Novel compounds and organic light emitting devices comprising the same

Abstract

The present invention relates to novel compounds and organic light emitting devices comprising the same.

Description

Technical Field

[0001] This invention relates to novel compounds and organic light-emitting devices containing the same. Background Technology

[0002] In organic light-emitting diodes (OLEDs), materials used as the organic layer can be broadly classified according to function as luminescent materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Furthermore, these luminescent materials can be classified by molecular weight (high molecular weight and low molecular weight), by luminescence mechanism (fluorescent materials originating from single-state electron excitation and phosphorescent materials originating from triple-state electron excitation), and by emission color (blue, green, red, and yellow and orange luminescent materials for better representation of natural colors). To increase color purity and luminescent efficiency through energy transfer, host / dopant types can be used as luminescent substances. The principle is that if a small amount of a dopant with a smaller band gap and higher luminescent efficiency than the host, which constitutes the main luminescent layer, is mixed into the luminescent layer, excitons generated in the host are transported to the dopant, resulting in high-efficiency light emission. In this case, the wavelength of the host shifts towards the wavelength band of the dopant, thus allowing the desired wavelength of light to be obtained depending on the type of dopant and host used.

[0003] To date, a variety of compounds are known as materials for use in organic light-emitting devices (OLEDs). However, OLEDs utilizing these known materials suffer from high driving voltages, low efficiency, and short lifespans, necessitating the development of new materials. Therefore, continuous efforts are being made to develop OLEDs with low-voltage driving, high brightness, and long lifespans using materials with excellent properties.

[0004] Existing technical documents

[0005] Patent documents

[0006] Japanese Patent Publication No. 10-2015-530735 Summary of the Invention

[0007] This invention provides novel organic compounds, methods for their preparation, and organic light-emitting devices containing the same.

[0008] However, the problems to be solved by the present invention are not limited to those described above. Those skilled in the art to which this invention pertains can clearly understand other problems not described based on the following description.

[0009] A first embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0010] Chemical Formula 1

[0011]

[0012] In the above chemical formula 1, R1 and R2 are independently hydrogen, deuterium, or C1-C6 alkyl, respectively, and R3 to R5 are independently hydrogen, deuterium, or C6-C6 alkyl, respectively. 30 Aryl, C1-C6 alkyl, Ar1 and Ar2 are independently substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted C6-C 30 heteroaryl, Ar3 is substituted or unsubstituted C6-C 24 Aryl or substituted or unsubstituted C6-C 24 Heteroaryl groups, L1 and L2 are independently directly coupled and C6-C, respectively. 30 aryl or C6-C 30 The complex is a heteroarylene, where l is an integer from 1 to 4, m is an integer from 1 to 3, and o is an integer from 1 to 4.

[0013] A second embodiment of the present invention provides an organic light-emitting device comprising the compound of the present invention.

[0014] This invention utilizes arylamine bonds at the second position of phenyl-substituted dialkylfluorene and diarylfluorene to form highly occupied molecular orbitals (HOMOs) that facilitate hole injection and transport, and maintains high least unoccupied molecular orbitals (LUMOs) by substituting the diarylfluorene portion, thus easily blocking electrons. This allows for efficient exciton formation within the light-emitting layer, achieving a high-efficiency organic light-emitting device. Furthermore, the phenyl substitution of dimethylfluorene expands conjugation, resulting in excellent thin-film and interfacial alignment. This allows for rapid hole mobility to suppress roll-off and achieve long-lifetime devices. Additionally, maintaining a high Tg at lower molecular weights prevents film recrystallization and increases driving stability.

[0015] The compounds of this invention have high luminous efficiency and high color purity, making them suitable for organic light-emitting devices, organic light devices for solar power generation, etc., thereby greatly contributing to the organic light-emitting diode (OLED) industry for flexible displays, lighting equipment, etc. Attached Figure Description

[0016] Figure 1 A simplified diagram illustrating an example of an organic light-emitting device according to the present invention.

[0017] Explanation of reference numerals in the attached figures

[0018] 100: Substrate

[0019] 200: Hole injection layer

[0020] 300: Hole Transport Layer

[0021] 400: Emissive layer

[0022] 500: Electron transport layer

[0023] 600: Electron Injection Layer

[0024] 1000: Anode

[0025] 2000: Cathode Detailed Implementation

[0026] Hereinafter, with reference to the accompanying drawings, examples and embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the invention.

[0027] However, the present invention can be implemented in many different forms and is not limited to the examples and embodiments described herein. Furthermore, in the figures, parts unrelated to the description have been omitted for clarity, and similar reference numerals are used for similar parts throughout the specification.

[0028] Throughout this invention specification, the phrase "when one component is on top of another component" includes not only cases where one component is in contact with another component, but also cases where there are other components between the two components.

[0029] Throughout this specification, when a part "comprises" a structural element, unless specifically stated otherwise, it means that other structural elements may also be included, rather than excluding other structural elements. The terms "about," "substantially," etc., used throughout this specification, when referring to inherent preparation and material tolerances in their purported meaning, are used in their numerical or near-numerical sense to prevent unscrupulous infringers from improperly using disclosures of precise or absolute numerical values ​​used to aid in understanding the invention. The terms "~(of) step" or "~ step" as used throughout this specification do not mean "for the ~ step."

[0030] Throughout this specification, the term "combination of these" in the Markush form means a mixture or combination of one or more of the groups of structural elements described in the Markush form, and includes one or more of the groups of the aforementioned structural elements.

[0031] Throughout this invention specification, the phrase “A and / or B” means “A or B, or A and B”.

[0032] Throughout this specification, the term "aryl" means containing C 5-30Aromatic hydrocarbon cyclic groups, such as benzyl, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, phenylenyl, trunyl, fluorenylthiophenemethyl, benzo[fluorenyl], benzo[triphenylenyl], benzo[trunyl], anthracene, stilbeneyl, pyrene, etc., are aromatic rings. "Heteroaryl" refers to an aromatic ring containing at least one heteroelement, for example, meaning an aromatic ring containing pyrrolinyl, pyrazinyl, pyridyl, indole, isoindole, furanyl, benzo[furanyl], isobenzofuranyl, dibenzo[furanyl], or benzo[benzenethio]. Dibenzophenylthio, quinolino, isoquinolino, quinoxalino, carbazolyl, phenanthrene, acridine, phenanthrene-rholine, thiophene, and aromatic heterocyclic groups formed from pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, triazine rings, indole rings, quinolino rings, acridine rings, pyrrolidine rings, dioxane rings, piperidine rings, morpholine rings, piperazine rings, carbazolyl rings, furan rings, thiophene rings, oxazole rings, oxadiazole rings, benzoxazole rings, thiazole rings, thiadiazo rings, benzothiazole rings, triazole rings, imidazole rings, benzimidazole rings, pyran rings, and dibenzofuran rings.

[0033] Throughout this specification, the term "alkyl" may include straight-chain or branched saturated or unsaturated C1-C6 alkyl groups, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, or all such possible isomers, but may not be limited thereto.

[0034] Throughout this specification, in the term "substituted or unsubstituted," "substituted" means that it may be derived from a group selected from deuterium, halogen, amino, nitrile, nitro, or C1-C2. 20 Alkyl groups, C2-C 20 alkenyl, C1-C 20 alkoxy groups, C3-C 20 cycloalkyl, C3-C 20 Heterocyclic alkyl groups, C6-C 30 aryl and C5-C 30 One or more groups are substituted in the group consisting of heteroaryl groups.

[0035] Furthermore, throughout the entire specification of this invention, unless otherwise specified, the same symbols may have the same meaning.

[0036] A first embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0037] Chemical Formula 1

[0038]

[0039] R1 and R2 are each independently hydrogen, deuterium, or C1-C6 alkyl, and R3 to R5 are each independently hydrogen, deuterium, or C6-C6 alkyl. 30Aryl, C1-C6 alkyl, Ar1 and Ar2 are independently substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted C6-C 30 heteroaryl, Ar3 is substituted or unsubstituted C6-C 24 Aryl or substituted or unsubstituted C6-C 24 Heteroaryl groups, L1 and L2 are independently directly coupled and C6-C, respectively. 30 aryl or C6-C 30 The complex is a heteroarylene, where l is an integer from 1 to 4, m is an integer from 1 to 3, and o is an integer from 1 to 4.

[0040] In one embodiment of the present invention, the compound of chemical formula 1 may include a compound represented by chemical formula 2 or chemical formula 3.

[0041] Chemical formula 2

[0042]

[0043] Chemical formula 3

[0044]

[0045] In the aforementioned chemical formulas, R1 and R2 are independently hydrogen, deuterium, or C1-C6 alkyl groups, respectively, and R3 to R7 are independently hydrogen, deuterium, or C6-C6 alkyl groups, respectively. 30 Aryl, C1-C6 alkyl, Ar3 is substituted or unsubstituted C6-C 24 Aryl or substituted or unsubstituted C6-C 24 The heteroaryl group, L1 and L2, are independently C6-C. 30 Aryl or C6-C 30 The complex aryl group consists of l, which is an integer from 1 to 4; m and n, which are integers from 1 to 3; o, which is an integer from 1 to 4; and p and q, which are integers from 1 to 5.

[0046] In one embodiment of the present invention, the above-mentioned compound may comprise a compound represented by the following chemical formula 4 or chemical formula 5.

[0047] Chemical Formula 4

[0048]

[0049] Chemical formula 5

[0050]

[0051] In the above chemical formulas, R1 to R7, Ar3, m, n, o, p and q are as defined in chemical formulas 1 to 3, and r is an integer from 0 to 3.

[0052] In one embodiment of the present invention, the above-mentioned compound may comprise a compound of the following chemical formula 6.

[0053] Chemical Formula 6

[0054]

[0055] In the aforementioned chemical formulas, R1 to R7, Ar3, m, n, o, p, and q are as defined in chemical formulas 1 to 3. Specifically, the N of the aromatic amine may be attached to the second position of the dialkylfluorene, in which case a HOMO suitable for the hole transport layer can be achieved, thereby potentially increasing the driving voltage.

[0056] In one embodiment of the present invention, in the above chemical formulas 1 to 6, Ar3 can be selected from the group consisting of phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, dimethylfluorene, and combinations thereof. For example, it can be phenyl, biphenyl, or terphenyl. Furthermore, the aforementioned phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, or dimethylfluorene can be derived from C6-C6. 30 Aryl substitution, such as phenyl substitution. In this case, especially with LUMO which maintains electron barrier properties easily, the vapor deposition process can be controlled at low temperatures.

[0057] In one embodiment of the present invention, in the above chemical formulas 1 to 6, R1 and R2 can be hydrogen or C1-C6 alkyl, and R3 to R7 can be hydrogen.

[0058] In one embodiment of the present invention, in the above chemical formulas 1 to 6, when R1 and R2 are independently C1-C6 alkyl groups, the substituted phenyl group may be attached to the first to fourth positions of the dialkylfluorene, for example, it may be attached to the second or third position.

[0059] In one embodiment of the present invention, in the above chemical formulas 1 to 6, when R1 and R2 are independently C1-C6 alkyl groups, the aromatic amine can be coupled to the second position of the dialkylfluorene.

[0060] In one embodiment of the present invention, the compound of the above-mentioned chemical formula 1 can be prepared according to the following reaction formula 1, but may not be limited thereto.

[0061] Reaction 1

[0062]

[0063] In one embodiment of the present invention, the above-mentioned organic light-emitting compound may include the following compounds, but may not be limited thereto.

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] Among the specific compounds mentioned above, the following compounds can have a HOMO more suitable for hole transport layers by directly coupling at least two fluorene groups to N, and can have faster hole mobility. This results in a lower driving voltage and improved efficiency and lifetime.

[0075]

[0076]

[0077]

[0078] A second embodiment of the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1. The organic light-emitting device may comprise one or more organic layers containing the compound of the present invention between a first electrode and a second electrode.

[0079] In one embodiment of the present invention, the organic layer may be one or more of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, but may not be limited thereto. In this case, the compound of the present invention may be used alone or in combination with known organic light-emitting compounds.

[0080] In one embodiment of the present invention, the above-mentioned organic light-emitting device may include an organic layer containing a hole-transporting substance and an organic layer containing a compound represented by the above-mentioned chemical formula 1, but may not be limited thereto.

[0081] The aforementioned organic light-emitting device may include one or more organic layers such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between the anode and the cathode.

[0082] For example, the above-mentioned organic light-emitting devices can be based on Figure 1 The organic light-emitting device is fabricated according to the structure described in the document. The organic light-emitting device is constructed by stacking the following layers from bottom to top: 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 injection electrode 2000).

[0083] exist Figure 1 In this process, the substrate 100 can be a substrate used for organic light-emitting devices, and in particular, it can be a transparent glass substrate or a flexible plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and water resistance.

[0084] The hole injection electrode 1000 serves as the anode for injecting holes into an organic light-emitting device. To enable hole injection, a material with a low work function is used, which can be formed from transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene.

[0085] Hole injection layer 200 can be formed by depositing a hole injection layer material on the upper part of the aforementioned anode electrode using methods such as vacuum deposition, spin coating, casting, and the LB (Langmuir-Blodgett) method. When forming the hole injection layer using the aforementioned vacuum deposition method, the deposition conditions vary depending on the compound used as the material for the hole injection layer 200, the desired structure of the hole injection layer, and its thermal properties, but are generally suitable for deposition temperatures ranging from 50 to 500°C and 10... -8 Up to 10 -3 The vacuum degree of tor r, 0.01 to deposition rate, Appropriate selection should be made within the range of layer thickness up to 5 μm.

[0086] Next, a hole transport layer material is deposited on top of the hole injection layer 200 using methods such as vacuum deposition, spin coating, casting, and LB method, thereby forming a hole transport layer 300. When forming the hole transport layer using the vacuum deposition method, the deposition conditions vary depending on the compound used, but are generally, preferably, selected within a range almost identical to those for forming the hole injection layer. Then, a light-emitting layer material is deposited on top of the hole transport layer using methods such as vacuum deposition, spin coating, casting, and LB method, thereby forming a light-emitting layer 400. When forming the light-emitting layer using the vacuum deposition method, the deposition conditions vary depending on the compound used, but are generally, preferably, selected within a range almost identical to those for forming the hole injection layer. Furthermore, the light-emitting layer material can use known compounds as the host or dopant.

[0087] Furthermore, when used in conjunction with a phosphorescent dopant in the light-emitting layer, a hole suppression material (HBL) can be laminated using vacuum deposition or spin coating to prevent the diffusion of three-state excitons or holes into the electron transport layer. The hole suppression material that can be used is not particularly limited, but any known material used as a hole suppression material can be selected. Examples include diazole or triazole derivatives, phenanthroline derivatives, or the hole suppression material described in Japanese Patent Application Laid-Open No. 11-329734 (A1). Representatively, Balq (bis(8-hydroxy-2-methylquinoline)-aluminum biphenol salt), phenanthroline compounds (e.g., BCP (Basso Coupoline) from Universal Display Corporation (UDC)) can be used.

[0088] An electron transport layer 500 is formed on top of the light-emitting layer 400 as described above. This electron transport layer can be formed using methods such as vacuum deposition, spin coating, or casting. Furthermore, the deposition conditions for the electron transport layer vary depending on the compound used, but are generally, preferably, selected within a range of conditions almost identical to those for the formation of the hole injection layer.

[0089] Subsequently, an electron injection layer material can be deposited on the electron transport layer 500 to form an electron injection layer 600. At this time, the electron transport layer can be formed by conventional electron injection layer material through methods such as vacuum deposition, spin coating, and casting.

[0090] The hole injection layer 200, hole transport layer 300, light emission layer 400, and electron transport layer 500 of the above-mentioned device may use the compounds of the present invention or the following substances, or the compounds of the present invention and known substances may be used together.

[0091]

[0092] A cathode 2000 for injecting electrons is formed on the electron injection layer 600 using methods such as vacuum deposition or sputtering. Various metals can be used as the cathode. Specific examples include aluminum, gold, and silver.

[0093] The organic light-emitting device of the present invention can not only adopt an organic light-emitting device with an anode, hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer and cathode structure, but also adopt the structure of organic light-emitting devices with various structures. As needed, one or two intermediate layers can also be formed.

[0094] As described above, the thickness of each organic layer formed according to the present invention can be adjusted to the desired extent, preferably, specifically, 10 to 1000 nm, more specifically, 20 to 150 nm.

[0095] Furthermore, in this invention, the organic layer containing the compound represented by the above chemical formula 1 can adjust the thickness of the organic layer to molecular units, thus having the advantages of uniform surface and outstanding morphological stability.

[0096] The organic light-emitting compounds described in this embodiment can be applied to the contents of the first embodiment of the present invention, but may not be limited thereto.

[0097] The following describes the invention in more detail through embodiments, but the scope of the invention is not limited to these embodiments.

[0098] Example

[0099] Preparation Example 1

[0100] IM synthesis

[0101]

[0102] To synthesize the target compound, the above steps were performed to prepare IM.

[0103] The synthesis method of IM1 is as follows.

[0104]

[0105] In a round-bottom flask, 15.0 g of 2-bromo-9,9-dimethyl-9H-fluorene and 7.4 g of phenylboronic acid were dissolved in 200 mL of 1,4-dioxane. Then, 80 mL of K₂CO₃ (2M) and 1.9 g of Pd(PPh₃)₄ were added, and the mixture was refluxed with stirring. The reaction was confirmed by thin-layer chromatography (TLC), and the reaction was terminated by adding water. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, and purified by column chromatography to obtain 10.69 g (72% yield) of intermediate IM1-1.

[0106] In a round-bottom flask, 10.0 g of the above IM1-1 was dissolved in 100 mL of dimethylformamide (DMF), and then a solution of 6.6 g of NBS dissolved in 50 mL of DMF was slowly added dropwise while stirring for 6 hours. The reaction was confirmed by thin-layer chromatography (TLC), and the reaction was stopped after adding water. After filtration under reduced pressure, recrystallization was performed to obtain 8.7 g (yield 67%) of IM1.

[0107] Using the method described above for IM1, the following IM2 to IM4 were synthesized by changing the starting materials.

[0108]

[0109] OP synthesis

[0110]

[0111] To synthesize the target compound, the above steps are performed to prepare the OP.

[0112] The synthesis method of OP1 is as follows.

[0113]

[0114] In a round-bottom flask, 10.0 g of 2-bromo-9,9-diphenyl-9H-fluorene, 2.6 g of aniline, 3.6 g of t-BuONa, 0.9 g of Pd2(dba)3, and 1.1 ml of (t-Bu)3P were dissolved in 130 ml of toluene and then refluxed with stirring. The reaction was confirmed by thin-layer chromatography, and the reaction was terminated by adding water. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, purified by column chromatography, and recrystallized to obtain 7.22 g (70% yield) of OP1.

[0115] Using the method described in OP1 above, the starting materials were changed to synthesize the following OP2 to OP7.

[0116]

[0117] Synthesis Example 1: Synthesis of Compound 1

[0118]

[0119] In a round-bottom flask, 5.0 g of IM1, 6.5 g of OP1, 2.0 g of t-BuONa, 0.5 g of Pd2(dba)3, and 0.65 ml of (t-Bu)3P were dissolved in 110 ml of toluene and then refluxed with stirring. The reaction was confirmed by thin-layer chromatography, and the reaction was terminated by adding water. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, purified by column chromatography, and recrystallized to obtain 7.08 g (73% yield) of compound 1.

[0120] m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

[0121] Synthesis Example 2: Synthesis of Compound 2

[0122]

[0123] Compound 2 was synthesized by using IM2 instead of IM1, as in Synthesis Example 1 (yield 69%).

[0124] m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

[0125] Synthesis Example 3: Synthesis of Compound 3

[0126]

[0127] Compound 3 was synthesized (70% yield) by replacing IM1 with IM3, as in Synthesis Example 1.

[0128] m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

[0129] Synthesis Example 4: Synthesis of Compound 4

[0130]

[0131] Compound 4 was synthesized (65% yield) by replacing IM1 with IM4, as in Synthesis Example 1.

[0132] m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

[0133] Synthesis Example 5: Synthesis of Compound 5

[0134]

[0135] Compound 5 was synthesized (65% yield) by replacing OP1 with OP2, using the method described in Synthesis Example 1.

[0136] m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

[0137] Synthesis Example 6: Synthesis of Compound 6

[0138]

[0139] Compound 6 was synthesized (70% yield) by replacing OP1 with OP3, using the method described in Synthesis Example 1.

[0140] m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

[0141] Synthesis Example 7: Synthesis of Compound 7

[0142]

[0143] Compound 7 was synthesized (74% yield) by replacing OP1 with OP4, using the method described in Synthesis Example 1.

[0144] m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0145] Synthesis Example 8: Synthesis of Compound 8

[0146]

[0147] Compound 8 was synthesized (68% yield) by replacing OP1 with OP5, using the method described in Synthesis Example 1.

[0148] m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0149] Synthesis Example 9: Synthesis of Compound 9

[0150]

[0151] Compound 9 was synthesized (70% yield) by replacing OP1 with OP6, using the method described in Synthesis Example 1.

[0152] m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0153] Synthesis Example 10: Synthesis of Compound 10

[0154]

[0155] Compound 10 was synthesized by replacing OP1 with OP7, as in Synthesis Example 1 (yield 66%).

[0156] m / z: 829.37 (100.0%), 830.37 (69.6%), 831.38 (24.0%), 832.38 (5.4%)

[0157] Synthesis Example 11: Synthesis of Compound 11

[0158]

[0159] Compound 11 was synthesized by replacing OP1 with OP8, as in Synthesis Example 1 (yield 62%).

[0160] m / z: 793.37 (100.0%), 794.37 (66.3%), 795.38 (21.8%), 796.38 (4.7%)

[0161] Synthesis Example 12: Synthesis of Compound 12

[0162]

[0163] Compound 12 was synthesized (60% yield) by replacing OP1 with OP9, as in Synthesis Example 1.

[0164] m / z: 793.37 (100.0%), 794.37 (66.3%), 795.38 (21.8%), 796.38 (4.7%)

[0165] Synthesis Example 13: Synthesis of Compound 13

[0166]

[0167] In a round-bottom flask, 10.0 g of 3,6-dibromo-9,9-dimethyl-9H-fluorene and 2.1 g of phenylboronic acid were dissolved in 120 mL of 1,4-dioxane. Then, 40 mL of K₂CO₃ (2M) and 1.0 g of Pd(PPh₃)₄ were added, and the mixture was refluxed with stirring. The reaction was confirmed by thin-layer chromatography (TLC), and the reaction was terminated by adding water. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, and purified by column chromatography to obtain 5.06 g (51% yield) of intermediate IM₅. Using intermediate IM₅ instead of IM₁, compound 13 was synthesized (60% yield) as in Synthesis Example 1.

[0168] m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

[0169] Synthesis Example 14: Synthesis of Compound 14

[0170]

[0171] Compound 14 was synthesized (70% yield) by replacing OP1 with OP10, as in Synthesis Example 1.

[0172] m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0173] Synthesis Example 15: Synthesis of Compound 15

[0174]

[0175] In a round-bottom flask, 10.0 g of IM1 and 9.45 g of bis(pipinacol)diboron were dissolved in 200 mL of 1,4-dioxane. 8.5 mL of KOAc and 0.1 g of Pd(dppf)Cl2 were added, and the mixture was refluxed with stirring. The reaction was confirmed by thin-layer chromatography (TLC). Water was added, and the reaction was terminated. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, and purified by column chromatography to obtain 9.1 g (80% yield) of intermediate IM6-1. In a round-bottom flask, 9.0 g of IM6-1 and 7.1 g of 1-bromo-4-iodobenzene were dissolved in 200 mL of 1,4-dioxane. 35 mL of K2CO3 (2M) and 0.8 g of Pd(PPh3)4 were added, and the mixture was refluxed with stirring. The reaction was confirmed by thin-layer chromatography (TLC). Water was added, and the reaction was terminated. The organic layer was extracted with dichloromethane (MC), filtered under reduced pressure, and then purified by column chromatography to obtain 5.12 g (53% yield) of intermediate IM6. Subsequently, using intermediate IM6 instead of IM1, compound 15 was synthesized by the method described in Synthesis Example 1 (67% yield).

[0176] m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0177] Fabrication Example 2: Fabrication of Organic Light-Emitting Devices

[0178] Ultrasonic waves transmitted through distilled water The glass substrate with an indium tin oxide (ITO) thin film is washed. After washing with distilled water, it is ultrasonically cleaned using solvents such as isopropanol, acetone, or methanol. After drying, it is transferred to a plasma cleaner, where oxygen plasma is used to clean the substrate for 5 minutes. Then, a thermal evaporator is used as a hole injection layer on top of the indium tin oxide substrate. HI01 is used to form a film, HATCN was used to fabricate a film to serve as a hole transport layer. After compound 1 is film-formed, 3% BH01:BD01 is doped into the light-emitting layer as described above. A film is formed. Then, it is used as an electron transport layer. After film formation using ET01:Liq (1:1), LiF, An organic light-emitting device was prepared by forming a film of aluminum (Al) and then encapsulating the device in a glove box (Example 1).

[0179] Organic light-emitting devices were prepared by replacing compound 1 with compounds 2 to 15 (Examples 2 to 15) as described above.

[0180] Comparative example

[0181] Organic light-emitting devices were prepared in the same manner as in Preparation Example 2 above, except that Ref. 1 to Ref. 11 (Comparative Examples 1 to 11) were used instead of Compound 1.

[0182]

[0183]

[0184] Experimental Example 1: Performance Evaluation of Organic Light-Emitting Devices

[0185] Electrons and holes were injected by applying a voltage using a Kiethley 2400 source measurement unit, and the brightness during emission was measured using a Konica Minolta spectroradiometer (CS-2000). Thus, under atmospheric pressure conditions, the current density and brightness with respect to the applied voltage were measured to evaluate the performance of the organic light-emitting devices of the examples and comparative examples, and the results are shown in Table 1.

[0186] Table 1

[0187]

[0188]

[0189]

[0190] As shown in Table 1 above, it can be seen that in various embodiments of the present invention, compared with Comparative Examples 1 to 10, improved efficiency and extended lifetime are achieved. Comparing the embodiments of the present invention, it can be seen that: 1) compared with Comparative Examples 2, 3, 7, and 10, the case containing diphenylfluorene; 2) compared with Comparative Examples 2 and 6, the case expanding conjugation by substituting the plate-like dimethylfluorene phenyl group; 3) compared with Comparative Examples 4 and 5, the case maintaining the lowest unoccupied molecular orbital that easily blocks electrons by substituting the phenyl group; 4) compared with Comparative Examples 8, 9, and 10, the case having a HOMO that facilitates hole injection through second-position coupling of the fast-moving diphenylfluorene; and 5) compared with Comparative Example 11, the case containing Ar3 to maintain a relatively plate-like unit. Considering all of the above, the compounds of the present invention have low driving voltages for organic light-emitting devices and significantly improved efficiency and lifetime.

[0191] The foregoing description of the present invention is illustrative, and those skilled in the art will understand that modifications can be readily made in other specific ways without altering the technical concept or essential features of the invention. Therefore, it should be understood that the various embodiments described above are illustrative in all respects and not limiting. For example, the individual structural elements described as a single type can be implemented separately; similarly, the multiple structural elements described as separate can also be implemented in combination.

[0192] The scope of this invention is indicated by the appended patent claims, rather than by the detailed description above. The meaning and scope of the patent claims, as well as all modifications or variations derived therefrom, should be interpreted as being included within the scope of this invention.

Claims

1. A compound, characterized in that, Represented by the following chemical formula 1, Chemical Formula 1 In the above chemical formula 1, R1 and R2 are independently hydrogen, deuterium, or C1-C6 alkyl groups, respectively. R3 to R5 are each independently hydrogen, deuterium, or C1-C6 alkyl. Ar1 and Ar2 are independently benzyl, phenyl, naphthyl, and biphenyl, respectively. Ar3 is selected from the group consisting of phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, and dimethylfluorenyl. L1 and L2 are independently directly coupled or phenylene, naphthylene, and biphenylene, respectively. l is an integer of 1, m and n are integers from 1 to 3, and o is an integer from 1 to 4.

2. The compound according to claim 1, characterized in that, The above compounds include compounds represented by the following chemical formula 2 or chemical formula 3, Chemical formula 2 Chemical formula 3 Among the above chemical formulas, R1 and R2 are independently hydrogen, deuterium, or C1-C6 alkyl groups, respectively. R3 to R5 are each independently hydrogen, deuterium, or C1-C6 alkyl. R6 to R7 are hydrogen atoms, Ar3 is selected from the group consisting of phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, and dimethylfluorenyl. L1 and L2 are independently phenylene, naphthylene, and biphenylene, respectively. l is an integer of 1, m and n are integers from 1 to 3, o is an integer from 1 to 4, and p and q are integers from 1 to 5.

3. The compound according to claim 1, characterized in that, The above compounds include compounds represented by the following chemical formula 4 or chemical formula 5, Chemical Formula 4 Chemical formula 5 Among the above chemical formulas, R1 and R2 are independently hydrogen, deuterium, or C1-C6 alkyl groups, respectively. R3 to R5 are each independently hydrogen, deuterium, or C1-C6 alkyl. R6 to R7 are hydrogen atoms, Ar3 is selected from the group consisting of phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, and dimethylfluorenyl. m and n are integers from 1 to 3, o is integer from 1 to 4, p and q are integers from 1 to 5, and r is integer from 0 to 3, but r is not 3.

4. The compound according to claim 1, characterized in that, The above compounds include those represented by chemical formula 6. Chemical Formula 6 Among the above chemical formulas, R1 and R2 are independently hydrogen, deuterium, or C1-C6 alkyl groups, respectively. R3 to R5 are each independently hydrogen, deuterium, or C1-C6 alkyl. R6 to R7 are hydrogen atoms, Ar3 is selected from the group consisting of phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, and dimethylfluorenyl. m and n are integers from 1 to 3, o is integer from 1 to 4, and p and q are integers from 1 to 5.

5. The compound according to any one of claims 1 to 4, characterized in that, Ar3 is a phenyl, biphenyl, or terphenyl group.

6. The compound according to any one of claims 1 to 4, characterized in that, R1 and R2 are each independently hydrogen or C1-C6 alkyl, and R3 to R7 are hydrogen.

7. The compound according to any one of claims 1 to 4, characterized in that, When R1 and R2 are C1-C6 alkyl groups, the substituted phenyl group is attached to the second or third position.

8. The compound according to any one of claims 1 to 4, characterized in that, When R1 and R2 are C1-C6 alkyl groups respectively, the aromatic amine is coupled to the second position of the dialkylfluorene.

9. The compound according to any one of claims 1 to 4, characterized in that, The N-terminus of the aromatic amine is attached to the second position of the dialkylfluorene.

10. The compound according to claim 1, characterized in that, The above compound is one of the following compounds: 。 11. An organic light-emitting device, characterized in that, Between the first electrode and the second electrode is an organic layer containing one or more layers of the compound of claim 1.

12. The organic light-emitting device according to claim 11, characterized in that, The aforementioned organic layer is one or more of the hole injection layer, hole transport layer, and light-emitting auxiliary layer.

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