016-11-28 | 2018-06-07 | 원광대학교산학협력단 | Compound for hole transporting material and preparing method thereof |
| CN111607069A (en) * | 2020-06-09 | 2020-09-01 | 太原理工大学 | Conjugated microporous organic polymer based on spiro [3.3] heptane-2, 6-spirofluorene and preparation thereof |
| CN111607069B (en) * | 2020-06-09 | 2021-07-02 | 太原理工大学 | Conjugated microporous organic polymer based on spiro [3.3] heptane-2, 6-spirofluorene and preparation thereof |
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