KR101482632B1 - Spyro type organic material and organic electroluminescent device and organic eletroluminescent device utilizing the same - Google Patents

Abstract

The present invention relates to a spiro-type organic material represented by the following formula (1) and an organic electroluminescence device using the same, and more particularly, to a spiro-type organic material capable of emitting light with a short wavelength with high efficiency, And to provide an electroluminescent device.
[Chemical Formula 1]

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 R 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,

R 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, said R ₁ is phenyl and said 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, the R 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, R ₁ and R 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 (30.1 g), toluene (500 mL), potassium carbonate (132.9 g) and water (250 mL) were placed in a 2 L three- Lt; / RTI > Tetrakis (triphenylphosphine) palladium (0) (2.22 g) was added to the mixture, 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 35 g of a white powder.

2) Preparation of intermediate 1-3

Intermediate 1-2 (35 g) and tetrahydrofuran (525 mL) were placed in a 2 L three-neck round bottom flask, stirred under argon atmosphere and the temperature of the mixture was lowered to -78 ° C. N-Butyl lithium (44.1 mL) was slowly added thereto, followed by stirring at the same temperature for 2 hours. Fluorenone (19.9 g) was added to the above mixed solution, the temperature of the mixed solution was raised to room temperature, and then stirred for 12 hours. Water (200 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 1-4

Intermediate 1-3 (46 g), acetic acid (918 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 35.5 g of an intermediate compound 1-4 of white powder.

4) Preparation of intermediate 1

Intermediate 1-4 (33.5 g) was added to 335 mL of carbon tetrachloride under an argon atmosphere, and the mixture was stirred until completely dissolved. After confirming that the intermediate 1-4 was completely dissolved, bromine (13.4 mL) was added and refluxed for 72 hours. After completion of the reaction, the reaction mixture was filtered under reduced pressure at room temperature, washed with aqueous sodium hydroxide solution, and the filtered solid was vacuum dried to obtain 40.1 g of intermediate 1.

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 2-76

Intermediates 2-2 to 2-76 having the structures shown in Tables 1 to 5 below were prepared in a similar manner to the preparation of Intermediate 2-1.

Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure 2

7

12

3

8

13

4

9

14

5

10

15

6

11

16

Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure 17

22

27

18

23

28

19

24

29

20

25

30

21

26

31

Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure 32

37

42

33

38

43

34

39

44

35

40

45

36

41

46

Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure 47

52 57

48

53

58

49

54

59

50

55

60

51

56

61

Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure Manufacturing example
number Chemical structure 62

67

72

63

68

73

64

69

74

65

70

75

66

71

76

Example  One

The intermediate 1 (10.7 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, intermediate 2-1 (12 g) was added and dissolved in toluene (1 L). Palladium acetate (II) (0.22 g), BINAP (0.62 g) and sodium-t-butoxide 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 material produced by concentration was purified by silica gel column chromatography (eluent: n-hexane: dichloromethane = 3: 1) and recrystallized from tetrahydrofuran to obtain a green-yellow solid having the structure shown below.

^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 8.14 (d, 1H), 8.05 (d, 1H), 7.71 (m, 3H), 7.48 (d, 1H), 7.40 (d, 2H) , 7.34 (m, 4H), 7.24 (m, 6H), 7.14 (m, 5H), 7.00 (d, 2H), 6.95 6.62 (d, 1 H), 6.28 (d, 1 H)

Example  2 to 76

Preparations were carried out in the same manner as in Example 1, except that Intermediates 2-2 to 2-76 were used instead of Intermediate 2-1 to prepare the compounds of Examples 2 to 76, respectively. Structures and NMR data of Examples 2 to 76 prepared respectively are shown in Tables 6 to 20 below.

Example 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 (m, 4H), 7.11 (d, 2H), 6.87 (d, 2H), 6.77 (d, 2H), 6.69 3

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

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

(M, 3H), 7.17 (m, 3H), 7.11 (m, 2H), 7.30 (d, 2H), 7.05 (d, 2H), 7.01 (m, 3H), 6.87

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

(D, 2H), 7.33 (m, 4H), 7.27 (m, 6H), 7.22 (d, (m, 2H), 6.94 (d, 2H), 6.94 (d, 2H) 7

2H), 7.31 (d, IH), 7.17 (d, IH), 8.15 (m, (m, 2H), 7.01 (d, 2H), 6.98 (m, 3H), 6.74 (d, 2H), 6.63 (d, 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, 2H), 6.96 (d, 2H), 6.91 (m, 3H), 6.74 (d, 2H), 6.62 (d,

Example 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), 7.00 (d, 2H), 6.95 (d, 2H), 6.91 12

2H), 7.34 (m, 4H), 7.24 (m, 6H), 7.17 (d, IH) (m, 3H), 7.12 (d, 2H), 6.95 (d, 2H), 6.91 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, IH) 2H), 6.99 (d, 2H), 6.91 (m, 3H), 6.69 (d, 2H), 6.58 15

2H), 7.44 (m, 4H), 7.29 (m, 6H), 7.11 (d, IH) (m, 3H), 7.02 (d, 2H), 6.97 (d, 2H), 6.89

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

2H), 7.43 (m, 4H), 7.30 (m, 6H), 7.17 (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), 7.20 (d, IH) (d, 2H), 7.04 (d, 2H), 6.77 (m, 3H), 6.62 (d, 2H), 6.51 s, 18H) 18

2H), 7.24 (m, 6H), 7.21 (d, IH), 8.14 (d, IH) (d, 2H), 6.99 (d, 2H), 6.69 (m, 3H), 6.52 s, 18H) 19

(M, 6H), 7.14 (m, 6H), 7.02 (d, IH) (d, 2H), 6.95 (d, 2H), 6.88 (m, 6H) 20

2H), 7.34 (m, 4H), 7.22 (m, 6H), 7.14 (d, IH) (m, 3H), 7.10 (d, 2H), 6.96 (d, 2H), 6.90 (m, 3H)

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

2H), 7.31 (m, 4H), 7.27 (m, 6H), 7.13 (d, IH) (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), 7.11 (d, 2H), 6.96 (d, 2H), 6.91 23

2H), 7.42 (d, IH), 7.31 (m, 6H), 7.22 (d, (m, 3H), 7.07 (d, 2H), 6.97 (d, 2H), 6.89 24

2H), 7.30 (m, 4H), 7.24 (m, 6H), 7.21 (d, IH) (m, 3H), 7.16 (d, 2H), 6.87 (d, 2H), 6.92 25

2H), 7.31 (m, 4H), 7.28 (m, 6H), 7.21 (d, IH) (m, 3H), 7.14 (d, 2H), 7.00 (d, 2H), 6.90 (m,

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

2H), 7.31 (d, IH), 7.21 (m, 6H), 7.14 (m, (m, 3H), 7.10 (d, 2H), 6.96 (d, 2H), 6.90 (m, 3H) 27

2H), 7.43 (m, 4H), 7.30 (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), 6.92 (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, (d, 2H), 7.01 (d, 2H), 6.69 (m, 3H), 6.52 (d, 2H), 6.39 s, 18H) 30

2H), 7.40 (d, IH), 7.20 (d, IH) (m, 6H), 7.02 (d, 2H), 6.94 (d, 2H), 6.88 (m, 6H)

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

4H), 7.24 (m, 6H), 7.17 (m, 6H), 7.04 (d, 2H) (d, 2H), 6.92 (d, 2H), 6.86 (m, 6H), 6.71 (m, 4H) 32

2H), 7.32 (m, 4H), 7.22 (m, 6H), 7.15 (m, 6H), 7.02 (d, 2H), 6.94 (d, 2H), 6.84 (m, 6H), 6.66 (m, 4H) 33

2H), 7.34 (m, 4H), 7.26 (m, 6H), 7.5 (m, 6H), 7.05 (d, 2H), 6.93 (d, 2H), 6.84 (m, 6H) 34

2H), 7.14 (m, 2H), 6.94 (d, 2H), 8.24 (d, 2H) (d, 2H), 6.90 (m, 6H), 6.80 (m, 4H) 35

2H), 7.32 (d, IH), 7.22 (m, 6H), 7.14 (d, 2H) (m, 6H), 7.01 (d, 2H), 6.94 (d, 2H), 6.84

Example 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), 7.20 (d, IH), 7.52 (d, 2H), 8.02 (m, (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), 7.17 (d, 2H) (d, 2H), 6.93 (d, 2H), 6.84 (m, 6H), 6.72 (m, 4H) 39

2H), 7.22 (d, 2H), 7.91 (m, 4H), 7.84 (d, 2H), 7.42 (d, 2H), 7.01 (d, 2H), 6.90 (m, 6H), 6.82 (m, 4H), 6.54 40

2H), 7.41 (m, 4H), 7.33 (m, 6H), 7.14 (d, IH) (m, 6H), 7.03 (d, 2H), 6.95 (d, 2H), 6.88 (m, 6H)

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

2H), 7.33 (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) 2H), 6.92 (d, 2H), 6.88 (m, 6H), 6.72 (d, 2H), 6.54 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), 7.43 (m, 4H), 7.29 (m, 6H), 7.14 (d, (m, 6H), 7.07 (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), 6.96 (d, 2H), 6.78 (m, 6H), 6.72 (d, 2H), 6.44 s, 18H)

Example 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), 6.8 47

2H), 7.34 (m, 4H), 7.26 (m, 6H), 7.20 (d, IH) (m, 3H), 7.13 (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

2H), 7.37 (m, 4H), 7.26 (m, 6H), 7.23 (d, IH) (m, 3H), 7.12 (d, 2H), 6.95 (d, 2H), 6.91 50

2H), 7.41 (d, 2H), 7.34 (m, 4H), 7.27 (m, 6H), 7.21 (d, (d, 2H), 6.99 (d, 2H), 6.69 (m, 3H), 6.53 s, 18H)

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

2H), 7.40 (d, 2H), 7.31 (m, 4H), 7.24 (m, 6H), 7.20 (d, 2H), 6.69 (d, 2H), 6.69 (m, 3H), 6.52 s, 18H) 52

2H), 7.31 (m, 4H), 7.27 (m, 6H), 7.20 (d, IH) (m, 3H), 7.14 (d, 2H), 6.98 (d, 2H), 6.92 (m, 3H) 53

2H), 7.40 (m, 4H), 7.27 (m, 6H), 7.14 (d, IH) (m, 6H), 7.02 (d, 2H), 6.95 (d, 2H), 6.72 (m, 6H) 54

2H), 7.31 (d, IH), 7.21 (m, 6H), 7.13 (m, 6H), 7.01 (d, 2H), 6.92 (d, 2H), 6.84 (m, 6H), 6.64 (m, 4H), 6.54 55

2H), 7.34 (m, 4H), 7.27 (m, 6H), 7.14 (d, IH) (m, 3H), 7.02 (d, 2H), 6.97 (d, 2H), 6.91

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

2H), 7.35 (m, 4H), 7.21 (m, 6H), 7.17 (d, IH) (m, 3H), 7.12 (d, 2H), 6.95 (d, 2H), 6.91 57

2H), 7.37 (m, 4H), 7.27 (m, 6H), 7.15 (d, IH) (m, 3H), 7.10 (d, 2H), 6.92 (d, 2H), 6.80 58

2H), 7.34 (m, 4H), 7.23 (m, 6H), 7.19 (d, IH) (m, 3H), 7.12 (d, 2H), 6.87 (d, 2H), 6.91 59

2H), 7.31 (m, 10H), 7.22 (m, 3H), 7.14 (d, IH) (d, 2H), 6.99 (d, 2H), 6.91 (m, 3H) 60

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

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

2H), 7.32 (m, 4H), 7.21 (m, 6H), 7.16 (d, IH) (m, 3H), 7.00 (d, 2H), 6.94 (d, 2H), 6.81 (m, 3H) 62

2H), 7.38 (m, 4H), 7.27 (m, 6H), 7.14 (d, IH) (m, 6H), 7.02 (d, 2H), 6.95 (d, 2H), 6.70 (m, 6H) 63

2H), 7.39 (m, 4H), 7.27 (m, 6H), 7.20 (d, IH) (d, 2H), 6.80 (d, 2H), 6.80 (m, 3H), 6.52 s, 18H) 64

2H), 7.24 (m, 6H), 7.21 (d, IH), 8.14 (d, IH) (d, 2H), 6.69 (d, 2H), 6.69 (m, 3H), 6.52 s, 18H) 65

2H), 7.40 (m, 4H), 7.27 (m, 6H), 7.14 (d, IH) (m, 6H), 7.02 (d, 2H), 6.95 (d, 2H), 6.72 (m, 6H)

Example Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 66

(M, 3H), 7.14 (m, 3H), 7.06 (d, 2H), 8.04 (d, 2H), 6.94 (d, 2H), 6.80 (m, 3H) 67

2H), 7.32 (m, 4H), 7.01 (m, 9H), 8.21 (d, (D, 2H), 6.94 (d, 2H), 6.94 (d, 2H) 68

2H), 7.37 (m, 4H), 7.26 (m, 6H), 7.23 (d, IH) (m, 3H), 7.12 (d, 2H), 6.95 (d, 2H), 6.91 69

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 70

2H), 7.29 (m, 3H), 7.22 (m, 3H), 7.11 (d, IH) (d, 2H), 6.98 (d, 2H), 6.81 (m, 3H), 6.68

Example Chemical structure ^{1 H NMR (500 MHz, CDCl} 3, TMS) δ (PPM) 71

2H), 7.34 (m, 4H), 7.24 (m, 6H), 7.21 (d, IH) (d, 2H), 6.74 (d, 2H), 6.74 (m, 3H), 6.52 s, 18H) 72

2H), 7.41 (d, 2H), 7.33 (m, 4H), 7.22 (m, 6H), 7.19 (d, (m, 5H), 7.12 (d, 2H), 7.00 (d, 2H), 6.56 (m, 3H), 6.42 (d, 2H), 6.33 s, 18H) 73

2H), 7.37 (m, 4H), 7.27 (m, 6H), 7.11 (d, (m, 6H), 6.99 (d, 2H), 6.95 (d, 2H), 6.798 74

(D, 2H), 7.32 (m, 4H), 7.20 (m, 7H), 7.11 (m, 3H), 7.03 (d, 2H), 6.98 (d, 2H), 6.81 (m, 2H), 6.71 75

6H), 7.13 (m, 6H), 7.01 (d, 2H), 8.04 (m, 2H) (d, 2H), 6.92 (d, 2H), 6.84 (m, 6H) 76

2H), 7.32 (m, 4H), 7.22 (m, 6H), 7.11 (d, IH) (m, 3H), 7.04 (d, 2H), 6.95 (d, 2H), 6.83 (m, 3H), 6.71 (d, 2H), 6.61 s, 36H)

Experimental Example

Experimental Example  One: Example  Preparation of organic electroluminescent device using

The ITO transparent electrode with a 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 was repeatedly washed twice with 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 resultant organic electroluminescent device was measured at a voltage of 4 V to form a current density of 6.9 mA / cm 2. The current density was 351 cd / m 2 corresponding to x = 0.148 and y = 0.113 based on the 1931 CIE color coordinate system. A spectrum close to pure blue was observed and the efficiency was 5.08 cd / A.

Experimental Example  2: Example  10 for the fabrication of organic electroluminescent devices

An organic electroluminescent device was prepared using the same method as Experimental Example 1 except that the compound of Example 10 was used instead of the compound of Example 1 which is a luminescent dopant material.

The resultant organic electroluminescent device was measured at a voltage of 4V. As a result, the current density was 6.1 mA / cm 2. At this time, the brightness of 298 cd / m 2 corresponding to x = 0.143 and y = 0.107 on the basis of 1931 CIE color coordinates A spectrum close to pure blue was observed and the efficiency was 4.91 cd / A.

Experimental Example  3: Example  71 for organic electroluminescence device fabrication

An organic electroluminescent device was prepared in the same manner as in Experimental Example 1 except that the compound of Example 71 was used instead of the compound of Example 1 which is a luminescent dopant material.

The resultant organic electroluminescent device was measured at a voltage of 4V. As a result, the current density was 6.7 mA / cm 2. At this time, the brightness of 337 cd / m 2 corresponding to x = 0.143 and y = 0.108 on the basis of 1931 CIE color coordinates A spectrum close to pure blue was observed and the efficiency was 5.03 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 4.65 cd / A.

Claims (9)

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

In this formula,
And R 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,
R 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 said R ₁ is phenyl and said 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 the phenyl of R < ₁ > is substituted with any one substituent selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl.
3. The method of claim 2,
Wherein the phenyl of R < ₁ > is substituted with two trifluoromethyls.
The method according to claim 1,
Wherein said R < ₂ > is phenyl and said 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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≪ / 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.