KR20190096099A - Novel compound and organic electroluminescent device including the same - Google Patents

Abstract

The present application relates to a novel compound and an organic light emitting device comprising the same. The novel compound according to an embodiment of the present invention is applied to an organic light emitting device, thereby being able to increase luminous efficiency and quantum efficiency of the organic light emitting device. The compound according to an embodiment of the present invention can emit fluorescence or delayed fluorescence, thereby being able to be used as an organic light emitting material.

Description

Novel compound and organic light emitting device including the same {NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME}

The present application relates to a novel compound and an organic light emitting device comprising the same.

The material used as the organic material layer in the organic light emitting diode can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function. The light emitting material may be classified into a polymer and a low molecule according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. The luminescent material may be classified into blue, green, and red luminescent materials and yellow and orange luminescent materials required to achieve better natural colors according to the emission color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.

To date, various compounds are known as materials used in such organic light emitting diodes. However, in the case of organic light emitting diodes using materials known to date, development of new materials is continuously required due to high driving voltage, low efficiency, and short lifetime. Therefore, efforts have been made to develop organic light emitting devices having low voltage driving, high brightness and long life using materials having excellent properties.

Korea Patent Publication 10-2015-0086721

The present application provides a novel organic compound, and an organic light emitting device comprising the same.

However, the problem to be solved by the present application is not limited to the problem described above, other problems that are not described will be clearly understood by those skilled in the art from the following description.

A first aspect of the present application provides a compound represented by the following Chemical Formula 1:

[Formula 1]

In Chemical Formula 1,

L ₁ and L ₂ are each independently phenyl or biphenyl,

n and m are each independently an integer of 0 to 3,

D is any one of the following Chemical Formulas 1-1 to 1-4,

In Chemical Formulas 1-1 to 1-4,

X is O, S, or N,

Y is O, S, or CR ₁ R ₂ , R ₁ and R ₂ are each independently hydrogen, an alkyl group of C ₁ to C ₁₀ , a substituted or unsubstituted C ₆ to C ₂₄ aryl group, or a substituted or unsubstituted A substituted C ₃ ~ C ₂₄ heteroaryl group,

Ar ₁ to Ar ₈ are each independently hydrogen, a substituted or unsubstituted C ₆ -C ₂₄ aryl group, or a substituted or unsubstituted C ₃ -C ₂₄ heteroaryl group.

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

The compound according to the embodiment of the present invention may emit fluorescence or delayed fluorescence and thus may be used as an organic light emitting material.

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

The compound according to an embodiment of the present invention may include a strong electron pulling body such as CF ₃ to reduce the electron density of phenyl or biphenyl to have a high HOMO energy level, and maintain a broad blue E _g to maintain a high color blue. (Deep Blue) can be emitted. In addition, due to the electron induction effect of CF _{3 it} can have a high luminous efficiency by separating the HOMO and LUMO molecular orbital distribution.

In addition, the compound according to an embodiment of the present invention is used as a thermally activated delayed fluorescence host material to minimize the difference between the excitation singlet energy and the excitation triplet energy (ΔE _ST ) to have a high luminous efficiency. Can be.

1 shows a schematic view of an organic light emitting device according to an embodiment of the present disclosure.

Hereinafter, with reference to the accompanying drawings will be described in detail the embodiments and embodiments of the present application to be easily carried out by those of ordinary skill in the art.

As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention. In the drawings, parts irrelevant to the description are omitted in order to clearly describe the present invention, and like reference numerals designate like parts throughout the specification.

Throughout this specification, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

Throughout this specification, when a part is said to "include" a certain component, it means that it can further include other components, without excluding the other components unless specifically stated otherwise. As used throughout this specification, the terms "about", "substantially" and the like are used at, or in the sense of, numerical values when a manufacturing and material tolerance inherent in the stated meanings is indicated, Accurate or absolute figures are used to assist in the prevention of unfair use by unscrupulous infringers. As used throughout this specification, the term "step to" or "step of" does not mean "step for."

Throughout this specification, the term "combination of these" included in the expression of the makushi form means one or more mixtures or combinations selected from the group consisting of constituents described in the expression of the makushi form, wherein the constituents It means to include one or more selected from the group consisting of.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B."

Throughout this specification, the term “aryl” refers to a C _5-30 aromatic hydrocarbon ring group, for example phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, perylene It means containing an aromatic ring such as nil, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzocrisenyl, anthracenyl, stilbenyl, pyrenyl, etc., " heteroaryl " As an aromatic ring of C _3-30 containing a hetero element, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindoleyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Benzothiophenyl, dibenzothiophenyl, quinolyl group, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine ring, pyrazine ring, pyrimidine ring , 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, benzooxa It may be meant to include a heterocyclic group formed from a sol ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzoimidazole ring, pyran ring, dibenzofuran ring .

The term "substituted" throughout this specification refers to deuterium, halogen, amino, nitrile, nitro or C ₁ -C ₂₀ alkyl groups, C ₂ -C ₂₀ alkenyl groups, C ₁ -C ₂₀ alkoxy groups, It means that it can be substituted with one or more groups selected from the group consisting of C ₃ ~ C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C ₃₀ aryl group and C ₃ ~ C ₃₀ heteroaryl group can do.

A first aspect of the present application provides a compound represented by the following Chemical Formula 1:

[Formula 1]

In Chemical Formula 1,

L ₁ and L ₂ are each independently phenyl or biphenyl,

n and m are each independently an integer of 0 to 3,

D is any one of the following Chemical Formulas 1-1 to 1-4,

In Chemical Formulas 1-1 to 1-4,

X is O, S, or N,

Y is O, S, or CR ₁ R ₂ , R ₁ and R ₂ are each independently hydrogen, an alkyl group of C ₁ to C ₁₀ , a substituted or unsubstituted C ₆ to C ₂₄ aryl group, or a substituted or unsubstituted A substituted C ₃ ~ C ₂₄ heteroaryl group,

Ar ₁ to Ar ₈ are each independently hydrogen, a substituted or unsubstituted C ₆ -C ₂₄ aryl group, or a substituted or unsubstituted C ₃ -C ₂₄ heteroaryl group.

According to an embodiment of the present invention, the compound may emit fluorescence or delayed fluorescence and thus may be used as an organic light emitting material.

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

The compound according to an embodiment of the present invention may include a strong electron pulling body such as CF ₃ to reduce the electron density of phenyl or biphenyl to have a high HOMO energy level, and maintain a broad blue E _g to maintain a high color blue. (Deep Blue) can be emitted. In addition, due to the electron induction effect of CF _{3 it} can have a high luminous efficiency by separating the HOMO and LUMO molecular orbital distribution.

In addition, the compound according to an embodiment of the present invention is used as a thermally activated delayed fluorescence host material to minimize the difference between the excitation singlet energy and the excitation triplet energy (ΔE _ST ) to have a high luminous efficiency. Can be.

In one embodiment of the present invention, Chemical Formula 1-1 may be represented by any one of the following structural formulas.

In one embodiment of the present invention, Chemical Formula 1-2 may be represented by any one of the following structural formulas.

In one embodiment of the present invention, L ₁ and L ₂ may be each independently phenyl or biphenyl, the biphenyl may have a linking structure of ortho, meta, para.

In one embodiment of the present invention, Ar ₁ to Ar ₈ may be independently selected from the group consisting of the following structural formula and a combination of the following structural formula.

According to an embodiment of the present invention, the compound represented by Formula 1 may be embodied as follows:

According to an embodiment of the present invention, the compound represented by Chemical Formula 1 may be specifically any one of the following compounds. The following compounds may be substituted with strong electron pulling bodies to reduce the electron density of the phenyl ring, thereby realizing high color purity dark blue while maintaining a wide energy bend gap.

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

The second aspect of the present application provides an organic light emitting device comprising the compound represented by Formula 1. The organic light emitting device may include one or more organic material layers containing a compound according to the present application between the first electrode and the second electrode.

In one embodiment of the present invention, the organic material layer may be a light emitting layer, but may not be limited thereto. In addition, the compounds of the present invention may be used alone or in combination with known compounds when forming the organic layer.

In one embodiment of the present invention, the organic light emitting device is a hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML), electron transport layer (ETL), electron injection between the anode (anode) and the cathode (cathod) One or more organic material layers, such as a layer (EIL), may be included.

For example, the organic light emitting device may be manufactured as shown in FIG. 1. The organic light emitting device is an anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / light emitting layer 400 / electron transport layer 500 / electron injection layer 600 / cathode (electron) from below The injection electrodes 2000 may be stacked in this order.

In FIG. 1, the substrate 100 may be a substrate used in an organic light emitting device, and in particular, may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. have.

The hole injection electrode 1000 is used as an anode for hole injection of the organic light emitting device. 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), and graphene.

A hole injection layer 200 may be formed on the anode by depositing a hole injection layer material by a method such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB). When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal properties of the desired hole injection layer, and generally 50-500 deposition. Temperature, a vacuum of 10 ⁻⁸ to 10 ⁻³ torr, a deposition rate of 0.01 to 100 kPa / sec, and a layer thickness of 10 Pa to 5 μm may be appropriately selected.

Next, a hole transport layer 300 may be formed by depositing a hole transport layer material on the hole injection layer 200 by a method such as vacuum deposition, spin coating, cast, or LB. In the case of forming the hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in the same condition range as the formation of the hole injection layer.

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

The light emitting layer 400 may be formed by depositing a light emitting layer material on the hole transport layer 300 or the light emitting auxiliary layer by a method such as vacuum deposition, spin coating, cast, or LB. In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition 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 a compound according to the present invention. The compounds according to the invention can be used alone and known compounds can be used together as a host or dopant.

Although not limited thereto, a host material having an excitation singlet energy or excitation triplet energy higher than either of the excitation singlet energy and the excitation triplet energy of the compound according to the present invention can be used.

According to one embodiment of the invention, the compound according to the invention can be used as a dopant. In addition, known materials can be used as dopants and the compounds according to the invention can be used as assist dopants. When the compound of the present invention is used as an assist dopant, dark blue light emission can be exhibited.

In addition, when used together with a phosphorescent dopant in the light emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, the hole suppressing material (HBL) may be further laminated by vacuum deposition or spin coating. The hole-suppressing material that can be used at this time is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1) can be cited. Oxy-2-methylquinolinolato) -aluminum biphenoxide), a phenanthrolines-based compound (e.g., BCP (vasocuproin) from UDC) can be used.

The electron transport layer 500 is formed on the light emitting layer 400 formed as described above. The electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like. In addition, although the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.

Subsequently, an electron injection layer 600 may be formed by depositing an electron injection layer material on the electron transport layer 500, wherein the electron transport layer may be formed by vacuum deposition, spin coating, or casting a conventional electron injection layer material. It can form by a method, such as a method.

The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500 of the organic light emitting device may use a compound according to the present invention or may use the following materials, or according to the present invention Compounds and known materials can be used together.

The cathode 2000 for electron injection is formed on the electron injection layer 600 by a method such as vacuum deposition or sputtering. Various metals may be used as the cathode. Specific examples include materials such as aluminum, gold, and silver.

The organic light emitting device of the present invention is not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device of the cathode structure, but also the structure of an organic light emitting device of various structures, 1 It is also possible to form a layer or two intermediate layers.

As described above, the thickness of each organic material layer formed in accordance with the present invention can be adjusted according to the required degree, specifically 10 to 1,000 nm, more specifically 20 to 150 nm.

In addition, the present invention has an advantage that the organic material layer including the compound represented by Formula 1 has a uniform surface and excellent shape stability because the thickness of the organic material layer can be adjusted in molecular units.

With respect to the organic light emitting compound according to the present aspect may be applied to the contents described with respect to the first aspect of the present application, but may not be limited thereto.

Hereinafter, the embodiments of the present application will be described in more detail, and the scope of the present application is not limited by the present embodiment.

EXAMPLE

Intermediate synthesis

According to one embodiment of the invention, the intermediate SubC may be synthesized as follows, but is not limited thereto.

Synthesis Example 1: Intermediate Sub C1 Synthesis

Was dissolved in 2,8-round DIBROMODIBENZOFURAN (subA) bottom flask 5 g, 9H-carbazole (sub2 ) 7.3 g, t-BuONa 5.5 g, Pd (OAC) 2 0.5 g, 50 ml of toluene was stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column and recrystallized to obtain 6.4 g (yield 50%) of intermediate 9- (8-bromodibenzo [b, d] furan-2-yl) -9H-carbazole. Sub C2 to sub C22 were synthesized as shown in Table 1 by varying starting materials Sub A and Sub B in the same manner as in sub C1.

Synthesis Examples 2 to 22: Intermediate Sub C2 to Sub C22 Synthesis

Intermediates Sub C1 to Sub C22 were synthesized by using the same method as the intermediate Sub C1, but different from starting materials Sub A and Sub B as shown in Table 1 below.

Sub A Sub B Sub C yield
(%) Sub C1

60 Sub C2

52 Sub C3

55 Sub C4

49 Sub C5

44 Sub C6

60 Sub C7

48 Sub C8

54 Sub C9

45 Sub C10

43 Sub C11

52 Sub C12

51 Sub C13

41 Sub C14

48 Sub C15

59 Sub C16

44 Sub C17

57 Sub C18

49 Sub C19

46 Sub C20

43 Sub C21

49 Sub C22

56

Compound synthesis

The final compound Product P according to the present invention can be synthesized as follows, but is not limited thereto.

Synthesis Example of Final Compound Product P1

5 g of 9- (8-bromodibenzo [b, d] furan-2-yl) -9H-carbazole (Sub C1) and 3 g of bis (4- (trifluoromethyl) phenyl) amine (Sub D1) in a round bottom flask It was dissolved in 2.3 g of BuONa, 0.2 g of Pd (OAc) ₂ and 50 ml of Toluene, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, purified by column and recrystallized, and then purified by 8- (9H-carbazol-9-yl) -N, N-bis (4- (trifluoromethyl) phenyl) dibenzo [b, d] furan-2- 6.4 g (54% yield) of amine (Product P1) were obtained.

m / z: 636.16 (100.0%), 637.17 (41.4%), 638.17 (8.6%), 639.17 (1.2%)

Product P2 Synthesis Example of Final Compound

Product P2 was synthesized in the same way as Product P1 using Sub C2 instead of Sub C1 (59% yield).

m / z: 801.22 (100.0%), 802.22 (55.2%), 803.23 (14.7%), 804.23 (2.8%)

Product P3 Synthesis Example of Final Compound

Product P3 was synthesized using Sub C3 instead of Sub C1 in the same way as Product P1 (62% yield).

m / z: 817.22 (100.0%), 818.22 (54.5%), 819.22 (15.4%), 820.23 (2.5%), 818.21 (1.1%)

Final Compound Product P4 Synthesis Example

Product P4 was synthesized in the same way as Product P1 using Sub C4 instead of Sub C1 (62% yield).

 m / z: 833.19 (100.0%), 834.20 (54.5%), 835.20 (15.2%), 835.19 (5.1%), 836.20 (2.9%), 836.19 (2.5%), 834.19 (1.9%)

Final Compound Product P5 Synthesis Example

Product P5 was synthesized using Sub C5 instead of Sub C1 in the same way as Product P1 (60% yield).

m / z: 586.15 (100.0%), 587.15 (37.8%), 588.15 (7.0%)

Final Compound Product P6 Synthesis Example

Product P6 was synthesized using Sub C6 instead of Sub C1 in the same way as Product P1 (65% yield).

m / z: 751.21 (100.0%), 752.21 (50.1%), 753.21 (12.9%), 754.22 (2.0%), 752.20 (1.1%)

Final Compound Product P7 Synthesis Example

Product P7 was synthesized in the same way as Product P1 using Sub C7 instead of Sub C1 (66% yield).

m / z: 751.21 (100.0%), 752.21 (50.1%), 753.21 (12.9%), 754.22 (2.0%), 752.20 (1.1%)

Final Compound Product P8 Synthesis Example

Product P8 was synthesized using Sub C8 instead of Sub C1 in the same way as Product P1 (66% yield).

m / z: 678.21 (100.0%), 679.21 (45.1%), 680.22 (9.8%), 681.22 (1.5%)

Product P9 Synthesis Example of Final Compound

Product P9 was synthesized in the same way as Product P1 using Sub C9 instead of Sub C1 (62% yield).

m / z: 918.32 (100.0%), 919.32 (64.3%), 920.32 (21.0%), 921.33 (4.2%), 919.31 (1.5%)

Synthesis Example of Final Compound Product P10

Product P10 was synthesized in the same way as Product P1 using Sub C10 instead of Sub C1 (yield 63%).

m / z: 802.24 (100.0%), 803.25 (55.6%), 804.25 (15.3%), 805.25 (2.9%)

Final Compound Product P11 Synthesis Example

Product P11 was synthesized in the same way as Product P1 using Sub C11 instead of Sub C1. (Yield 59%)

m / z: 668.14 (100.0%), 669.14 (42.2%), 670.14 (9.1%), 670.13 (4.5%), 671.13 (1.9%), 671.15 (1.1%)

Product P12 Synthesis Example of Final Compound

Product P12 was synthesized in the same way as Product P1 using Sub C12 instead of Sub C1. (Yield 65%)

m / z: 751.21 (100.0%), 752.21 (50.1%), 753.21 (12.9%), 754.22 (2.0%), 752.20 (1.1%)

Final Compound Product P13 Synthesis Example

Product P13 was synthesized using Sub C13 instead of Sub C1 in the same way as Product P1 (yield 61%).

m / z: 876.27 (100.0%), 877.27 (62.0%), 878.28 (18.3%), 879.28 (3.6%)

Final Compound Product P14 Synthesis Example

Product P14 was synthesized in the same way as Product P1 using Sub C14 instead of Sub C1 (yield 58%).

m / z: 711.21 (100.0%), 712.21 (48.7%), 713.22 (11.2%), 714.22 (1.7%)

Final Compound Product P15 Synthesis Example

Product P15 was synthesized using Sub C15 instead of Sub C1 in the same way as Product P1 (59% yield).

m / z: 753.26 (100.0%), 754.26 (51.2%), 755.26 (13.2%), 756.27 (2.1%), 754.25 (1.1%)

Final Compound Product P16 Synthesis Example

Product P16 was synthesized using Sub C16 instead of Sub C1 in the same way as Product P1 (56% yield).

m / z: 918.32 (100.0%), 919.32 (64.3%), 920.32 (21.0%), 921.33 (4.2%), 919.31 (1.5%)

Final Compound Product P17 Synthesis Example

Product P17 was synthesized using Sub C17 instead of Sub C1 in the same way as Product P1 (57% yield).

m / z: 652.14 (100.0%), 653.14 (42.6%), 654.15 (8.3%), 654.14 (5.2%), 655.14 (1.9%), 655.15 (1.2%)

Final Compound Product P18 Synthesis Example

Product P18 was synthesized using Sub C18 instead of Sub C1 in the same way as Product P1 (75% yield).

m / z: 816.20 (100.0%), 817.21 (55.5%), 818.21 (15.6%), 818.20 (4.9%), 819.21 (2.9%), 819.20 (2.5%), 817.20 (1.5%)

Final Compound Product P19 Synthesis Example

Product P19 was synthesized using Sub C19 instead of Sub C1 in the same way as Product P1 (74% yield).

m / z: 694.19 (100.0%), 695.19 (45.5%), 696.19 (10.3%), 696.18 (4.5%), 697.19 (2.2%), 697.20 (1.4%)

Final Compound Product P20 Synthesis Example

Product P20 was synthesized using Sub C20 instead of Sub C1 in the same way as Product P1 (70% yield).

m / z: 859.25 (100.0%), 860.25 (57.7%), 861.25 (17.2%), 861.24 (4.5%), 862.26 (3.0%), 862.24 (2.6%), 860.24 (1.9%)

Final Compound Product P21 Synthesis Example

Product P21 was synthesized using Sub C21 instead of Sub C1 in the same way as Product P1 (yield 47%).

m / z: 743.18 (100.0%), 744.19 (47.9%), 745.19 (11.6%), 745.18 (5.1%), 746.18 (2.2%), 744.18 (1.9%), 746.19 (1.9%)

Final Compound Product P22 Synthesis Example

Product P22 was synthesized using Sub C22 instead of Sub C1 in the same way as Product P1 (yield 54%).

m / z: 908.24 (100.0%), 909.24 (62.8%), 910.25 (18.3%), 910.24 (5.9%), 911.25 (3.7%), 911.24 (3.0%)

Manufacture of delayed fluorescent organic light emitting device

Example 1 (Used as Delayed Fluorescent Dopant)

A glass substrate coated with a 150 nm thick thin film of indium tin oxide (ITO) was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes and then PEDOT: PSS 60 nm on the ITO substrate The hole injection layer was formed by spin coating to a thickness of. Using a thermal evaporator, a film of TAPC 20 nm was formed as a hole transport layer and mCP 10 nm was formed as an exciton blocking layer, followed by mCP as the host material and 5% of the product P1 synthesized through the synthesis example as a delayed fluorescent dopant material. The film was doped with 25 nm. After forming TPBI 30 nm into an electron transport layer, LiF 1 nm and aluminum (Al) 100 nm were formed, and this element was encapsulated in a glove box, and the organic light emitting element was produced.

Examples 2 to 22

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound P2 to P22 were used instead of Compound P1 to form a film.

Comparative Examples 1 to 8

Using the same method as in Example 1, an organic light emitting device was manufactured using the following Ref.1 to Ref.8 instead of compound P1.

Example 23 (Used as Delayed Fluorescent Assist Dopant)

A glass substrate coated with a 150 nm thick thin film of indium tin oxide (ITO) was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes and then PEDOT: PSS 60 nm on the ITO substrate The hole injection layer was formed by spin coating to a thickness of. Using a thermal evaporator, 20 nm of TAPC was formed into the hole transport layer and 10 nm of mCP into the exciton blocking layer, followed by mCP as the host material and as a delayed fluorescent assist dopant material. A 25 nm film was formed by doping with% and doping with BD01 as a dopant material at 5%. Next, after forming TPBI 30 nm into an electron transport layer, LiF 1 nm and aluminum (Al) 100 nm were formed, and this element was encapsulated in a glove box, and the organic light emitting element was produced.

Examples 24 and 33

An organic light-emitting device was manufactured in the same manner as in Example 23, except that Compound P2 to P11 were used instead of Compound P1 to form a film.

 [Evaluation of Organic Light Emitting Device]

Inject electrons and holes by applying voltage to a Keithley 2400 source measurement unit and measure the luminance when light is emitted using the Konica Minolta Spectroradiometer (CS-2000) Thus, the performance of the organic light emitting diodes of Examples and Comparative Examples was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in the following [Table 2].

Light emitting layer Driving voltage (V) External quantum efficiency (%) efficiency
(Cd / A) Color coordinates Host Assist 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 Comparative Example 7 mCP Ref 7 5.8 6.2 7.25 0.17 0.37 Comparative Example 8 mCP Ref 8 6 6.9 8.9 0.20 0.37 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 P20 5.6 15.2 31.4 0.15 0.21 Example 21 mCP P21 5.7 15.5 31.6 0.15 0.22 Example 22 mCP P22 5.7 14.9 31.6 0.15 0.22 Example 23 mCP P1 BD01 5.5 16.8 44.2 0.14 0.11 Example 24 mCP P2 BD01 5.6 15.9 40.1 0.14 0.11 Example 25 mCP P3 BD01 5.5 16.4 42.8 .0.14 0.12 Example 26 mCP P4 BD01 5.6 15.8 43.1 0.14 0.11 Example 27 mCP P5 BD01 5.5 15.9 41.6 0.14 0.11 Example 28 mCP P6 BD01 5.6 16.5 42.3 0.14 0.12 Example 29 mCP P7 BD01 5.6 16.1 42.1 0.14 0.12 Example 30 mCP P8 BD01 5.5 15.8 41.5 0.14 0.12 Example 31 mCP P9 BD01 5.5 16.1 43.2 0.14 0.12 Example 32 mCP P10 BD01 5.6 15.7 42.2 0.14 0.12 Example 33 mCP P11 BD01 5.6 15.8 42.4 0.14 0.11

As described above, the light emitting layer was constructed using a thermally active delayed fluorescent compound, and the results of performance evaluation thereof are shown in Table 2 above. As shown in Table 2, 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 a general fluorescent device.

This shows that the compounds according to the present embodiments enable efficient triplet energy transfer to singlet energy through thermally activated delayed fluorescence. In addition, the embodiments of the present invention have a lower driving voltage compared to Comparative Examples 1 to 6, the efficiency and the external quantum efficiency was found to increase the results. In addition, referring to Examples 23 to 33 used as an assist dopant, it was confirmed that the light emission of dark blue was excellent and the physical properties were excellent in all aspects.

The above description of the present application is intended for illustration, and it will be understood by those skilled in the art that the present invention may be easily modified in other specific forms without changing the technical spirit or essential features of the present application. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined form.

The scope of the present application is indicated by the following claims rather than the above description, and it should be construed that all changes or modifications derived from the meaning and scope of the claims and their equivalents are included in the scope of the present application. .

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

Claims (9)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
L ₁ and L ₂ are each independently phenyl or biphenyl,
n and m are each independently an integer of 0 to 3,
D is any one of the following Chemical Formulas 1-1 to 1-4,

In Chemical Formulas 1-1 to 1-4,
X is O, S, or N,
Y is O, S, or CR ₁ R ₂ , R ₁ and R ₂ are each independently hydrogen, an alkyl group of C ₁ to C ₁₀ , a substituted or unsubstituted C ₆ to C ₂₄ aryl group, or a substituted or unsubstituted A substituted C ₃ ~ C ₂₄ heteroaryl group,
Ar ₁ to Ar ₈ are each independently hydrogen, a substituted or unsubstituted C ₆ -C ₂₄ aryl group, or a substituted or unsubstituted C ₃ -C ₂₄ heteroaryl group. The method of claim 1,
Formula 1-1 is a compound represented by any one of the following structural formula.

Ar ₁ is each independently hydrogen, a substituted or unsubstituted C ₆ -C ₂₄ aryl group, or a substituted or unsubstituted C ₃ -C ₂₄ heteroaryl group. The method of claim 1,
Formula 1-2 is a compound represented by any one of the following structural formula.

Ar ₃ is each independently hydrogen, a substituted or unsubstituted C ₆ -C ₂₄ aryl group, or a substituted or unsubstituted C ₃ -C ₂₄ heteroaryl group. The method of claim 1,
Ar ₁ to Ar ₈ are each independently selected from the group consisting of the following structural formula and a combination of the following structural formula.

The method of claim 1,
The compound is any one of the following chemicals.

The compound according to any one of claims 1 to 5, wherein the compound is an organic light emitting material that emits fluorescence or delayed fluorescence. An organic light-emitting device comprising at least one organic material layer comprising a compound according to any one of claims 1 to 5 between the first electrode and the second electrode. The method of claim 7, wherein
The organic material layer is an organic light emitting device. The method of claim 8,
And the light emitting layer comprises a host material having an excitation singlet energy or an excitation triplet energy higher than any one of the excitation singlet energy and the excitation triplet energy of the compound.

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