KR20150051831A - Spyro type organic material and organic electroluminescent device and organic eletroluminescent device utilizing the same - Google Patents

Abstract

The present invention relates to a spyro type organic material represented by chemical formula 1, and to an organic electroluminescent device using the same, and more specifically, to a spyro type organic material which can obtain luminescence of short wavelength with high efficiency, and to an organic electroluminescent device using the same. In the formula, Ar_1 and Ar_2 are the same as defined in the specification.

Description

[0001] The present invention relates to a spirotic organic material and an organic electroluminescent device using the spirotic organic material,

The present invention relates to a spiropy type organic material and an organic electroluminescence device using the same. More particularly, the present invention relates to a spiropy type organic material which can obtain light of a short wavelength which can be used for an organic electroluminescence device, And an organic electroluminescent device using the same.

Organic semiconductors are being developed for many types of electronic equipment applications. The organic electroluminescent device has a simple structure compared to other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP), and a field emission display (FED) And has a high response speed and a low driving voltage, so that it is being actively developed to be used as a light source for a flat panel display such as a wall-mounted TV or a backlight of a display, a lighting, and a billboard.

In the organic electroluminescent device, when a direct current voltage is applied, holes injected from the anode recombine with electrons injected from the cathode to form an exciton, which is an electron-hole pair, and the energy of the exciton is transferred to the light emitting material .

In order to improve the efficiency and stability of organic electroluminescent devices, CW Tang, et al. (KW Tang, SA Vanslyke, Applied Physics Letters, vol. 51, p. 913, 1987), studies on organic materials for multilayer thin film structure organic electroluminescent devices have been actively conducted.

On the other hand, spyro-type compounds are known to have excellent thermal stability and device characteristics. However, a substance having a blue light emitting layer in a short wavelength region using a spiromolecular compound has not been reported.

Thus, the present inventors have studied an aromatic compound capable of achieving light emission with a short wavelength at a high efficiency, confirming that an asymmetric spiro-type compound can solve the above problems, thereby completing the present invention.

Disclosed herein is a spiro-type organic material capable of emitting light having a short wavelength with high efficiency, and an organic electroluminescent device using the same.

In order to solve the above problems, the present invention provides a compound represented by the following general formula (1).

[Chemical Formula 1]

In this formula,

And Ar ₁ is phenyl, said phenyl being optionally substituted with one or two substituents, unsubstituted or substituted, or halogen, C _{1 -4} haloalkyl, cyano, independently selected from the group consisting of phenyl and trimethylsilyl,

Ar ₂ is phenyl or naphthyl, said phenyl is substituted with halogen, C _{1 -4} haloalkyl, cyano, and any one or two substituents independently selected from the group consisting of trimethyl silyl.

The compound represented by Formula 1 has a structure of spiro [benzo [de] anthracene-7,9'-fluorene] (spiro [benzo [de] anthracene- Which is stronger than the structure of the compound and is difficult to crystallize. In addition, it has an asymmetric structure and is characterized in that it can emit blue light because its secondary amine derivative is substituted.

Preferably, Ar ₁ is phenyl and the phenyl is unsubstituted or substituted with one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl do.

Also preferably, said phenyl is substituted with any one substituent selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl.

Also preferably, the phenyl is substituted with two trifluoromethyls.

Also preferably, Ar ₂ is phenyl and the phenyl is substituted with any one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano, and trimethylsilyl.

Also preferably, the phenyl is substituted with any one substituent selected from the group consisting of fluoro, trifluoromethyl, cyano, and trimethylsilyl.

Also preferably, the phenyl is substituted with two trifluoromethyls.

Representative examples of the compound represented by the above formula (1) are as follows:

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In addition, the present invention provides, for example, a process for preparing a compound represented by the above-mentioned formula (1), as shown in Reaction Scheme 1 below. In the following Reaction Scheme 1, Ar ₁ and Ar ₂ are as defined above.

[Reaction Scheme 1]

Step 1 is a step of reacting a compound represented by formula (2) with a compound represented by formula (3) to prepare a compound represented by formula (1). The solvent may be toluene, and the reaction is preferably carried out in the presence of palladium acetate (II), BINAP (2,2'-bis (diphenylphosphino) -1,1'-binaphthyl), sodium-t-butoxide or the like.

The compound represented by Formula 2 may be prepared, for example, as shown in Reaction Scheme 2 below. In the present invention, the compound represented by Formula 2 is prepared and used in the following Production Examples.

[Reaction Scheme 2]

Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. The organic electroluminescent device according to the present invention is characterized in that at least one layer of the organic thin film layer is represented by the above formula (1), wherein the organic thin film layer comprises a single layer or a plurality of organic thin film layers sandwiching a cathode and an anode, An organic electroluminescent device comprising an organic electroluminescent device comprising a compound.

The compound of the spiro structure and the organic electroluminescent device using the same according to the present invention can emit light having a short wavelength with high efficiency and can be applied to various organic electroluminescent devices such as a flat panel display such as a wall- Can be used.

Hereinafter, the present invention will be described in more detail with reference to Examples. These embodiments are only for describing the present invention more specifically, and the scope of the present invention is not limited by these examples.

Manufacturing example  1: Preparation of intermediate 1

1) Preparation of intermediate 1-2

(50 g), 4-chlorophenylboronic acid (21 g), toluene (1000 mL), potassium carbonate (96 g) and water (250 mL) were placed in a 2 L 3-neck round bottom flask Lt; / RTI > Tetrakis (triphenylphosphine) palladium (0) (0.81 g) was added to the mixed solution, and the mixture was heated at 110 ° C for 8 hours. The reaction solution was cooled to room temperature and extracted twice with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent. The material formed by concentration was separated by column using hexane and washed with methanol to obtain 40 g of a white powder.

2) Preparation of intermediate 1-3

Intermediate 1-2 (40 g) and tetrahydrofuran (600 mL) were placed in a 2 L three-neck round bottom flask, stirred under an argon atmosphere, and the temperature of the mixture was lowered to -78 ° C. N-Butyl lithium (50 mL) was slowly added thereto, followed by stirring at the same temperature for 2 hours. Fluorenone (32.6 g) was added to the above mixed solution, the temperature of the mixed solution was raised to room temperature, and the mixture was stirred for 12 hours. Water (300 mL) was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted twice with ethyl acetate, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent.

3) Preparation of intermediate 1

Intermediate 1-3 (60 g), acetic acid (1200 mL) and hydrochloric acid (48 mL) were added to a 2 L three-necked round bottom flask, followed by stirring at 110 ° C for 8 hours and cooling. The reaction solution was filtered, washed sequentially with water and methanol, and then dried to obtain 42 g of an intermediate compound 1-4 of white powder.

Manufacturing example  2: Preparation of intermediate 2

1) Preparation of intermediate 2-1

4-Aminobenzonitrile (15 g) was added to a 2 L three-neck round bottom flask and stirred for 30 minutes under argon atmosphere. After stirring for 30 minutes, bromobenzene (18.1 g) was added and dissolved in toluene (1 L). Tris (dibenzylideneacetone) dipalladium (0) (1.06 g) and tri-t-butylphosphine (0.23 g) , And sodium-t-butoxide (24.4 g) were added thereto, and the mixture was refluxed with stirring for 18 hours. After filtration under hot conditions, the solid on the filter was washed with hot toluene, dichloromethane and the filtrate was concentrated under reduced pressure. The reaction mixture was extracted with water and methylene chloride, dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent. The resulting material was purified by silica gel column chromatography (eluent: n-hexane: ethyl acetate = 4: 1) and then recrystallized from dichloromethane and hexane to obtain a white solid of the following formula.

2) Preparation of intermediate 2-2 to 2-63

Intermediates 2-2 to 2-63 having the structures shown in Tables 1 to 4 below were prepared in a similar manner to the preparation of Intermediate 2-1.

Intermediate
number Chemical structure Intermediate
number Chemical structure Intermediate
number Chemical structure 2-2

2-7

2-12

2-3

2-8

2-13

2-4

2-9

2-14

2-5

2-10

2-15

2-6

2-11

2-16

Intermediate
number Chemical structure Intermediate
number Chemical structure Intermediate
number Chemical structure 2-17

2-22

2-27

2-18

2-23

2-28

2-19

2-24

2-29

2-20

2-25

2-30

2-21

2-26

2-31

Intermediate
number Chemical structure Intermediate
number Chemical structure Intermediate
number Chemical structure 2-32

2-37

2-42

2-33

2-38

2-43

2-34

2-39

2-44

2-35

2-40

2-45

2-36

2-41

2-46

Intermediate
number Chemical structure Intermediate
number Chemical structure Intermediate
number Chemical structure 2-47

2-53

2-59

2-48

2-54

2-60

2-49

2-55

2-61

2-50

2-56

2-62

2-51

2-57

2-63

2-52

2-58

Example  One

Intermediate 2-1 (15 g) was added to a 1 L three-neck round bottom flask and stirred under argon atmosphere for 30 minutes. After stirring for 30 minutes, intermediate 1 (19 g) was added and dissolved in toluene (370 mL). Palladium acetate (II) (0.35 g), tri-t-butylphosphine (0.8 g), sodium-t-butoxide g) was added thereto, and the mixture was refluxed with stirring for 18 hours. After the reaction was completed, the reaction solution was filtered in a hot state. The solid on the filter was washed with hot toluene and dichloromethane, and the filtrate was concentrated under reduced pressure. The resulting material was purified by silica gel column chromatography (eluent: n-hexane: dichloromethane = 1: 1) and then recrystallized from tetrahydrofuran to obtain a light green solid (11 g) having the following structure .

^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 8.11 (d, 1H), 8.08 (d, 1H), 7.74 (m, 3H), 7.48 (d, 1H), 7.40 (d, 2H) (D, 2H), 7.34 (m, 4H), 7.24 (m, 6H), 7.14 6.62 (d, 1 H), 6.28 (d, 1 H)

Example  2 to 63

Preparations were carried out in the same manner as in Example 1, except that Intermediates 2-2 to 2-63 were used instead of Intermediate 2-1, respectively, to give the compounds of Examples 2 to 63. Structures and NMR data of Examples 2 to 63 prepared respectively are shown in Tables 5 to 17 below.

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 2

2H), 7.32 (d, 2H), 7.30 (m, 5H), 7.22 (m, 7H), 7.14 (d, (m, 4H), 7.11 (d, 2H), 6.87 (d, 2H), 6.77 (d, 2H), 6.71 3

2H), 7.31 (m, 4H), 7.21 (m, 6H), 7.19 (d, (m, 6H), 7.06 (d, 2H), 7.01 (d, 2H), 6.98 (m, 3H) 4

(M, 6H), 7.14 (m, 5H), 7.00 (d, IH) (d, 2H), 6.95 (d, 2H), 6.91 (m, 3H) 5

7H), 7.17 (m, 3H), 7.11 (m, 2H), 7.30 (m, 2H) (d, 2H), 7.05 (d, 2H), 7.04 (m, 3H), 6.91

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 6

2H), 7.31 (d, IH), 7.27 (m, 6H), 7.22 (m, (m, 2H), 6.94 (d, 2H), 6.94 (d, 2H) 7

2H), 7.36 (d, IH), 7.16 (d, IH), 8.13 (d, (d, 2H), 7.02 (d, 2H), 6.98 (m, 3H), 6.74 (d, 2H), 6.63 8

2H), 7.44 (m, 4H), 7.17 (m, 6H), 7.20 (d, IH) (d, 2H), 6.83 (d, 2H), 6.88 (m, 3H), 6.71 s, 18H) 9

2H), 7.32 (m, 4H), 7.23 (m, 6H), 7.17 (m, 5H), 7.07 (d, (d, 2H), 6.99 (d, 2H), 6.90 (m, 3H), 6.80 (d, 2H), 6.65 10

2H), 7.34 (m, 4H), 7.27 (m, 6H), 7.14 (d, IH) 2H), 6.94 (d, 2H), 6.91 (m, 3H), 6.74 (d, 2H)

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 11

2H), 7.34 (m, 4H), 7.24 (m, 6H), 7.14 (d, IH) (m, 3H), 7.02 (d, 2H), 6.97 (d, 2H), 6.91 (m, 12

2H), 7.34 (m, 4H), 7.24 (m, 6H), 7.17 (d, IH) (m, 3H), 7.15 (d, 2H), 6.93 (d, 2H), 6.90 13

2H), 7.37 (m, 4H), 7.27 (m, 6H), 7.20 (d, IH) (m, 3H), 6.97 (d, 2H), 6.98 (d, 2H), 6.94 14

2H), 7.32 (m, 4H), 7.30 (m, 6H), 7.22 (d, (m, 3H), 7.11 (d, 2H), 6.99 (d, 2H), 6.91 15

2H), 7.44 (m, 4H), 7.31 (m, 6H), 7.11 (d, IH) (m, 3H), 7.02 (d, 2H), 6.97 (d, 2H), 6.89

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 16

4H), 7.30 (m, 6H), 7.20 (m, 6H), 7.02 (d, (d, 2H), 6.95 (d, 2H), 6.91 (m, 6H) 17

2H), 7.34 (m, 4H), 7.24 (m, 6H), 7.21 (d, IH) (d, 2H), 7.06 (d, 2H), 6.77 (m, 3H), 6.62 (d, 2H), 6.51 s, 18H) 18

2H), 7.31 (d, IH), 7.25 (m, 6H), 7.21 (d, 2H), 6.99 (d, 2H), 6.69 (m, 3H), 6.52 (d, 2H), 6.41 s, 18H) 19

(M, 6H), 7.14 (m, 6H), 7.02 (d, IH) (d, 2H), 6.95 (d, 2H), 6.91 (m, 6H) 20

2H), 7.32 (d, IH), 7.22 (m, 6H), 7.14 (d, (m, 3H), 7.07 (d, 2H), 6.96 (d, 2H), 6.90

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 21

2H), 7.28 (m, 4H), 7.25 (m, 6H), 7.13 (d, (m, 3H), 7.10 (d, 2H), 6.96 (d, 2H), 6.91 22

2H), 7.34 (m, 4H), 7.27 (m, 6H), 7.14 (d, IH) (m, 3H), 7.10 (d, 2H), 6.99 (d, 2H), 6.91 (m, 3H) 23

2H), 7.47 (m, 4H), 7.31 (m, 6H), 7.25 (d, IH) (m, 3H), 7.07 (d, 2H), 6.99 (d, 2H), 6.89 24

2H), 7.30 (m, 4H), 7.24 (m, 6H), 7.21 (d, IH) (m, 3H), 7.16 (d, 2H), 6.90 (d, 2H), 6.92 25

2H), 7.31 (m, 4H), 7.28 (m, 6H), 7.21 (d, IH) (m, 3H), 7.14 (d, 2H), 7.03 (d, 2H), 6.90 (m,

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 26

2H), 7.31 (m, 4H), 7.21 (m, 6H), 7.11 (d, (m, 3H), 7.07 (d, 2H), 6.96 (d, 2H), 6.90 27

2H), 7.43 (m, 4H), 7.27 (m, 6H), 7.17 (d, IH) (m, 6H), 7.02 (d, 2H), 6.94 (d, 2H), 6.80 (m, 6H) 28

(M, 2H), 7.20 (d, IH), 7.41 (d, IH) (d, 2H), 6.91 (d, 2H), 6.80 (m, 3H), 6.71 (d, 2H), 6.54 29

2H), 7.39 (d, 2H), 7.34 (m, 4H), 7.28 (m, 6H), 7.21 (d, (m, 5H), 7.07 (d, 2H), 7.01 (d, 2H), 6.69 (m, 3H), 6.52 (d, 2H), 6.39 s, 18H) 30

2H), 7.42 (m, 4H), 7.23 (m, 6H), 7.20 (d, IH) (m, 6H), 7.02 (d, 2H), 6.94 (d, 2H), 6.88 (m, 6H)

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 31

2H), 7.37 (m, 4H), 7.26 (m, 6H), 7.17 (m, 6H), 7.04 (d, 2H) (d, 2H), 6.94 (d, 2H), 6.86 (m, 6H), 6.71 (m, 4H) 32

6H), 7.15 (m, 6H), 7.02 (d, 2H), 8.02 (m, 2H) (d, 2H), 6.94 (d, 2H), 6.84 (m, 6H), 6.66 (m, 4H) 33

(D, 2H), 7.32 (d, 2H), 7.97 (m, 4H) (d, 2H), 6.95 (d, 2H), 6.84 (m, 6H), 6.72 (m, 4H) 34

2H), 8.24 (m, 2H), 8.14 (m, 2H), 8.14 (m, (d, 2H), 6.90 (m, 6H), 6.80 (m, 4H) 35

2H), 7.31 (d, IH), 7.22 (m, 6H), 7.19 (d, (m, 6H), 7.01 (d, 2H), 6.94 (d, 2H), 6.84

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 36

6H), 7.13 (m, 6H), 6.99 (d, 2H), 8.18 (d, 2H) (d, 2H), 6.91 (d, 2H), 6.85 (m, 6H) 37

2H), 7.34 (m, 4H), 7.25 (m, 6H), 7.13 (m, 6H), 7.01 (d, 2H), 6.92 (d, 2H), 6.84 (m, 6H), 6.66 (m, 4H), 6.54 38

6H), 7.51 (m, 6H), 7.05 (m, 4H), 7.18 (d, 2H) (d, 2H), 6.93 (d, 2H), 6.84 (m, 6H), 6.72 (m, 4H) 39

2H), 7.22 (m, 6H), 7.54 (m, 6H), 7.22 (d, 2H) (d, 2H), 7.03 (d, 2H), 6.92 (m, 6H), 6.82 (m, 4H), 6.54 40

2H), 7.41 (m, 4H), 7.33 (m, 6H), 7.14 (d, IH) (m, 6H), 7.05 (d, 2H), 6.97 (d, 2H), 6.88 (m, 6H)

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 41

2H), 7.35 (m, 4H), 7.23 (m, 6H), 7.17 (d, IH) (m, 6H), 7.04 (d, 2H), 6.94 (d, 2H), 6.81 (m, 6H) 42

2H), 7.37 (m, 4H), 7.23 (m, 6H), 7.11 (d, IH) (m, 6H), 7.02 (d, 2H), 6.91 (d, 2H), 6.87 (m, 6H) 43

2H), 7.41 (m, 4H), 7.27 (m, 6H), 7.17 (d, IH) 2H), 6.79 (d, 2H), 6.79 (m, 6H), 6.69 (d, 2H), 6.57 44

2H), 7.44 (d, IH), 7.31 (m, 6H), 7.14 (d, (m, 6H), 7.09 (d, 2H), 6.95 (d, 2H), 6.88 (m, 6H) 45

2H), 7.41 (m, 4H), 7.32 (m, 6H), 7.11 (d, IH) (d, 2H), 6.98 (d, 2H), 6.78 (m, 6H), 6.74 (d, 2H), 6.44 s, 18H)

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 46

2H), 7.31 (m, 4H), 7.31 (m, 6H), 7.12 (d, IH) (m, 6H), 7.03 (d, 2H), 6.93 (d, 2H), 6.81 (m, 6H) 47

2H), 7.34 (m, 4H), 7.26 (m, 6H), 7.20 (d, IH) (m, 3H), 7.15 (d, 2H), 6.98 (d, 2H), 6.94 48

2H), 7.31 (m, 4H), 7.25 (m, 6H), 7.19 (d, IH) (m, 3H), 7.11 (d, 2H), 6.92 (d, 2H), 6.93 49

8.33 (d, 1 H), 8.19 (d, 1 H), 8.01 (m, 3H), 7.68 (d, 1H), 7.48 (m, 3H), 7.12 (d, 2H), 6.95 (d, 2H), 6.91 50

2H), 7.32 (d, IH), 7.27 (m, 6H), 7.23 (d, (d, 2H), 6.99 (d, 2H), 6.69 (m, 3H), 6.53 s, 18H)

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 51

2H), 7.31 (m, 4H), 7.23 (m, 6H), 7.18 (d, IH) (d, 2H), 6.69 (d, 2H), 6.69 (m, 3H), 6.52 s, 18H) 52

2H), 7.31 (m, 4H), 7.27 (m, 6H), 7.18 (d, IH) (m, 3H), 7.12 (d, 2H), 6.98 (d, 2H), 6.92 53

2H), 7.40 (d, IH), 7.25 (m, 6H), 7.14 (d, (m, 6H), 7.02 (d, 2H), 6.95 (d, 2H), 6.72 (m, 6H) 54

2H), 7.97 (d, IH), 7.47 (d, 2H), 7.32 (m, 4H), 7.01 (m, 9H), 7.12 (d, 2H), 6.94 (d, 2H), 6.92 (m, 3H) 55

2H), 7.36 (m, 4H), 7.26 (m, 6H), 7.23 (d, IH) (m, 3H), 7.12 (d, 2H), 6.95 (d, 2H), 6.91

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 56

2H), 7.34 (m, 4H), 7.23 (m, 6H), 7.20 (d, IH) (m, 3H), 7.09 (d, 2H), 6.98 (d, 2H), 6.88 57

2H), 7.29 (m, 3H), 7.24 (m, 3H), 7.11 (d, (d, 2H), 6.98 (d, 2H), 6.81 (m, 3H), 6.68 58

2H), 7.34 (m, 4H), 7.24 (m, 6H), 7.21 (d, IH) (d, 2H), 6.84 (d, 2H), 6.74 (m, 3H), 6.52 s, 18H) 59

2H), 7.41 (d, 2H), 7.33 (m, 4H), 7.22 (m, 6H), 7.19 (d, (d, 2H), 7.03 (d, 2H), 6.56 (m, 3H), 6.42 (d, 2H), 6.33 s, 18H) 60

2H), 7.37 (m, 4H), 7.27 (m, 6H), 7.11 (d, IH) (m, 6H), 6.99 (d, 2H), 6.97 (d, 2H), 6.79

Example
number Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 61

7H), 7.12 (m, 3H), 7.05 (m, 2H), 7.20 (d, (d, 2H), 6.98 (d, 2H), 6.81 (m, 2H), 6.71 62

6H), 7.13 (m, 6H), 7.01 (d, 2H), 8.04 (m, 2H) (d, 2H), 6.93 (d, 2H), 6.85 (m, 6H) 63

2H), 7.32 (m, 4H), 7.22 (m, 6H), 7.13 (d, IH) (m, 3H), 7.06 (d, 2H), 6.96 (d, 2H), 6.84 s, 36H)

Experimental Example

Experimental Example  One: Example  Preparation of organic electroluminescent device using

The ITO transparent electrode with a thin film thickness of 100 nm was cleaned by ultrasonic wave for 10 minutes in a distillation shoe in which the detergent dissolved in a size of 40 mm × 40 mm × 0.7 m and washed twice in distilled water for 10 minutes.

After the distilled water was washed, solvents such as isopropyl alcohol, acetone and methanol were sequentially ultrasonically washed and dried. After the wet refining, the substrate was dry-cleaned using oxygen / argon plasma, and then a glass substrate having a transparent electrode line was mounted on a substrate holder of a vacuum evaporation apparatus. On the surface of the ITO side on which the transparent electrode line was formed, Was thermally vacuum deposited to a thickness of 3 nm to form a hole injection layer.

(A)

A layer of a compound represented by the following formula (B) capable of hole transporting was vacuum deposited on the compound layer represented by the formula (A) at 80 nm.

[Chemical Formula B]

The compound of Example 1 of the present invention was mixed and vapor-deposited as a blue dopant at a concentration of 5% together with a compound represented by the following formula (C) as a light emitting host on the compound layer represented by the formula (B) to form a light emitting layer with a thickness of 20 nm.

≪ RTI ID = 0.0 &

A compound represented by the following formula (D) serving as an electron injecting and transporting layer was vacuum deposited on the light emitting layer to a thickness of 25 nm.

[Chemical Formula D]

Lithium fluoride (LiF) with a thickness of 0.7 nm and aluminum with a thickness of 120 nm were sequentially deposited on the electron injection and transport layer to form a cathode. The resulting organic light emitting device was sagged at a voltage of 4 V, resulting in a current density of 6.2 mA / cm 2. At this time, the brightness of 217 cd / m 2 corresponding to x = 0.145 and y = 0.093 on the basis of 1931 CIE color coordinates A spectrum close to pure blue was observed and the efficiency was 3.50 cd / A.

Experimental Example  2: Example  9 for the fabrication of organic electroluminescent devices

An organic electroluminescent device was prepared in the same manner as in Experimental Example 1 except that the compound of Example 9 was used instead of the compound of Example 1 which is a luminescent dopant material.

The organic EL device thus fabricated was measured at a voltage of 4 V. As a result, a current density of 6.1 mA / cm 2 was formed. The luminance of 236 cd / m 2 corresponding to x = 0.144 and y = 0.097 on the basis of 1931 CIE color coordinates A spectrum close to pure blue was observed and the efficiency was 3.87 cd / A.

Experimental Example  3: Example  31 Fabrication of Organic Electroluminescent Devices

An organic electroluminescent device was produced in the same manner as in Experimental Example 1 except that the compound of Example 31 was used instead of the compound of Example 1 which is a luminescent dopant material.

The organic EL device thus fabricated had a current density of 5.8 mA / cm < 2 > at a voltage of 4 V. The current density was 218 cd / m < 2 > corresponding to x = 0.145 and y = A spectrum close to pure blue was observed and the efficiency was 3.76 cd / A.

Comparative Example

An organic electroluminescent device was prepared using the same method as in Experimental Example 1 except that the compound represented by the following Formula E was used instead of the compound of Example 1 which is a luminescent dopant material.

(E)

The resultant organic electroluminescent device was measured at a voltage of 4V. As a result, the current density was 1.46 mA / cm 2. At this time, the brightness of 68.1 cd / m 2 corresponding to x = 0.130 and y = 0.180 on the basis of 1931 CIE color coordinates A spectrum close to pure blue was observed and the efficiency was 4.66 cd / A.

The above results are summarized in Table 18 below.

Current density
(mA / cm 2) brightness
(cd / m 2) Luminous efficiency
(cd / A) Color coordinates @ 4V CIEx CIEy Example 1 6.2 217 3.50 0.145 0.093 Example 9 6.1 236 3.87 0.144 0.097 Example 31 5.8 218 3.76 0.145 0.091 Comparative Example 1.46 68.1 4.66 0.130 0.180

Claims (9)

A compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
And Ar ₁ is phenyl, said phenyl being optionally substituted with one or two substituents, unsubstituted or substituted, or halogen, C _{1 -4} haloalkyl, cyano, independently selected from the group consisting of phenyl and trimethylsilyl,
Ar ₂ is phenyl or naphthyl, said phenyl is substituted with halogen, C _{1 -4} haloalkyl, cyano, and any one or two substituents independently selected from the group consisting of trimethyl silyl.
The method according to claim 1,
Wherein Ar ₁ is phenyl and the phenyl is unsubstituted or substituted with one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl .
3. The method of claim 2,
Wherein said phenyl is substituted with any one substituent selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl.
3. The method of claim 2,
≪ / RTI > wherein said phenyl is substituted with two trifluoromethyls.
The method according to claim 1,
Wherein Ar ₂ is phenyl and the phenyl is substituted with any one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano, and trimethylsilyl.
6. The method of claim 5,
Wherein said phenyl is substituted with any one substituent selected from the group consisting of fluoro, trifluoromethyl, cyano, and trimethylsilyl.
6. The method of claim 5,
≪ / RTI > wherein said phenyl is substituted with two trifluoromethyls.
The compound according to claim 1, wherein the compound is

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And

≪ / RTI > is a compound of formula < RTI ID = 0.0 >
9. An organic electroluminescent device comprising a compound according to any one of claims 1 to 8.