KR20180068431A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to an organic compound to which arylamine is applied on both sides of phenylene substituted with phenyl, and more specifically, to a novel compound in which diphenylfluorene, spirobifluorene, triphenylene, dibenzofuran or dibenzothiophene is introduced into one side. The present invention also relates to an organic light emitting device including the novel compound. The organic light emitting device of the present invention can realize low driving voltage, and has high efficiency and long life.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, and an organic light emitting device including the same. BACKGROUND OF THE INVENTION [0002]

The present invention relates to a novel compound and an organic light emitting device comprising the same.

A material used as an organic material layer in an organic light emitting diode can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material can be classified into a polymer and a low molecular weight according to the molecular weight, and can be classified into a phosphorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from an electron triplet excited state according to an emission mechanism, Materials can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural colors depending on luminescent colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant and the host.

Various compounds have been known as materials for use in such organic light emitting devices. However, in the case of organic light emitting devices using known materials, development of new materials is continuously required due to high driving voltage, low efficiency, and short lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a material having excellent characteristics.

Japanese Patent Laid-Open No. 10-2015-530735

The present invention is to provide a novel organic compound, a method for producing the same, and an organic light emitting device including the same.

However, the problems to be solved by the present invention are not limited to the problems described above, and other problems not described can be clearly understood by those skilled in the art from the following description.

A first aspect of the invention provides a compound represented by formula 1:

[Chemical Formula 1]

In Formula 1,

또는

이고,Ar ₁ is

or

ego,

Ar ₂ to Ar ₄ are each independently a phenyl, biphenyl or naphthyl which may be substituted,

L ₁ and L ₂ are each independently a C ₅ -C ₃₀ arylene group which may be directly bonded or substituted.

A second aspect of the present invention provides an organic light emitting device comprising a compound according to the present invention.

The present invention relates to an organic compound to which an arylamine is applied on both sides of phenylene substituted with phenyl, and more particularly, to an organic compound to which phenylamine substituted with phenyl is substituted by arylamine, by introducing diphenylfluorene, spirobifluorene, triphenylene, dibenzofuran or dibenzothiophene, HOMO which is easy to inject and transport holes can be formed to form a low driving voltage, thereby realizing a high efficiency and long life organic light emitting device. In addition, it is possible to maintain high triplet energy, thereby achieving high efficiency through formation of an exciton in the light emitting layer, facilitating application of a phosphorescent device, and maintaining a high Tg even at relatively low molecular weight through substitution position or phenyl ring control, And thus the driving stability and lifetime are increased.

The compound of the present invention has a high luminous efficiency and a high color purity. Thus, the compound of the present invention can contribute greatly to the OLED industry such as flexible display and illumination by applying it to an organic electroluminescent device, an organic photonic device for solar power generation,

1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, embodiments and examples of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains.

It should be understood, however, that the present invention may be embodied in many different forms and is not limited to the embodiments and examples described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are denoted by like reference characters throughout the specification.

Throughout this specification, when a member is "on " another member, it includes not only when the member is in contact with the other member, but also when there is another member between the two members.

Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. The terms "about "," substantially ", etc. used to the extent that they are used throughout the specification are intended to be taken to mean the approximation of the manufacturing and material tolerances inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure. The word " step (or step) "or" step "used to the extent that it is used throughout the specification does not mean" step for.

Throughout this specification, the term "combination thereof" included in the expression of the machine form means one or more combinations or combinations selected from the group consisting of the constituents described in the expression of the machine form, And the like.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B".

Throughout this specification, the term "aryl" refers to C _5-30 aromatic hydrocarbon ring groups such as benzyl, phenyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, Means an aromatic ring such as phenyl, naphthyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, As the aromatic ring containing a hetero element, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, di Thienyl, and pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, pyrimidinyl rings, pyridazinyl rings, pyrimidinyl rings, pyridazinyl rings, A triazine ring, an indole ring, a quinoline ring, an arc A pyridine ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, Means an aromatic heterocyclic group formed from a thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring.

Throughout the specification, the term "alkyl" may be linear or branched, including saturated or unsaturated C ₁ -C ₆ alkyl, such as methyl, ethyl, propyl, butyl, pentyl, But is not limited to, all possible isomers.

"Optionally substituted" term throughout the present specification is a deuterium, a halogen, an amino group, a nitrile group, a nitro group or a C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ of the alkoxy group, Means a group selected from the group consisting of a C ₃ to C ₂₀ cycloalkyl group, a C ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₃₀ aryl group and a C ₅ to C ₃₀ heteroaryl group do.

A first aspect of the invention provides a compound represented by formula 1:

[Chemical Formula 1]

In Formula 1,

또는

이고,Ar ₁ is

or

ego,

Ar ₂ to Ar ₄ are each independently phenyl, biphenyl or naphthyl,

L ₁ and L ₂ are each independently a C ₅ -C ₃₀ arylene group which may be directly bonded or substituted.

In Ar ₁ , * means a linking site

The Ar ₁ is _one of diphenylfluorene, spirobifluorene, triphenylene, dibenzofuran or dibenzothiophene, and forms a low driving voltage by forming HOMO which is easy to inject and transport holes, and has a high efficiency and long life Can be realized.

In one embodiment of the present invention, the compound of Formula 1 may include a compound represented by the following Formula 2 or 3:

(2)

(3)

In the above formulas,

Ar ₂ to Ar ₄ , L ₁ and L ₂ are as defined in formula (1)

Dashed lines are un-bonded or direct bonded.

In one embodiment of the present invention, the compound of Formula 1 may include a compound represented by Formula 4:

[Chemical Formula 4]

In the above formulas,

Ar ₂ to Ar ₄ are as defined in formula (1)

L ₁ and L ₂ are both direct bonds,

X is S or O;

In one embodiment of the present invention, when both of L ₁ and L ₂ in the formula (4) are C ₅ -C ₃₀ arylene groups which may be substituted, for example, phenylene, mobility is slower, the efficiency is decreased and the driving voltage is increased .

In one embodiment of the present invention, L ₁ and L ₂ each independently may be a direct bond or phenylene.

In one embodiment of the present invention, L < _{1 >} and L < _{2 >} may all be a direct bond or phenyl. For example, in the above general formulas (1) to (4), L ₁ and L ₂ may all be a direct bond, and in this case, the compounds have better mobility and can further increase the efficiency and lower the driving voltage

In one embodiment of the invention, the compound may have a molecular weight of from about 550 to about 810, such as from about 550 to about 750, from about 550 to about 700, from about 550 to about 650, from about 600 to about 810, from about 650 to about 810, from about 700 to about 810, or from about 600 to about 750. When the molecular weight is less than 550, the compound is difficult to produce, and when the molecular weight is more than 810, the deposition temperature increases during deposition.

In one embodiment of the present invention, the compound of Formula 1 may include, but is not limited to, the following compounds:

For example, the compound of Formula 1 may include the following compounds. The following compounds have better mobility and thus can be more efficient and have a higher driving voltage:

The second aspect of the present invention provides an organic light emitting device comprising the compound represented by Formula 1. The organic light emitting device may include one or more organic layers including a compound according to the present invention between the first electrode and the second electrode.

In one embodiment of the present invention, the organic material layer may be at least one of a hole injecting layer, a hole transporting layer, and a light-emitting auxiliary layer, but the present invention is not limited thereto. May be used together with a luminescent compound.

In one embodiment of the present invention, the organic light emitting device may include, but not limited to, an organic material layer containing a hole transporting material and an organic material layer containing a compound represented by the general formula (1).

In one embodiment of the present invention, the organic material layer containing the compound represented by Formula 1 may be a light-emitting auxiliary layer.

The organic light emitting device includes an organic layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode One or more can be included.

For example, the organic light emitting device can be manufactured according to the structure shown in FIG. The organic light emitting device includes an anode (hole injection electrode 1000), a hole injection layer 200, a hole transport layer 300, a light emitting layer 400, an electron transport layer 500, an electron injection layer 600, The injection electrode 2000) are stacked in this order.

1, the substrate 100 may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. have.

The hole injection electrode 1000 is used as an anode for hole injection of the organic light emitting element. A material having a low work function is used to allow injection of holes and may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene

A hole injecting layer material may be deposited on the anode electrode by a method such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) method. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions depend on the compound used as the material of the hole injection layer 200, the structure and the thermal properties of the desired hole injection layer, and the like. Generally, deposition of 50-500 Temperature, a degree of vacuum of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness range of 10 Å to 5 μm.

Next, a hole transporting layer material may be deposited on the hole injection layer 200 by a method such as vacuum deposition, spin coating, casting, or LB method to form the hole transporting layer 300. When the hole transporting layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The hole transporting layer may be one or more, for example, two layers of a hole transporting layer and a light emitting auxiliary layer. Any one of the hole transporting layer and the light emitting auxiliary layer may include the compound of Formula 1 according to the present invention.

Thereafter, the light emitting layer material may be deposited on the hole transporting layer by vacuum evaporation, spin coating, casting, LB method, or the like to form the light emitting layer 400. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The light emitting layer material may be a known compound as a host or a dopant.

When the phosphorescent dopant is used together with the phosphorescent dopant, a hole blocking material (HBL) may be further deposited by vacuum evaporation or spin coating to prevent triplet excitons or holes from diffusing into the electron transport layer. The hole blocking material that can be used at this time is not particularly limited, but any known hole blocking material may be used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open Publication No. 11-329734 (A1) can be exemplified. Typically, Balq (bis Phenanthrolines based compounds such as UDC company BCP (bassocouroin), and the like can be used.

An electron transport layer 500 is formed on the light emitting layer 400 formed as described above. The electron transport layer may be formed by vacuum deposition, spin coating, casting, or the like. The deposition conditions of the electron transporting layer depend on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer.

Then, an electron injection layer material may be deposited on the electron transport layer 500 to form an electron injection layer 600. The electron injection layer may be formed by vacuum deposition, spin coating, casting, And the like.

The hole injecting layer 200, the hole transporting layer 300, the light emitting layer 400 and the electron transporting layer 500 of the device can be formed using the compound according to the present invention or the following compounds, Known materials can be used together.

A cathode 2000 for electron injection is formed on the electron injection layer 600 by a vacuum evaporation method or a sputtering method. As the cathode, various metals may be used. Specific examples thereof include aluminum, gold, and silver.

The organic light emitting device of the present invention can have an organic light emitting device having various structures as well as an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode structure, Layer or an intermediate layer of two layers may be further formed.

As described above, the thickness of each organic material layer formed according to the present invention can be controlled depending on the required degree, specifically 10 to 1,000 nm, more specifically 20 to 150 nm.

In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.

The organic light emitting compound according to the present invention may be applied to the first aspect of the present invention, but the present invention is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited by these Examples.

[ Example ]

Manufacturing example 1: intermediate  I-1 synthesis

Under an argon or nitrogen atmosphere, diphenylamine 8.46g (50mM), 3,5- dibromo-1,1'-biphenyl, _{21.84g (70mM), Pd 2 (} dba) 3 1.6g (1.7mM), 50 300 ml of toluene was added to 2 ml (4 mM) of P (t-Bu) 3 and 14.7 g (152 mM) of NaOtBu, and the mixture was heated under reflux for 7 hours. After completion of the reaction, the reaction mixture was immediately filtered, extracted with dichloromethane, and then filtered with MgSO ₄ . The solvent of the filtered organic layer was removed and then purified by column chromatography to obtain 16.41 g of intermediate I-1 (5-bromo-N, N-diphenyl- [1,1'-biphenyl] -3-amine). (Yield: 82%)

m / z: 399.06 (100.0%), 401.06 (97.1%), 402.06 25.4%, 400.07 16.3%, 400.07 9.5%, 403.07 1.8%, 401.07 1.6% ), 401.07 (1.4%)

Manufacturing example  2: Synthesis of intermediate I-2

The reaction was carried out in the same manner as in Preparation Example 1, except that 12.27 g of N-phenyl- [1,1'-biphenyl] -4-amine was used instead of diphenylamine to obtain Intermediate I-2 (N - Biphenyl] -4-yl) -5-bromo-N-phenyl- [1,1'-biphenyl] -3-amine). (Yield: 82%)

m / z: 475.09 (100.0%), 477.09 (97.1%), 478.09 (30.4%), 476.10 (17.4%), 476.10 (16.1%), 477.10 (4.5% ), 479.10 (1.2%)

Manufacturing example  3: Synthesis of intermediate I-3

Except that 16.08 g of di ([1,1'-biphenyl] -4-yl) amine was used in place of diphenylamine to obtain Intermediate I-3 (N, N-di [1,1'-biphenyl] -4-yl) -5-bromo- [1,1'-biphenyl] -3-amine). (Yield: 80%).

m / z: 551.12 (100.0%), 553.12 (97.1%), 554.13 (38.2%), 552.13, 22.9%, 552.13 (16.0%), 555.13 (6.8%), 553.13 )

Manufacturing example  4: Intermediate I-4 Synthesis

(50 mM) of I-1, 7.5 g (80 mM) of aniline, 1.2 g (1.3 mM) of Pd ₂ (dba) 3, 1.5 ml (3 mM) of P (t- Bu) 3, After the addition of 11.05 g (115 mM), 200 ml of toluene was added and the mixture was heated under reflux for 5 hours. After completion of the reaction, the reaction mixture was immediately filtered, extracted with dichloromethane, and then filtered with MgSO ₄ . The solvent of the filtered organic layer was removed and then purified by column chromatography to obtain 16.92 g of Intermediate I-4 (N3, N3, N5-triphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 82%)

m / z: 412.19 (100.0%), 413.20 (32.1%), 414.20 (2.9%

Manufacturing example  5: Synthesis of Intermediate I-5

(N3 - ([1,1'-biphenyl] -4-yl) -N3, N5 (I-2) was obtained in the same manner as in Production Example 4, except that 23.82 g of I- -Diphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 83%)

m / z: 488.23 (100.0%), 489.23 (38.7%), 490.23 (7.8%)

Manufacturing example  6: Synthesis of Intermediate I-6

(N3, N3-di ([1,1'-biphenyl] -4-yl) thiophene was obtained in the same manner as in Production Example 3, except that 27.63 g of I- -N5-phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 81%).

m / z: 564.26 (100.0%), 565.26 (44.3%), 566.26 (11.2%

Synthetic example  1: Synthesis of compound 1

27.82 g (70 mM) of 2-bromo-9,9-diphenyl-9H-fluorene and 20.63 g (50 mM) of I-4 were placed under argon or nitrogen atmosphere and the reaction was carried out in the same manner as in Preparation Example 1, (N3- (9,9-diphenyl-9H-fluoren-2-yl) -N3, N5, N5-triphenyl- [1,1'- biphenyl] -3,5-diamine) . (Yield: 80%).

m / z: 728.32 (100.0%), 729.32 (59.8%), 730.33 (17.2%), 731.33

Synthetic example  2: Synthesis of compound 2

The reaction was carried out in the same manner as in Synthesis Example 1, except that 24.43 g of I-5 was used in place of I-4, to thereby yield Compound 2 (N3 - ([1,1'-biphenyl] 9-diphenyl-9H-fluoren-2-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 80%).

m / z: 804.35 (100.0%), 805.35 (66.3%), 806.36 (21.2%), 807.36

Synthetic example  3: Synthesis of compound 3

Except that 27.82 g of 3-bromo-9,9-diphenyl-9H-fluorene was used instead of 2-bromo-9,9-diphenyl-9H-fluorene in the same manner as in Synthesis Example 1 N3, N5, N5-triphenyl- [1,1'-biphenyl] -3,5-diamine) 29.52 (9,9-diphenyl-9H- g. (Yield: 81%).

m / z: 728.32 (100.0%), 729.32 (59.3%), 730.33 (17.5%), 731.33

Synthetic example  4: Synthesis of compound 4

The reaction was carried out in the same manner as in Synthesis Example 3 except that 24.43 g of I-5 was used in place of I-4, to obtain a compound 4 (N3 - ([1,1'-biphenyl] 9-diphenyl-9H-fluoren-3-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 83%)

m / z: 804.35 (100.0%), 805.35 (66.2%), 806.36 (21.5%), 807.36 (3.4%

Synthetic example  5: Synthesis of compound 5

Except that 27.82 g of 4-bromo-9,9-diphenyl-9H-fluorene was used instead of 2-bromo-9,9-diphenyl-9H-fluorene in the same manner as in Synthesis Example 1 The compound 5 (N3- (9,9-diphenyl-9H-fluoren-4-yl) -N3, N5, N5-triphenyl- [1,1'- biphenyl] -3,5- diamine) 29.89 g. (Yield: 82%)

m / z: 728.32 (100.0%), 729.32 (59.8%), 730.33 (17.3%), 731.33

Synthetic example  6: Synthesis of Compound 6

The reaction was carried out in the same manner as in Synthesis Example 5 except that 24.43 g of I-5 was used in place of I-4, to thereby yield Compound 6 (N3 - ([1,1'-biphenyl] Diphenyl-9H-fluoren-4-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 81%).

m / z: 804.35 (100.0%), 805.35 (66.2%), 806.36 (21.5%), 807.36 (3.4%

Synthetic example  7: Synthesis of Compound 7

Except that 27.67 g of 2-bromo-9,9'-spirobi [fluorene] was used instead of 2-bromo-9,9-diphenyl-9H-fluorene in the same manner as in Synthesis Example 1 (9,9'-spirobi [fluorene] -2-yl) -N3, N5, N5-triphenyl- [1,1'- biphenyl] -3,5-diamine) 29.81 g. (Yield: 82%)

m / z: 726.30 (100.0%), 727.31 (59.3%), 728.31 (17.3%), 729.31

Synthetic example  8: Compound 8 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 7 except that 24.43 g of I-5 was used in place of I-4 to give Compound 8 (N3- (9,9'-spirobi [fluorene] -2-yl) -N5- ( [1,1'-biphenyl] -4-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 81%).

m / z: 802.33 (100.0%), 803.34 (66.1%), 804.34 (21.6%), 805.34 (3.4%

Synthetic example  9: Synthesis of Compound 9

Except that 27.67 g of 3-bromo-9,9'-spirobi [fluorene] was used instead of 2-bromo-9,9-diphenyl-9H-fluorene in the same manner as in Synthesis Example 1 (9,9'-spirobi [fluorene] -3-yl) -N3, N5, N5-triphenyl- [1,1'- biphenyl] -3,5- diamine) 30.17 g. (Yield: 83%)

m / z: 726.30 (100.0%), 727.31 (59.2%), 728.31 (17.5%), 729.31

Synthetic example  10: Compound 10 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 9, except that 24.43 g of I-5 was used in place of I-4 to give Compound 10 (N3- (9,9'-spirobi [fluorene] -3- [1,1'-biphenyl] -4-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 82%)

m / z: 802.33 (100.0%), 803.34 (65.7%), 804.34 (21.5%), 805.34

Synthetic example  11: Compound 11 Synthesis

Except that 27.67 g of 4-bromo-9,9'-spirobi [fluorene] was used instead of 2-bromo-9,9-diphenyl-9H-fluorene in the same manner as in Synthesis Example 1 The compound 11 (N3- (9,9'-spirobifluoren-4-yl) -N3, N5, N5-triphenyl- [1,1'- biphenyl] -3,5- diamine) 29.08 g. (Yield: 80%).

m / z: 726.30 (100.0%), 727.31 (59.3%), 728.31 (17.5%), 729.31

Synthetic example  12: Compound 12 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 11 except that 24.43 g of I-5 was used in place of I-4 to obtain Compound 12 (N3- (9,9'-spirobi [fluorene] -4- [1,1'-biphenyl] -4-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 82%)

m / z: 802.33 (100.0%), 803.34 (66.4%), 804.34 (21.7%), 805.34

Synthetic example  13: Compound 13 Synthesis

Except that 17.3 g of 2-bromodibenzo [b, d] furan was used instead of 2-bromo-9,9-diphenyl-9H-fluorene and 24.43 g of I- (Dibenzo [b, d] furan-2-yl) -N3, N5-di Phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 79%).

m / z: 654.27 (100.0%), 655.27 (51.7%), 656.27 (13.3%), 657.28

Synthetic example  14: Compound 14 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 13, except that 28.24 g of I-6 was used instead of I-5, to thereby yield Compound 14 (N3, N3-di [(1,1'-biphenyl- (Dibenzo [b, d] furan-2-yl) -N5-phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 81%).

m / z: 730.30 (100.0%), 731.30 (58.6%), 732.31 (16.6%), 733.31

Synthetic example  15: Compound 15 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 13 except that 17.3 g of 3-bromodibenzo [b, d] furan was used instead of 2-bromodibenzo [b, d] furan to obtain Compound 15 (N3 - (Dibenzo [b, d] furan-3-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5-diamine ). (Yield: 80%).

m / z: 654.27 (100.0%), 655.27 (51.6%), 656.27 (13.4%), 657.28

Synthetic example  16: Compound 16 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 15, except that 28.24 g of I-6 was used in place of I-5 to give Compound 16 (N3, N3-di [(1,1'-biphenyl- (Dibenzo [b, d] furan-3-yl) -N5-phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 80%).

m / z: 730.30 (100.0%), 731.30 (58.1%), 732.31 (16.8%), 733.31

Synthetic example  17: Compound 17 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 13 except that 17.3 g of 4-bromodibenzo [b, d] furan was used instead of 2-bromodibenzo [b, d] furan to obtain Compound 17 (N3 - (Dibenzo [b, d] furan-4-yl) -N3, N5-diphenyl- [1,1'- biphenyl] -3,5-diamine ). (Yield: 82%)

m / z: 654.27 (100.0%), 655.27 (51.5%), 656.27 (13.5%), 657.28

Synthetic example  18: Compound 18 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 17, except that 28.24 g of I-6 was used in place of I-5 to give Compound 18 (N3, N3-di [(1,1'-biphenyl- (Dibenzo [b, d] furan-4-yl) -N5-phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 81%).

m / z: 730.30 (100.0%), 731.30 (58.2%), 732.31 (16.8%), 733.31

Synthetic example  19: Compound 19 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 13, except that 18.42 g of 2-bromodibenzo [b, d] thiophene was used instead of 2-bromodibenzo [b, (Dibenzo [b, d] thiophen-2-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5 -Diamine). ≪ / RTI > (Yield: 81%).

m / z: 670.24 (100.0%), 671.25 (51.5%), 672.25 (13.4%), 672.24 (4.6%), 673.24

Synthetic example  20: Compound 20 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 19 except that 28.24 g of I-6 was used in place of I-5 to give Compound 20 (N3, N3-di [(1,1'-biphenyl- (Dibenzo [b, d] thiophen-2-yl) -N5-phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 80%).

m / z: 746.28 (100.0%), 747.28 (58.5%), 748.28 (16.8%), 748.27 (4.3%), 749.27

Synthetic example  21: Compound 21 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 13, except that 18.42 g of 3-bromodibenzo [b, d] thiophene was used instead of 2-bromodibenzo [b, (Dibenzo [b, d] thiophen-3-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5 -Diamine). ≪ / RTI > (Yield: 83%)

m / z: 670.24 (100.0%), 671.25 (51.5%), 672.25 (13.5%), 672.24 (4.6%), 673.24

Synthetic example  22: Compound 22 Synthesis

The reaction was carried out in the same manner as in Synthetic Example 21 except that 28.24 g of I-6 was used instead of I-5, to give Compound 22 (N3, N3-di [(1,1'-biphenyl- (Dibenzo [b, d] thiophen-3-yl) -N5-phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 82%)

m / z: 746.28 (100.0%), 747.28 (58.8%), 748.28 (16.9%), 748.27 (4.1%), 749.27

Synthetic example  23: Compound 23 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 13, except that 18.42 g of 4-bromodibenzo [b, d] thiophene was used instead of 2-bromodibenzo [b, (Dibenzo [b, d] thiophen-4-yl) -N3, N5-diphenyl- [1,1'-biphenyl] -3,5 -Diamine). ≪ / RTI > (Yield: 79%).

m / z: 670.24 (100.0%), 671.25 (51.7%), 672.25 (13.4%), 672.24 (4.2%), 673.24

Synthetic example  24: Compound 24 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 23, except that 28.24 g of I-6 was used in place of I-5 to obtain a compound 24 (N3, N3-di [(1,1'-biphenyl- (Dibenzo [b, d] thiophen-4-yl) -N5-phenyl- [1,1'-biphenyl] -3,5-diamine). (Yield: 80%).

m / z: 746.28 (100.0%), 747.28 (58.1%), 748.28 (16.4%), 748.27 (4.7%), 749.27 (2.9%

Synthetic example  25: Compound 25 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 2 except that 21.5 g of 2-bromotriphenylene was used instead of 2-bromo-9,9-diphenyl-9H-fluorene to obtain Compound 25 (N3 - ([ (Triphenylen-2-yl) - [1,1'-biphenyl] -3,5-diamine) . (Yield: 80%).

m / z: 714.30 (100.0%), 715.31 (58.1%), 716.31 (16.8%), 717.31

Synthetic example  26: Compound 26 Synthesis

The reaction was carried out in the same manner as in Synthesis Example 25 except that 24.43 g of I-6 was used in place of I-5 to obtain Compound 26 (N3, N3-di [(1,1'-biphenyl- Phenyl-N5- (triphenylene-2-yl) - [1,1'-biphenyl] -3,5-diamine). (Yield: 78%).

m / z: 790.33 (100.0%), 791.34 (65.1%), 792.34 (20.9%), 793.34

Manufacturing example  7: Fabrication of organic light emitting device

A thin glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator) to form a hole injection layer HI 600 Å, HATCN 50 Å, and HT 350 Å as a hole transport layer, and then Compound 1 was formed as a light emitting auxiliary layer in a thickness of 150 Å. Next, the light emitting layer was doped with 7% of GH: Ir (ppy) ₃ to form a 250 Å layer. Next, an ET: Liq (1: 1) 300 Å film was formed as an electron transport layer, and LiF 10 Å and aluminum (Al) 1000 Å were film-formed. The device was encapsulated in a glove box to fabricate an organic light- Respectively.

Organic light emitting devices (Examples 2 to 26) were prepared in the same manner as above using Compound 2 to 26 instead of Compound 1.

Comparative Example

An organic light emitting device was prepared in the same manner as in Production Example 7, except that the following Ref.1 to Ref.7 (Comparative Examples 1 to 7) were used instead of Compound 1.

Experimental Example  1: Performance evaluation of organic light emitting device

A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light emitting devices of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Table 1.

Table 1 Driving voltage
Op.V Current density
mA / cm ² Current efficiency
Cd / A Color coordinates
CIEx Color coordinates
CIEy LT97
@ 10000nit Example 1 4.89 10.00 51.02 0.328 0.628 105 Example 2 5.08 10.00 53.47 0.322 0.632 116 Example 3 5.02 10.00 48.66 0.324 0.627 122 Example 4 5.01 10.00 52.03 0.318 0.637 137 Example 5 4.99 10.00 47.74 0.324 0.631 114 Example 6 4.98 10.00 49.87 0.324 0.632 129 Example 7 4.94 10.00 51.23 0.318 0.636 111 Example 8 4.81 10.00 50.24 0.322 0.634 122 Example 9 4.86 10.00 48.72 0.341 0.622 133 Example 10 5.05 10.00 48.36 0.336 0.625 142 Example 11 5.04 10.00 47.61 0.339 0.623 124 Example 12 5.09 10.00 49.84 0.337 0.623 136 Example 13 4.75 10.00 47.82 0.341 0.622 124 Example 14 4.86 10.00 51.50 0.335 0.624 138 Example 15 4.98 10.00 52.51 0.339 0.621 129 Example 16 4.73 10.00 53.81 0.335 0.623 142 Example 17 4.59 10.00 51.72 0.340 0.620 133 Example 18 4.86 10.00 50.04 0.334 0.624 147 Example 19 4.79 10.00 51.27 0.331 0.626 127 Example 20 5.01 10.00 51.86 0.333 0.624 142 Example 21 4.67 10.00 53.59 0.347 0.617 128 Example 22 5.07 10.00 53.13 0.333 0.625 140 Example 23 4.69 10.00 53.50 0.310 0.640 124 Example 24 4.59 10.00 50.44 0.314 0.637 138 Example 25 4.80 10.00 51.95 0.307 0.643 142 Example 26 4.76 10.00 54.17 0.304 0.646 155 Comparative Example 1 5.07 10.00 39.72 0.347 0.624 95 Comparative Example 2 5.15 10.00 38.64 0.349 0.623 97 Comparative Example 3 5.35 10.00 35.26 0.348 0.636 84 Comparative Example 4 5.21 10.00 36.78 0.354 0.640 86 Comparative Example 5 5.20 10.00 34.57 0.354 0.640 80 Comparative Example 6 5.25 10.00 35.74 0.342 0.634 79 Comparative Example 7 5.23 10.00 36.36 0.346 0.638 81

As shown in Table 1, in Comparative Examples 1 and 2 in which phenyl-substituted phenylene was used between two nitrogen atoms and biphenylene substituted with one phenyl, Comparative Example 5 to Comparative Example 7 in which phenylene was used, Examples 13 to 24 in which dibenzofuran or dibenzothiophene was substituted and Comparative Example 3 in which dibenzofuran or dibenzothiophene was substituted in two , And Comparative Example 4, high efficiency and long life characteristics are exhibited, and the voltage is also lowered. As a result, the compound of the present invention can lower the driving voltage of the organic light emitting device, increase the efficiency, and improve the lifetime. Particularly, when phenylene is added between dibenzofuran or an arylamine into which dibenzothiophene is introduced, specifically, when L ₁ and L ₂ are both phenylene in the structure of the formula (1) In Comparative Examples 1 and 2 using Ref.1 and Ref.2, it was confirmed that the mobility was slower, the efficiency was decreased, and the driving voltage was increased.

It will be understood by those of ordinary skill in the art that the foregoing description of the embodiments is for illustrative purposes and that those skilled in the art can easily modify the invention without departing from the spirit or essential characteristics thereof. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.

The scope of the present invention is defined by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be interpreted as being included in the scope of the present invention .

100: substrate
200: Hole injection layer
300: hole transport layer
400: light emitting layer
500: electron transport layer
600: electron injection layer
1000: anode
2000: cathode

Claims (11)

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

In the above formulas,
Ar ₁ is

or

ego,
Ar ₂ to Ar ₄ are each independently phenyl, biphenyl or naphthyl,
L ₁ and L ₂ are each independently a C ₅ -C ₃₀ arylene group which may be directly bonded or substituted. The method according to claim 1,
Wherein said compound comprises a compound represented by the following formula 2 or 3:
(2)

(3)

In the above formulas,
Ar ₂ to Ar ₄ , L ₁ and L ₂ are as defined in claim 1,
Dashed lines are un-bonded or direct bonded. The method according to claim 1,
Wherein said compound comprises a compound represented by the following Formula 4:
[Chemical Formula 4]

In the above formulas,
Ar < ₂ > to Ar < ₄ > are as defined in claim 1,
L ₁ and L ₂ are both a direct bond or phenylene,
X is S or O; 4. The method according to any one of claims 1 to 3,
Lt; _{1 >} and L < ₂ > are each independently a direct bond or phenylene. 4. The method according to any one of claims 1 to 3,
Lt; _{1 >} and L < _{2 >} are both direct bonds. 4. The method according to any one of claims 1 to 3,
Lt; RTI ID = 0.0 > 550 < / RTI > The method according to claim 1,
Wherein said compound comprises any one of the following compounds: < RTI ID = 0.0 >

And at least one organic layer comprising at least one compound according to claim 1 between the first electrode and the second electrode. 9. The method of claim 8,
Wherein the organic material layer is one or more layers of a hole injecting layer, a hole transporting layer, and a light emitting auxiliary layer. 9. The method of claim 8,
Wherein the organic light emitting element comprises an organic material layer containing a hole transporting material and an organic material layer containing a compound represented by the general formula (1). 11. The method of claim 10,
Wherein the organic material layer containing the compound represented by Formula 1 is a light-emission-assisting layer.

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