KR20110018195A - Anthracene derivatives and organic light-emitting diode including the same - Google Patents

Abstract

PURPOSE: Anthracene derivatives are provided to ensure low driving voltage and excellent luminous efficiency and to improve brightness and lifetime of an organic electroluminescence device. CONSTITUTION: Anthracene derivatives are represented by chemical formula 1. In chemical formula 1, A is a single bond or substituted or unsubstituted C6-60 aryl group; B is substituted or unsubstituted C2-40 heteroaryl group containing 1-3 nitrogens or substituted or unsubstituted amino group; l or m are an integer of 1-5; R is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C3-10 alkylsilyl group, substituted or unsubstituted C1-40 alkyl group, and substituted or unsubstituted C6-40 arylsilyl group.

Description

Anthracene derivatives and organic light-emitting diodes including the same

The present invention relates to an anthracene derivative and an organic light emitting device including the same, and more particularly, to an anthracene derivative having excellent brightness and long life and an organic light emitting device including the same.

Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional cathode ray tube (CRT). It has disadvantages such as limited viewing angle and the necessity of back light. In contrast, the organic light emitting diode (OLED), a new flat panel display device, is a display using a self-luminous phenomenon, has a large viewing angle, can be thinner and shorter than a liquid crystal display, and has a fast response speed. have.

Representative organic electroluminescent devices have been limited to various uses since their performance limitations since they were announced by Gurnee in 1969 (US 3,172,862, US 3,173,050), but in 1987, Eastman Kodak co After the presentation of multi-layer organic electroluminescent devices (CW Tang et al., Appl. Phys. Lett., 51, 913 (1987); J. Applide Phys., 65, 3610 (1989)) Overcoming, it has developed rapidly. Currently, organic light emitting diodes have excellent characteristics such as low driving voltage (for example, 10V or less), wide viewing angle, high speed response, and high contrast compared to plasma display panels or inorganic electroluminescent display. It can be used as a pixel, as a pixel for television video displays or as a surface light source, and can be formed on flexible, transparent plastic substrates, making it very thin and light and having good color. It is emerging as a suitable device for the next generation flat panel display (FPD).

In the organic light emitting device, when an electron and a hole are injected into a light emitting layer formed between an anode as a hole injection electrode and a cathode as an electron injection electrode, excitons generated by pairing electrons and holes are coupled to a ground state from an excited state. As a device that disappears and disappears and emits light, application to a full color display is expected in recent years. In order to realize such a full color, it is necessary to arrange pixels on the panel which emit light of three primary colors of green, red, and blue, i) blue, green, and red. A method of arranging three types of organic light emitting elements showing luminescence of ii) a method of separating luminescence from elements exhibiting white luminescence which is a mixture of RGB into three primary colors through a color filter, and iii) an organic light emitting element exhibiting blue luminescence A method of converting light emission from green and red light into a light emission source has been proposed. In all cases, blue light emission is essential and there is an urgent need for a blue light emitting material having high luminance, high efficiency and high color purity. . In this context, in 1965, Hellrich and Pope first reported blue organic electroluminescence using anthracene single crystals. However, high voltage was required for light emission using anthracene single crystal, and thus, the lifespan of the organic light emitting diode was shortened, and thus, there were many difficulties in practical use. On the other hand, anthracene and its derivatives have been employed in various conventional organic electroluminescent devices, and 9,10-di (2-naphthyl) anthracene, which is well known as an abbreviation of "ADN" (US Patent No. 5,935,721). Has been used as a host of the most widely used light emitting layer, has also been disclosed a technique employing an anthracene derivative in the hole transport layer (European Patent Publication No. 1 009 044), an anthracene derivative as an electron transporting material and a blue light emitting material The technique employed has also been disclosed (Japanese Patent Laid-Open No. 11-345686), and anthracene and its derivatives have also been employed in organic electroluminescent devices for various purposes.

As described above, many studies have been conducted in which anthracene is employed in the organic light emitting display device. However, until now, the present invention has not sufficiently satisfied characteristics such as brightness, driving stability, and lifespan. Development is urgent.

The first technical problem to be achieved by the present invention is to provide an anthracene derivative having excellent brightness and long life.

In addition, the second technical problem to be achieved by the present invention is to provide an organic light emitting device comprising the anthracene derivative.

In order to achieve the above technical problem, the present invention provides an anthracene derivative represented by the following formula (1).

 (Formula 1)

Where

A is a single bond or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

B is a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms containing 1 to 3 nitrogens, a substituted or unsubstituted amino group,

l or m is an integer of 1 to 5, when l or m is 2 or more, a plurality of A or B are each independently the same or different,

R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C3-C10 alkylsilyl group, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C6-C40 It is selected from the group consisting of an arylsilyl group.

According to one embodiment of the present invention, the A and B substituents are hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, C3-C10 alkylsilyl group, C1-C40 alkyl group, C1-C1- Alkoxy group of 40, alkylamino group of 1-40 carbon atoms, aryl group of 6-40 carbon atoms, aryloxy group of 6-40 carbon atoms, arylamino group of 6-40 carbon atoms, arylsilyl group of 6-40 carbon atoms, 3- One or more may be selected from the group consisting of 40 heteroaryl groups, and may be substituted monovalent, divalent or fused.

According to another embodiment of the present invention, the substituents of A and B may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.

The present invention also provides an anthracene derivative represented by the following formula (2).

Where

A is a single bond, each substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

C is a substituted or unsubstituted C 2-40 heteroaryl group containing 1 to 3 nitrogens,

D is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms containing 1 to 3 nitrogens,

l and m are integers of 1 to 5, when l or m is 2 or more, a plurality of A, C or D are each independently the same or different,

R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C3-C10 alkylsilyl group, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C6-C40 It is selected from the group consisting of an arylsilyl group.

According to one embodiment of the present invention, the substituents of A, C and D are a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an alkylsilyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 40 carbon atoms, and a carbon number 1-40 alkoxy group, C1-40 alkylamino group, C6-40 aryl group, C6-40 aryloxy group, C6-40 arylamino group, C6-40 arylsilyl group, carbon number One or more may be selected from the group consisting of 3-40 heteroaryl groups, and may be substituted monovalent, divalent, or fused.

In addition, according to another embodiment of the present invention, the substituents of A, C and D may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.

The present invention also provides an anode, in order to achieve the second technical problem; Cathode; And it provides an organic electroluminescent device having a layer comprising an anthracene derivative represented by the formula (1) or (2) interposed between the anode and the cathode.

According to an embodiment of the present invention, the organic light emitting device is selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode The above layer may be further included, and the anthracene derivative is preferably included in the electron transport layer between the anode and the cathode.

When the anthracene derivative according to the present invention is used in the organic material layer of the organic light emitting device, the luminance of the organic light emitting device is improved, and the service life is extended, which is very economical.

Hereinafter, the present invention will be described in more detail.

Anthracene derivative according to an embodiment of the present invention is characterized in that the compound represented by the following formula (1).

(Formula 1)

Where

A is a single bond or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

B is a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms containing 1 to 3 nitrogens, a substituted or unsubstituted amino group,

l or m is an integer of 1 to 5, when l or m is 2 or more, a plurality of A or B are each independently the same or different,

R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C3-C10 alkylsilyl group, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C6-C40 It is selected from the group consisting of an arylsilyl group.

According to one embodiment of the present invention, the A and B substituents are hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, C3-C10 alkylsilyl group, C1-C40 alkyl group, C1-C1- Alkoxy group of 40, alkylamino group of 1-40 carbon atoms, aryl group of 6-40 carbon atoms, aryloxy group of 6-40 carbon atoms, arylamino group of 6-40 carbon atoms, arylsilyl group of 6-40 carbon atoms, 3- One or more may be selected from the group consisting of 40 heteroaryl groups, and may be substituted monovalent, divalent or fused.

According to another embodiment of the present invention, the substituents of A and B may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.

In addition, the anthracene derivative according to an embodiment of the present invention is characterized in that the compound represented by the following formula (2).

Where

A is a single bond, each substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

C is a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms containing 1 to 3 nitrogens,

D is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms containing 1 to 3 nitrogens,

l and m are integers of 1 to 5, when l or m is 2 or more, a plurality of A, C or D are each independently the same or different,

R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C3-C10 alkylsilyl group, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C6-C40 It is selected from the group consisting of an arylsilyl group.

According to one embodiment of the present invention, the substituents of A, C and D are a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an alkylsilyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 40 carbon atoms, and a carbon number 1-40 alkoxy group, C1-40 alkylamino group, C6-40 aryl group, C6-40 aryloxy group, C6-40 arylamino group, C6-40 arylsilyl group, carbon number One or more may be selected from the group consisting of 3-40 heteroaryl groups, and may be substituted monovalent, divalent, or fused.

In addition, according to another embodiment of the present invention, the substituents of A, C and D may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.

An aryl group, which is a substituent used in the compounds of the present invention, means a carbocyclic aromatic system comprising one or more rings, which rings may be attached or fused together in a pendant manner. Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl, and the like, and at least one hydrogen atom may be a halogen atom, a hydroxy group, a nitro group, a cyano group, or a silyl group (in this case, "Alkylsilyl group"), amino group (-NH ₂ , -NH (R), -N (R ') (R''),R' and R "are independently of each other an alkyl group having 1 to 10 carbon atoms, In this case, "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C1-C24 alkenyl group , Alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or heteroarylalkyl group having 2 to 24 carbon atoms It may be substituted by.

Heteroaryl group which is a substituent used in the compound of the present invention means a ring aromatic system having 2 to 24 carbon atoms containing 1, 2 or 3 hetero atoms selected from N, O, P or S, and the remaining ring atoms are carbon, The rings may be attached or fused together in a pendant manner. At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the case of the allyl group.

Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like. The atom may be substituted with the same substituent as in the case of the allyl group.

The cycloalkyl group, which is a substituent used in the compound of the present invention, means a monovalent monocyclic system having 3 to 24 carbon atoms. At least one hydrogen atom of the cycloalkyl group may be substituted with the same substituent as in the case of the allyl group.

Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like. At least one hydrogen atom of the alkoxy group may be substituted with the same substituent as in the case of the allyl group.

Specific examples of the silyl group which is a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl and methylcyclo Butylsilyl, dimethylfurylsilyl, and the like, and at least one hydrogen atom in the silyl group may be substituted with the same substituent as in the alkyl group.

Phenoxy, naphthoxy, phenanthoxy, pyoxy, biphenoxy and the like of the aryloxy group which is a substituent used in the compound of the present invention, and one or more hydrogen atoms of the aryloxy group may be used in the case of the allyl group. Substituents similar to the above can be substituted.

Specifically, the anthracene derivative according to the present invention may be any one compound selected from the group consisting of compounds represented by Formulas (3) to (148), but the present invention is not limited thereto.

(3) (4) (5)

(6) (7) (8)

(9) (10) (11)

(12) (13) (14)

               (15) (16)

(17) (18)

(19) (20) (21)

(22) (23)

(24) (25) (26)

(27) (28) (29)

(30) (31) (32)

(33) (34)

(35) (36)

(37) (38) (39)

(40) (41) (42)

(43) (44) (45)

(46) (47) (48)

(49) (50) (51)

(52) (53) (54)

(55) (56) (57)

(58) (59) (60)

(61) (62) (63)

(64) (65) (66)

(67) (68)

(69) (70) (71)

(72) (73)

(74) (75)

(76)

(77)

(78)

(79) (80)

(81) (82)

(83) (84) (85)

(86) (87) (88)

(89) (90) (91)

(92) (93) (94)

(95) (96) (97)

(98) (99) (100)

(101) (102)

(103) (104)

(105) (106)

(107) (108)

(109) (110) (111)

(112) (113) (114)

(115) (116) (117)

(118) (119) (120) (121)

(122) (123) (124)

(125) (126) (127)

(128) (129)

(130) (131) (132)

(133) (134) (135)

(136) (137) (138)

(139) (140) (141)

(142) (143) (144)

(145) (146)

(147) (148)

An organic light emitting display device according to the present invention includes an anode; Cathode; And an layer interposed between the anode and the cathode and comprising an anthracene derivative of the formula (1) or (2).

According to an embodiment of the present invention, the anode and the cathode may include one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer. In this case, the anthracene derivative is preferably included in the electron transport layer between the anode and the cathode.

In addition, according to another embodiment of the present invention, at least one or more of the hole injection layer, hole transport layer, hole blocking layer, light emitting layer, electron transport layer, electron injection layer and electron blocking 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 represented by Chemical Formula (1) or at least one sum of x and y of 1931 CIE (x, y) of 0.3 or more. The above compound may be further included.

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic light emitting layer. Silver is laminated to facilitate the injection of holes from the anode, and the electron transport molecule having a small ionization potential is used as the material of the hole transport layer. It is used a lot.

The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl-[1 , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (a-NPD) and the like can be used.

A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc or Starburst type amines such as TCTA, m-MTDATA, etc., which are listed in the following formulae, can be used.

In addition, the electron transport layer used in the organic light emitting device according to the present invention can be recombined in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the organic light emitting layer and inhibits the movement of holes that are not bonded in the organic light emitting layer. It increases your chances. The electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and, for example, oxadiazole derivatives such as PBD, BMD, BND or Alq ₃ may be used.

Meanwhile, an electron injection layer (EIL) may be further stacked on the upper portion of the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. The electron injection layer material may also be stacked. If it is conventionally used in the art can be used without particular limitation, for example, materials such as LiF, NaCl, CsF, Li ₂ O, BaO and the like can be used.

The organic light emitting display device according to an embodiment of the present invention may be used for a display device, a display device, and a monochrome or white lighting device.

1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting diode according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and if necessary, the hole injection layer 30 and the electron The injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a method of manufacturing the present invention, as follows. First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, transparent and conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), and zinc oxide (ZnO) are used as the anode electrode material.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30. Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and 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. can do. The hole blocking layer serves to prevent such a problem by using a material having a very low HOMO level when the hole is introduced into the cathode through the organic light emitting layer to reduce the lifetime and efficiency of the device. In this case, the hole blocking material used is not particularly limited, but has an ion transporting potential and has a higher ionization potential than the light emitting compound, and BAlq, BCP, TPBI, etc. may be used.

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a cathode forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form a cathode 80 electrode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

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

Synthesis Example 1 Synthesis of Compound of Chemical Formula 55

Synthesis Example 1- (1) Synthesis of 9-phenyl anthracene

15 g (0.058 mol) of 9-bromoanthracene, 7.8 g (0.0641 mol) phenylboronic acid, 2 g (0.116 mol) of potassium carbonate (K ₂ CO ₃ ), tetrakistriphenylphosphinepalladium (Pd) in a 500 ml round bottom flask (PPh ₃ ) ₄ ) 1.35 g (0.0012 mol), 20 mL of water, 100 mL of toluene and 100 mL of tetrahydrofuran were added thereto, and the mixture was refluxed for 24 hours. After the reaction was completed, the resultant was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure. Then, the solid obtained by column chromatography using hexane and dichloromethane as a developing solvent was dried and dried to be 9.64 g ( Yield 65%) of a white solid.

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

In a 500 ml round bottom flask, 9 g (0.0354 mol) of 9-phenyl anthracene was dissolved in 150 ml of chloroform, and a solution of 5.94 g (0.0372 mol) of bromine diluted in 100 ml of chloroform was slowly added dropwise. After dropping, the mixture is stirred for 12 hours. After the reaction was completed, 300ml of water was extracted and the organic layer was anhydrous treated. The filtrate was concentrated under reduced pressure, and the resulting solid was dissolved in 100 ml of dichloromethane and 200 ml of hexane was added to precipitate the solid. The resulting solid is filtered and then cut into 50 ml of toluene, cooled, to precipitate crystals and filtered. 10 g (yield 85%) of light yellow solid 9-phenyl-10-bromo anthracene was obtained.

Synthesis Example 1- (3) Synthesis of 9-phenyl anthracene-10-boronic acid

In a 500 ml round bottom flask, 10 g (0.03 mol) of 9-phenyl-10-bromo anthracene was dissolved in 100 ml of tetrahydrofuran under a nitrogen atmosphere and cooled to minus 70 degrees. After cooling, 20.6 ml (0.033 mol) of n-butyllithium (1.6 M hexane solution) was slowly added dropwise. After stirring for 1 hour while maintaining a low temperature, trimethyl borate 4.67g (0.045mol) was added dropwise and stirred at room temperature for 12 hours. After completion of the reaction, 100 ml of 2N HCl solution was added dropwise, followed by extraction with ethyl acetate and water. The organic layer is anhydrous and then depressurized to remove the organic solvent. The resulting solid is dissolved in 30 ml of ethyl acetate, 200 ml of hexane is added and recrystallized. The resulting solid was filtered to give 5.7 g (64% yield) of light brown 9-phenyl anthracene-10-boronic acid.

Synthesis Example 1- (4) Synthesis of Compound of Chemical Formula 55

5 g (0.0168 mol) of 9-phenyl anthracene-10-boronic acid, 5.4 g (0.0151 mol) of bromo-3 (3-quinolinyl) biphenyl in a 250 ml round bottom flask, 4.17 g of potassium carbonate (K ₂ CO ₃ ) (0.0302 mol), tetrakistriphenylphosphinepalladium (Pd (PPh ₃ ) ₄ ) 0.35 g (0.0003 mol), 20 mL of water, 100 mL of toluene and 100 mL of tetrahydrofuran were added and refluxed for 24 hours. After completion of the reaction, the resultant of the reaction was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure. Then, the solid obtained by column chromatography using hexane and dichloromethane as a developing solvent was dried, and the yield was 3.46 g. 44% of a white solid was obtained.

MS (MALDI-TOF): m / z 532 [M] ⁺

Synthesis Example 2 Synthesis of Compound of Formula 04

Synthesis Example 1- (4) except that 1-bromo-3 (3-pyridinyl) biphenyl was used instead of 3-bromo- (3-quinolinyl) biphenyl, and ET04 was synthesized in the same manner. 3.5 g (43% yield) was obtained as a white solid.

MS (MALDI-TOF): m / z 482 [M] ⁺

 Synthesis Example 3 Synthesis of Compound of Formula 15

Same procedure as in Synthesis Example 1- (4) except that 1-bromo-3,5-bis (3-pyridinylphenyl) benzene was used instead of 3-bromo- (3-quinolinyl) biphenyl Synthesis was carried out to give 2.9 g (44.7%) of ET15 as a white solid.

MS (MALDI-TOF): m / z 635 [M] ⁺

Synthesis Example 4 Synthesis of Compound of Chemical Formula 64

Synthesis Example 1- (4) except that 1-bromo-4 (4-pyridinyl) biphenyl was used instead of 3-bromo- (3-quinolinyl) biphenyl to synthesize ET64. 4.1 g (46.3% yield) was obtained as a white solid.

MS (MALDI-TOF): m / z 482 [M] ⁺

Synthesis Example 4 Synthesis of Compound of Formula 146

Synthesis was carried out in the same manner as in Synthesis Example 1- (1), except that 3-methyl phenylboronic acid was used instead of phenylboronic acid to obtain 3.2 g of ET146 (yield 43%) as a white solid.

MS (MALDI-TOF): m / z 546 [M] ⁺

Example Preparation of Organic Light Emitting Diode

The light emitting area of the ITO glass was patterned to a size of 2 mm x mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure is 1x10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), ADN + C545T (3%) (300 kPa), the compound according to the present invention. (350 kV), LiF (5 kV), and Al (1,000 kV) were formed in this order and measured at 0.4 mA.

Comparative example

The organic light emitting diode device for the Comparative Example was prepared in the same manner except that Alq ₃ was used instead of the compound prepared by the invention in the device structure of the Experimental Example.

ETL Dopant Host Doping
density% V A J
(mA / cm ² ) Cd / A CIEx CIEy Alq3 C545T ADN 3 6.24 0.0004 10 17.86 0.26 0.63 Formula 04 C545T ADN 3 4.97 0.0004 10 25.62 0.29 0.64 Formula 15 C545T ADN 3 5.29 0.0004 10 23.84 0.26 0.64 Formula 55 C545T ADN 3 4.85 0.0004 10 27.20 0.28 0.64 Formula 64 C545T ADN 3 5.37 0.0004 10 30.63 0.28 0.64 Formula 146 C545T ADN 3 5.38 0.0004 10 29.11 0.38 0.65

As shown in the above table, the organic compound obtained by the present invention has a low driving voltage and excellent luminous efficiency compared to Alq ₃ , which is widely used as an ETL material.

1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.

<Description of the symbols for the main parts of the drawings>

10: substrate 20: anode

30: hole injection layer 40: hole transport layer

50: organic light emitting layer 60: electron transport layer

70: electron injection layer 80: cathode

2 is a graph showing the change in luminance according to the current density change of the organic light emitting display device according to Experimental Example 1 to Experimental Example 5 and the embodiment of the present invention.

Claims (10)

Anthracene derivatives represented by the following Formula 1;  (Formula 1)

Where A is a single bond or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, B is a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms containing 1 to 3 nitrogens, a substituted or unsubstituted amino group, l or m is an integer of 1 to 5, when l or m is 2 or more, a plurality of A or B are each independently the same or different, R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C3-C10 alkylsilyl group, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C6-C40 It is selected from the group consisting of an arylsilyl group. The method of claim 1, The substituents of A and B include hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, C3-10 alkylsilyl group, C1-40 alkyl group, C1-40 alkoxy group and C1-40 An alkylamino group of 6, an aryl group of 6-40 carbon atoms, an aryloxy group of 6-40 carbon atoms, an arylamino group of 6-40 carbon atoms, an arylsilyl group of 6-40 carbon atoms, or a heteroaryl group of 3-40 carbon atoms An anthracene derivative, wherein the anthracene derivative is selected from the foregoing and substituted monovalently, divalently, or by fusion. The method of claim 2, The substituents of A and B combine with each other to form a substituted or unsubstituted saturated or unsaturated ring anthracene derivative. Anthracene derivatives represented by the following formula (2);

Where A is a single bond, each substituted or unsubstituted aryl group having 6 to 60 carbon atoms, C is a substituted or unsubstituted C 2-40 heteroaryl group containing 1 to 3 nitrogens, D is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms containing 1 to 3 nitrogens, l and m are integers of 1 to 5, when l or m is 2 or more, a plurality of A, C or D are each independently the same or different, R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C3-C10 alkylsilyl group, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C6-C40 It is selected from the group consisting of an arylsilyl group. The method of claim 4, wherein Substituents of A, C and D include a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an alkylsilyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, and a carbon atom 1 Group consisting of -40 alkylamino group, aryl group having 6-40 carbon atoms, aryloxy group having 6-40 carbon atoms, arylamino group having 6-40 carbon atoms, arylsilyl group having 6-40 carbon atoms, heteroaryl group having 3-40 carbon atoms An anthracene derivative, wherein the anthracene derivative is selected from one or more, and is monovalent, divalent, or fused. The method of claim 5, The substituents of A, C and D are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring anthracene derivative. The method of claim 1, Anthracene derivatives, characterized in that any one compound selected from the group consisting of the compound represented by Formula 3 to Formula 148;

(3) (4) (5)

(6) (7) (8)

(9) (10) (11)

(12) (13) (14)

               (15) (16)

(17) (18)

(19) (20) (21)

(22) (23)

(24) (25) (26)

(27) (28) (29)

(30) (31) (32)

(33) (34)

(35) (36)

(37) (38) (39)

(40) (41) (42)

(43) (44) (45)

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(49) (50) (51)

(52) (53) (54)

(55) (56) (57)

(58) (59) (60)

(61) (62) (63)

(64) (65) (66)

(67) (68)

(69) (70) (71)

(72) (73)

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(76)

(77)

(78)

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(83) (84) (85)

(86) (87) (88)

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(92) (93) (94)

(95) (96) (97)

(98) (99) (100)

(101) (102)

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(105) (106)

(107) (108)

(109) (110) (111)

(112) (113) (114)

(115) (116) (117)

(118) (119) (120) (121)

(122) (123) (124)

(125) (126) (127)

(128) (129)

(130) (131) (132)

(133) (134) (135)

(136) (137) (138)

(139) (140) (141)

(142) (143) (144)

(145) (146)

(147) (148) Anode; Cathode; And an layer interposed between the anode and the cathode, the layer comprising an anthracene derivative according to claim 1 or 4. The method of claim 8, further comprising at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode. An organic electroluminescent device. The organic electroluminescent device according to claim 9, wherein the anthracene derivative is included in an electron transport layer between the anode and the cathode.

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