Novel compounds and organic light-emitting elements comprising the same

Abstract

The present application provides a compound represented by the following Chemical Formula 1 and an organic light emitting element including the same.

Description

Technical Field

[0001] This invention relates to a novel compound and an organic light-emitting element comprising the novel compound. Background Technology

[0002] Recently, self-emissive, low-voltage driven organic light-emitting elements have gained attention as a new generation of display elements compared to the mainstream flat panel display element, liquid crystal display (LCD). These advantages include superior viewing angle and contrast ratio, no need for backlighting, lightweight and thin design, low power consumption, and wide color reproduction range.

[0003] Materials used as organic layers in organic light-emitting elements can be broadly classified according to their function into light-emitting layer materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0004] Furthermore, the aforementioned luminescent materials can be classified into polymers and single molecules based on their molecular weight, and into fluorescent materials derived from singlet excited states of electrons, phosphorescent materials derived from triplet excited states of electrons, and delayed fluorescent materials derived from electron movement from triplet excited states to singlet excited states based on their luminescence mechanism. Additionally, luminescent materials can be classified into blue, green, yellow, and vermilion luminescent materials, which are needed to achieve a more superior natural color than red luminescent materials, based on their luminescence color.

[0005] Furthermore, to improve color purity and energy transfer-based luminescence efficiency, host / dopant type substances can also be used as luminescent materials. The principle is that by incorporating a small amount of a dopant (a luminescent material with a smaller energy band gap than the host) into the luminescent layer, excitons generated in the host can be transferred to the dopant and emit light. Using the principle described above, the desired wavelength of light can be obtained depending on the type of host and dopant.

[0006] To date, a variety of compounds have been known as suitable materials for the aforementioned organic light-emitting elements (OLEDs). However, OLEDs using these known materials suffer from problems such as high driving voltage, low efficiency, and short lifespan, necessitating the development of new materials. Therefore, researchers have consistently focused on developing OLEDs with excellent properties that enable low-voltage driving, high brightness, and long lifespan. Summary of the Invention

[0007] The purpose of this invention is to provide a novel compound and organic light-emitting element that forms a deep highest occupied molecular orbital (HOMO) while having a high lowest occupied molecular orbital (LUMO) and T1, thereby easily achieving electron interception and exciton movement interception and excellent charge balance within the light-emitting layer.

[0008] Furthermore, the present invention aims to provide a novel compound and organic light-emitting element that has a fast Hall mobility, and can ensure excellent molecular arrangement during thin film formation due to enhanced π conjugation, thereby achieving low driving voltage and high efficiency, and can achieve long lifespan by suppressing decay phenomena.

[0009] Furthermore, the object of the present invention is to provide a novel compound and an organic light-emitting element that can prevent the recrystallization of the thin film and thereby improve driving stability due to having a high glass transition temperature (Tg).

[0010] Next, we will provide a detailed explanation of the topics mentioned above, as well as any additional topics.

[0011] As a means to solve the above problems,

[0012] An embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0013] <Chemical Formula 1>

[0014]

[0015] In the above chemical formula 1,

[0016] Ar1 is a phenyl group or an unsubstituted C7-C30 fused aryl group, but does not contain a fluorenyl group;

[0017] Ar2 and Ar3 are substituted or unsubstituted C6-C30 aryl groups;

[0018] Ar4 and Ar5 are substituted or unsubstituted C6-C30 aryl groups;

[0019] L is a substituted or unsubstituted C6-C50 arylene or a substituted or unsubstituted C2-C50 heteroarylene;

[0020] R1 to R3 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 mercapto, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C6-C50 aryl, or substituted or unsubstituted C2-C50 heteroaryl.

[0021] l is an integer from 0 to 4;

[0022] m is an integer from 0 to 4; and,

[0023] n is an integer from 0 to 5, and m+n is 1 or more.

[0024] Furthermore, as an embodiment of the present invention, an organic light-emitting element is provided, comprising:

[0025] Electrode 1;

[0026] An organic layer is located on the first electrode described above; and,

[0027] The second electrode is located on the aforementioned organic layer;

[0028] The organic layer described above contains the compounds described above.

[0029] The aforementioned organic layer can be one or more of the following: hole injection layer, hole transport layer, and light-emitting auxiliary layer. Specifically, it can be a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer.

[0030] According to the present invention, the compound is introduced into an extended aryl structure (Ar2 to Ar5 in Formula 1) at position 1, 3 or 4 of the fluorenyl group via a linker (L in Formula 1) and is then bound to an amino group on one side. This allows for the formation of deeper highest occupied molecular orbitals (HOMOs) while increasing π-conjugation and thereby achieving a faster Hall mobility. Furthermore, it ensures excellent molecular alignment during thin film formation, thereby achieving a lower driving voltage and high efficiency. It also enables an organic light-emitting element with a long lifespan by suppressing decay phenomena.

[0031] Furthermore, a higher glass transition temperature (Tg) can be achieved by extending the aryl group (Ar2 or Ar5 in Formula 1) between the fluorenyl and amino groups, thereby preventing the recrystallization of the film and thus realizing an organic light-emitting element with excellent driving stability.

[0032] Furthermore, by including an unextended aryl structure (Ar1 in Formula 1) on the other side of the amine group to maintain a very deep highest occupied molecular orbital (HOMO) and a relatively high lowest occupied molecular orbital (LUMO) as well as T1, the exciton confinement effect within the luminescent layer can be maximized, thereby further improving the efficiency of the organic light-emitting element.

[0033] Next, we will explain in detail the effects described above and the additional effects. Attached Figure Description

[0034] FIG. 1This is a schematic cross-sectional view illustrating the structure of an organic light-emitting element according to an embodiment of the present invention.

[0035] [Symbol Explanation]

[0036] 100: Substrate

[0037] 200: Hole injection layer

[0038] 300: Hole Transport Layer

[0039] 400: Emissive layer

[0040] 500: Electron transport layer

[0041] 600: Electron Injection Layer

[0042] 1000: Electrode 1 (Anode)

[0043] 2000: Second electrode (cathode) Detailed Implementation

[0044] Before providing a detailed description of the invention, it should be understood that the terminology used in this specification is for describing specific embodiments only and is not intended to limit the scope of the invention, which should be defined only by the scope of the appended claims. Unless otherwise expressly stated, all technical and scientific terms used in this specification have the same meaning as commonly understood by one of ordinary skill in the art.

[0045] Throughout this specification and the claims, unless otherwise expressly stated, the terms "comprise," "comprises," or "comprising" are used only to indicate that the mentioned object, step, or series of objects and steps are included, and do not preclude any other object, step, or series of objects or steps.

[0046] Throughout this specification and the claims, the term "aryl" refers to substances such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrene, triphenylene, and phenylenetriene. Benzyl, fluoranyl, benzo[a]fluorene, benzo[a]triphenylene, benzo[a] Aromatic ring groups of C6 to C50, such as aryl, anthracene, piracene, and pyrene.

[0047] In addition, the term "heteroaryl" can refer to an aromatic ring of C2 to C50 containing at least one heteroelement, such as pyrrole, pyrazinyl, pyridyl, indolyl, isoindolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazoyl, phenanthridine, acridine, phenanthridine, thiopheneyl, as well as pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, quinoline, acridine, pyrrolidine, dioxane, piperidine, morpholine, piperazine, carbazole, furan, thiophene, oxazole, oxadiazole, benzoxazole, thiazole, thiadiazole, benzothiazole, benzotriazole, imidazole, benzimidazole, pyran, dibenzofuran, etc.

[0048] In addition, Ar in the chemical formula x (where x is an integer) unless otherwise explicitly defined, L represents a substituted or substituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group, L x (where x is an integer) unless otherwise explicitly defined, R represents a directly bonded, substituted or unsubstituted C6–C50 arylene, or a substituted or unsubstituted C2–C50 heteroarylene, R x (where x is an integer) Unless otherwise explicitly defined, it means hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 mercapto, substituted or unsubstituted C6-C50 aryl, or substituted or unsubstituted C2-C50 heteroaryl.

[0049] Throughout this specification and the claims, the term "substituted or unsubstituted" may refer to a group consisting of deuterium, halogen, amino, cyano, nitrile, nitro, nitrosyl, aminosulfonyl, isothiocyanate, thiocyanate, carboxyl, or C1-C30 alkyl, C1-C30 alkylsulfinyl, C1-C30 alkylsulfonyl, C1-C30 alkylthioalkyl, C1-C12 fluoroalkyl, C2-C30 alkenyl, C1-C30 alkoxy, C1 The substituted or unsubstituted group is selected from the group consisting of N-alkylamino (C12), N,N-dialkylamino (C2-C20), substituted or unsubstituted thiol (C1-C30), N-alkylaminosulfonyl (C1-C6), N,N-dialkylaminosulfonyl (C2-C12), silyl (C3-C30), cycloalkyl (C3-C20), heterocycloalkyl (C3-C20), aryl (C6-C50), and heteroaryl (C2-C50). Furthermore, throughout this specification, unless otherwise expressly stated, the same symbols may have the same meaning.

[0050] Furthermore, unless otherwise expressly stated to the contrary, various embodiments of the present invention may be combined with certain other embodiments. The embodiments of the present invention and their effects will now be described.

[0051] The present invention will now be described in detail.

[0052] The compounds according to the present invention are represented by the following chemical formula 1.

[0053] <Chemical Formula 1>

[0054]

[0055] In the above chemical formula 1,

[0056] Ar1 is a phenyl group or an unsubstituted C7-C30 fused aryl group, but does not contain a fluorenyl group;

[0057] Ar2 and Ar3 are substituted or unsubstituted C6-C30 aryl groups;

[0058] Ar4 and Ar5 are substituted or unsubstituted C6-C30 aryl groups;

[0059] L is a substituted or unsubstituted C6-C50 arylene or a substituted or unsubstituted C2-C50 heteroarylene;

[0060] R1 to R3 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 mercapto, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C6-C50 aryl, or substituted or unsubstituted C2-C50 heteroaryl.

[0061] l is an integer from 0 to 4;

[0062] m is an integer from 0 to 4; and,

[0063] n is an integer from 0 to 5, and m+n is 1 or more.

[0064] At this time, R1 and R2 can each be independently a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C6-C50 aryl, or a substituted or unsubstituted C2-C50 heteroaryl.

[0065] In the above content, the substituent during substitution can be one of the substituents mentioned above, specifically methyl or phenyl, but is not limited to this.

[0066] As described above, the compound represented by Formula 1 according to the present invention has an amino group bound to one side of the extended aryl structure (Ar2 to Ar5 in Formula 1) and then to the fluorene group at positions 1, 3, or 4 via a linker (L in Formula 1). This structure allows for the formation of deeper highest occupied molecular orbitals (HOMOs) suitable for the luminescent auxiliary layer, while simultaneously increasing π-conjugation and thereby achieving faster Hall mobility. Furthermore, it ensures excellent molecular alignment during film formation, resulting in a high driving voltage and high efficiency. It also achieves a long lifetime by suppressing decay phenomena. In particular, when R1 and R2 are methyl or phenyl, the decrease in Hall mobility can be suppressed by minimizing the volume characteristics of the fluorene group, thus effectively improving the driving voltage. Moreover, because film deposition can be performed at lower temperatures, its thermal stability is excellent.

[0067] Specifically, the above chemical formula 1 can be represented by the following chemical formula 2:

[0068] <Chemical Formula 2>

[0069]

[0070] In the above chemical formula 2,

[0071] The definitions of Ar1 to Ar5, R3, l, m, and n are the same as those in Chemical Formula 1 above.

[0072] R1 and R2 are each independently a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C6-C50 aryl, or a substituted or unsubstituted C2-C50 heteroaryl;

[0073] o can be an integer from 1 to 3.

[0074] Specifically, m+n can be an integer from 1 to 3.

[0075] As described above, the compound represented by chemical formula 2 according to the present invention has a structure in which one or more phenylene groups are included as the linking group (L) and R1 and R2 are defined as alkyl, aryl or heteroaryl groups, which can form a high least occupied molecular orbital (LUMO), and thus electron interception can be easily achieved when it is applied to a light-emitting auxiliary layer.

[0076] Furthermore, the above chemical formula 1 can be represented by the following chemical formula 3:

[0077] <Chemical Formula 3>

[0078]

[0079] In the above chemical formula 3,

[0080] The definitions of Ar1 to Ar5, R3, m, and n are the same as those in Chemical Formula 1 above.

[0081] R1 and R2 are each independently a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group.

[0082] The phenylene group is attached to any of the * positions of the fluorene group.

[0083] As described above, the compound represented by chemical formula 3 according to the present invention defines the linker (L) as a phenylene group and defines the phenylene group as being bonded to the 3rd or 4th position of the fluorene group. By minimizing the warpage of the molecule, a higher least occupied molecular orbital (LUMO) and a deeper highest occupied molecular orbital (HOMO) can be formed. Therefore, when it is applied to the light-emitting auxiliary layer, the electronic balance in the light-emitting layer can be easily adjusted, thereby improving efficiency and lifespan.

[0084] The above chemical formula 1 can be represented by the following chemical formula 4 or chemical formula 5:

[0085] <Chemical Formula 4>

[0086]

[0087] <Chemical Formula 5>

[0088]

[0089] In the aforementioned chemical formulas 4 and 5,

[0090] The definitions of Ar1 to Ar5, m, and n are the same as those in Chemical Formula 1 above.

[0091] R1 and R2 are each independently a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C6-C50 aryl, or a substituted or unsubstituted C2-C50 heteroaryl.

[0092] The compound represented by Formula 4 according to the present invention has a structure in which the linker group of the fluorene group and the amino group, i.e., the phenylene group, is defined as p-phenylene (1,4-phenylene) and is defined as being bound to the fluorene group at position 3. Therefore, excellent thin film alignment of the molecule can be ensured and mobility can be effectively improved by minimizing the warpage of the fluorene group.

[0093] Furthermore, the compound represented by Formula 5 according to the present invention has a structure in which the linker (L) between the fluorene group and the amino group, i.e., the phenylene group, is defined as p-phenylene (1,4-phenylene) and is defined as being bound to the 4th position of the fluorene group. This structure can maintain a deeper highest occupied molecular orbital (HOMO) and a higher lowest occupied molecular orbital (LUMO) as well as T1. Therefore, excitons can be easily formed within the luminescent layer and the decrease in mobility can be minimized, thereby maintaining the driving voltage more effectively and improving efficiency.

[0094] Furthermore, in any of the above chemical formulas 1 to 5, Ar1 can be phenyl or naphthyl.

[0095] In the case described above, efficiency can be effectively improved by forming higher least occupied molecular orbitals (LUMO) and T1 while having deeper highest occupied molecular orbitals (HOMO), and it is also more advantageous in terms of thermal stability because the deposition temperature can be reduced.

[0096] Furthermore, the aforementioned Ar2 and Ar3 are phenylene oxides; and,

[0097] The Ar4 and Ar5 mentioned above can each be phenyl, naphthyl, or triphenylene, independently.

[0098] As an example, in the above chemical formula 1 It can be any of the substituents in the structures represented by A-1 to A-7 below:

[0099]

[0100]

[0101] The compound according to the invention is as The presence of any one of the substituents A-1 to A-7 described above minimizes the volumetric characteristics of the terminal extension. Therefore, the compounds according to the invention ensure excellent thin-film alignment of the molecules and effectively improve Hall mobility, thus contributing to improved lifespan by suppressing the decay phenomenon of organic light-emitting elements.

[0102] Specifically, The substituents may be structures represented by A-1 or A-6, and the aforementioned substituents may contain one or more o-phenylene (1,2-phenylene) or one or more m-phenylene (1,3-phenylene).

[0103] The compounds according to the present invention that meet the above conditions have deeper highest occupied molecular orbitals (HOMO) and higher lowest occupied molecular orbitals (LUMO) and T1, and therefore can very effectively improve the efficiency of organic light-emitting elements.

[0104] Furthermore, in any of the above chemical formulas 1 to 5, R1 and R2 can each be methyl or phenyl independently.

[0105] The compounds according to the present invention that satisfy the above conditions can suppress the decrease in mobility by minimizing the volume characteristics of the fluorene group. This effectively improves the driving voltage of organic light-emitting elements containing the above compounds, and also ensures excellent thermal stability of the elements during manufacturing due to their lower deposition temperature.

[0106] The following compounds are specific examples of compounds according to the present invention. These examples are merely illustrative of the invention and are not intended to limit the invention.

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] Furthermore, another embodiment of the present invention provides an organic light-emitting element comprising a compound represented by the above-described chemical formula 1. The organic light-emitting element may include one or more organic layers containing the compound according to the present invention between the first electrode and the second electrode.

[0144] In one embodiment of the present invention, the aforementioned organic layer may be one or more of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, for example, it may be a light-emitting auxiliary layer, but it is not limited thereto. In this case, the compound of the present invention may be used alone or in combination with known organic light-emitting compounds.

[0145] In this invention, the light-emitting auxiliary layer refers to the layer formed between the hole transport layer and the light-emitting layer. The hole transport layer can be referred to as such as the second hole transport layer or the third hole transport layer, depending on its number.

[0146] Specifically, the organic light-emitting element of the present invention may include one or more organic layers such as a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between the first electrode and the second electrode.

[0147] FIG. 1 This is a schematic diagram illustrating the structure of an organic light-emitting element according to an embodiment of the present invention.

[0148] like FIG. 1 As shown, the organic light-emitting element of the present invention can be manufactured by stacking the first electrode (hole injection electrode) 1000, hole injection layer 200, hole transport layer 300, light-emitting layer 400, electron transport layer 500, electron injection layer 600 and second electrode (electron injection electrode) 2000 sequentially from bottom to top on the upper part of the substrate 100.

[0149] In addition, although not shown in the figure, a hole blocking layer (not shown) may be included between the light-emitting layer 400 and the electron transport layer 500, and an electron blocking layer (not shown) may be included between the hole transport layer 300 and the light-emitting layer 400.

[0150] Furthermore, a cover layer (not shown) may be included between the substrate 100 and the first electrode 1000, and a cover layer (not shown) may also be included on the upper part of the second electrode 2000.

[0151] FIG. 1 The substrate 100 can be used as a substrate in organic light-emitting elements, especially a transparent glass substrate or a flexible plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and water resistance.

[0152] The first electrode 1000 is used as the anode for injecting holes in the organic light-emitting element. To achieve hole injection, a material with the lowest possible work function is used, and transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene can be used.

[0153] Above the first electrode, a hole injection layer 200 can be formed by depositing a hole injection layer material using methods such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett (LB) method. When forming the hole injection layer using vacuum deposition, the deposition conditions will vary depending on the compound used as the hole injection layer material, the desired hole injection layer structure, and its thermal properties. Typically, deposition temperatures ranging from 50 to 500°C and 10...-8 Up to 10 -3 The vacuum level of the Torr is 0.01 to... deposition rate per second and Appropriate selection should be made within the range of layer thickness up to 5 μm.

[0154] Next, on top of the aforementioned hole injection layer 200, a hole transport layer 300 can be formed by depositing a hole transport layer material using methods such as vacuum deposition, spin coating, casting, or the Langmuir-Brønder (LB) method. When forming the hole transport layer using the aforementioned vacuum deposition method, the deposition conditions will vary depending on the compound used, but are generally preferably selected within a range of conditions almost identical to those used for forming the hole injection layer. There can be more than one hole transport layer; for example, it can be two layers, such as a first hole transport layer and a second hole transport layer (luminescent auxiliary layer). At least one of the aforementioned first hole transport layer and second hole transport layer can include a compound of Chemical Formula 1 according to the present invention.

[0155] Next, on top of the aforementioned hole transport layer or luminescent auxiliary layer, a luminescent layer 400 can be formed by depositing a luminescent layer material using methods such as vacuum deposition, spin coating, casting, or the Langmuir-Brønder (LB) method. When forming the luminescent layer using the aforementioned vacuum deposition method, the deposition conditions will vary depending on the compound used, but it is generally preferable to select conditions within a range almost identical to those used for forming the hole injection layer. Furthermore, known compounds can be used as the main agent or dopant as the luminescent layer material.

[0156] Furthermore, when phosphorescent dopants are used simultaneously in the emitting layer, to prevent triplet excitons or holes from diffusing into the electron transport layer, a stacked hole-blocking material (HBL) can be added using vacuum deposition or spin coating. In this case, the hole-blocking material used is not particularly limited, and any known material used as a hole-blocking material can be selected. For example, oxadiazole derivatives or benzotriazole derivatives, o-diazepinel derivatives, or hole-blocking materials described in Japanese Patent Application Publication No. 11-329734 (A1) can be used. Among these, the most representative include Balq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum) and phenanthrolines (e.g., UDC's BCP).

[0157] An electron transport layer 500 will be formed on top of the light-emitting layer 400 formed as described above. This electron transport layer can be formed by methods such as vacuum deposition, spin coating, or casting. Furthermore, the deposition conditions of the electron transport layer will vary depending on the compound used, but it is generally preferable to select conditions within a range that are almost identical to those for the formation of the hole injection layer.

[0158] Next, an electron injection layer 600 can be formed by depositing an electron injection layer material on top of the electron transport layer 500. At this time, the electron injection layer can be formed using a common electron injection layer material through methods such as vacuum deposition, spin coating, or casting.

[0159] The hole injection layer 200, hole transport layer 300, light emission layer 400, and electron transport layer 500 of the above-mentioned organic light-emitting element may use compounds according to the present invention or substances as described in Table 1 below, or may use compounds according to the present invention and known substances simultaneously.

[0160] Table 1

[0161]

[0162] Above the electron-injected layer 600, a second electrode 2000 can be formed using methods such as vacuum deposition or spin coating. Various metals can be used as the second electrode. Specific examples include materials such as aluminum, gold, and silver.

[0163] As an organic light-emitting element according to the present invention, not only can an organic light-emitting element composed of a first electrode (anode), a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a second electrode (cathode) be used, but also organic light-emitting elements with various structures can be used, and one or two intermediate layers can be added as needed.

[0164] The thickness of each organic layer formed by the present invention as described above can be adjusted according to the required degree, specifically from 10 to 1000 nm, and more specifically from 30 to 100 nm.

[0165] Furthermore, the present invention allows for the adjustment of the thickness of an organic layer, comprising a compound represented by the above-described chemical formula 1, at the molecular level, thus providing the advantages of uniform surface and excellent morphological stability.

[0166] Next, the present invention will be described in more detail through examples of the synthesis of compounds according to an embodiment of the present invention and examples of the manufacture of organic light-emitting elements. The following examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples.

[0167] <Synthetic Example 1> Synthesis of Compound 74

[0168]

[0169] 70 mL of toluene was added to a round-bottom flask, and 3.0 g of 3-(4-bromophenyl)-9,9-diphenyl-9H-fluorene, 2.0 g of N-phenyl-[1,1':3',1”-terphenyl]-4-amine, 0.9 g of t-BuONa, 0.2 g of Pd2(dba)3, and 0.3 mL of (t-Bu)3P were dissolved in the solution before reflux and stirring. The extent of the reaction was confirmed by thin-layer chromatography (TLC), and the reaction was terminated after the addition of water. The organic layer was extracted with dichloromethane (MC), purified by column chromatography after vacuum filtration, and recrystallized to obtain 3.1 g of compound 74 (yield 69%).

[0170] m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

[0171] <Synthetic Example 2> Synthesis of Compound 148

[0172]

[0173] The same procedure as in Synthesis Example 1 was followed, wherein compound 148 was synthesized by replacing N-phenyl-[1,1':3',1”-terphenyl]-4-amine with N,5'-diphenyl-[1,1':3',1”-terphenyl]-4-amine (yield 65%).

[0174] m / z: 789.34 (100.0%), 790.34 (66.3%), 791.35 (21.7%), 792.35 (4.7%)

[0175] <Synthetic Example 3> Synthesis of Compound 194

[0176]

[0177] The same procedure as in Synthesis Example 1 was followed, wherein compound 194 was synthesized by substituting 3-(4-bromophenyl)-9,9-diphenyl-9H-fluorene with 4-(4-bromophenyl)-9,9-diphenyl-9H-fluorene (66% yield).

[0178] m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

[0179] <Synthetic Example 4> Synthesis of Compound 195

[0180]

[0181] The same procedure as in Synthesis Example 1 was followed, in which compound 195 was synthesized by replacing 3-(4-bromophenyl)-9,9-diphenyl-9H-fluorene and N-phenyl-[1,1':2',1”-terphenyl]-4-amine with 4-(4-bromophenyl)-9,9-diphenyl-9H-fluorene and N-phenyl-[1,1':3',1”-terphenyl]-4-amine (yield 63%).

[0182] m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

[0183] <Synthetic Example 5> Synthesis of Compound 199

[0184]

[0185] The same procedure as in Synthesis Example 1 was followed, wherein 4-(4-bromophenyl)-9,9-diphenyl-9H-fluorene and N-phenyl-[1,1':4',1”-terphenyl]-4-amine were used to replace 3-(4-bromophenyl)-9,9-diphenyl-9H-fluorene and N-phenyl-[1,1':3',1”-terphenyl]-4-amine to synthesize compound 199 (yield 61%).

[0186] m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

[0187] Manufacture of organic light emitting element

[0188] The organic light-emitting element of the present invention was manufactured using the substances listed in Table 2 below.

[0189] Table 2

[0190]

[0191] <Example 1>

[0192] Using distilled water to coat with A glass substrate with a thick indium tin oxide (ITO) thin film is ultrasonically cleaned. After washing with distilled water, it is ultrasonically cleaned and dried using solvents such as isopropanol, acetone, and methanol. Next, 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 to deposit a thin film onto the indium tin oxide (ITO) substrate. HI01 and The HATCN membrane was used as a hole injection layer to form... The HT01 membrane is used as a hole transport layer to form a... After using the film of the compound prepared in Synthesis Example 1 as a light-emitting auxiliary layer, a 3% doped BH01:BD01 was prepared. The film serves as the light-emitting layer. Next, a... After using an ET01:Liq (1:1) film as an electron transport layer, it was fabricated LiF membrane, Organic light-emitting elements are manufactured by encapsulating aluminum (Al) films in a glove box.

[0193] Example 2 to Example 5

[0194] Organic light-emitting elements were manufactured by depositing light-emitting auxiliary layers using the compounds produced by Synthesis Examples 2 to 5, respectively, in the same manner as in Example 1 above.

[0195] Comparative Examples 1 to 6

[0196] Organic light-emitting elements were fabricated by depositing light-emitting auxiliary layers using comparative compounds 1 (Ref. 1) to 6 (Ref. 6) as shown in Table 3 below, respectively.

[0197] Table 3

[0198]

[0199] Performance Evaluation of Organic Light-Emitting Components

[0200] Electrons and holes were injected by applying a voltage to a Kiethley 2400 source measurement unit, and the brightness of the emitted light was measured using a Konica Minolta spectroradiometer (CS-2000). The performance of the organic light-emitting elements of the examples and comparative examples, i.e., the current density and brightness relative to the applied voltage, were evaluated under atmospheric pressure conditions. The results are shown in Table 4.

[0201] Table 4

[0202] Op.V mA / cm 2 ]] Cd / A QE (%) CIEx CIEy LT95 Example 1 3.50 10 7.8 6.7 0.139 0.110 153 Example 2 3.50 10 8.0 6.9 0.140 0.109 155 Example 3 3.54 10 8.7 7.5 0.140 0.110 175 Example 4 3.54 10 8.5 7.3 0.142 0.110 170 Example 5 3.55 10 8.3 7.1 0.140 0.109 167 Comparative Example 1 3.60 10 5.9 4.8 0.140 0.111 107 Comparative Example 2 3.75 10 6.4 5.3 0.141 0.109 113 Comparative Example 3 4.03 10 6.8 5.7 0.140 0.110 120 Comparative Example 4 4.00 10 6.6 5.4 0.142 0.110 128 Comparative Example 5 4.15 10 6.9 6.0 0.140 0.112 82 Comparative Example 6 3.70 10 6.3 5.1 0.140 0.112 100

[0203] By comparing the embodiments of the present invention, it can be found that the organic light-emitting elements of the embodiments can not only achieve a lower driving voltage, but also have a very good effect on improving luminous efficiency.

[0204] Specifically, compared to Comparative Example 1, the organic light-emitting element of the embodiments contains a compound with a deeper highest occupied molecular orbital (HOMO) in the light-emitting auxiliary layer, and compared to Comparative Examples 2 and 3, it contains a compound with a structure in which π-conjugation is extended on one side of the amino group through further extended aryl groups. Therefore, the organic light-emitting element of the embodiments can maintain a faster Hall mobility, thereby achieving lower voltage and higher efficiency.

[0205] Furthermore, compared to Comparative Example 4, the compound in the luminescent auxiliary layer of the above embodiments contains an unextended aryl group on the other side of the amino group, thus maintaining a deeper highest occupied molecular orbital (HOMO) while exhibiting a higher lowest occupied molecular orbital (LUMO) and T1. Moreover, it can be confirmed that the above compounds have a superior film alignment compared to Comparative Example 5, which contains an extended substituent in the fluorene group, thus improving its Hall mobility. Simultaneously, compared to Comparative Example 6, where the aryl group as the amino group contains a methylfluorene group, an increase in the highest occupied molecular orbital (HOMO) can be prevented. Therefore, the compounds of the embodiments can more effectively improve Hall mobility compared to the compounds of the comparative examples, while also easily achieving electron interception and exciton movement interception with excellent charge balance within the luminescent layer. Furthermore, the above compounds can achieve lower driving voltage, higher efficiency, and longer lifetime by suppressing decay phenomena.

Claims

1. A compound represented by the following chemical formula 5: Chemical formula 5 In the above chemical formula 5, Ar1 can be phenyl or naphthyl in each group; R1 to R2 are phenyl groups; m is an integer from 0 to 4; and, n is an integer from 0 to 5, and m+n is 1. For any one of the substituents represented by the following structures A-1 and A-5:

2. The compound according to claim 1, characterized in that: The above The substituent is represented by structure A-1.

3. The compound according to claim 1, characterized in that: The compound of chemical formula 5 above is any one of the compounds represented by the following chemical formulas:

4. An organic light-emitting element, characterized in that, include: Electrode 1; An organic layer is located on the first electrode mentioned above; as well as, The second electrode is located on the aforementioned organic layer; The aforementioned organic layer comprises a compound according to any one of claims 1 to 3.

5. The organic light-emitting element according to claim 4, characterized in that: The aforementioned organic layer is any one or more of the following: hole injection layer, hole transport layer, and light-emitting auxiliary layer.

6. The organic light-emitting element according to claim 5, characterized in that: The aforementioned organic layer is a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer.

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