KR20190079765A - Novel compound and organic electroluminescent device including the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic light emitting device including the same. The novel compound according to an embodiment of the present invention is applied to an organic light emitting device and can increase light emitting efficiency and quantum efficiency of the organic light emitting device. The organic light emitting device of the present invention comprises one or more organic layers including the compound between a first electrode and a second electrode.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and an organic light-

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 represented by formula 1:

[Chemical Formula 1]

In Formula 1,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ to C ₃₀ aryl group or a substituted or unsubstituted C ₃ to C ₃₀ heteroaryl group,

L is phenyl, pyridine, or pyrimidine,

D is a structure represented by the following formula (1-1) (wherein the dotted line is a bonding position).

[Formula 1-1]

In Formula 1-1,

X is a direct bond, O, S, or CR ₃ R _4,

R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, substituted or unsubstituted C ₁ -C ₃₀ alkyl, substituted or unsubstituted C ₆ -C ₁₈ aryl, C ₃ -C ₁₈ heteroaryl 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 can increase the electron transporting ability by a strong electron attracting effect of phosphine oxide, and thus the efficiency of the organic light emitting device can be increased.

In addition, phosphine can prevent the expansion of conjugated bonds to maintain high singlet energy and triplet energy, and thus can be applied in a dark blue color.

In addition, the donor and acceptor are bonded with a linking group such as phenyl, pyridine or pyrimidine to separate the molecular orbital distribution of HOMO and LUMO and to have appropriate overlapping, The difference in energy (DELTA _EST ) can be minimized. Thus, the efficiency of the organic light emitting device can be increased.

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 represented by formula 1:

[Chemical Formula 1]

In Formula 1,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ to C ₃₀ aryl group or a substituted or unsubstituted C ₃ to C ₃₀ heteroaryl group,

L is phenyl, pyridine, or pyrimidine,

D is represented by the following formula (1-1) (wherein the dotted line represents the bonding position).

[Formula 1-1]

In Formula 1-1,

X is a direct bond, O, S, or CR ₃ R _4,

R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, a substituted or unsubstituted C ₁ to C ₃₀ alkyl, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, the C is a ₃ ~ C ₃₀ heteroaryl group.

According to an embodiment of the present invention, in Formula 1-1, R ₁ and R ₂ may be bonded to positions 1 to 4 of the 3-ring condensed ring. More specifically, R ₁ and R ₂ may be bonded to the 3-position. In this case, since the non-covalent electron pair of N and R ₁ and R ₂ interact with each other and are stabilized, a more efficient and long-lasting organic light- , And can be easily manufactured.

In one embodiment of the present invention, the formula (1-1) may be represented by any one of the following formulas (1-1-1) to (1-1-9).

In the above formulas 1-1-1 to 1-1-9,

R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted C ₁ to C ₃₀ alkyl, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a substituted or unsubstituted C ₃ to C ₃₀ A heteroaryl group,

Ar ₃ is a substituted or unsubstituted C ₆ -C ₁₈ aryl group or a substituted or unsubstituted C ₃ -C ₁₈ heteroaryl group.

The compound according to an 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 can increase the electron transporting ability due to the strong electron withdrawing effect of phosphine oxide, and thus the efficiency of the organic light emitting device .

In addition, phosphine can prevent the expansion of conjugated bonds to maintain high singlet energy and triplet energy, and thus can be applied in a dark blue color.

In addition, the donor and acceptor are bonded with a linking group such as phenyl, pyridine or pyrimidine to separate the molecular orbital distribution of HOMO and LUMO and to have appropriate overlapping, The difference in energy (DELTA _EST ) can be minimized. Thus, the efficiency of the organic light emitting device can be increased.

In one embodiment of the present invention, Ar ₁ and Ar ₂ may each independently be phenyl, biphenyl, naphthyl, or pyridine.

According to an embodiment of the present invention, in Formula 1-1, R ₁ and R ₂ are each independently hydrogen, phenyl, dibenzofurane, dibenzothiophene or carbazole. In the above formulas 1-1-1 to 1-1-9, R ₁ and R ₂ are each independently hydrogen, phenyl, dibenzofuran, dibenzothiophene or carbazole.

According to an embodiment of the present invention, in the formulas 1-1-3 and 1-1-4, R ₁ represents Dibenzofurane or dibenzothiophene, and in the above formula 1-1-6, R ₁ or R ₂ may be a carbazole.

In one embodiment of the present invention, Ar ₃ in Formula 1-1-5 may be phenyl, biphenyl or naphthyl.

In one embodiment of the present invention, P and D may be combined into the meta, para or ortho position of L.

According to one embodiment of the present invention, the compound represented by Formula 1 may be any one of the following compounds.

More specifically, according to one embodiment of the present invention, the compound represented by Formula 1 may be any one of the following compounds. The following compounds can realize a more efficient organic light emitting device.

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

Synthesis Example 1: Intermediate (Sub C1) synthesis

According to one embodiment of the present invention, SubC1 can be synthesized as follows, but is not limited thereto.

10 g of 3,9'-bicarbazole (SM B1), 5.8 g of t-BuONa, 0.8 g of Pd2 (dba) 3 and 1.6 ml of (t-Bu) 3P were added to a round bottom flask Dissolved in 70 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 12.1 g (yield: 81%) of intermediate product 9- (4-Bromophenyl) -9H-3,9'- bicarbazole (Sub C1).

Synthesis Examples 2 to 5: Intermediate (Sub C2 to Sub C5) synthesis

Intermediates Sub C2 to Sub C5 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.

SME SM B Sub C yield
(%) Sub C2

79 Sub C3

77 Sub C4

76 Sub C5

75

Compound synthesis

Compound P1 Synthesis

5 g of Sub C1, 3.1 g of diphenylphosphine oxide, 2.9 g of K2CO3 and 30 g of toluene (0.9 g) of Ni (dppp) Cl2 were dissolved in a round bottom flask, followed by stirring 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. 4.5 g (yield 75%) of 9- (4- (diphenylphosphoryl) phenyl) -9H-3,9'-bicarbazole

m / z: 608.20 (100.0%), 609.21 (45.8%), 610.21 (10.4%), 611.21

Compound P2 Synthesis

Synthesis of 9- (3- (diphenylphosphoryl) phenyl) -9H-3,9'-bicarbazole (Product P2) was synthesized in the same manner as Product P1 using Sub C2 instead of Sub C1 (yield 74%).

m / z: 608.20 (100.0%), 609.21 (45.8%), 610.21 (10.4%), 611.21

Compound P3 Synthesis

Synthesis of 9- (5- (diphenylphosphoryl) pyridin-3-yl) -9H-3,9'-bicarbazole (Product P3) was obtained in the same manner as Product P1 using Sub C3 instead of Sub C1.

m / z: 609.20 (100.0%), 610.20 (44.7%), 611.20 (10.3%), 612.21 (1.4%), 610.19

Compound P4 synthesis

3-yl) -9H-3,9'-dicarboxylic acid was prepared in the same manner as Product P1 using Sub C3 and 3,3'-phosphoryldipyridine instead of Sub C1 and diphenylphosphine oxide. bicarbazole (Product P4) was synthesized (yield: 71%).

m / z: 611.19 (100.0%), 612.19 (42.5%), 613.19 (9.7%), 612.18 (1.8%), 614.20

Compound P5 Synthesis

(Dibenzo [b, d] furan-2-yl) -9- (5- (diphenylphosphoryl) pyridin-3-yl) -9H-carbazole (Product P4) was synthesized (yield: 71%).

m / z: 610.18 (100.0%), 611.18 (45.1%), 612.19 (10.2%), 613.19

Compound P6 Synthesis

(Diphenylphosphoryl) pyridin-3-yl) -9'-phenyl-9H, 9'H-3,3'-bicarbazole (Product P6) was obtained in the same manner as Product P1 using Sub C5 instead of Sub C1. (Yield: 71%).

m / z: 685.23 (100.0%), 686.23 (52.3%), 687.24 (12.9%), 688.24

Manufacture of retarded fluorescent organic light emitting device

Example 1 (used as a delayed fluorescence host)

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 and doped with P1 and a fluorescent dopant material BD01 synthesized through a synthesis example as a host material at 5% Respectively. 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 6

An organic luminescent device was fabricated using the same method as in Example 1, but using Compound P2 to P6 instead of Compound P1.

Comparative Examples 1 to 4

Using the same method as in Example 1, an organic light emitting device was produced by using the following mCP and the following Ref.1 to Ref.3, respectively, in place of the compound P1.

Example 7 (used as retarded fluorescent assist 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 20% P 3 synthesized through a synthesis example as a delayed fluorescence assist dopant material, And BDOl as a dopant material was doped with 5% to form a 25 nm layer. 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 8

An organic electroluminescent device was fabricated using the same method as in Example 7, except that Compound P4 was used instead of Compound P3.

Example 9 (used as an exciton blocking layer)

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. The P10 and P10 synthesized as a host material were synthesized by a thermal evaporator using a TAPC 20 nm exciton blocking layer as a hole transport layer. 5% 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.

 [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- Exciton
Jersey floor Driving
Voltage
(V) External quantum efficiency (%) efficiency
(Cd / A) Color coordinates Host Assist
Dopant Dopant CIEx CIEy Comparative Example 1 mCP - BD01 mCP 6 4.9 7.6 0.15 0.12 Comparative Example 2 Ref 1 - BD01 mCP 6 4.3 6.8 0.15 0.12 Comparative Example 3 Ref 2 - BD01 mCP 6 8.1 29.1 0.14 0.11 Comparative Example 4 Ref 3 - BD01 mCP 5.7 6.4 20.5 0.14 0.12 Example 1 P1 - BD01 mCP 5.5 13.7 30.9 0.14 0.11 Example 2 P2 - BD01 mCP 5.4 14.3 31.4 0.14 0.11 Example 3 P3 - BD01 mCP 5.5 14.9 31.5 0.14 0.11 Example 4 P4 - BD01 mCP 5.6 14.6 30.4 0.14 0.11 Example 5 P5 - BD01 mCP 5.4 13.7 30.2 0.14 0.11 Example 6 P6 - BD01 mCP 5.5 14.5 30.5 0.14 0.11 Example 7 mCP P3 BD01 mCP 5.6 15.9 43.1 0.14 0.11 Example 8 mCP P4 BD01 mCP 5.6 16.1 42.1 0.14 0.11 Example 9 P3 - BD01 P1 5.3 16.9 41.5 0.14 0.11

As described above, the light-emitting layer was formed using the thermally-activatable fluorescent compound, and the performance evaluation results thereof are shown in Table 2 above. As shown in Table 2, the embodiments according to the present invention all exhibited a quantum efficiency exceeding 5% (when the light extraction efficiency is 20%), which is the maximum external quantum efficiency that can be obtained from a general fluorescent device.

This shows that the compounds according to the present embodiments are capable of efficient sequential transition of triplet energy to singlet energy through thermoactive delayed fluorescence properties. In addition, the embodiments of the present invention can show the increase in the efficiency and the external quantum efficiency as compared with the comparative examples 1 to 4. [

In addition, it can be used as an assist dopant and an exciton blocking layer. When used as an exciton blocking layer, it can be confirmed that excitons are effectively blocked and excellent physical properties are obtained.

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

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

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

Claims (11)

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

In Formula 1,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ to C ₃₀ aryl group or a substituted or unsubstituted C ₃ to C ₃₀ heteroaryl group,
L is phenyl, pyridine, or pyrimidine,
D is represented by the following formula (1-1) (wherein the dotted line represents the bonding position).
[Formula 1-1]

In Formula 1-1,
X is a direct bond, O, S, or CR < ₃ > R < ₄ &
R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, a substituted or unsubstituted C ₁ to C ₃₀ alkyl, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, the C is a ₃ ~ C ₃₀ heteroaryl group. The method according to claim 1,
Wherein R ₁ and R ₂ in Formula 1-1 are bonded at the 3-position. 3. The method according to claim 1 or 2,
The compound represented by any one of formulas (1-1-1) to (1-1-9) shown below in the formula (1-1).

In the above formulas 1-1-1 to 1-1-9,
R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted C ₁ to C ₃₀ alkyl, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a substituted or unsubstituted C ₃ to C ₃₀ A heteroaryl group,
Ar ₃ is a substituted or unsubstituted C ₆ -C ₁₈ aryl group or a substituted or unsubstituted C ₃ -C ₁₈ heteroaryl group. 3. The method according to claim 1 or 2,
Wherein Ar ₁ and Ar ₂ are each independently phenyl, biphenyl, naphthyl, or pyridine. 3. The method according to claim 1 or 2,
Wherein R ₁ and R ₂ are each independently hydrogen, phenyl, dibenzofuran, dibenzothiophene or carbazole. The method of claim 3,
Wherein Ar < ₃ > is phenyl, biphenyl or naphthyl. 3. The method according to claim 1 or 2,
Wherein said compound is any one of the following compounds.

8. A compound according to any one of claims 1 to 7, wherein the compound is an organic luminescent material emitting fluorescence or retarded fluorescence. And at least one organic layer comprising a compound according to any one of claims 1 to 7 between a first electrode and a second electrode. 10. The method of claim 9,
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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