KR20180043726A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to a novel compound represented by chemical formula 1, and an organic light emitting device comprising the same. In the present invention, phenyl-substituted diarylfluorene and arylamine containing a phenyl group and a condensed aryl group are applied so that a high efficiency organic light emitting device with easy HOMO formation which facilitates injection and transport of holes, and easy electron blocking due to high LUMO retention through phenyl substitution can be realized.

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 is hydrogen, deuterium, a C ₁ -C ₆ alkyl group or a C ₆ -C ₃₀ aryl group,

Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁₀ -C ₂₅ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, Ar ₃ and Ar ₄ may or may not form a ring with each other,

L are each independently a direct bond, a C ₆ -C ₃₀ arylene group, or a C ₅ -C ₃₀ heteroarylene group,

Ar is a substituted or unsubstituted C ₆ -C ₁₀ aryl group, a substituted or unsubstituted C ₁₀ -C ₂₅ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

l is an integer of 1 to 4, and m is an integer of 1 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 process for preparing a compound represented by the general formula (I), which comprises applying a phenyl-substituted diarylfluorene and an arylamine containing a phenyl group and a condensed aryl group to form a HOMO that facilitates injection and transport of holes, So that an exciton in the light emitting layer can be efficiently formed, thereby realizing a highly efficient organic light emitting device. Also, some of the aryls bonded to amines have aryl groups or condensed aryls each having 6 to 10 carbon atoms introduced therein, so that the thin film and the interfacial alignment of molecules are excellent. Thus, the roll-off phenomenon and the long- , It is possible to maintain the high Tg even in a relatively simple molecule, and it is possible to prevent the recrystallization of the thin film, thereby increasing the driving stability.

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 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.

The term throughout the present specification, "substituted or unsubstituted" in the "optionally substituted" is heavy hydrogen, 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 Substituted with at least one group selected from the group consisting of an alkoxy group of C ₃ to C ₂₀ , a cycloalkyl group of C ₃ to C ₂₀ , a heterocycloalkyl group of C ₃ to C ₂₀ , an aryl group of C ₆ to C ₃₀ , and a heteroaryl group of C ₅ to C ₃₀ It means that you can.

In addition, throughout the present specification, the same symbols may have the same meanings unless otherwise specified.

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

[Chemical Formula 1]

In Formula 1,

R ₁ is hydrogen, deuterium, a C ₁ -C ₆ alkyl group or a C ₆ -C ₃₀ aryl group,

Ar ₁ to Ar ₄ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, Ar ₃ and Ar ₄ may or may not form a ring with each other,

L are each independently a direct bond, a C ₆ -C ₃₀ arylene group, or a C ₅ -C ₃₀ heteroarylene group,

Ar is a substituted or unsubstituted C ₆ -C ₁₀ aryl group, a substituted or unsubstituted C ₁₀ -C ₂₅ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

l is an integer of 1 to 4, and m is an integer of 1 to 3.

In one embodiment of the present invention, Ar ₃ and Ar ₄ may combine with each other to form a ring, for example, fluorene may be formed.

In one embodiment of the present invention, when Ar is an aryl group, it may be, for example, phenyl, and when Ar is a condensed aryl group, it may be naphthyl, phenanthrene, triphenylene, and the like. These substituents limit the formation of high LUMO, leading to good molecular thin-film and interfacial alignment, and low temperature control during the deposition process.

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

(2)

(3)

In the above formulas,

Ar, Ar _1, Ar _2, Ar _4, L, l and m are as defined in Formula 1, R ₂ to R ₅ are each independently hydrogen, deuterium, C ₁ -C ₆ alkyl, C ₆ -C ₃₀ aryl group or C ₅ -C ₃₀ hetero aryl group.

In one embodiment of the invention, the compound may comprise a compound of formula 4 or 5:

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas,

Ar, R &_lt; 1 >, l and m are as defined in formula (1)

R ₆ and R ₇ are each independently hydrogen, deuterium or a C ₁ -C ₆ alkyl group,

R ₈ to R ₁₁ are each independently hydrogen, deuterium, a C ₁ -C ₆ alkyl group, a C ₆ -C ₃₀ aryl group or a C ₅ -C ₃₀ heteroaryl group,

Ar ₅ is a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

n is an integer of 0 to 3;

In one embodiment of the invention, the compound may comprise a compound of formula 6 or 7:

[Chemical Formula 6]

(7)

In the above formulas,

Ar, R &_lt; 1 >, l and m are as defined in formula (1)

R ₆ to R ₁₁ and Ar ₅ are as defined in formulas (2) to (5).

In one embodiment of the present invention, in the general formulas (1) to (7), Ar may be specifically an unsubstituted C ₆ -C ₁₀ aryl group or an unsubstituted C ₁₀ -C ₂₅ condensed aryl group.

In one embodiment of the present invention, Ar in the above Chemical Formulas 1 to 7 may be phenyl or naphthyl.

In one embodiment of the present invention, l in the above Chemical Formulas 1 to 7 may be 1 and R ₁ may be hydrogen.

In one embodiment of the present invention, R ₃ , R ₄ , R ₉ and R ₁₀ in each of Formulas 3, 5 and 7 may each independently be hydrogen, methyl or phenyl.

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 specific compounds:

The following compounds in the above specific compounds can bind N directly to the 2-position of at least one fluorene to have higher hole mobility, thereby lowering the driving voltage and improving the efficiency and lifetime.

Further, the following compounds in the above specific compounds can have higher hole mobility by binding L, phenylene or N to the 2-position of the diarylfluorene or diphenylfluorene, thereby lowering the driving voltage and increasing the efficiency And the lifetime can be further improved.

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 claim 1 between a first electrode and a 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).

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 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 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. 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  One

IM  synthesis

Preparation of IM for the synthesis of the target compound was synthesized by following the same procedure as the above reaction formula.

The synthesis method of IM1 is as follows.

Dissolved in 2-bromo-9,9-dimethyl -9H- fluorene-phenylboronic acid and 15.0g of 1,4-dioxane, 200ml round bottom flask with 5.1g K ₂ CO ₃ (2M) 60ml and Pd (PPh ₃ ) ₄ were placed, 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 10.43 g (yield: 63%) of intermediate IM1-1.

The starting materials IM2 to IM4 were synthesized in the same manner as IM1.

Synthesis of OP

h is a halogen atom.

Preparation of OP was carried out in the same manner as in the above reaction scheme.

The synthesis method of the following OP1 is as follows.

To a round bottom flask was added 2-bromo-9,9-diphenyl--9H- fluorene 10.0g, aniline 3.8g, t-BuONa 5.3g, Pd 2 (dba) 3 1.4g and (t-Bu) ₃ P 1.6 ml were dissolved in 150 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 7.73 g (yield: 74%) of OP1.

The starting materials OP2 to OP8 were synthesized in the same manner as in OP1 above.

Synthetic example  One : Compound 1  Synthesis of

5.0 g of IM1, 3.3 g of OP1, 1.5 g of t-BuONa, 0.4 g of Pd ₂ (dba) ₃ and 0.5 ml of (t-Bu) ₃ P were dissolved in 100 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 5.01 g of Compound 1 (yield 70%).

m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%

Synthetic example  2 : Compound 2  Synthesis of

Compound 2 was synthesized using IM2 instead of IM1 in the same manner as in Synthesis Example 1 (yield: 74%).

m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%

Synthetic example  3: Compound 3  synthesis

Compound 3 was synthesized using IM3 instead of IM1 in the same manner as in Synthesis Example 1 (yield: 70%).

m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%

Synthetic example  4 : Compound 4  synthesis

Compound 4 was synthesized using IM4 instead of IM1 in the same manner as in Synthesis Example 1 (yield 65%).

m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%

Synthetic example  5: Compound 5  synthesis

Compound 5 was synthesized in the same manner as in Synthesis Example 1 using OP2 instead of OP1 (Yield: 71%).

m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%

Synthetic example  6: Compound 6  synthesis

Compound 6 was synthesized in the same manner as in Synthesis Example 1 using OP3 instead of OP1 (yield: 75%).

m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%

Synthetic example  7: Compound 7  synthesis

Compound 7 was synthesized by using OP4 instead of OP1 in the same manner as in Synthesis Example 1. (Yield: 70%).

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

Synthetic example  8 : Compound 8  synthesis

Compound 8 was synthesized using OP5 instead of OP1 in the same manner as in Synthesis Example 1 (yield: 62%).

m / z: 687.29 (100.0%), 688.30 (57.7%), 689.30 (16.4%), 690.30

Synthetic example  9: Compound 9  synthesis

Compound 9 was synthesized using OP6 instead of OP1 in the same manner as in Synthesis Example 1 (yield 65%).

m / z: 687.29 (100.0%), 688.30 (57.7%), 689.30 (16.4%), 690.30

Synthetic example  10: Compound 10  synthesis

Compound 10 was synthesized in the same manner as in Synthesis Example 1 using OP7 instead of OP1 (Yield: 70%).

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

Synthetic example  11: Compound 11  synthesis

Compound 11 was synthesized using OP8 instead of OP1 in the same manner as in Synthesis Example 1 (yield: 72%).

m / z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%

Production Example 2: Production 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 HI01 of 600 angstroms, a HATCN of 50 angstroms, and a hole transport layer of compound 1 600 angstroms. The light emitting layer was doped with BH01: BD01 of 3% to form 250 angstroms. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transporting layer, and LiF 10 Å and aluminum (Al) 1000 Å were film-formed. The device was encapsulated in a glove box, Respectively.

Organic light-emitting devices (Examples 2 to 11) were prepared using Compound 2 to 11 instead of Compound 1 in the same manner as above.

Comparative Example

An organic light emitting device was prepared in the same manner as in Preparation Example 2, except that the following Ref.1 to Ref.8 (Comparative Examples 1 to 8) 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.

Op. V mA / cm2 Cd / A lm / w CIEx CIEy LT95 Example 1 3.901 10 7.47 6.84 0.140 0.109 192 Example 2 3.890 10 7.45 6.80 0.140 0.110 189 Example 3 3.890 10 7.45 6.79 0.141 0.110 190 Example 4 3.900 10 7.40 6.82 0.140 0.110 188 Example 5 3.900 10 7.31 6.65 0.141 0.110 170 Example 6 3.895 10 7.30 6.60 0.140 0.110 165 Example 7 3.926 10 7.43 6.73 0.140 0.110 185 Example 8 3.931 10 7.40 6.70 0.140 0.111 180 Example 9 3.933 10 7.44 6.72 0.139 0.111 185 Example 10 3.930 10 7.40 6.70 0.141 0.110 188 Example 11 3.940 10 7.40 6.70 0.140 0.110 190 Comparative Example 1 4.110 10 6.55 5.60 0.14 0.111 100 Comparative Example 2 4.002 10 5.17 4.06 0.143 0.113 108 Comparative Example 3 4.115 10 5.13 4.04 0.141 0.113 70 Comparative Example 4 4.112 10 6.36 5.28 0.141 0.112 73 Comparative Example 5 4.011 10 5.15 4.10 0.141 0.111 18 Comparative Example 6 4.020 10 6.50 5.64 0.142 0.112 110 Comparative Example 7 4.060 10 5.32 4.23 0.141 0.113 115 Comparative Example 8 4.250 10 6.72 6.00 0.140 0.115 30

As shown in Table 1 above, the embodiments of the present invention show a result of increasing efficiency and lifetime as compared with Comparative Examples 1 to 11. Comparing the examples of the present invention, it can be seen that 1) Compared with Comparative Example 5, when having a diphenylfluorene moiety, 2) Compared to Comparative Examples 1 and 2, the conjugation through diphenylfluorene- 3) Compared with the comparative examples 3 and 4, when the LUMO which facilitates the electron blocking through the phenyl substitution was maintained, 4) Compared with the comparative examples 6, 7 and 8, Phenyl or naphthyl, and the compound of the present invention in which the other side is not phenyl 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.

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 (12)

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

In Formula 1,
R ₁ is hydrogen, deuterium, a C ₁ -C ₆ alkyl group or a C ₆ -C ₃₀ aryl group,
Ar ₁ To Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, and Ar ₃ And Ar < ₄ > may or may not form a ring with each other,
L are each independently a direct bond, a C ₆ -C ₃₀ arylene group, or a C ₅ -C ₃₀ heteroarylene group,
Ar is a substituted or unsubstituted C ₆ -C ₁₀ aryl group, a substituted or unsubstituted C ₁₀ -C ₂₅ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,
l is an integer of 1 to 4, and m is an integer of 1 to 3. 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 ₁ , Ar ₁ , Ar ₂ , Ar ₄ , L, l and m are as defined in claim 1,
R ₂ to R ₅ are each independently hydrogen, deuterium, C ₁ -C ₆ alkyl, C ₆ -C ₃₀ aryl or C ₅ -C ₃₀ heteroaryl. The method according to claim 1,
Wherein said compound comprises a compound represented by the following formula 4 or 5:
[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas,
Ar, R &_lt; 1 >, l and m are as defined in claim 1,
R ₆ and R ₇ are each independently hydrogen, deuterium or a C ₁ -C ₆ alkyl group,
R ₈ to R ₁₁ are each independently hydrogen, deuterium, a C ₁ -C ₆ alkyl group, a C ₆ -C ₃₀ aryl group or a C ₅ -C ₃₀ heteroaryl group,
Ar ₅ is a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,
n is an integer of 0 to 3; The method according to claim 1,
Wherein said compound comprises a compound of formula 6 or 7:
[Chemical Formula 6]

(7)

In the above formulas,
Ar, R &_lt; 1 >, l and m are as defined in claim 1,
R ₆ and R ₇ are each independently hydrogen, deuterium or a C ₁ -C ₆ alkyl group,
R ₈ to R ₁₁ are each independently hydrogen, deuterium, a C ₁ -C ₆ alkyl group, a C ₆ -C ₃₀ aryl group or a C ₅ -C ₃₀ heteroaryl group,
Ar ₅ is a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group. 5. The method according to any one of claims 1 to 4,
Ar is an unsubstituted C ₆ -C ₁₀ aryl group or an unsubstituted C ₁₀ -C ₂₅ fused aryl group. 6. The method of claim 5,
And Ar is phenyl or naphthyl. 5. The method according to any one of claims 1 to 4,
l is 1 and the R ₁ is hydrogen. 5. The method according to any one of claims 2 to 4,
R ₃ , R ₄ , R ₉ and R ₁₀ are each independently hydrogen, methyl or phenyl. The method according to claim 1,
Wherein said compound is any one of the following compounds.

The method according to claim 1,
Wherein said compound is any one of the following compounds.

And at least one organic compound layer comprising a compound according to claim 1 between a first electrode and a second electrode. 12. The method of claim 11,
Wherein the organic material layer is at least one of a hole injection layer, a hole transport layer,

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