KR20180131091A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to a novel compound and to an organic electroluminescent device including the same, wherein the novel compound according to one embodiment of the present invention contains a linking group located between a position 2 of fluorene and arylamine, wherein the arylamine has a substituent having two or more aryl groups and a phenyl substituent, and the organic light emitting device containing the compound according to the present invention can realize low voltage, 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.

Korean Patent Publication No. 10-2015-0086721

The present invention provides 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,

L is a substituted or unsubstituted C _6-30 arylene group or a substituted or unsubstituted C _6-30 heteroarylene group,

Ar _a And Ar _b are each independently a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 nitrogen-containing heteroaryl group (provided that it is not substituted with deuterium)

R, R ', R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted C _1-30 An alkyl group, a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 heteroaryl group,

R ₃ is hydrogen or a substituted or unsubstituted C _1-30 alkyl group,

1 is an integer of 0 to 4, m is 0 to 3, n is 0 to 5, p is 1 to 3, q is an integer of 1 to 3, and p + q is an integer of 2 to 4.

The second aspect of the present invention provides an organic light emitting device comprising an organic compound layer containing a compound according to the present invention between a first electrode and a second electrode.

The compound according to an embodiment of the present invention can form an easy deep HOMO level in the luminescent auxiliary layer and can maintain a high LUMO which is easy to block electrons by bonding an arylamine through a linking group to the 2-position of fluorene . Accordingly, the compound according to one embodiment of the present invention can be used in an organic light emitting device to realize low voltage and high efficiency of an organic light emitting device.

In addition, the compound according to an embodiment of the present invention has a substituent group in which the arylamine is linked with two or more aryl groups, and the pi-conjugation can be increased. OFF can be suppressed and the lifetime of the organic light emitting device can be realized.

In addition, the compound according to an embodiment of the present invention has a substituent having an arylamine fixed to the phenyl, so that the HOMO level and the LUMO level of the compound are maintained at a high value of T1, thereby maximizing the exciton confinement effect in the light emitting layer. Can be achieved.

Further, since the linkage between the fluorene and the arylamine and the arylamine have a substituent connected by two or more aryls, the Tg is improved to prevent the recrystallization of the thin film, and the driving stability of the organic light emitting device can be improved.

1 is a schematic view of an organic light emitting 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 a C _6-30 aromatic hydrocarbon ring group, such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, Means an aromatic ring such as phenyl, naphthyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, Examples of the C _3-30 aromatic ring containing a hetero element include pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Benzothiophenyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine rings, pyrazine rings, pyrimidine rings , Pyridazine ring, triazine ring, indole ring, quinoline ring , Acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazine May include a heterocyclic group formed from a heterocyclic ring, a thiazole ring, a thiadiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring or a dibenzofuran ring .

The term "which may be substituted" in the whole specification of the present application is 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, C ₃ ~ C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C ₃₀ aryl group and C ₃ ~ may mean that which may be substituted with one or more groups selected from the group consisting of a heteroaryl group of C ₃₀ have.

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

[Chemical Formula 1]

In Formula 1,

L is a substituted or unsubstituted C _6-30 arylene group or a substituted or unsubstituted C _3-30 heteroarylene group,

Ar _a And Ar _b are each independently a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 nitrogen-containing heteroaryl group (provided that it is not substituted with deuterium)

R, R ', R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted C _1-30 An alkyl group, a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 heteroaryl group,

R ₃ is hydrogen or a substituted or unsubstituted C _1-30 alkyl group,

1 is an integer of 0 to 4, m is 0 to 3, n is 0 to 5, p is 1 to 3, q is an integer of 1 to 3, and p + q is an integer of 2 to 4.

In the compound of Formula 1 according to an embodiment of the present invention, arylamine is bonded through a linking group to the 2-position of fluorene, and the arylamine is substituted with one substituent having two or more aryl groups and a substituent 1 I have a dog.

The compound according to an embodiment of the present invention is characterized in that the arylamine is bonded to the fluorene at the 2-position of the fluorene through the linking group to form an easy deep HOMO level in the luminescent auxiliary layer and a high LUMO have. Accordingly, the compound according to one embodiment of the present invention can be used in an organic light emitting device to realize low voltage and high efficiency of an organic light emitting device.

In addition, the compound according to an embodiment of the present invention has a substituent group in which the arylamine is linked with two or more aryl groups, and the pi-conjugation can be increased. OFF can be suppressed and the lifetime of the organic light emitting device can be realized.

In addition, the compound according to an embodiment of the present invention has a substituent having an arylamine fixed to the phenyl, so that the HOMO level and the LUMO level of the compound are maintained at a high value of T1, thereby maximizing the exciton confinement effect in the light emitting layer. Can be achieved.

Further, since the linkage between the fluorene and the arylamine and the arylamine have a substituent connected by two or more aryls, the Tg is improved to prevent the recrystallization of the thin film, and the driving stability of the organic light emitting device can be improved.

In one embodiment of the present invention, the Ar < _{a >} And Ar _b may be a substituted or unsubstituted C _6-30 aryl group or a heteroaryl group containing C _3-30 nitrogen, but the aryl group and the heteroaryl group are not substituted with deuterium. Substitution with deuterium is not only complicated in the synthesis process, but also in such a case, it may be difficult to obtain a high purity compound required for the hole transport layer. This may adversely affect the lifetime of the organic light emitting device.

In one embodiment of the present invention, the nitrogen-containing heteroaryl group is not limited thereto, but may be, for example, pyridine, pyrazine, triazine, or quinoline.

Further, in one embodiment of the present invention, the compound may be represented by the following general formula (2).

(2)

In Formula 2, o is an integer of 1 to 4.

When the linker (L) has at least one phenylene, it is possible to form a deep HOMO level easily in the luminescent auxiliary layer and maintain a high LUMO level which facilitates blocking of electrons.

According to an embodiment of the present invention, R and R 'in the above formula (1) or (2) are independently a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 Or a heteroaryl group. In this case, a deeper HOMO can be maintained, and the molecular arrangement is excellent, so that a high Tg can be formed. Thus, the efficiency and lifetime of the organic light emitting device can be increased.

According to an embodiment of the present invention, R 1 and R 'in the general formula (1) or (2) are independently hydrogen, a substituted or unsubstituted C _1-30 Alkyl group, a substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _6-30 heteroaryl group, Ar _a and Ar _b each independently represent a substituted or unsubstituted C _6-30 Lt; / RTI > Ar _a And when Ar _b is a substituted or unsubstituted C _6-30 aryl group, the deep HOMO level can be maintained and the low voltage and high efficiency effect can be more excellent. More specifically, the Ar < _{a >} And Ar _b may be a phenyl group.

According to one embodiment of the present invention, the compound may be represented by the following general formula (3).

(3)

In Formula 3,

R ₄ and R ₅ are each independently hydrogen, substituted or unsubstituted C _1-24 An alkyl group, a substituted or unsubstituted C _6-24 aryl group or a substituted or unsubstituted C _3-24 heteroaryl group,

o is an integer of 1 to 4;

According to an embodiment of the present invention, the - (Ar _a ) _p - (Ar _b ) _q may be represented by any one of the following formulas [1-1] to [1-6].

In the above formulas [1-1] to [1-6]

Ar ₁ To Ar ₄ are each independently a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 heteroaryl group containing nitrogen, but not substituted with deuterium. Further, according to one embodiment of the present invention, Ar ₁ to Ar ₄ in the above formulas [1-1] to [1-6] may be a phenyl group.

Further, according to an embodiment of the present invention, since HOMO having a sufficiently high HOMO as the hole transport layer is used as the connecting position of the fluorene, the proper balance of the exciton forming region in the light emitting layer is maintained to achieve low voltage and high efficiency of the organic light emitting device .

In one embodiment of the present invention, the compound represented by Formula 1 may be specifically, but not limited to, the following compounds:

The above compounds 1 to 210 have a stable Tg, which is excellent in thermal stability, and is effective in preventing lifetime recrystallization during device operation.

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 at least one organic compound layer containing 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 a hole injection layer, a hole transport layer, and a light emission assisting layer, but may not be limited thereto. Further, when forming the organic material layer, the compound according to the present invention may be used alone or in combination with a known 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 compound represented by Formula 1 as an emission auxiliary layer. In addition, the compound represented by Formula 1 may be a compound specifically specified as described above.

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 layers may be included.

For example, the organic light emitting device can be fabricated as 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, Implantation electrode 2000) may be 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 may be used to inject 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 탆.

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 transport layer 300 may be made of the compound according to the present invention. As described above, the compound according to the present invention may be used alone or a known compound may be used together. In addition, according to one embodiment of the present invention, the hole transport layer 300 may have one or more layers, and may include a hole transport layer formed only of a known material.

In addition, according to an embodiment of the present invention, a light emitting auxiliary layer may be formed on the hole transport layer 300. The light-emitting auxiliary layer may be a compound according to the present invention, and various compounds represented by the general formula (1) may be used together. In addition, the compound according to the present invention and a known compound can be used together to form a light-emitting auxiliary layer.

The light emitting layer material may be deposited on the hole transport layer 300 or the light emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. 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 organic light emitting diode can be formed using the compound according to the present invention or the following materials. The compound and a known substance 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 according to the required degree, specifically 10 to 1,000 nm, and 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]

Intermediate synthesis

Intermediate IM was synthesized by the reaction as described above for synthesis of the target compound.

Synthetic example  1: Synthesis of intermediate (IM1)

In a round bottom flask, 8.5 g of 9,9-dimethyl-9H-fluoren-2-yl boronic acid and 10.0 g of 1-bromo-4-iodobenzene were dissolved in 200 ml of 1,4-dioxane, and 50 ml of K2CO3 (2M) PPh ₃ ) ₄ were added, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 8.27 g (yield 67%) of intermediate IM1-1.

8.0 g of IM1-1, 2.4 g of aniline, 3.3 g of t-BuONa, 0.85 g of Pd ₂ (dba) ₃ and 1.0 ml of (t-Bu) ₃ were dissolved in 110 ml of toluene, and the mixture was refluxed with stirring. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 6.04 g (yield: 73%) of IM1.

Synthesis Examples 2 to 4 Synthesis of Intermediates (IM2 to IM4)

Intermediates IM2 to IM4 were synthesized using the same method as Intermediate IM1 except that starting materials were changed as shown in Table 1 below.

Synthetic example Starting material Intermediate 2

9,9-dimethyl-9H-fluoren-2-yl)boronic acid

9,9-dimethyl-9H-fluoren-2-yl) boronic acid

4-bromo-4'-iodo-1,1'-biphenyl

3

9,9-diphenyl-9H-fluoren-2-yl) boronic acid

1-bromo-4-iodobenzene

4

9,9-diphenyl-9H-fluoren-2-yl) boronic acid

4-bromo-4'-iodo-1,1'-biphenyl

Compound synthesis

Synthesis of Compound 1

To a round bottom flask was added IM1 3.0g, 4-bromo-1,1 ': 4', 1 '' - terphenyl 2.5g, t-BuONa 1.2g, Pd 2 (dba) 3 0.3g, (t-Bu) 3 P0 Were dissolved in 60 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 3.34 g of Compound 1 (yield: 70%).

Synthesis of Compound 2

4 ', 4' ', 4' ', 1' ', 4' 'and 4' 'were used instead of 4-bromo-1,1' '-quaterphenyl. < / RTI >

Synthesis of Compound 3

Compound 3 was synthesized using IM2 instead of IM1, using the same method as Compound 1.

Synthesis of Compound 4

IM2 and 4-bromo-1,1 ': 3', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 4 was synthesized.

Synthesis of Compound 5

IM2 and 4-bromo-1,1 ': 2', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 5 was synthesized.

Synthesis of Compound 6

Compound 6 was synthesized using IM3 and 4-bromo-1,1'-biphenyl instead of IM1 and 4-bromo-1,1 ': 4', 1 "-terphenyl.

Synthesis of Compound 7

Compound 7 was synthesized using IM3 instead of IM1, using the same method as compound 1. [

Synthesis of Compound 8

IM3 and 4-bromo-1,1 ': 3', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 8 was synthesized.

Synthesis of Compound 9

IM3 and 4-bromo-1,1 ': 2', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 9 was synthesized.

Synthesis of Compound 10

IM3 and 3-bromo-1,1 ': 4', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 10 was synthesized.

Synthesis of Compound 11

IM3 and 3-bromo-1,1 ': 3', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 11 was synthesized.

Synthesis of Compound 12

IM3 and 3-bromo-1,1 ': 2', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 12 was synthesized.

Synthesis of Compound 13

IM3 and 2-bromo-1,1 ': 4', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 13 was synthesized.

Synthesis of Compound 14

IM3 and 2-bromo-1,1 ': 3', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 14 was synthesized.

Synthesis of Compound (15)

IM3 and 2-bromo-1,1 ': 2', 1 "-terphenyl were used instead of IM1 and 4-bromo-1,1 ': 4' Compound 15 was synthesized.

Synthesis of Compound 16

Compound 16 was synthesized using IM4 and 4-bromo-1,1'-biphenyl instead of IM1 and 4-bromo-1,1 ': 4', 1 "-terphenyl.

Synthesis of Compound 17

Compound 17 was synthesized using IM4 and IM-4 and 3-bromo-1,1'-biphenyl instead of IM1 and 4-bromo-1,1 ': 4', 1 "-terphenyl.

Synthesis of compound 18

Compound 18 was synthesized using IM4 and IM-4 and 2-bromo-1,1'-biphenyl instead of IM1 and 4-bromo-1,1 ': 4', 1 "-terphenyl.

Synthesis of Compound 19

IM3 and 4-bromo-5'-phenyl-1,1 ': 3', 1 ': 4', 1''-terphenyl were used instead of IM1 and 4-bromo- '-terphenyl was used to synthesize Compound 19.

Synthesis of Compound 20

IM3 and 2-bromo-5'-phenyl-1,1 ': 3', 1 ': 4', 1''-terphenyl were used instead of IM1 and 4-bromo- ' -terphenyl. < / RTI >

The specific formulas of the compounds 1 to 20 synthesized above are shown in Table 2 below.

compound The yield(%) FD-MS One

70 m / z: 589.28 (100.0%), 590.28 (49.1%), 591.28 (11.8%), 592.29 2

72

m / z: 665.31 (100.0%), 666.31 (56.0%), 667.31 (15.1%), 668.32 3

75 m / z: 665.31 (100.0%), 666.31 (56.0%), 667.31 (15.1%), 668.32 4

70 m / z: 665.31 (100.0%), 666.31 (56.0%), 667.31 (15.1%), 668.32 5

70 m / z: 665.31 (100.0%), 666.31 (56.0%), 667.31 (15.1%), 668.32 6

75 m / z: 637.28 (100.0%), 638.28 (53.4%), 639.28 (14.0%), 640.29 7

70 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 8

68 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 9

72 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 10

65 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 11

60 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 12

62 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 13

70 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 14

65 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 15

65 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 16

72 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 17

60 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 18

69 m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 19

65 m / z: 789.34 (100.0%), 790.34 (66.3%), 791.35 (21.7%), 792.35 20

61 m / z: 789.34 (100.0%), 790.34 (66.3%), 791.35 (21.7%), 792.35

Organic Light Emitting Device Manufacturing

Example  One

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 washed 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 HATCN 50 Å, a hole transporting layer BPA 250 Å, and a light emitting auxiliary layer 100 Å were formed by using an evaporator as a light emitting layer. The light emitting layer was doped with BH 01: BDO 3 to a thickness of 250 Å. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were formed, and the device was encapsulated in a glove box to produce an organic light emitting device.

Examples 2 to 20

An organic luminescent device was fabricated by the same method as in Example 1 except for using Compound 2 to Compound 20 instead of Compound 1.

Comparative Examples 1 to 9

Using the same method as in Example 1, instead of compound 1, organic electroluminescent devices were prepared by using Ref.1 to Ref.9 of the following [Table 4], respectively.

[Evaluation of performance 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 Examples and Comparative Examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under atmospheric pressure. The results are shown in Table 5.

Op. V mA / cm2 Cd / A QE (%) CIEx CIEy LT95 Example 1 3.96 10 7.22 6.14 0.140 0.109 115 Example 2 3.95 10 7.25 6.10 0.140 0.110 112 Example 3 3.94 10 7.29 6.19 0.141 0.110 115 Example 4 3.95 10 7.25 6.12 0.140 0.110 110 Example 5 3.94 10 7.27 6.15 0.141 0.110 115 Example 6 3.91 10 7.34 6.23 0.140 0.110 142 Example 7 3.89 10 7.45 6.33 0.140 0.110 156 Example 8 3.90 10 7.53 6.40 0.140 0.111 162 Example 9 3.89 10 7.50 6.42 0.139 0.111 166 Example 10 3.92 10 7.60 6.49 0.141 0.110 162 Example 11 3.93 10 7.62 6.50 0.140 0.110 169 Example 12 3.92 10 7.59 6.50 0.140 0.110 160 Example 13 3.89 10 7.49 6.35 0.140 0.110 165 Example 14 3.90 10 7.52 6.43 0.139 0.111 169 Example 15 3.89 10 7.50 6.40 0.141 0.110 170 Example 16 3.91 10 7.37 6.25 0.140 0.110 147 Example 17 3.93 10 7.40 6.27 0.140 0.110 150 Example 18 3.90 10 7.37 6.23 0.141 0.110 152 Example 19 3.94 10 7.41 6.29 0.140 0.110 165 Example 20 3.95 10 7.43 6.30 0.140 0.109 160 Comparative Example 1 4.40 10 6.45 5.60 0.14 0.111 13 Comparative Example 2 4.20 10 6.77 4.06 0.143 0.113 55 Comparative Example 3 4.22 10 6.90 4.04 0.141 0.113 18 Comparative Example 4 4.10 10 7.10 5.28 0.141 0.112 60 Comparative Example 5 4.13 10 7.00 4.10 0.141 0.111 85 Comparative Example 6 4.18 10 6.95 5.64 0.142 0.112 76 Comparative Example 7 4.05 10 7.05 4.23 0.141 0.113 105 Comparative Example 8 4.11 10 7.06 6.00 0.140 0.115 97 Comparative Example 9 4.30 10 7.00 5.97 0.140 0.112 81

As shown in Table 5, it can be seen that the embodiments of the present invention are superior in physical properties in all respects, such as low driving voltage, increased efficiency and lifetime, as compared with Comparative Examples 1 to 8. [

More specifically, when comparing Examples of the present invention with Comparative Examples 1 and 2 which do not have a linking group between fluorene and arylamine, the embodiment of the present invention has a linking group between fluorene and arylamine, It is possible to form an easy deep HOMO level and maintain a high LUMO which is easy to cut off the electron, so that it shows lower voltage and higher efficiency than Comparative Examples 1 and 2.

Compared with Comparative Examples 3 and 4 in which all of the arylamine aryl groups had a phenyl group or a methylphenyl group, the examples of the present invention showed that two or more aryl groups were introduced into one of the two aryl substituents of the arylamine, Can be increased, and the thin film and the molecular arrangement are excellent. Thus, it has a faster hole mobility than that of Comparative Examples 3 and 4, and has a long lifetime through roll-off suppression.

Compared with Comparative Examples 6 and 7, in which one of the two aryl substituents of the arylamine is naphthyl, and the two aryl substituents of the arylamine are all biphenyl, The LUMO level was maintained by the phenyl group, which facilitates the blocking of electrons, and the high T1 was formed, maximizing the exciton confinement effect in the luminescent layer and exhibiting high efficiency.

Compared with Comparative Example 8 in which the arylamine has a dibenzofurane group, the embodiment of the present invention does not include a heterocyclic group having a heteroatom such as O, S, etc. serving as an electron donor and can maintain a deep HOMO level, And high efficiency.

Compared with Comparative Example 9 in which the number of fluorenes is 3 as a connecting position, the embodiment of the present invention has a HOMO that is appropriately deep as a hole transport layer, maintains an appropriate balance of the exciton formation region in the emission layer, Respectively.

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 (10)

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

In Formula 1,
L is a substituted or unsubstituted C _6-30 arylene group or a substituted or unsubstituted C _3-30 heteroarylene group,
Ar _a And Ar _b are each independently a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 nitrogen-containing heteroaryl group (provided that it is not substituted with deuterium)
R, R ', R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted C _1-30 An alkyl group, a substituted or unsubstituted C _6-30 aryl group, or a substituted or unsubstituted C _3-30 heteroaryl group,
R ₃ is hydrogen or a substituted or unsubstituted C _1-30 alkyl group,
1 is an integer of 0 to 4, m is 0 to 3, n is 0 to 5, p is 1 to 3, q is an integer of 1 to 3, and p + q is an integer of 2 to 4. The method according to claim 1,
The compound is a compound represented by the following formula 2:
(2)

In Formula 2,
o is an integer of 1 to 4; 3. The method according to claim 1 or 2,
Wherein R and R 'are each independently a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 heteroaryl group. The method according to claim 1,
The compound is a compound represented by the following formula 3:
(3)

In Formula 3,
R ₄ and R ₅ are each independently hydrogen, substituted or unsubstituted C _1-24 An alkyl group, a substituted or unsubstituted C _6-24 aryl group or a substituted or unsubstituted C _3-24 heteroaryl group,
o is an integer of 1 to 4; The method according to claim 1,
Wherein the - (Ar _a ) _p - (Ar _b ) _q is a compound represented by any one of the following formulas [1-1] to [1-6]

In the above formulas [1-1] to [1-6]
Ar ₁ To Ar ₄ are each independently a substituted or unsubstituted C _6-30 aryl group or a substituted or unsubstituted C _3-30 heteroaryl group containing nitrogen (provided that it is not substituted with deuterium). 6. The method of claim 5,
The Ar ₁ To Ar < ₄ > is a phenyl group. The method according to claim 1,
Wherein said compound is any one of the following compounds:

An organic light-emitting device comprising an organic material layer containing a compound according to any one of claims 1 to 7 between a first electrode and a 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 material layer is a light emission-assisting layer.

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