KR20190043839A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to a novel compound applied to an organic light emitting device to improve luminous efficiency and quantum efficiency thereof, and to an organic light emitting device including the same. The novel compound is represented by chemical formula 1. In chemical formula 1, Ar_1 and Ar_2 are each independently a substituted or unsubstituted C_6-C_30 aryl group or a substituted or unsubstituted C_5-C_30 heteroaryl group, and X_1 to X_3 are each independently carbon or nitrogen, and at least one thereof is nitrogen.

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.

Korean Patent Publication No. 10-2015-0086721

The present invention provides a novel organic compound, and an organic light emitting device including the organic compound.

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 of formula 1:

[Chemical Formula 1]

In Formula 1,

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

X ₁ to X ₃ are each independently carbon or nitrogen, at least one of them is nitrogen,

X ₄ to X ₈ are each independently carbon or nitrogen, at least one is nitrogen,

L is phenylene, pyridine, or pyrimidine,

A is a substituted or unsubstituted C ₆ -C ₃₀ aryl or C ₅ -C ₃₀ hetero arylene group.

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 one embodiment of the present invention can emit fluorescence or retardation fluorescence and can be used as an organic light emitting material.

The compound according to the present invention can be used alone in the light emitting layer of an organic light emitting device or in combination with a known compound, and the compound according to the present invention can be used as a dopant of a known host material. In addition, a known substance may be used as a dopant, and the compound of the present invention may be used as an assist dopant.

The compound according to one embodiment of the present invention connects a donor and an acceptor to an ortho or meta position to separate HOMO and LUMO molecular orbital distribution using steric hindrance, And the acceptor interactions can be minimized. Thus, the difference between the singlet energy and the excitation triplet energy (ΔE _ST ) can be minimized.

In addition, the compound according to one embodiment of the present invention has phenyl phosphine or phenylpyrimidine positioned between the donor and the acceptor, so that the HOMO and LUMO are partially overlapped with each other, the charge transport efficiency is improved, 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 "aryl" refers to a C _5-30 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 .

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

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

[Chemical Formula 1]

In Formula 1,

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

X ₁ to X ₃ are each independently carbon or nitrogen, at least one of them is nitrogen,

X ₄ to X ₈ are each independently carbon or nitrogen, at least one is nitrogen,

L is phenylene, pyridine, or pyrimidine,

A is a substituted or unsubstituted C ₆ -C ₃₀ aryl or C ₅ -C ₃₀ hetero arylene group.

In one embodiment of the present invention, A may be represented by any one of the following formulas, and R is hydrogen, a substituted or unsubstituted aryl group of C ₅ -C ₁₂ , a heteroaryl group, or C ₁ -C Or a substituted or unsubstituted alkyl group having 1 to ₁₀ carbon atoms.

In one embodiment of the present invention, L may be connected to a meta or ortho position with respect to the ring having X ₁ to X ₃ .

Further, in one embodiment of the present invention, A may be connected to a meta or ortho position with respect to a ring having X ₄ to X ₈ .

The compounds according to the present invention can be obtained by linking a donor and an acceptor to ortho or meta positions to separate HOMO and LUMO molecular orbital distribution using steric hindrance to form donor and acceptor Interaction can be minimized. Thus, the difference between the singlet energy and the excitation triplet energy (ΔE _ST ) can be minimized.

In one embodiment of the present invention, Ar ₁ and Ar ₂ may be phenyl.

In one embodiment of the present invention, L may be phenylene.

The compound according to an embodiment of the present invention has phenyl phosphine or phenylpyrimidine positioned between the donor and the acceptor, so that HOMO and LUMO are partially overlapped with each other, thereby improving the charge transport efficiency in the molecule and improving the luminous efficiency .

Further, in one embodiment of the present invention, the compound may be represented by any one of the following formulas (2-1) to (2-4).

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

In addition, according to one embodiment of the present invention, the compound represented by Formula 1 may be any one of the following compounds, and the following compounds may exhibit superior performance.

In one embodiment of the present invention, the compound is an organic light emitting material that emits fluorescence or retardation fluorescence, and can be used in an organic light emitting device.

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 layer may be an emissive layer, but may not be limited thereto. The compounds of the present invention may be used alone or in combination with known compounds when forming an organic layer.

In one embodiment of the present invention, the organic light emitting device includes a hole injecting layer (HIL), a hole transporting layer (HTL), a light emitting layer (EML), an electron transporting layer (ETL) Layer (EIL) or the like.

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 μm.

Next, a hole transporting layer material may be deposited on the hole injection layer 200 by a method such as vacuum deposition, spin coating, casting, or LB method to form the hole transporting layer 300. When the hole transporting layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer.

The hole transport layer 300 may be formed of a known material, and the emission layer may be formed on the hole transport layer 300.

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 vacuum deposition, spin coating, casting, or LB method. 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.

According to an embodiment of the present invention, the light emitting layer may be formed of the compound according to the present invention. The compound according to the present invention can be used alone, and known compounds can be used together as a host or a dopant.

A host material having excited singlet energy or excited triplet energy higher than either of the excited singlet energy and excited triplet energy of the compound according to the present invention can be used.

According to one embodiment of the present invention, the compound according to the present invention can be used as a dopant. In addition, a known substance may be used as a dopant, and the compound of the present invention may be used as an assist dopant. When the compound of the present invention is used as an assist dopant, it can exhibit luminescence of a dark blue color.

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 SubC was synthesized as follows to synthesize the target compound.

Synthesis Example 1 : Intermediate (Sub C1) synthesis

5 g of 3,5-dibromopyridine (Sub A1), 7.3 g of 3- (9H-carbazol-9-yl) phenylboronic acid (Sub B1), 5.5 g of K ₂ CO ₃ , 0.5 g of Pd (PPh ₃ ) ₄ 0.5 g, and 1,4-dioxane (50 ml), 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 purified by column, and recrystallized to obtain 6.4 g (yield 81%) of intermediate product 9- (3- (5-bromopyridin-3- yl) phenyl) -9H-carbazole.

Intermediate To a round bottom flask was added 9- (3- (5-bromopyridin- 3-yl) phenyl) -9H-carbazole 6.4 g, bis (pinacolato) diboron 4.9 g, KOAc 3.2 g, Pd (dppf) Cl 2 0.4 g, Dioxane (40 ml), 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 purified by column and recrystallized to obtain the intermediate product 9- (3- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- 3-yl) phenyl) -9H-carbazole (Sub C1) (yield 82%, integrated yield 65%).

Synthetic example  2 to 17: Intermediate (Sub C2 to Sub C17) synthesis

Intermediates Sub C2 to Sub C17 were synthesized by using the same method as Intermediate Sub C1 except that the starting materials Sub A and Sub B were changed as shown in Table 1 below.

Suba Sub B Sub C yield
(%) Sub C2

65 Sub C3

66 Sub C4

64 Sub C5

62 Sub C6

65 Sub C7

71 Sub C8

65 Sub C9

70 Sub C10

63 Sub C11

62 Sub C12

71 Sub C13

64 Sub C14

68 Sub C15

67 Sub C16

72 Sub C17

70

Compound synthesis

The compounds according to the present invention can be synthesized by the following reaction, but are not limited thereto.

Compound P1 Synthesis

A round bottom flask was charged with 9- (3- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridin- 3 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (Sub D1), 3.3 g of K ₂ CO ₃ , 0.3 g of Pd (PPh ₃ ) ₄ , ml, 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 purified by column, and recrystallized to obtain 6.4 g (yield 75%) of 9- (3- (5-bromopyridin-3- yl) phenyl) -9H-carbazole (Product P1).

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P2 Synthesis

Compound P2 was synthesized by the same method as Compound P1 using 4-chloro-2,6-diphenylpyrimidine instead of Sub D1 (yield: 74%).

m / z: 550.22 (100.0%), 551.22 (42.5%), 552.22 (9.3%), 551.21 (1.5%), 553.23

Compound P3 Synthesis

Product P3 was synthesized in the same manner as Product P1 using Sub C2 instead of Sub C1 (yield: 74%).

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P4 synthesis

Product P4 was synthesized in the same manner as Product P1 using Sub C3 instead of Sub C1 (yield: 71%).

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P5 Synthesis

Product P5 was synthesized in the same manner as Product P1 using Sub C3 and 2-chloro-4,6-di (pyridin-4-yl) -1,3,5-triazine instead of Sub C1 and Sub D1 65%)

m / z: 553.20 (100.0%), 554.20 (41.5%), 555.21 (7.5%), 556.21 (1.1%

Compound P6 Synthesis

Product P6 was synthesized in the same manner as Product P1 using Sub C4 instead of Sub C1 (yield 71%).

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P7 Synthesis

Product P7 was synthesized in the same manner as Product P1 using Sub C5 instead of Sub C1 (yield 70%).

m / z: 552.21 (100.0%), 553.21 (40.3%), 554.21 (8.7%), 553.20 (2.2%), 555.22

Compound P8 Synthesis

Product P8 was synthesized in the same manner as Product P1 using Sub C6 instead of Sub C1 (yield: 73%).

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P9 Synthesis

Product P9 was synthesized in the same manner as Product P1 using Sub C7 instead of Sub C1 (yield: 72%).

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P10 Synthesis

Product P10 was synthesized in the same manner as Product P1 using Sub C8 instead of Sub C1. (Yield: 72%)

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P11 Synthesis

Product P11 was synthesized in the same manner as Product P1 using Sub C9 instead of Sub C1. (Yield: 72%)

m / z: 551.21 (100.0%), 552.21 (42.9%), 553.22 (8.3%), 554.22

Compound P12 Synthesis

Product P12 was synthesized in the same manner as Product P1 using Sub C10 instead of Sub C1 (yield 70%).

m / z: 716.27 (100.0%), 717.27 (56.3%), 718.28 (14.5%), 719.28 (2.5%), 718.27

Compound P13 Synthesis

Product P13 was synthesized in the same manner as Product P1 using Sub C11 instead of Sub C1 (yield: 72%).

m / z: 716.27 (100.0%), 717.27 (56.3%), 718.28 (14.5%), 719.28 (2.5%), 718.27

Compound P14 Synthesis

Product P14 was synthesized in the same manner as Product P1 using Sub C12 instead of Sub C1 (yield: 73%).

m / z: 716.27 (100.0%), 717.27 (56.3%), 718.28 (14.5%), 719.28 (2.5%), 718.27

Compound P15 Synthesis

Product P15 was synthesized in the same manner as Product P1 using Sub C13 instead of Sub C1 (yield: 72%).

m / z: 716.27 (100.0%), 717.27 (56.3%), 718.28 (14.5%), 719.28 (2.5%), 718.27

Compound P16 Synthesis

Product P16 was synthesized in the same manner as Product P1 using Sub C14 instead of Sub C1 (yield 75%).

m / z: 716.27 (100.0%), 717.27 (56.3%), 718.28 (14.5%), 719.28 (2.5%), 718.27

Compound P17 Synthesis

Product P17 was synthesized in the same manner as Product P1 using Sub C15 instead of Sub C1 (yield 72%).

m / z: 716.27 (100.0%), 717.27 (56.3%), 718.28 (14.5%), 719.28 (2.5%), 718.27

Compound P18 synthesis

Product P18 was synthesized in the same manner as Product P1 using Sub C16 instead of Sub C1 (yield: 72%).

m / z: 716.27 (100.0%), 717.27 (56.3%), 718.28 (14.5%), 719.28 (2.5%), 718.27

Compound P19 Synthesis

Product P19 was synthesized in the same manner as Product P1 using Sub C17 instead of Sub C1 (yield: 72%).

m / z: 881.33 (100.0%), 882.33 (67.5%), 883.33 (23.9%), 884.34 (4.9%

Manufacture of retarded fluorescent organic light emitting device

Example 1 (used as a first fluorescent dopant)

A glass substrate coated with a thin film of indium tin oxide (ITO) having a thickness of 150 nm was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried and transferred to a plasma cleaner, and then the substrate was cleaned using oxygen plasma for 5 minutes. PEDOT: PSS 60 nm To form a hole injection layer. TAPC 20 nm as a hole transport layer and mCP 10 nm as an exciton blocking layer were formed by using a thermal evaporator. Then, mCP as a host material and 5% of a compound P1 synthesized by a synthesis example as a retarded fluorescent dopant material, To form a 25 nm film. A film of TPBI 30 nm was formed as an electron transport layer, and then LiF 1 nm and aluminum (Al) 100 nm were formed. Encapsulation of this device in a glove box was performed to fabricate an organic light emitting device.

Examples 2 to 19

Using the same method as in Example 1, an organic light emitting device formed by using P2 to P19 instead of Compound P1 was fabricated.

Comparative Examples 1 to 6

Using the same method as in Example 1, instead of Compound P1, the following Ref.1 to Ref.6 were used to fabricate an organic light emitting device.

Example  20 ( Delayed fluorescence  Assist By dopant  use)

A glass substrate coated with a thin film of indium tin oxide (ITO) having a thickness of 150 nm 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, and then the substrate was cleaned using oxygen plasma for 5 minutes. Then, PEDOT: PSS Spin coating to form a hole injection layer. A layer of TAPC 20 nm as a hole transporting layer and a layer of mCP 10 nm as an exciton blocking layer were formed using a thermal evaporator, and mCP as a host material and 20% of a compound P1 synthesized through a synthesis example as a delayed fluorescence assist dopant material Doping, and BDOl as a dopant material to a thickness of 25 nm. Next, TPBI 30 nm was formed as an electron transport layer, and LiF 1 nm and aluminum (Al) 100 nm films were formed. Encapsulation of this device in a glove box was performed to fabricate an organic light emitting device.

Example  21-28

An organic electroluminescent device was fabricated using the same method as in Example 20 except for using Compound P2 to P11 instead of Compound P1.

 [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 atmospheric pressure. The results are shown in Table 2 below.

The light- Driving voltage
(V) External quantum efficiency (%) efficiency
(Cd / A) Color coordinates Host Assist The second dopant CIEx CIEy Comparative Example 1 mCP - Ref 1 6 9.3 14.6 0.15 0.22 Comparative Example 2 mCP - Ref 2 6 6.8 9.8 0.15 0.20 Comparative Example 3 mCP - Ref 3 6 8.5 13.8 0.15 0.20 Comparative Example 4 mCP - Ref 4 6 7.1 10.2 0.16 0.22 Comparative Example 5 mCP - Ref 5 6 9.1 14.3 0.16 0.23 Comparative Example 6 mCP - Ref 6 6 11 29.1 0.20 0.44 Example 1 mCP - P1 5.5 14.2 30.9 0.15 0.20 Example 2 mCP - P2 5.4 14.7 31.3 0.15 0.20 Example 3 mCP - P3 5.5 15.3 31.6 0.15 0.20 Example 4 mCP - P4 5.6 14.8 30.3 0.15 0.20 Example 5 mCP - P5 5.4 13.9 30.1 0.15 0.20 Example 6 mCP - P6 5.5 14.9 30.5 0.15 0.20 Example 7 mCP - P7 5.5 15.1 31.5 0.15 0.20 Example 8 mCP - P8 5.6 14.3 30.9 0.15 0.20 Example 9 mCP - P9 5.5 14.3 30.7 0.15 0.20 Example 10 mCP - P10 5.5 14.8 31.2 0.15 0.20 Example 11 mCP - P11 5.6 15.2 31.8 0.15 0.20 Example 12 mCP - P12 5.6 15.1 31.5 0.15 0.22 Example 13 mCP - P13 5.6 15.7 31.9 0.15 0.22 Example 14 mCP - P14 5.7 15.3 31.8 0.15 0.22 Example 15 mCP - P15 5.6 14.8 31.3 0.15 0.22 Example 16 mCP - P16 5.6 14.9 31.5 0.15 0.22 Example 17 mCP - P17 5.6 15.2 31.7 0.15 0.22 Example 18 mCP - P18 5.7 15.1 31.8 0.15 0.22 Example 19 mCP - P19 5.7 14.6 31.1 0.15 0.23 Example 20 mCP P1 BD01 5.5 16.8 44.2 0.14 0.11 Example 21 mCP P2 BD01 5.6 15.9 40.1 0.14 0.11 Example 22 mCP P6 BD01 5.6 16.5 42.3 0.14 0.12 Example 23 mCP P7 BD01 5.6 16.1 42.1 0.14 0.12 Example 24 mCP P8 BD01 5.5 15.8 41.5 0.14 0.12 Example 25 mCP P9 BD01 5.5 16.1 43.2 0.14 0.12 Example 26 mCP P10 BD01 5.6 15.7 42.2 0.14 0.12 Example 28 mCP P11 BD01 5.6 15.8 42.4 0.14 0.11

As described above, a light-emitting layer was formed using a thermally-active retarding fluorescent compound, and the results are shown in Table 1 above. As shown in Table 1, the embodiments according to the present invention all exhibited quantum efficiencies exceeding 5% (when the light extraction efficiency is 20%), which is the maximum external quantum efficiency that can be obtained from general fluorescent devices.

It can be seen that the compounds according to the present invention are capable of efficient sequential transition of triplet energy to singlet energy through thermal activation delay fluorescence properties. In addition, the examples of the present invention are superior in efficiency and external quantum efficiency to those of the comparative examples 1 to 6, exhibit a luminescence of a dark blue color when used as an assist dopant, and are excellent in physical properties in all aspects.

More specifically, Comparative Examples 1 to 3, in which no cyclic compound containing nitrogen was included between phenylcarbazole and triazine, and pyrimidine between phenylcarbazole and triazine, but phenylcarbazole was used as pyrimidine etra Compared with Comparative Examples 4 and 5 and Comparative Example 6 in which triazine ecabazole is directly bonded to the para and para positions, the embodiments according to the present invention have ortho or meta linked structures High quantum efficiency, and improved luminous efficiency.

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,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,
X ₁ to X ₃ are each independently carbon or nitrogen, at least one of them is nitrogen,
X ₄ to X ₈ are each independently carbon or nitrogen, at least one is nitrogen,
L is phenylene, pyridine, or pyrimidine,
A is a substituted or unsubstituted C ₆ -C ₃₀ aryl or C ₅ -C ₃₀ hetero arylene group. The method according to claim 1,
And A is the formula 1-1) to (1-6, any one is shown, of the formula R is hydrogen, C ₅ -C ₁₂ substituted of unsubstituted aryl group, a heteroaryl group, or C ₁ -C ₁₀ of Or a substituted or unsubstituted alkyl group.

The method according to claim 1,
Wherein L is connected to the meta or ortho position with respect to the ring having X ₁ to X ₃ . The method according to claim 1,
Wherein A is linked to a meta or ortho position to a ring having X ₄ to X ₈ . The method according to claim 1,
Wherein Ar < _{1 >} and Ar < ₂ > are phenyl. The method according to claim 1,
Wherein L is phenylene. The method according to claim 1,
Wherein said compound is represented by any one of the following formulas (2-1) to (2-4).

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

9. A compound according to any one of claims 1 to 8 which is an organic luminescent material that emits fluorescence or retarded fluorescence. And at least one organic layer comprising a compound according to any one of claims 1 to 9 between a first electrode and a second electrode. 11. The method of claim 10,
Wherein the organic material layer is a light emitting layer. 11. The method of claim 10,
Wherein the light emitting layer comprises a host material having excited singlet energy or excited triplet energy higher than either of excited singlet energy and excited triplet energy of the compound.

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