KR101681214B1 - Host compounds and organic electroluminescent devices using the same - Google Patents

Abstract

(1)
(상기 식에서, A_, B, C₁, C₂, a, 및 b는 발명의 상세한 설명 및 청구범위에 정의된 바와 같다)The present invention relates to a host compound represented by the following formula (1) and an organic electroluminescent device including the host compound. The organic electroluminescent device comprising the host compound according to the present invention has an excellent effect on brightness, color purity and lifetime .

(One)
(Wherein A _, B, C ₁ , C ₂ , a, and b are as defined in the description and claims of the invention)

Description

Host compounds and organic electroluminescent devices using the same,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a host compound and an organic electroluminescent device using the host compound. More particularly, the present invention relates to a blue or green host compound having excellent brightness, color purity and lifetime characteristics, and an organic electroluminescent device using the same.

In recent years, the demand for a flat display device having a small space occupancy has been increased due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT, And a back light is necessarily required. On the contrary, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminescent phenomenon, has a large viewing angle, is thinner and thinner than a liquid crystal display, And in recent years, application to a full-color display or illumination is expected. For this purpose, there is an increasing need for high luminance, high efficiency, high color purity and long life luminescent materials.

Since the representative organic electroluminescent device was known by Gurnee in 1969 (US 3,172,862, US 3,173,050), its performance limitations have limited its use to various applications. However, in 1987, Eastman Kodak co (Applied Phys. Lett., 51, 913 (1987); J. Applied Phys., 65, 3610 (1989)). And has developed at a rapid pace. Although many studies have been made on an organic electroluminescent device, until now, characteristics such as brightness, driving stability and lifetime which are required until now have not been sufficiently satisfied. Therefore, it is urgent to develop various technologies to solve this problem. Although various anthracene derivatives are used in hole transporting layers of organic electroluminescent devices in Eastman Kodak Co., Ltd. (2000-0048009) in 2000, there is an energy transfer principle of doping a host with a dopant, There is a need for much research on new compounds as blue and green light-emitting layer host materials.

SUMMARY OF THE INVENTION The present invention provides a host compound having excellent brightness, color purity and long life.

A second object of the present invention is to provide an organic electroluminescent device using the host compound.

In order to achieve the first technical object, the present invention provides a host compound represented by the following formula (1).

(1)

(One)

In this formula,

A, B, C ₁ and C ₂ each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted group having 3 to 20 carbon atoms A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms. The substituent is preferably selected from the group consisting of a substituted or unsubstituted aryl group, a heteroaryl group, a germanium group, a boron group,

a is an integer of 0 to 7, b is an integer of 1 to 7, and when a and b are two or more, a plurality of A and B may be independently the same or different.

According to another embodiment of the present invention, the substituents of A, B, C ₁ and C ₂ may be a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, , A substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a germanium group, a boron group, An unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms, and deuterium.

According to another aspect of the present invention, there is provided a plasma display panel comprising: an anode; Cathode; And a layer containing a host compound according to Formula (1) between the anode and the cathode.

According to an embodiment of the present invention, the host compound according to the present invention is preferably included in the host among the light emitting layer between the anode and the cathode.

According to another embodiment of the present invention, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer is further interposed between the anode and the cathode And at least one or more layers of the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer, and the electron injecting layer may be formed by a solution process.

According to another embodiment of the present invention, the light emitting layer may further include at least one compound selected from the compounds of the formulas BD1 to BD68 or GD1 to GD60 described in the following examples.

According to another embodiment of the present invention, the light emitting layer may be a mixture of one or more compounds represented by the formula (1).

Further, the organic electroluminescent device according to the present invention can be usefully used for a display device, a display device, and a monochromatic or white illumination device.

The organic electroluminescent device comprising the compound of the formula (1) according to the present invention in the thin film layer between the anode and the cathode is a blue and green host material having excellent luminance, color purity and lifetime characteristics, have.

1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention.
Description of the Related Art
10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

The host compound according to the present invention is characterized by being represented by the following chemical formula (1).

(1)

(One)

In this formula,

A, B, C ₁ and C ₂ each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted group having 3 to 20 carbon atoms A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms. The substituent is preferably selected from the group consisting of a substituted or unsubstituted aryl group, a heteroaryl group, a germanium group, a boron group,

a is an integer of 0 to 7, b is an integer of 1 to 7, and when a and b are two or more, plural A and B are independently the same or different.

According to another embodiment of the present invention, the substituents of A, B, C ₁ and C ₂ may be a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, , A substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a germanium group, a boron group, An unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms, and deuterium.

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " Substituted or unsubstituted amino group (-NH2, -NH (R), -N (R ') (R "), R' and R" A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms An alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms Heterocyclic group, which may be substituted with a heteroaryl group containing 6 to 30 carbon atoms of the aryl group, having 6 to 60 carbon atoms in the arylalkyl group, having 4 to 40 carbon atoms or a heteroaryl group of from 4 to 40.

Specific examples of the cycloalkyl group used as the substituent in the compound of the present invention include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, ≪ / RTI >

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And can be substituted with substituents similar to those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

Specific examples of the aryl group as the substituent group used in the compound of the present invention include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, Examples of the aryl group include phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, , Anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, tetrahydronaphthyl group and the like, which may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the heteroaryl group used as the substituent in the compound of the present invention include pyridinyl, pyrimidinyl, triazinyl, indolinyl, quinolinyl, pyrrolidinyl, piperidinyl, An oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, or a benzoimidazole group, And at least one of the hydrogen atoms of the heteroaryl group may be substituted with the same substituent as the alkyl group.

The blue or green host compound according to one embodiment of the present invention may be any one compound selected from the group consisting of, for example, the following formulas (H1) to (H72), but is not limited to these exemplified compounds.

(H1) (H2) (H3)

(H4) (H5) (H6)

(H7) (H8) (H9)

(H10) (H11) (H12)

(H13) (H14) (H15)

(H16) (H17) (H18)

(H19) (H2O) (H21)

(H22) (H23) (H24)

(H25) (H26) (H27)

(H28) (H29) (H30)

(H31) (H32) (H33)

(H34) (H35) (H36)

(H37) (H38) (H39)

(H40) (H41) (H42)

(H43) (H44) (H45)

(H46) (H47) (H48)

(H49) (H50) (H51)

(H52) (H53) (H54)

(H55) (H56) (H57)

(H58) (H59) (H60)

(H61) (H62) (H63)

(H64) (H65) (H66)

(H67) (H68) (H69)

(H70) (H71) (H72)

The organic electroluminescent device according to the present invention includes an anode; Cathode; And a layer containing a blue or green host compound according to the above formula (1) between the anode and the cathode. At this time, the anthracene compound according to an embodiment of the present invention is preferably included in the light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, a hole blocking layer, a light emitting layer, an electron transporting layer, An electron injection layer, and an electron blocking layer.

According to another embodiment of the present invention, at least one or more layers of the hole injection layer, the hole transport layer, the hole blocking layer, the light emitting layer, the electron transport layer, the electron injection layer and the electron blocking layer are formed by a solution process An organic electroluminescent device is provided.

According to another embodiment of the present invention, the light emitting layer may further include at least one compound selected from compounds represented by the following formulas (BD1 to BD68) or (GD1 to GD60), thereby improving performance.

BD1 BD2 BD3

BD4 BD5 BD6

BD7 BD8 BD9

BD10 BD11 BD12

BD13 BD14 BD15

BD16 BD17 BD18

BD19 BD20 BD21

BD22 BD23 BD24

BD25 BD26 BD27

BD28 BD29 BD30

BD31 BD32 BD33

BD34 BD35 BD36

BD37 BD38 BD39

BD40 BD41 BD42

BD43 BD44 BD45

BD46 BD47 BD48

BD49 BD50 BD51

BD52 BD53

BD54 BD55 BD56

BD57 BD58 BD59

BD60 BD61 BD62

 BD63 BD64 BD65

BD66 BD67 BD68

           GD1 GD2 GD3

GD4 GD5 GD6

GD7 GD8 GD9

GD10 GD11 GD12

GD13 GD14 GD15

GD16 GD17 GD18

GD19 GD20 GD21

GD22 GD23 GD24

GD25 GD26 GD27

 GD28 GD29 GD30

GD31 GD32 GD33

GD34 GD35 GD36

GD37 GD38 GD39

GD40 GD41 GD42

GD43 GD44 GD45

GD46 GD47 GD48

GD49 GD50 GD51

GD52 GD53 GD54

GD55 GD56 GD57

GD58 GD59 GD60

Also, the organic electroluminescent device according to the present invention is preferably used for a display device, a display device, and a monochromatic or white illumination device.

As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.

In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).

A HIL (Hole Injection Layer) may be additionally deposited on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, CuPc or starburst type amines such as TCTA and m-MTDATA may be used.

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material for the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

On the other hand, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

According to an embodiment of the present invention, it is preferable that the organic electroluminescent device according to the present invention is used in a display device, a display device, and a monochromatic or white illumination device. The compounds according to the present invention can be used not only in organic electroluminescent devices but also in organic thin film transistors (OTFTs) and radio frequency identification (RFID) devices.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic light emitting diode according to the present invention includes an anode 20, a hole transporting layer 40, an organic light emitting layer 50, an electron transporting layer 60 and a cathode 80, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic electroluminescent device of the present invention and its manufacturing method will be described as follows. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), and zinc oxide (ZnO), which are transparent and excellent in conductivity, are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30. A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. When the holes pass through the organic light emitting layer and enter the cathode, the lifetime and efficiency of the hole blocking layer are reduced. Therefore, the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO level. The hole blocking material used herein is not particularly limited, but it is required to have an ionization potential higher than that of a light emitting compound while having an electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

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

Synthesis Example 1: Synthesis of formula H1

Synthesis Example 1- (1): Synthesis of 9- (1-naphthyl) anthracene

500ml round bottom flask, 9-bromo-anthracene 20g (0.078mol), 1- naphthalenesulfonic acid 16.0 g (0.093mol), potassium carbonate _{(K 2 CO 3) 21.5 g} (0.156mol), tetrakis (triphenylphosphine) In the palladium _{(Pd (PPh 3) 4)} 4.49 g (0.004mol), 20mL of water, 100ml of toluene and 100mL of tetrahydrofuran and refluxed for 24 hours. After the completion of the reaction, the reaction product was separated to remove the water layer. The organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and dichloromethane as eluent. The solid was dried to obtain 9.64 g Yield 65%) as a white solid.

Synthesis Example 1- (2) Synthesis of 9-bromo-10- (1-naphthyl) anthracene

20 g (0.066 mol) of 9- (1-naphthyl) anthracene is dissolved in 250 ml of chloroform, and 12.6 g (0.076 mol) of bromine in 50 ml of chloroform is slowly added dropwise to a 500 ml round bottom flask. The mixture was stirred for 12 hours. After completion of the reaction, 300 ml of water is added to extract the organic layer, and then the organic layer is dried. The filtrate is concentrated under reduced pressure, and the resulting solid is dissolved in 100 ml of dichloromethane, and then 200 ml of hexane is added to precipitate a solid. The resultant solid was filtered, and the filtrate was extracted with 50 ml of toluene, followed by cooling to precipitate crystals and filtration. 28 g (yield 88%) of pale yellow solid 9-bromo-10- (1-naphthyl) anthracene was obtained.

Synthesis Example 1- (3) Synthesis of 2,7-dibromo-9,9'-dimethylfluorene

This compound was obtained by the method of a known document Journal of Organic Chemistry , 2004, 69 , 987-990.

Synthesis Example 1- (4) Synthesis of 2-bromo-7-phenyl-9,9'-dimethylfluorene

500ml phenylboronic acid To a round bottom flask was added 10g (0.082mol), 2,7- dibromo -9,9'- dimethyl fluorene 57.7g (0.164mol), potassium carbonate _{(K 2 CO 3) 13.6 g} (0.0984mol ), tetra kiss was added triphenylphosphine palladium _{(Pd (PPh 3) 4)} 4.74 g (0.004mol), 20mL of water, 100ml of toluene and 100mL of tetrahydrofuran and refluxed for 24 hours. After the completion of the reaction, the reaction product was separated into layers, the water layer was removed, and the organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and dichloromethane as eluent. The solid was dried to obtain 19 g Yield 66%) as a white solid.

Synthesis Example 1- (5) Synthesis of 7-phenyl-9,9'-dimethylfluorenyl-2-boronic acid

50 g (0.143 mol) of 2-bromo-7-phenyl-9,9'-dimethylfluorene is dissolved in 250 ml of tetrahydrofuran in a 500 ml round-bottomed flask under a nitrogen atmosphere. After cooling, add 107 mL (0.172 mol) of n-butyllithium (1.6 M hexane solution) slowly dropwise. After stirring for 1 hour while keeping the temperature low, 27 mL (0.215 mol) of trimethylborate is added dropwise and the mixture is stirred at room temperature for 1 hour. After completion of the reaction, 100 ml of a 2N HCl solution is added dropwise, and then ethyl acetate and water are added to extract. The organic layer is treated with anhydrous water and then the organic solvent is removed by decompression. The resulting solid was dissolved in 30 ml of ethyl acetate and recrystallized with 200 ml of hexane. The resulting solid was filtered to obtain 34 g (yield: 75.6%) of 7-phenyl-9,9'-dimethylfluorenyl-2-boronic acid as white.

Synthesis Example 1- (6) Synthesis of Formula H1

(0.021 mol) of 9-bromo-10- (1-naphthyl) anthracene, 7.21 g (0.023 mol) of 7-phenyl-9,9'-dimethylfluorenyl boronic acid, _{K 2 CO 3) 3.46 g (} 0.025mol), tetrakis (triphenylphosphine) palladium (Pd (PPh ₃₎ In the ₄₎ 1.21 g, 20mL water, 50ml of toluene and 50mL of tetrahydrofuran and refluxed for 24 hours. After completion of the reaction, the reaction product was separated to remove the water layer. The organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and dichloromethane as eluent. The solid was dried to obtain 9.7 g Yield: 81%) as a white solid.

MS (MALDI-TOF): m / z 572 [M] ^< ^{+ &}

Synthesis Example 2: Synthesis of Formula H8

Synthesis Example 2- (1): Synthesis of 7-phenyl (d-5) -9,9'-dimethylfluorenyl-2-boronic acid

Phenyl (d-5) -9,9'-dimethylfluorenyl-2-pyrrolidone was prepared in the same manner as in Synthesis Example 1- (4), except that phenyl (d- Boronic acid was synthesized.

Synthesis Example 2- (2): Synthesis of Formula H8

(D-5) -9,9'-dimethylfluorenyl-2-boron instead of 7-phenyl-9,9'-dimethylfluorenyl-2-boronic acid in Synthesis Example 1- (6) 8.4 g (85% yield) of a white solid of the formula H8 was obtained in the same manner as the acid except for using the acid.

MS (MALDI-TOF): m / z 577 [M] ^< ^{+ &}

Synthesis Example 3: Synthesis of formula H31

Synthesis Example 3- (1) Synthesis of 3,6-dibromo-9,9'-dimethylfluorene

The compound was obtained by the method of Macromolecules , 2008, 41 , 3765-3768.

Synthesis Example 3- (2) Synthesis of 6-phenyl-9,9'-dimethylfluorenyl-3-boronic acid

Except that 3,6-dibromo-9,9'-dimethylfluorene was used instead of 2,7-dibromo-9,9'-dimethylfluorene in the above Synthesis Example 1- (4) 6-phenyl-9,9'-dimethylfluorenyl 3-boronic acid was synthesized.

Synthesis Example 3- (3): Synthesis of Formula H31

Except that 6-phenyl-9,9'-dimethylfluorenyl-3-boronic acid was used instead of 7-phenyl-9,9'-dimethylfluorenyl-2-boronic acid in Synthesis Example 1- (6) And a white solid of 7.1 g (yield 78%) of the formula H31 was obtained in the same manner.

MS (MALDI-TOF): m / z 572 [M] ^< ^{+ &}

Synthesis Example 4: Synthesis of formula H39

Synthesis Example 4- (1): Synthesis of 6- (pentafluorophenyl) -9,9'-dimethylfluorenyl-3-boronic acid

6- (Pentafluorophenyl) -9,9'-dimethylfluorenyl 3-boronic acid was obtained in the same manner as in Synthesis Example 3- (2) except that pentafluorophenylboronic acid was used instead of phenylboronic acid. Were synthesized.

Synthesis Example 4- (2): Synthesis of Formula H39

A solution of 6- (pentafluorophenyl) -9,9'-dimethylfluorenyl-3-boron in place of 7-phenyl-9,9'-dimethylfluorenyl-2-boronic acid in Synthesis Example 1- (6) 11.2 g (82% yield) of a white solid of the formula H39 was obtained in the same manner as the acid except for using the acid.

MS (MALDI-TOF): m / z 662 [M] ^< ⁺ & gt ^;

Synthesis Example 5: Synthesis of formula H60

Synthesis Example 5- (1) Synthesis of 3,6-dibromo-9,9'-diphenylfluorene

The above compound was obtained in a known document Organic Letters , 2001, 3 , 2285-2288 using 3,6-dibromofluoren-9-one instead of 2,7-dibromofluoren-9-one.

Synthesis Example 5- (2) Synthesis of 6- (3,5-diphenyl) phenyl-9,9'-diphenylfluorenyl-3-boronic acid

Except that 3,6-dibromo-9,9'-diphenylfluorene was used instead of 2,7-dibromo-9,9'-dimethylfluorene in Synthesis Example 1- (4) 6- (3,5-diphenyl) phenyl-9,9'-diphenylfluorenyl-3-boronic acid was synthesized in the same manner except that 3,5-diphenylphenyl-1-boronic acid was used .

Synthesis Example 5- (3): Synthesis of Chemical Formula H60

The procedure of Synthesis Example 1- (6) was repeated except that 6- (3,5-diphenyl) phenyl-9,9'-diphenylfluorenylsuccinimide was used in place of 7-phenyl-9,9'-dimethylfluorenyl- -3-boronic acid, 5.2 g (yield 59%) of a pale yellow solid of the formula H60 was obtained in the same manner.

MS (MALDI-TOF): m / z 724 [M] ^< ^{+ &}

Synthesis Example 6: Synthesis of formula H61

Synthesis Example 6- (1) Synthesis of 4-bromo-1-phenylnaphthalene

(0.065 mol) of 1,4-dibromonaphthalene, 8.75 g (0.072 mol) of phenylboronic acid, 10.8 g (0.078 mol) of potassium carbonate (K ₂ CO ₃ ), and tetrakistriphenylphosphine In the palladium _{(Pd (PPh 3) 4)} 3.77 g, 20mL water, 50ml of toluene and 50mL of tetrahydrofuran and refluxed for 24 hours. After the completion of the reaction, the reaction product was separated to remove the aqueous layer. The organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and dichloromethane as eluent. The solid was dried to obtain 14.7 g Yield: 8%) as a white solid.

Synthesis Example 6- (2) Synthesis of Compound 61

Was obtained in the same manner as in Synthesis Example 1- (6) except that 9-bromo-10- (4-phenyl-1-naphthyl) anthracene was used instead of 9-bromo- H61 (5.3 g, yield 49%) as a pale yellow solid.

MS (MALDI-TOF): m / z 648 [M] ^< ⁺ & gt ^;

Example: Fabrication of organic electroluminescent device

Examples 1 to 6

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr. Subsequently, CuPc (800 Å) and α-NPD (300 Å) + BD1 compound 3% were mixed to form a film (250 ANGSTROM) Next, Alq ₃ (350 Å), LiF (5 Å), and Al (500 Å) were sequentially deposited to form an organic electroluminescent device. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA.

Comparative Examples 1 and 2

As used in the above embodiment An organic electroluminescent device was fabricated in the same manner except that the compound of the formula H73 or H74 was used instead of the host compound of the present invention. The luminescent characteristics of the organic electroluminescent device were measured at 0.4 mA. The chemical formulas of H73 and H74 are as follows.

         H73 H74

In Table 1, voltage, current, luminance, color coordinates and lifetime of the organic EL device manufactured according to Examples 1 to 5 and Comparative Example 1 were measured and the results are shown. T80 means the time required for the luminance to be reduced to 80% of the initial luminance.

division Host Dopant V J (mA / cm ² ) Cd / m ² CIEx CIEy T80 Example 1 H1 BD1 4.70 10 453 0.140 0.144 350 Example 2 H8 BD1 5.36 10 566 0.141 0.142 420 Example 3 H31 BD1 6.10 10 484 0.144 0.145 394 Example 4 H39 BD1 4.74 10 435 0.141 0.142 356 Example 5 H60 BD1 4.15 10 405 0.138 0.143 340 Example 6 H61 BD1 4.20 10 453 0.137 0.148 430 Comparative Example 1 H73 BD1 5.11 10 369 0.144 0.151 230 Comparative Example 2 H74 BD1 5.40 10 490 0.137 0.176 207

Examples 7 to 11

A device was prepared in the same manner as in Example 1, except that the following host and dopant compound were used for the light emitting layer.

division Host Dopant V J (mA / cm ² ) Cd / m ² CIEx CIEy T80 Example 7 H9 BD19 5.25 10 570 0.141 0.139 367 Example 8 H9 BD30 4.45 10 411 0.138 0.138 425 Example 9 H9 BD35 4.21 10 430 0.138 0.146 386 Example 10 H9 BD42 5.53 10 673 0.138 0.148 510 Example 11 H9 BD47 5.47 10 633 0.135 0.148 451

Examples 12 to 17 and Comparative Examples 3 and 4

A device was prepared in the same manner as in Example 1, except that the following host and dopant compound were used for the light emitting layer.

division Host Dopant V J (mA / cm ² ) Cd / m ² CIEx CIEy T80 Example 12 H1 GD31 3.89 10 2693 0.267 0.658 861 Example 13 H8 GD31 3.87 10 2712 0.270 0.659 964 Example 14 H31 GD31 3.97 10 2890 0.278 0.652 786 Example 15 H39 GD31 3.92 10 2918 0.277 0.655 954 Example 16 H60 GD31 3.75 10 2644 0.302 0.652 1021 Example 17 H61 GD31 4.20 10 2711 0.297 0.659 946 Comparative Example 3 H73 GD31 4.39 10 2395 0.331 0.640 568 Comparative Example 4 H74 GD31 4.38 10 2018 0.300 0.633 530

Examples 18 to 22

A device was prepared in the same manner as in Example 1, except that the following host and dopant compound were used for the light emitting layer.

division Host Dopant V J (mA / cm ² ) Cd / m ² CIEx CIEy T80 Example 18 H9 GD05 3.75 10 2685 0.304 0.653 981 Example 19 H9 GD23 4.21 10 2968 0.320 0.649 1214 Example 20 H9 GD36 4.11 10 3079 0.312 0.646 1031 Example 21 H9 GD45 4.01 10 2933 0.338 0.637 758 Example 22 H9 GD51 3.61 10 2772 0.328 0.624 859

As can be seen from the results of Tables 1 and 2, the organic EL device according to the present invention is superior in efficiency and lifetime in the blue color to that of the conventional anthracene host, Showed good luminescence characteristics in the light blue region. Also, in the case of green, the luminance showed a maximum performance of 1.45 times as compared with Comparative Example 4. In the case of the lifetime characteristics, the maximum lifetime characteristic was 1.9 times that of Comparative Example 4. In the case of most of the exemplified GD compounds, Characteristics.

Claims (10)

A host compound represented by the following formula (1):

(One)
(Wherein,
A, C ₁ and C ₂ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms,
B is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 40 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, provided that when B is a substituted or unsubstituted anthracene group, ),
a is an integer of 0 to 7, b is an integer of 1 to 7, and when a and b are two or more, plural A and B are independently the same or different.) The method according to claim 1,
The substituents of A, B, C ₁ and C ₂ may be deuterium, a halogen group, a cyano group, an alkyl group having 1 to 7 carbon atoms, a halogenalkyl group having 1 to 7 carbon atoms, an alkylsilyl group having 1 to 7 carbon atoms, An aryl group having 6 to 24 carbon atoms, and a heteroaryl group having 2 to 24 carbon atoms. The method according to claim 1,
A host compound, which is a compound selected from the group consisting of the following formulas (H1) to (H72):

(H1) (H2) (H3)

(H4) (H5) (H6)

(H7) (H8) (H9)

(H10) (H11) (H12)

(H13) (H14) (H15)

(H16) (H17) (H18)

(H19) (H2O) (H21)

(H22) (H23) (H24)

(H25) (H26) (H27)

(H28) (H29) (H30)

(H31) (H32) (H33)

(H34) (H35) (H36)

(H37) (H38) (H39)

(H40) (H41) (H42)

(H43) (H44) (H45)

(H46) (H47) (H48)

(H49) (H50) (H51)

(H52) (H53) (H54)

(H55) (H56) (H57)

(H58) (H59) (H60)

(H61) (H62) (H63)

(H64) (H65) (H66)

(H67) (H68) (H69)

(H70) (H71) (H72) Anode;
Cathode; And
An organic electroluminescent device comprising a layer containing a host compound according to any one of claims 1 to 3 between the anode and the cathode. 5. The method of claim 4,
Wherein the layer containing the compound is a light emitting layer between the anode and the cathode. 6. The method of claim 5,
Further comprising at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer between the anode and the cathode. The method according to claim 6,
Wherein at least one of the light emitting layer, the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer electron transporting layer, and the electron injecting layer is formed by a solution process. 6. The method of claim 5,
Wherein the light emitting layer further comprises at least one compound selected from compounds represented by the following formulas (BD1 to BD68).

BD1 BD2 BD3

BD4 BD5 BD6

BD7 BD8 BD9

BD10 BD11 BD12

BD13 BD14 BD15

BD16 BD17 BD18

BD19 BD20 BD21

BD22 BD23 BD24

BD25 BD26 BD27

BD28 BD29 BD30

BD31 BD32 BD33

BD34 BD35 BD36

BD37 BD38 BD39

BD40 BD41 BD42

BD43 BD44 BD45

BD46 BD47 BD48

BD49 BD50 BD51

BD52 BD53

BD54 BD55 BD56

BD57 BD58 BD59

BD60 BD61 BD62

BD63 BD64 BD65

BD66 BD67 BD68 6. The method of claim 5,
Wherein the light emitting layer further comprises at least one compound selected from compounds represented by the following formulas (GD1) to (GD60).

GD1 GD2 GD3

GD4 GD5 GD6

GD7 GD8 GD9

GD10 GD11 GD12

GD13 GD14 GD15

GD16 GD17 GD18

GD19 GD20 GD21

GD22 GD23 GD24

GD25 GD26 GD27

GD28 GD29 GD30

GD31 GD32 GD33

GD34 GD35 GD36

GD37 GD38 GD39

GD40 GD41 GD42

GD43 GD44 GD45

GD46 GD47 GD48

GD49 GD50 GD51

GD52 GD53 GD54

GD55 GD56 GD57

GD58 GD59 GD60 5. The method of claim 4,
A display element, a display element, and a device for monochromatic or white illumination.

Images