KR20180079718A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to a novel arylamine compound into which carbazole and aryl substituted fluorene structures are introduced, and an organic light emitting device comprising the same. The compound is represented by chemical formula 1, wherein R_1 to R_5 each independently represent hydrogen, deuterium or an optionally substituted C1-C6 alkyl group.

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 may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from an electron triplet excited state according to a light emitting mechanism, The light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color. 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,

R ₁ to R ₅ are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

R and R 'are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

Ar, Ar ₁ and Ar ₂ are each independently a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

l and o are integers of 0 to 4, m is an integer of 0 or 1, and n is an integer of 0 to 3.

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 a novel arylamine into which carbazole and aryl substituted fluorene structures have been introduced and specifically discloses a novel arylamine having a carbazole and an aryl substituted fluorene structure by applying an arylamine bond to a carbazole position 3 and an aryl substituted fluorene position 1 or 4, High HOMO formation which is easy to transport and high LUMO at the same time, excellent thin film formation and interfacial arrangement of molecules, and fast hole mobility improves the hole transporting property, thereby suppressing roll-off phenomenon and realizing low voltage, high efficiency and long- It is possible. In addition, it provides stability when driven at a high Tg, maintains a high T1 through the combination of an aryl-substituted fluorene 1 or 4 and an arylamine, and can exhibit high efficiency when a phosphorescent device is applied.

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

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 _5-30 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 Means an aromatic 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.

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.

The term " optionally substituted "or" substituted "as used throughout this application is intended to encompass a variety of substituents such as deuterium, halogen, amino, nitrile, nitro, silane, alkyl or C ₁ -C ₂₀ alkyl, alkenyl or C ₂ -C ₂₀ An alkoxy group or a C ₁ to C ₂₀ alkoxy group, a cycloalkyl group or a C ₃ to C ₂₀ cycloalkyl group, a heterocycloalkyl group or a C ₃ to C ₂₀ heterocycloalkyl group, an aryl group or a C ₆ to C ₃₀ An aryl group and a heteroaryl group or a C ₅ to C ₃₀ heteroaryl group.

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

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₅ are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

R and R 'are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

Ar, Ar ₁ and Ar ₂ are each independently a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

l and o are integers of 0 to 4, m is an integer of 0 or 1, and n is an integer of 0 to 3.

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

 (2)

In Formula 2,

R ₁ to R ₇ are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

R and R 'are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

Ar is a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted.

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

(3)

In Formula 3,

R ₁ to R ₇ are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

R and R 'are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

Ar is a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroarylene group which may be substituted.

In one embodiment of the present invention, in the general formulas (1) to (3), Ar may be a C ₆ -C ₂₄ aryl group which may be substituted or a C ₅ -C ₂₄ heteroarylene group which may be substituted. It is possible to suppress the bulky characteristics and make the molecular arrangement excellent when forming the thin film, thereby maximizing the efficiency and the life span improvement.

In one embodiment of the present invention, Ar in the formulas (1) to (3) is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorene, diphenylfluorene, dimethylfluorene, phenanthrene, triphenylene, dibenzo Furan, dibenzothiophene, and combinations thereof, and may not be spirobifluorene. For example, Ar may be selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthyl, diphenylfluorene, dimethylfluorene, phenanthrene, triphenylene, dibenzofuran and dibenzothiophene Phenyl linked to the phenyl, or dimethylfluorene, dibenzofuran or dibenzothiophene linked to the phenyl. The Ar may be selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthyl, diphenylfluorene, dimethylfluorene, phenanthrene, triphenylene, dibenzofuran and dibenzothiophene, And may include various connection structures of the groups. In this case, it is possible to maintain the LUMO, which is particularly easy to cut off, and to be controlled at a low temperature during the deposition process.

In one embodiment, the R ₃ in the above Chemical Formulas 1 to 3 is phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorene, diphenyl fluorene, dimethyl fluorene, triphenylene, di Benzofuran, dibenzothiophene, and combinations thereof. For example, R ₃ may be selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthyl, diphenylfluorene, And a phenyl group linked to a group selected from the group consisting of triphenylene, triphenylene, dibenzofuran and dibenzothiophene. The R ₃ may be selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, diphenylfluorene, dimethylfluorene, phenanthrene, triphenylene, dibenzofuran and dibenzothiophene, And various connection structures of the groups.

In one embodiment of the present invention, the compound of Formula 1 may be prepared as shown in Reaction Scheme 1 below, but not limited thereto:

[Reaction Scheme 1]

In one embodiment of the present invention, the organic light emitting compound may include, but is not limited to, the following compounds:

In addition, when the compound is applied to an organic light emitting device, the compound may have HOMO that is easy to inject holes from the electrode, thereby facilitating hole transport and increasing efficiency and lifetime.

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 injection layer, a hole transporting layer, and a light-emitting auxiliary layer. For example, the organic material layer may be a hole transporting layer, but the present invention is not limited thereto. The compounds may be used alone or in combination with known organic luminescent compounds.

In one embodiment of the present invention, the organic light emitting device may include an organic material layer containing a hole transporting material and an organic material layer containing a compound represented by the general formula (1), wherein the organic material layer May be, but not limited to, 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), an emission 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, 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 vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and the like. In general, the deposition temperature is 50-500 [ A vacuum of 10 < ^-8 > to 10 < ^-3 > torr, a deposition rate of 0.01 to 100 ANGSTROM / sec, and a layer thickness range of 10 ANGSTROM to 5 mu m.

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 may be one or more, for example, two layers of a first hole transport layer and a second hole transport layer (emission auxiliary layer). Any one of the first hole transporting layer and the second hole transporting 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 evaporation, spin coating, Casting method or 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 16 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  One

Synthesis of OP

Preparation of OP for synthesis of target compound was synthesized by the above step.

The synthesis method of the following OP1 is as follows.

To a round bottom flask was added 4-bromo-9,9-diphenyl--9H- fluorene 10.0g, aniline 2.6g, t-BuONa 3.6g, Pd 2 (dba) 3 0.9g, (t-Bu) 3 P 1.1 ml were dissolved in 130 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 7.01 g (yield: 68%) of OP1.

The starting materials OP2 to OP9 were synthesized in the same manner as in OP1 above.

Synthetic example  1: Synthesis of Compound 1

The 3-bromo-9-phenyl -9H- carbazol 3.0g, OP1 4.2g, t-BuONa 1.4g, Pd 2 (dba) 3 0.4g, (t-Bu) 3 P 0.5ml To a round bottom flask was added 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 4.54 g (yield 75%) of Compound 1.

m / z: 650.27 (100.0%), 651.28 (53.4%), 652.28 (14.0%), 653.28

Synthetic example  2: Synthesis of Compound 2

Compound 2 was synthesized in the same manner as Compound 1 using OP2 instead of OP1 (Yield: 70%).

m / z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31

Synthetic example  3: Synthesis of Compound 3

Compound 3 was synthesized in the same manner as Compound 1 using OP3 instead of OP1 (yield 65%).

m / z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31

Synthetic example  4: Synthesis of compound 4

Compound 4 was synthesized in the same manner as Compound 1 using OP4 instead of OP1 (yield: 73%).

m / z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31

Synthetic example  5: Synthesis of Compound 5

Compound 5 was synthesized in the same manner as Compound 1 using OP5 instead of OP1 (yield: 63%).

m / z: 766.33 (100.0%), 767.34 (63.2%), 768.34 (20.1%), 769.34

Synthetic example  6: Synthesis of Compound 6

By using 9 - ([1,1'-biphenyl] -4-yl) -3-bromo-9H-carbazole in place of 3-bromo-9-phenyl-9H- Compound 6 was synthesized (yield 65%).

m / z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31

Synthetic example  7: Synthesis of Compound 7

Compound 7 was synthesized by using OP6 instead of OP1 in the same manner as compound 1 (yield: 58%).

m / z: 650.27 (100.0%), 651.28 (53.4%), 652.28 (14.0%), 653.28

Synthetic example  8: Synthesis of Compound 8

Compound 8 was synthesized in the same manner as Compound 1 using OP7 instead of OP1 (yield 60%).

m / z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31

Synthetic example  9: Synthesis of Compound 9

Compound 9 was synthesized in the same manner as Compound 1 using OP8 instead of OP1 (yield: 60%).

m / z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31

Synthetic example  10: Compound 1 0's  synthesis

Compound 10 was synthesized in the same manner as Compound 1 using OP9 instead of OP1 (yield: 55%).

m / z: 726.30 (100.0%), 727.31 (59.9%), 728.31 (17.6%), 729.31

Manufacturing example  2: 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 DNTPD 600 Å, a HATCN 50 Å and a hole transport layer 1 700 Å, and then the light emitting layer was doped with BH 01: BDO 0 3% to form 250 Å. Next, ET01: Liq (1: 1) 300 Å was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were film-formed and the device was encapsulated in a glove box, ).

An organic light emitting device was prepared in the same manner as above using Compound 2 to 10 (Examples 2 to 10) instead of Compound 1.

Comparative Example

An organic luminescent device was prepared in the same manner as in Production Example 2, except that the following Ref.1 to Ref.9 (Comparative Examples 1 to 9) were used instead of Compound 1.

Experimental Example 1: 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 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.

As shown in Table 1, the examples of the present invention can show the result that the efficiency and lifetime increase as compared with Comparative Examples 1 to 9, and that the physical properties are excellent in all respects. Compared with Comparative Examples 1, 2 and 4, the compounds of the present invention are bonded to carbazole 3 and diphenylfluorene at positions 1 and 4, HOMO. Compared with Comparative Examples 3 and 4, the compound of the present invention is superior in the formation of the thin film and the interfacial arrangement due to substitution of diphenylfluorene 1 or 4 instead of dimethylfluorene, mobility). Compared with Comparative Examples 5 and 6, the compounds of the present invention were able to increase mobility by including units that were not relatively bulky Ar, and compared to Comparative Examples 7, 8 and 9, The compounds were coupled with a phenyl linkage between carbazole and diphenylfluorene and arylamine to prevent poor pi-conjugation. As described above, it can be seen that the compound of the present invention has a low driving voltage of the organic light emitting device, and the efficiency and lifetime are greatly improved.

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.

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 (9)

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

In the above formulas,
R ₁ to R ₅ are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
R and R 'are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
Ar, Ar ₁ and Ar ₂ are each independently a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
l and o are integers of 0 to 4, m is an integer of 0 or 1, and n is an integer of 0 to 3. The method according to claim 1,
Wherein the compound comprises a compound represented by the following formula (2): < EMI ID =
(2)

In the above formulas,
R ₁ to R ₇ are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
R and R 'are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
Ar is a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted. The method according to claim 1,
Wherein the compound comprises a compound represented by Formula 3:
(3)

In the above formulas,
R ₁ to R ₇ are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
R and R 'are each independently hydrogen, deuterium or an optionally substituted C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group which may be substituted, a C ₂ -C ₆ alkenyl group which may be substituted, A C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
Ar is a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroarylene group which may be substituted. 4. The method according to any one of claims 1 to 3,
Wherein Ar is a C ₆ -C ₂₄ aryl group which may be substituted or a C ₅ -C ₂₄ heteroarylene group which may be substituted. 4. The method according to any one of claims 1 to 3,
Wherein Ar is selected from phenyl, biphenyl, terphenyl, naphthyl, fluorene, diphenyl fluorene, dimethyl fluorene, phenanthrene, triphenylene, dibenzofuran, dibenzothiophene, compound. 4. The method according to any one of claims 1 to 3,
R ₃ is selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorene, diphenylfluorene, dimethyl fluorene, triphenylene, dibenzofuran, dibenzothiophene and combinations thereof , Compound. The compound of claim 1, wherein said compound comprises the following compound:

And at least one organic compound layer comprising a compound according to claim 1 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.

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