KR101548076B1 - Organic electroluminescence device using the triphenylene derivative - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organic light emitting compound and an organic electroluminescent device including the same. More specifically, the present invention relates to a novel organic light emitting compound used as a hole or electron injection and transportation, .

Description

TECHNICAL FIELD [0001] The present invention relates to a triphenylene compound and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a triphenylene-based organic electroluminescent device having a specific structure and an organic electroluminescent device having improved characteristics such as luminous efficiency, luminance, thermal stability, driving voltage and lifetime by incorporating the above material into one or more organic layers .

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1965 based on observation of the organic thin film emission of Bernanose in the 1950s, (Tang) and a functional layer of a light emitting layer. In order to produce high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The phosphorescent dopant as well as phosphorescent host materials have been studied extensively.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. In particular, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials are metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ , And CBP is a phosphorescent host material. However, existing materials have advantages in terms of light emitting properties, but they are not satisfactory in terms of lifetime in OLED devices because of low glass transition temperature and poor thermal stability. Therefore, development of materials with higher performance is required.

Korean Patent Publication No. 2010-0105099

SUMMARY OF THE INVENTION The present invention has been conceived to solve the above-mentioned problems, and an object thereof is to provide a novel organic compound having an improved glass transition temperature and excellent thermal stability.

Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound and having improved various characteristics such as luminous efficiency, luminance, power efficiency, thermal stability, driving voltage, and device lifetime.

The present invention provides a compound represented by the following formula (1), preferably a triphenylene-based organic electroluminescent device.

X is _{CR 16 R 17, O, S} , SiR 18 R 19, S (= O), and S (= O) is selected from the group consisting of _2;

R ₁ to R ₁₉ are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C _A C ₅ to C ₄₀ aryl group, a C ₁ to C ₄₀ heteroaryl group, a C ₁ to C ₄₀ alkoxy group, a C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyl An amino group, a C ₅ to C ₄₀ arylamino group, a C ₅ to C ₄₀ diarylamino group, a C ₅ to C ₄₀ heteroarylamino group, a C ₂ to C ₄₀ diheteroarylamino group, a C ₆ to C ₄₀ arylalkyl group , A C ₆ to C ₄₀ heteroarylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₁ to C ₄₀ halogenalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₃ to C ₄₀ alkylsilyl group, a C _A C ₃ to C ₄₀ arylsilyl group, and a C ₃ to C ₄₀ heteroarylsilyl group;

Wherein R ₁ to R ₁₉ may each be fused to adjacent substituents or may form a ring.

The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode, wherein the compound And at least one compound selected from the group consisting of an organic electroluminescent device and an organic electroluminescent device.

Here, the organic material layer containing the compound represented by the formula (1) is preferably at least one selected from the group consisting of a light emitting layer, a hole injecting layer and a hole transporting layer, and more preferably a host material for phosphorescence or fluorescence of the light emitting layer.

The compound represented by the general formula (1) of the present invention is excellent in luminance, power efficiency, heat resistance, hole or electron transporting and injection performance, and can exhibit increased color purity and luminous efficiency as a light emitting layer. Layer, a transport layer, and a phosphorescent and fluorescent host or dopant of the light emitting layer.

Therefore, when using the novel compounds of the present invention, it is possible to produce a very good organic electroluminescent device (OLED) exhibiting low driving voltage, high current efficiency and long life.

1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

In the present invention, a material for a conventional organic light emitting device [for example, N4, N4'-di (naphthalene-1-yl) -N4, N4'- diphenylbiphenyl-4,4'- dicarbazolybiphenyl (hereinafter abbreviated as CBP)], and has a wide energy bandgap and a triphenylene-based compound having a specific structure.

The compound represented by Formula 1 has an effect of forming a triplet energy state stably through orbital mixing by connecting a fused heterocyclic moiety to a triphenylene base skeleton At the same time, the energy level is controlled by various substituents, resulting in a broad band gap (sky blue ~ red). As a result, the phosphorescence characteristics of the device can be improved and the electron and / or hole transporting ability, luminous efficiency, driving voltage, lifetime characteristics and the like can be improved. Therefore, it can be applied not only as a light emitting layer but also as a hole transporting layer, an electron transporting layer and a host by introducing various substituents. Particularly, it can exhibit excellent characteristics as a host material due to a wide band gap derived from a triphenylene base skeleton and can exhibit excellent properties as a hole transport layer (HTL) material due to the introduction of a substituent such as a tertiary amine have.

In addition, the molecular weight of the compound is significantly increased due to various aromatic ring substituents introduced into the triphenylene-based skeleton, whereby the glass transition temperature is improved and thus the polymer has higher thermal stability than the conventional NPB or CBP have. Therefore, the device including the triphenylene compound of the present invention can exhibit improvement in durability and lifetime.

In addition, when the compound is used as a hole transport layer and a blue, green and / or red phosphorescent host material or a fluorescent host material of an organic light emitting device, it is possible to exert an excellent effect in terms of efficiency and life as compared with NPB and CBP. Therefore, the compound represented by the formula (1) according to the present invention can greatly contribute to improvement of the performance and lifetime of the organic light emitting device, and particularly, such lifetime improvement of the device has a great effect in maximizing the performance of the full color organic light emitting panel.

The compounds represented by formula (1) of the present invention may be represented by the following formulas (2) to (7), respectively.

In this formula,

R ₁ to R ₁₉ are the same as defined in the above formula (1).

In the triphenylene compound according to the present invention, the compound of the formula (1) containing S as X can be further formulated by the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.

In the triphenylene type compound according to the present invention, the compound of the formula (1) containing O as X can be further specified by the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.

In the triphenylene compound according to the present invention, the compound of the formula (1) containing CR ₁₆ R ₁₇ as X can be further formulated into the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.

In the triphenylene compound according to the present invention, the compound of the formula (1) containing SiR ₁₈ R ₁₉ as X can be further formulated into the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.

In the triphenylene compound according to the present invention, the compound of the formula (1) containing S = O as X can be further formulated into the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.

In the triphenylene type compound according to the present invention, the compound of the formula (1) containing SO ₂ as X can be further specified by the following illustrated formulas. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.

The compounds represented by the general formulas (1) to (7) of the present invention can be synthesized according to a general synthesis method. (see Chem . Rev. , 60 : 313 (1960), J. Chem. SOC . 4482 (1955), Chem. Rev. 95: 2457 (1995)). .

Another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by Formula 1, preferably Formula 2 to Formula 7, according to the present invention.

Specifically, the present invention provides a fuel cell comprising: an anode; A cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1, preferably Formula 2 to Formula 7, Or a compound thereof. At this time, the compounds represented by Chemical Formulas 1 to 7 may be included singly or in plurality.

The organic material layer containing the compound represented by the formula (1) of the present invention, preferably the compounds represented by the formulas (2) to (7) may be any one or more of a hole injecting layer, a hole transporting layer, and a light emitting layer. And may be included in the organic EL device as the hole injection layer and the hole transport layer material. In this case, the organic EL device can maximize the hole injection / transport capability. And can be used as a light emitting layer material of an organic EL device, thereby providing an improved efficiency and a service life.

In the present invention, the light emitting layer may include a phosphorescent guest material or a fluorescent guest material. Preferably, the compounds represented by Chemical Formulas 1 to 7 may be included in the organic light emitting device as blue, green and / or red phosphorescent host, fluorescent host, hole transport material and / or hole transport material.

At this time, the triphenylene compound according to the present invention is preferable as a host material. Here, the compound of the formula (1) wherein a substituent such as a tertiary amine is introduced is preferable as a hole transporting layer (HTL) material.

Also, the compound represented by Formula 1 according to the present invention, preferably compounds represented by Formula 2 to Formula 7, has a high glass transition temperature of 150 ° C or higher. Therefore, when the compound is used as the organic material layer of the organic light emitting device, the crystallization in the organic light emitting device is minimized, so that the driving voltage of the device can be lowered and the light emitting efficiency, thermal stability and lifetime characteristics can be improved.

Non-limiting examples of the structure of the organic EL device according to the present invention may include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode sequentially laminated. At least one of the light emitting layer, the hole injecting layer, and the hole transporting layer may include the compound represented by Formula 1. An electron injection layer may be disposed on the electron transport layer.

In addition, the organic light emitting device according to the present invention may have an insulating layer or an adhesive layer interposed between the electrode and the organic material layer as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

In the organic light emitting device of the present invention, the organic material layer containing the compounds represented by Chemical Formulas 1 to 7 may be formed by a vacuum evaporation method or a solution coating method. Examples of the application of the solution include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The organic electroluminescent device according to the present invention can be manufactured by using a conventional material and method known in the art, except that at least one layer of the organic material layer includes the compound represented by the above formula (1) ≪ / RTI >

For example, the substrate may be a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, or a sheet.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of metal and oxides such as 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 not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, and the electron injecting layer are not particularly limited, and conventional materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Synthesis Example 1: Synthesis of compound 2-bromo-7- (2- (methylsulfinyl) phenyl) triphenylene ]

5.0 g (11.54 mmol) of 2- (7-bromotriphenylen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 1-bromo-2- (methylsulfinyl) benzene 2.78 g (12.70 mmol) was dissolved in 75 ml of toluene, and 2M K ₂ CO ₃ (8 ml) was added to remove gas. Then 0.73 g of Pd (PPh ₃ ) ₄ (5 mol%) was added and stirred at 90 ° C for 24 hours. After the reaction mixture was cooled to room temperature, the reaction mixture was extracted with dichloromethane, the water was removed with MgSO ₄ , and the residue was purified by column chromatography using EA / Hexane (1: 3) to obtain 2-bromo-7- (2- (methylsulfinyl) ) triphenylene (yield: 68%).

^{1 H NMR: 2.65 (s,} 3H), 7.52 (d, 2H), 7.84 (m, 3H), 8.00 (m, 4H), 8.16 (d, 2H), 8.95 (d, 2H), 9.05 (s, 1H).

[Synthesis Example 2: Synthesis of compound 6-bromobenzo [d] triphenyleno [2,3-b] thiophene]

3.49 g (7.84 mmol) of 2-bromo-7- (2- (methylsulfinyl) phenyl) triphenylene, 100 ml of CF ₃ SO ₃ H and 0.55 g (3.92 mmol) of phosphorus pentoxide were placed in a flask under nitrogen flow for 72 hours Lt; / RTI > 500 ml of ice-water was placed in a flask, and the yellow precipitate was dried after filtration. The dried material was added to 500 ml of pyridine, and the mixture was refluxed for 12 hours. Then, the mixture was cooled, extracted with dichloromethane, and then dehydrated with MgSO ₄ . EA / hexane (1: 7) as eluent to obtain 2.87 g (yield: 88%) of 6-bromobenzo [d] triphenyleno [2,3- b] thiophene as a target compound.

¹ H NMR: 7.52 (d, 2H), 7.84 (m, 3H), 8.00 (m, 4H), 8.16 (d, 2H), 8.95

[ Synthesis Example 3: Synthesis of compound (2- (7-bromotriphenylen-2-yl) phenyl) dimethyl silane ]

7-bromotriphenylen-2-ylboronic acid 10 g (28.49 mmol), (2-bromophenyl) dimethylsilane 5.11 g (23.74 mmol), Pd (PPh 3) 4 1.37 g (5 mol%), K 2 CO 3 9.84 g (71.23 mmol) and THF / distilled water (200 ml / 100 ml), 7.13 g (yield: 68%) of 2- (7-bromotriphenylen- .

^{1 H NMR: 0.66 (s,} 6H), 3.82 (s, 1H), 7.53 (d, 2H), 7.81 (m, 3H), 7.99 (m, 4H), 8.14 (d, 2H), 8.96 (d, 2H), 9.04 (s, 1 H).

Synthesis Example 4: Synthesis of compound 6-bromo-10,10-dimethyl-10H-benzo [d] triphenyl eno [2,3- b]

In a nitrogen atmosphere (2- (7-bromotriphenylen-2 -yl) phenyl) dimethylsilane 3.0 g (6.80 mmol) and RhCl (PPh _{3) 3} were dissolved 31.3 mg (0.034 mmol) in 1,4-dioxane 10ml, 135 ℃ Lt; / RTI > for 1 hour. After removal of the solvent, 2.52 g (yield 83%) of the target compound, 6-bromo-10,10-dimethyl-10H-benzo [d] triphenylenol [2,3-b] silole was obtained by column chromatography with EA: Hexane (1: ).

^{1 H NMR: 0.68 (s,} 6H), 7.54 (d, 2H), 7.83 (m, 3H), 7.98 (m, 4H), 8.15 (d, 2H), 8.95 (d, 2H), 9.02 (s, 1H).

[Synthesis Example 5: Synthesis of compound 2-bromo-7- (2-isopropylphenyl) triphenylene]

7-bromotriphenylen-2-ylboronic acid 10 g (28.5 mmol), 1-bromo-2-isopropylbenzene 6.18 g (34.2 mmol), Pd (PPh 3) 4 1.98 g (5 mol%), K 2 CO 3 11.82 g ( 77.7 mmol) and THF / distilled water (200 ml / 100 ml) were used in the same manner as in Synthesis Example 1 to obtain 7.6 g of 2-bromo-7- (2-isopropylphenyl) triphenylene .

^{1 H NMR: 1.23 (s,} 6H) 2.87 (m, 1H), 7.54 (d, 2H), 7.86 (m, 3H), 8.02 (m, 4H), 8.19 (d, 2H), 8.94 (d, 2H ), 9.04 (s, 1 H).

Synthesis Example 6: Synthesis of compound 6-bromo-10,10-dimethyl-10H-indeno [2,1-b ]

The purpose with 2-bromo-7- (2- isopropylphenyl) triphenylene 7.6 g (17.9 mmol) and _{RhCl (PPh 3) 3 164.8 mg} (0.18 mmol), and 1,4-dioxane 10ml same manner as in Example 4 using 6.2 g (yield 82%) of 6-bromo-10,10-dimethyl-10H-indeno [2,1-b]

^{1 H NMR: 1.78 (s,} 6H), 7.57 (d, 2H), 7.84 (m, 3H), 8.02 (m, 4H), 8.15 (d, 2H), 8.93 (d, 2H), 9.02 (s, 1H).

[Synthesis Example 7: Synthesis of compound 2- (2-benzhydrylphenyl) -7-bromotriphenylene]

*

7-bromotriphenylen-2-ylboronic acid 10 g (28.5 mmol), ((2-bromophenyl) methylene) dibenzene 11.05 g (34.2 mmol), Pd (PPh 3) 4 1.98 g (5 mol%), K 2 CO 3 11.82 (yield: 76%) of the target compound, 2- (2-benzhydrylphenyl) -7-bromotriphenylene, was obtained in the same manner as in Synthesis Example 1, except that the starting material was replaced with THF / distilled water (200 ml / 100 ml) .

^{1 H NMR: 5.48 (s,} 1H), 7.55 (d, 2H), 7.87 (m, 5H), 8.11 (m, 6H), 8.18 (d, 2H), 8.52 (m, 6H), 8.87 (d, 2H), 9.03 (s, 1 H).

Synthesis Example 8: Synthesis of compound 6-bromo-10,10-diphenyl-10H-indeno [2,1-b ]

2- (2-benzhydrylphenyl) -7- bromotriphenylene 11.95 g (21.7 mmol) and _{RhCl (PPh 3) 3 200 mg} (0.22 mmol), and 1,4-dioxane 10ml purpose in the same manner as in Example 4 using compound 9.86 g (yield: 83%) of 6-bromo-10,10-diphenyl-10H-indeno [2,1- b] triphenylene was obtained.

^{1 H NMR: 7.56 (d,} 2H), 7.88 (m, 5H), 8.08 (m, 6H), 8.19 (d, 2H), 8.50 (m, 6H), 8.85 (d, 2H), 9.04 (s, 1H).

[Synthesis Example 9: Synthesis of compound Inv5-16] - Example 1

6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 5 g (12.10 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid 4.17 g (14.52 mmol), Pd (PPh 3) 4 0.7 g ( (Yield: 81%) of the target compound Inv5-16 was obtained in the same manner as in Synthesis Example 1 using 1.45 g (36.29 mmol) of NaOH and THF / distilled water (100 ml / 50 ml) .

GC-Mass (calculated: 575.17 g / mol, measured: 575 g / mol)

[Synthesis Example 10: Synthesis of compound Inv5-57] - Example 2

4.56 g (14.52 mmol) of 4- (1-phenyl- 1H-benzo [d] imidazol-2-yl) phenylboronic acid were added to a solution of 5 g (12.10 mmol) of 6-bromobenzo [ _{Pd (PPh 3) 4 0.69 g} (5 mol%), NaOH 1.45 g (36.29 mmol), and THF / distilled water (100ml / 50ml) using the test in the same manner as in synthesis example 1, the desired compound 6.2 Inv5-57 g (yield: 85%).

GC-Mass (theory: 602.18 g / mol, measurement: 602 g / mol)

[Synthesis Example 11: Synthesis of compound Inv5-14] - Example 3

6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 6.18 g (14.95 mmol), 9H-carbazole 3 g (17.94 mmol), Pd 2 (dba) 3 0.68 g (5 mol%), P (t- 3.06 g (Yield: 41%) of the target compound Inv5-14 was obtained in the same manner as in Synthesis Example 3, except that 0.3 g (1.5 mmol) of ₃ , 3.59 g (37.38 mmol) of NaO ).

GC-Mass (theory: 499.14 g / mol, measurement: 499 g / mol)

[Synthesis Example 12: Synthesis of compound Inv5-35] - Example 4

6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 5 g (12.10 mmol), quinolin-3-ylboronic acid 2.51 g (14.52 mmol), Pd (PPh 3) 4 0.69 g (5 mol%), NaOH 1.45 g (36.29 mmol) of the title compound, and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 4.41 g (yield 79%) of the target compound Inv5-35.

GC-Mass (calculated: 461.58 g / mol, measured: 461 g / mol)

[Synthesis Example 13: synthesis of compound Inv5-51] - Example 5

A solution of 4.0 g (14.52 mmol) of 4,6-di (pyridin-4-yl) pyrimidin-2-ylboronic acid, 5 g (12.10 mmol) of 6-bromobenzo [d] triphenyleno [2,3- b] thiophene, _{3) 4 0.69 g (5 mol} %), NaOH 1.45 g (36.29 mmol), and THF / distilled water (100ml / 50ml) and the experiment in the same manner as in synthesis example 1, the desired compound using the Inv5-51 5.69 g (yield 83%).

GC-Mass (calculated: 566.16 g / mol, measured: 566 g / mol)

[Synthesis Example 14: synthesis of compound Inv7-35] - Example 6

6-bromo-10,10-dimethyl- 10H-indeno [2,1-b] triphenylene 5 g (11.188 mmol), quinolin-3-ylboronic acid 2.45 g (14.17 mmol), Pd (PPh 3) 4 0.68 g ( (Yield: 78%) of the target compound Inv7-35 was obtained in the same manner as in Synthesis Example 1, except that 1.9 g (5 mol%) of NaOH, 1.42 g (35.43 mmol) of NaOH and THF / distilled water .

GC-Mass (calculated: 471.20 g / mol, measured: 471 g / mol)

[Synthesis Example 15: synthesis of compound Inv7-106] - Example 7

6-bromo-10,10-diphenyl- 10H-indeno [2,1-b] triphenylene 5 g (9.13 mmol), b 3.04 g (10.96 mmol), Pd (PPh 3) 4 0.53 g (5 mol%), 4.35 g (yield 80%) of the target compound Inv7-106 was obtained by conducting the same method as in Synthesis Example 1 using 1.10 g (27.40 mmol) of NaOH and THF / distilled water (100 ml / 50 ml)

GC-Mass (calculated: 595.23 g / mol, measured: 595 g / mol)

[Synthesis Example 16: synthesis of compound Inv8-42] - Example 8

A solution of 5 g (11.38 mmol), 2,3'-bipyridin-6-ylboronic acid (2.73 g, 13.65 mmol), 6-bromo-10,10-dimethyl- _{Pd (PPh 3) 4 0.66 g} (5 mol%), NaOH 1.37 g (34.14 mmol), and THF / distilled water (100ml / 50ml) using the test in the same manner as in synthesis example 1, the desired compound 4.55 Inv8-42 g (yield: 82%).

GC-Mass (calculated: 487.18 g / mol, measured: 487 g / mol)

[Synthesis Example 17: synthesis of compound Inv9-14] - Example 9

5 g (10.83 mmol) of Inv 5-14 was dissolved in 100 ml of dichloromethane under nitrogen flow, and 1.88 g (10.83 mmol) of mCPBA dissolved in dichloromethane was added dropwise at -30 ° C. After stirring for 1 hour, the temperature was raised to room temperature, the reaction was terminated with sodium carbonate, and the organic layer was separated. The separated organic layer was dehydrated with MgSO ₄ and columned with EA / Hexane (1: 1) to obtain 2.41 g (yield: 45%) of the objective compound Inv9-14.

GC-Mass (calculated: 493.11 g / mol, measured: 493 g / mol)

[Synthesis Example 18: Synthesis of Compound Inv9-51] - Example 10

In the same manner as in Synthesis Example 88, 5 g (8.82 mmol) of Inv5-51, 1.53 g (8.82 mmol) of mCPBA and 150 ml of dichloromethane were used to obtain 2.36 g (yield 46%) of the target compound Inv9-51 .

GC-Mass (calculated: 582.67 g / mol, measured: 582 g / mol)

[Synthesis Example 19: synthesis of compound Inv10-35] - Example 11

In the same manner as in Synthesis Example 88, 5 g (10.83 mmol) of Inv5-35, 4.7 g (27.08 mmol) of mCPBA and 150 ml of dichloromethane were used to obtain 2.36 g (yield 35%) of the target compound Inv10-35 .

GC-Mass (calculated: 493.11 g / mol, measured: 493 g / mol)

[Synthesis Example 20: Synthesis of compound Inv 5-20] - Example 12

A mixture of 7.85 g (19.00 mmol) of 6-bromobenzo [d] triphenyleno [2,3-b] thiophene, 0.87 g (5 mol%) of Pd ₂ (dba) ₃ , 5 g (22.80 mmol) of N-phenylnaphthalen- In the same manner as in Synthesis Example 3, using 0.38 g (1.90 mmol) of P (t-bu) ₃ , 4.57 g (47.50 mmol) of NaO (t-bu) and 200 ml of toluene, (Yield 66%).

GC-Mass (calculated: 551.17 g / mol, measured: 551 g / mol)

[Synthesis Example 21: synthesis of compound Inv5-64] - Example 13

6-bromobenzo [d] triphenyleno [ 2,3-b] thiophene 5 g (12.10 mmol), 4- (naphthalen-2-yl (phenyl) amino) phenylboronic acid 4.92 g (14.51 mmol), Pd (PPh 3) 4 5.92 g (yield 78%) of the target compound Inv5-64 was obtained in the same manner as in Synthesis Example 1, except that 0.7 g (5 mol%) of NaOH, 1.45 g (36.29 mmol) of NaOH and THF / distilled water (100 ml / . GC-Mass (calculated: 627.20 g / mol, measured: 627 g / mol)

[Synthesis Example 22: synthesis of compound Inv7-18] - Example 14

6-bromo-10,10-dimethyl- 10H-indeno [2,1-b] triphenylene 6.55 g (15.47 mmol), dinaphthalen-2-ylamine 5 g (18.56 mmol), Pd 2 (dba) 3 0.71 g (5 mol%), P (t- bu) 3 0.31 g (1.55 mmol), NaO (t-bu) 3.72 g (38.67 mmol), and the target compound in the same manner as in Preparation example 3 using Toluene of 200 ml Inv7 -18 (6.15 g, yield 65%).

GC-Mass (calculated: 611.26 g / mol, measured: 611 g / mol)

[Synthesis Example 23: synthesis of compound Inv7-127] - Example 15

A solution of 3.72 g (10.96 mmol) of 6-bromo-10,10-diphenyl-10H-indeno [2,1-b] triphenylene 5 g (9.13 mmol), 4- (naphthalen- _{Pd (PPh 3) 4 0.53 g} (5 mol%), NaOH 1.10 g (27.40 mmol), and THF / distilled water (100ml / 50ml) using the test in the same manner as in synthesis example 1, the desired compound 5.5 Inv7-127 g (yield: 79%). GC-Mass (calculated: 761.31 g / mol, measured: 761 g / mol)

[Synthesis Example 24: synthesis of compound Inv8-61] - Example 16

A solution of 5 g (11.38 mmol) of 4- (diphenylamino) phenylboronic acid, 3.95 g (13.65 mmol), Pd (PPh ₃ ), and ₃ -bromo-10,10- _{) 4 0.66 g (5 mol%} ), NaOH 1.37 g (34.14 mmol), and THF / distilled water (100ml / 50ml) Inv8-61 5.57 of the aimed compound by experiment in the same manner as in synthesis example 1 by using g (yield: 81 %). GC-Mass (theory: 603.24 g / mol, measured: 603 g / mol)

[Examples 1 to 11] Preparation and evaluation of organic EL devices

An organic EL device was prepared in the following manner.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum evaporator.

(40 nm) / Inv compound + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (10 nm) using the compounds of the present invention as a host on the ITO 1 nm) / Al. Then, their luminescent characteristics were evaluated. The results are shown in Table 1 below. Here, the compounds to be applied to the host are shown in Table 1 below.

[Comparative Example 1]

(40 nm) / CBP + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (1 nm) / Al on the electrode prepared in the same manner as in the above- And the luminescent characteristics were evaluated in the same manner as in Examples 1 to 11.

For reference, the structures of NPB, CBP and Ir (ppy) ₃ and BCP are as follows.

NPB

CBP

Ir (ppy) 3

BCP

Voltage (V) Brightness (cd / m ² ) Color Efficiency (cd / A) Inv5-16 (Example 1) 7.76 172 green 17.2 Inv5-57 (Example 2) 7.99 161 green 16.1 Inv7-35 (Example 6) 7.95 170 green 17.0 Inv7-106 (Example 7) 8.13 165 green 16.5 Inv8-42 (Example 8) 7.97 169 green 16.9 Inv9-14 (Example 9) 7.96 168 green 16.8 Inv9-51 (Example 10) 7.97 164 green 16.4 Inv10-35 (Example 11) 7.95 171 green 17.1 Comparative Example 7.94 174 green 17.4

As a result of the experiment, it was confirmed that the organic light emitting devices of Examples 1 to 11 using the triphenylene type compound of the present invention showed superior performance in terms of voltage and efficiency as compared with the organic EL device of Comparative Example 1 using CBP .

[Examples 12 to 16] Preparation and evaluation of organic EL devices

An organic EL device was prepared in the following manner.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum evaporator.

(Invol) / CBP + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (1 nm) using the compounds of the present invention as the hole transport layer on the ITO / Al, and their luminescent properties were evaluated. The results are shown in Table 2 below. Here, the compound to be used as the hole transporting layer is shown in Table 2 below.

[Comparative Example 2]

(40 nm) / CBP + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (1 nm) / Al on the electrode prepared in the same manner as in the above- , And then the luminescent characteristics were evaluated in the same manner as in Example 1. [

Voltage (V) Brightness (cd / m ² ) Color Efficiency (cd / A) Inv5-20 (Example 12) 7.38 193 green 19.3 Inv5-64 (Example 13) 7.67 187 green 18.7 Inv7-18 (Example 14) 7.68 185 green 18.5 Inv7-127 (Example 15) 7.69 184 green 18.4 Inv8-61 (Example 16) 7.71 194 green 19.4 Comparative Example 7.94 174 green 17.4

As a result of the experiment, it was confirmed that the organic light emitting devices of Examples 12 to 16 using the triphenylene type compound according to the present invention had far superior performance in terms of voltage and efficiency than the organic EL devices of the comparative example using NPB there was.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

Claims (4)

A material for an organic electroluminescence device characterized by being represented by the following formula (4)
[Chemical Formula 4]

In the above formulas,
R ₁ to _{R 6, R 8 ~ R 11} , R 13 ~ R 14, R 16 to R ₁₇ are the same group, or different, and each independently represent hydrogen, deuterium, a halogen, a nitro group, a nitrile C ₁ ~ C with each other _A C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a C ₅ to C ₄₀ heteroaryl group, a C ₁ to C ₄₀ alkoxy group, a heteroaryl group of C ₆ ~ C ₄₀ of the aryloxy group, C ₅ ~ C ₄₀ heteroaryl group, C ₅ ~ C ₄₀ of the de-heteroaryl group, C ₆ ~ C ₄₀ aryl group, C ₆ ~ C ₄₀ of, A C ₃ to C ₄₀ cycloalkyl group, a C ₁ to C ₄₀ halogen alkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₄₀ arylsilyl group, and C _{A 5} to C ₄₀ heteroarylsilyl group,
R ₇ is a C ₆ to C ₄₀ aryl group or a C ₅ to C ₄₀ heteroaryl group,
R ₁₂ is hydrogen. An organic electroluminescent device comprising: (i) a cathode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic material layers comprises the material for an organic electroluminescence device according to any one of claims 1 to 6. [ The organic light emitting device according to claim 2, wherein the organic material layer is selected from the group consisting of a light emitting layer, a hole injecting layer, and a hole transporting layer. The organic electroluminescent device according to claim 2, wherein the organic material layer including the organic electroluminescence device material is a phosphorescent host or a fluorescent host material of the light emitting layer.

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