Novel Compound and Organic Light-Emitting Element Comprising the Above Novel Compound

Abstract

The present invention provides a compound represented by the following Chemical Formula 1 and an organic light-emitting device including the above compound. <Chemical Formula 1>

Description

Technical Field

[0001] The present invention relates to a novel compound and an organic light-emitting device comprising the above novel compound. Background Art

[0002] Recently, compared with liquid crystal displays (LCDs), which are the mainstream of flat panel display elements, self-emitting organic light-emitting devices that can be driven at low voltage have excellent viewing angles and contrast ratios, can be made lightweight and thin because they do not require a backlight, are advantageous in terms of power consumption, and have a wide color reproduction range. Therefore, they have attracted much attention as a new generation of display elements.

[0003] The materials used as organic layers in organic light-emitting devices can be generally classified into light-emitting layer materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials according to their functions.

[0004] In addition, the above light-emitting materials can be classified into polymers and single molecules according to their molecular weights, and can be classified 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 transfer from triplet excited states to singlet excited states according to their light-emitting mechanisms. The light-emitting materials can also be classified into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials required for achieving more excellent natural colors according to their light-emitting colors.

[0005] In addition, in order to improve color purity and light-emitting efficiency based on energy transfer, host / dopant type substances can also be used as light-emitting substances. The principle is that by mixing a small amount of a light-emitting substance, i.e., a dopant, whose energy band gap is smaller than that of the host material, into the light-emitting layer, excitons generated in the host material are transferred to the dopant to emit light. By means of the above principle, light of a desired wavelength can be obtained according to the types of the host material and the dopant.

[0006] So far, many compounds have been known as substances applicable to the above organic light-emitting devices. However, since organic light-emitting devices using currently known substances have problems such as high driving voltage, low efficiency, and short lifespan, the development of new materials is still needed. Therefore, people have been working on developing organic light-emitting devices that can be driven at low voltage, have high brightness, and long lifespan by using substances with excellent properties. Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] An object of the present invention is to provide a novel compound and an organic light-emitting device that can achieve excellent molecular alignment when forming a thin film by forming a deeper highest occupied molecular orbital (HOMO) and increasing π-conjugation, and can have a relatively fast Hall mobility.

[0009] Furthermore, an object of the present invention is to provide a novel compound and an organic light-emitting device that can maximize the exciton migration blocking effect in the light-emitting layer by virtue of a relatively high lowest unoccupied molecular orbital (LUMO) and T1, thereby achieving high efficiency, and can achieve a long service life effect by suppressing the roll-off phenomenon.

[0010] Furthermore, an object of the present invention is to provide a novel compound and an organic light-emitting device that can have a relatively high glass transition temperature (Tg) by extending the fluorene moiety and the ortho-linking group, thereby preventing recrystallization of the thin film and improving driving stability.

[0011] Next, the above-mentioned problems and additional problems will be described in detail.

[0012] Means for Solving the Problems

[0013] As a means for solving the above problems, an embodiment of the present invention provides a compound represented by the following Chemical Formula 1.

[0014] <Chemical Formula 1>

[0015]

[0016] In the above Chemical Formula 1,

[0017] Ar1 is a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C5-C50 heteroarylene group,

[0018] Ar2 is a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C5-C50 heteroaryl group,

[0019] L1 is a direct bond, a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group,

[0020] R, R`, and R`` are each independently hydrogen, deuterium, a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C1-C30 silyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group, and R` and R`` may form a ring or not form a ring by bonding to each other.

[0021] R1 to R5 are each independently hydrogen, deuterium, a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C3-C30 silyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group, and adjacent R1, R2, R3, R4, and R5 may form a ring by bonding to each other.

[0022] l, n, o, and p are each independently an integer from 0 to 4.

[0023] m is an integer from 0 to 3.

[0024] Advantages of the Invention

[0025] The compound and the organic light-emitting device according to the present invention have a structure in which a fluorene group and a linking group extended to the ortho position at the 9-position of the fluorene group are bonded to the nitrogen of an aromatic amine, and can ensure excellent molecular alignment and have a fast Hall mobility when forming a thin film by forming a deep highest occupied molecular orbital (HOMO) and increasing π-conjugation.

[0026] In addition, the present invention can maximize the exciton migration blocking effect in the light-emitting layer by virtue of a relatively high lowest unoccupied molecular orbital (LUMO) and T1, thereby achieving high efficiency, and can realize an organic light-emitting device having a long service life effect by suppressing the roll-off phenomenon.

[0027] In addition, it can have a relatively high glass transition temperature (Tg) through the extension of the fluorene group portion and the ortho-linking group, thereby enabling an organic light-emitting device that can prevent recrystallization of the thin film and ensure excellent driving stability.

[0028] Next, the above-described effects and additional effects will be described in detail. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1It is a schematic cross-sectional view of the structure of an organic light-emitting device according to an embodiment of the present invention.

[0030] Explanation of Reference Numerals

[0031] 100: Substrate

[0032] 200: Hole injection layer

[0033] 300: Hole transport layer

[0034] 400: Light-emitting layer

[0035] 500: Electron transport layer

[0036] 600: Electron injection layer

[0037] 1000: First electrode (anode)

[0038] 2000: Second electrode (cathode) Detailed implementation

[0039] Before a detailed description of the present invention, it should be understood that the terms used in this specification are only for describing specific embodiments and are not intended to limit the scope of the present invention, and the scope of the present invention should only be limited by the scope of the appended claims. Unless otherwise clearly stated, the meanings of all technical terms and scientific terms used in this specification are the same as those generally understood by persons with ordinary knowledge.

[0040] Throughout this specification and the claims, unless otherwise clearly stated, the term "comprise (comprise, comprises, comprising)" only indicates the inclusion of the mentioned objects, steps or a series of objects and steps, and does not pre-exclude any other objects, steps or a series of objects or a series of steps.

[0041] Throughout this specification and the claims, the term "aryl" may refer to a C5-50 aromatic hydrocarbon ring group including aromatic rings such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, phenylenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthryl, stilbenyl, and pyrenyl; "heteroaryl" refers to a C2-50 aromatic ring including one or more heteroelements and composed of heterocyclic groups such as pyrrolyl, pyrazinyl, pyridyl, indolyl, isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothienyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and those formed by pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, triazine rings, indole rings, quinoline rings, acridine rings, pyrrolidine rings, dioxane rings, piperidine rings, morpholine rings, piperazine rings, carbazole rings, furan rings, thiophene rings, oxazole rings, oxadiazole rings, benzofuran rings, thiazole rings, thiadiazole rings, benzothiophene rings, triazole rings, imidazole rings, benzimidazole rings, pyran rings, and dibenzofuran rings.

[0042] In addition, unless otherwise clearly defined, Arx (where x is an integer) in a chemical formula represents a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group; unless otherwise clearly defined, Lx (where x is an integer) represents a direct bond, a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group; unless otherwise clearly defined, Rx (where x is an integer) represents hydrogen, deuterium, halogen, nitro, nitrile, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group.

[0043] Throughout this specification and the claims, the term "substituted or unsubstituted" means being substituted or unsubstituted by any one or more groups selected from the group consisting of deuterium, halogen, amino, cyano, nitrile, nitro, nitroso, sulfamoyl, isothiocyanate, thiocyanate, carboxyl, or C1-C30 alkyl, C1-C30 alkylsulfinyl, C1-C30 alkylsulfonyl, C1-C30 alkylsulfanyl, C1-C12 fluoroalkyl, C2-C30 alkenyl, C1-C30 alkoxy, C1-C12 N-alkylamino, C2-C20 N,N-dialkylamino, substituted or unsubstituted C1-C30 sulfide group, C1-C6 N-alkylsulfamoyl, C2-C12 N,N-dialkylsulfamoyl, C3-C30 silyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C50 aryl, and C2-C50 heteroaryl, etc., but is not particularly limited thereto. In addition, throughout the specification of this application, unless otherwise clearly stated, the same symbols have the same meanings.

[0044] In addition, unless otherwise clearly stated to the contrary, multiple embodiments of the present invention can be combined with certain other embodiments. Next, the embodiments of the present invention and their effects will be described.

[0045] Next, the present invention will be described in detail.

[0046] The compound according to the present invention is represented by the following Chemical Formula 1.

[0047] <Chemical Formula 1>

[0048]

[0049] In the above Chemical Formula 1,

[0050] Ar1 is a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C5-C50 heteroarylene group,

[0051] Ar2 is a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C5-C50 heteroaryl group,

[0052] L1 is a direct bond, a substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group,

[0053] R, R`, and R`` are each independently hydrogen, deuterium, a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C1-C30 silyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. R` and R`` may form a ring or not form a ring by bonding to each other.

[0054] R1 to R5 are each independently hydrogen, deuterium, a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C3-C30 silyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. Adjacent R1, R2, R3, R4, and R5 may form a ring or not form a ring by bonding to each other.

[0055] l, n, o, and p are each independently an integer from 0 to 4.

[0056] m is an integer from 0 to 3.

[0057] In the above, the substituents during substitution may be deuterium, a halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group.

[0058] The compound of the present invention represented by Chemical Formula 1 as described above has a structure in which a fluorene group and a linking group extended ortho to the 9-position of the fluorene group are bonded to the nitrogen of an aromatic amine. It can achieve excellent molecular arrangement when forming a thin film and can have a relatively fast Hall mobility by forming a deeper highest occupied molecular orbital (HOMO) suitable for a light-emitting auxiliary layer and increasing π-conjugation. In addition, the present invention can maximize the exciton migration blocking effect in the light-emitting layer by virtue of a relatively high lowest unoccupied molecular orbital (LUMO) and T1 and thereby achieve high efficiency, and can achieve an organic light-emitting element with a long service life effect by suppressing the roll-off phenomenon. In addition, it can have a relatively high glass transition temperature (Tg) through the extension of the fluorene group part and the ortho-linking group, thereby realizing an organic light-emitting element that can prevent recrystallization of the thin film and thereby ensure excellent driving stability.

[0059] Specifically, the above chemical formula 1 can be represented by the following chemical formula 2.

[0060] <Chemical formula 2>

[0061]

[0062] In the above chemical formula 2,

[0063] the definitions of Ar2, R, R`, R``, R1 to R5, l, n, o, p, and m are the same as those in the above chemical formula 1, the definition of R6 is the same as that of R1 above, q is an integer from 1 to 4, and u is an integer from 0 to 4.

[0064] The compound of the above chemical formula 2 is a structure in which Ar1 in chemical formula 1 is composed of one or more phenylene groups and L1 is a direct bond, and it can form a relatively high T1 while having a relatively high lowest unoccupied molecular orbital (LUMO), thereby effectively blocking the movement of excitons in the light-emitting layer.

[0065] In addition, specifically, the above chemical formula 1 can also be represented by the following chemical formula 3.

[0066] <Chemical formula 3>

[0067]

[0068] In the above chemical formula 3,

[0069] the definitions of Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as those in the above chemical formula 1,

[0070] the definition of Ar is the same as that of Ar2 above.

[0071] The compound of the above chemical formula 3 is a structure in which R in chemical formula 1 is composed of Ar (i.e., aryl or heteroaryl), L1 is a direct bond, and there is no substituent in the phenyl group at the 9th position of the phenylfluorene group. Therefore, it can maintain a deeper highest occupied molecular orbital (HOMO) and maintain a relatively fast mobility by minimizing the twist of the linking group, thereby making it easy to achieve charge balance in the light-emitting layer, which is beneficial to the improvement of efficiency and service life.

[0072] In addition, the above chemical formula 3 can also be represented by the following chemical formula 3-1.

[0073] <Chemical formula 3-1>

[0074]

[0075] In the above chemical formula 3-1,

[0076] The definitions of Ar2, R`, R``, R1 to R5, l, n, o, p, m, and Ar are the same as those in Chemical Formula 3 above.

[0077] The compound of Chemical Formula 3-1 above has a structure where H is bonded to the phenyl group at the 9th position of the phenylfluorenyl group in Chemical Formula 3. By blocking the position where H is bonded, fluorene can only be bonded to the para or meta position that is not adjacent, thereby minimizing the twist of the linking group to ensure excellent thin-film alignment and maintaining a relatively fast mobility.

[0078] In addition, Chemical Formula 1 above can specifically be represented by Chemical Formula 4 below.

[0079] <Chemical Formula 4>

[0080]

[0081] In Chemical Formula 4 above,

[0082] The definitions of Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as those in Chemical Formula 1 above.

[0083] The definition of R7 is the same as that of R1 above.

[0084] v is an integer from 0 to 5.

[0085] The compound of Chemical Formula 4 above has a structure where an amino group is directly bonded to the 2nd position of one fluorene group and the other fluorene group is composed of a diphenylfluorenyl group. It can achieve the highest occupied molecular orbital (HOMO) suitable for the light-emitting auxiliary layer and effectively improve the Hall mobility, thereby effectively improving the service life by suppressing the roll-off phenomenon.

[0086] In addition, Chemical Formula 4 above can be represented by Chemical Formula 4-1 below.

[0087] <Chemical Formula 4-1>

[0088]

[0089] In Chemical Formula 4-1 above,

[0090] The definitions of Ar2, R`, R``, R1 to R5, and R7 are the same as those in Chemical Formula 4 above.

[0091] The compound of Chemical Formula 4-1 above has a structure where H is bonded to the phenyl group at the 9th position of the diphenylfluorenyl group in Chemical Formula 4. By blocking the position where H is bonded, fluorene can only be bonded to the para or meta position that is not adjacent, thereby minimizing the twist of the linking group to ensure excellent thin-film alignment and maintaining a relatively fast mobility.

[0092] In addition, in the above Chemical Formulas 1 to 4, the above R, R`, R``, and R1 to R7 may each independently be hydrogen, deuterium, a methyl group, or a phenyl group. Thereby, the decrease in mobility can be suppressed by minimizing the bulky characteristics of the molecule, and excellent thermal stability can be ensured with a lower deposition temperature while effectively improving the driving voltage.

[0093] In addition, in the above Chemical Formulas 1 to 4, the above R` and R`` may be methyl groups. Thereby, the bulky characteristics of the fluorene group can be minimized, the driving voltage can be effectively improved with a relatively high Hall mobility, and the service life can be effectively improved by suppressing the roll-off phenomenon.

[0094] In addition, in the above Chemical Formulas 1 to 4, Ar2 may be selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, a triphenylene group, a dimethylfluorene group, a diphenylfluorene group, a spirobifluorene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and a combination thereof. Specifically, it may be selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuran group, a dibenzothiophene group, or a combination thereof. More specifically, it may be a phenyl group, a naphthyl group, or a biphenyl group. Thereby, by forming a relatively high lowest unoccupied molecular orbital (LUMO) and T1, the deposition temperature can be reduced while effectively improving the efficiency, which is beneficial to thermal stability.

[0095] The following compounds are specific examples of the compounds according to the present invention. The following examples are merely illustrative for explaining the present invention, and the present invention is not limited thereby.

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[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] In addition, another embodiment of the present invention provides an organic light-emitting device including a compound represented by the above Chemical Formula 1. The above organic light-emitting device may include one or more organic layers containing the compound according to the present invention between a first electrode and a second electrode.

[0133] In one embodiment of the present invention, the above organic layer may be one or more of a hole injection layer, a hole transport layer, and a light-emission assisting layer. For example, it may be a light-emission assisting layer, but is not limited thereto. At this time, the compound of the present invention may be used alone or in combination with a known organic light-emitting compound.

[0134] In the present invention, the light-emission assisting layer refers to a layer formed between a hole transport layer and a light-emitting layer. The hole transport layer may also be referred to as a second hole transport layer, a third hole transport layer, etc. depending on the number of hole transport layers.

[0135] Specifically, the organic light-emitting device of the present invention 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 a first electrode and a second electrode.

[0136] Figure 1 is a schematic diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.

[0137] As Figure 1 shown, the organic light-emitting device of the present invention may be manufactured by sequentially laminating a substrate 100, a first electrode (hole injection electrode) 1000, a hole injection layer 200, a hole transport layer 300, a light-emitting layer 400, an electron transport layer 500, an electron injection layer 600, and a second electrode (electron injection electrode) 2000 from bottom to top.

[0138] In addition, although not shown, a hole blocking layer (not shown) may be further included between the light-emitting layer 400 and the electron transport layer 500, and an electron blocking layer (not shown) may be further included between the hole transport layer 300 and the light-emitting layer 400.

[0139] In addition, a cover layer (not shown) may be further included between the substrate 100 and the first electrode 1000, and a cover layer (not shown) may be further included on the upper portion of the second electrode 2000.

[0140] Figure 1 In, the substrate 100 may be a substrate used in an organic light-emitting device. In particular, a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, processability, and waterproofness may be used.

[0141] The first electrode 1000 is used as an anode for hole injection of an organic light-emitting element. To achieve hole injection, a material with a low work function is used, and it can be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.

[0142] On the upper part of the first electrode described above, a hole injection layer material can be deposited by methods such as vacuum deposition method, spin coating method, casting method, Langmuir-Blodgett (LB) method, etc. to form a hole injection layer 200. When forming the hole injection layer by the vacuum deposition method, its deposition conditions will vary according to the compound used as the material of the hole injection layer, the required structure of the hole injection layer, and thermal characteristics, but generally, it can be appropriately selected within the range of a deposition temperature of 50 to 500 °C, a -8 to 10 -3 vacuum degree of torr, a deposition rate of 0.01 to 100 / second, and a layer thickness of 10 to 5 μm.

[0143] Next, on the upper part of the hole injection layer 200 described above, a hole transport layer material can be deposited by methods such as vacuum deposition method, spin coating method, casting method, Langmuir-Blodgett (LB) method, etc. to form a hole transport layer 300. When forming the hole transport layer by the above vacuum deposition method, its deposition conditions will vary according to the compound used, but generally, it is advisable to select within a range of conditions almost the same as those for forming the hole injection layer. The hole transport layer can be one or more layers. For example, it can be two layers such as a first hole transport layer and a second hole transport layer (light-emitting auxiliary layer). At least one of the first hole transport layer and the second hole transport layer may include a compound according to Chemical Formula 1 of the present invention.

[0144] Next, on the upper part of the hole transport layer or the light-emitting auxiliary layer described above, a light-emitting layer material can be deposited by methods such as vacuum deposition method, spin coating method, casting method, Langmuir-Blodgett (LB) method, etc. to form a light-emitting layer 400. When forming the light-emitting layer by the above vacuum deposition method, its deposition conditions will vary according to the compound used, but generally, it is advisable to select within a range of conditions almost the same as those for forming the hole injection layer. In addition, as the light-emitting layer material, a known compound can be used as a host material or a dopant.

[0145] In addition, when phosphorescent dopants are used in the light-emitting layer simultaneously, in order to prevent the phenomenon of triplet excitons or holes diffusing into the electron transport layer, a hole blocking material (HBL) can be additionally laminated by vacuum deposition or spin coating. The hole blocking material that can be used at this time is not particularly limited, and any known substance used as a hole blocking material can be selected. For example, oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, or the hole blocking materials described in Japanese Patent Laid-Open No. 11-329734 (A1) can be used. Among them, the most representative ones include Balq (bis(8-hydroxy-2-methylquinoline)-phenylphenoxyaluminum), phenanthrolines compounds (for example: BCP (bathocuproine) of UDC Corporation), etc.

[0146] An electron transport layer 500 will be formed on the upper part of the light-emitting layer 400 formed in the above-described manner. At this time, the above electron transport layer can be formed by methods such as vacuum deposition, spin coating, casting, etc. In addition, the deposition conditions of the above electron transport layer will vary depending on the compound used, but it is generally advisable to select within a range almost the same as the conditions for forming the hole injection layer.

[0147] Next, an electron injection layer 600 can be formed by depositing an electron injection layer material on the upper part of the above electron transport layer 500. At this time, the above electron injection layer can be formed by methods such as vacuum deposition, spin coating, casting, etc. using a general electron injection layer material.

[0148] The hole injection layer 200, hole transport layer 300, light-emitting layer 400, and electron transport layer 500 of the above organic light-emitting element can use the compounds according to the present invention or the substances described in Table 1 below, or the compounds according to the present invention and known substances can also be used simultaneously.

[0149] [Table 1]

[0150]

[0151] Above the electron injection layer 600, a second electrode 2000 can be formed by methods such as vacuum deposition or spin coating. As the second electrode, various metals can be used. As specific examples, substances such as aluminum, gold, and silver are included.

[0152] As the organic light-emitting element according to the present invention, not only the organic light-emitting element composed of the first electrode (anode), hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, and second electrode (cathode) can be used, but also organic light-emitting elements with various structures can be used, and one or two intermediate layers can be additionally formed as needed.

[0153] As described above, the thickness of each organic layer formed by the present invention can be adjusted as required, specifically, it can be 10 to 1000 nm, more specifically, 30 to 100 nm.

[0154] In addition, in the present invention, the thickness of the organic layer including the compound represented by the above Chemical Formula 1 can be adjusted in molecular units, and thus has the advantages of having a uniform surface and excellent morphological stability.

[0155] Next, the present invention will be described in more detail by a synthesis example of a compound according to an embodiment of the present invention and a manufacturing example of an organic light-emitting element. The following examples are only used to illustrate the present invention, and the scope of the present invention is not limited to the following examples.

[0156] <Production Example 1> Synthesis of Compound 7

[0157]

[0158] In a round-bottom flask, 3.0 g of 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene, 1.8 g of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, 0.9 g of sodium tert-butoxide (t-BuONa), 0.2 g of Pd 2 (dba) 3 , 0.3 ml of tri-tert-butylphosphine ((t-Bu) 3 P) was dissolved in 80 ml of toluene and then refluxed with stirring. The reaction was confirmed by thin layer chromatography (TLC) and the reaction was terminated after adding water. The organic layer was extracted with MC (methylene chloride) and filtered under reduced pressure, then column purified and recrystallized to obtain 3.0 g of compound 7 (yield 70%).

[0159] m / z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

[0160] <Production Example 2> Synthesis of Compound 8

[0161]

[0162] Manufacture was carried out in the same manner as in Production Example 1, wherein Compound 8 (yield: 68%) was synthesized by using N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine in place of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine.

[0163] m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0164] <Production Example 3> Synthesis of Compound 10

[0165]

[0166] Manufacture was carried out in the same manner as in Production Example 1, wherein Compound 10 (yield: 71%) was synthesized by using N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine in place of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine.

[0167] m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%) m / z: 895.35 (100.0%), 896.35 (73.1%), 897.35 (27.0%), 898.36 (6.2%), 899.36 (1.2%)

[0168] <Production Example 4> Synthesis of Compound 11

[0169]

[0170] Production was carried out in the same manner as in Production Example 1, where 9,9-dimethyl-N-(naphthalen-1-yl)-9H-fluoren-2-amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine to synthesize Compound 11 (yield: 65%).

[0171] m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

[0172] <Production Example 5> Synthesis of Compound 92

[0173]

[0174] Production was carried out in the same manner as in Production Example 1, where 9-(2'-bromo-[1,1'-biphenyl]-3-yl)-9-phenyl-9H-fluorene and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used instead of 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine to synthesize Compound 92 (yield: 61%).

[0175] m / z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

[0176] <Production Example 6> Synthesis of Compound 259

[0177]

[0178] Manufacture was carried out in the same manner as in Production Example 1, wherein Compound 259 (yield: 68%) was synthesized using N,9,9-triphenyl-9H-fluoren-2-amine in place of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine.

[0179] m / z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)

[0180] <Production Example 7> Synthesis of Compound 289

[0181]

[0182] Manufacture was carried out in the same manner as in Production Example 1, wherein Compound 289 (yield: 68%) was synthesized using N-phenyl-9,9'-spirobi[fluoren]-2-amine in place of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine.

[0183] m / z: 799.32 (100.0%), 800.33 (67.5%), 801.33 (22.4%), 802.33 (4.9%)

[0184] <Production Example 8> Synthesis of Compound 1

[0185]

[0186] Manufacture was carried out in the same manner as in Production Example 1, wherein Compound 1 (yield: 58%) was synthesized using 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-methyl-9H-fluorene in place of 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene.

[0187] m / z: 615.29 (100.0%), 616.30 (51.3%), 617.30 (12.9%), 618.30 (2.1%)

[0188] <Production Example 9> Synthesis of Compound 434

[0189]

[0190] Production was carried out in the same manner as in Production Example 1, where 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-(naphthalen-2-yl)-9H-fluorene was used to replace 9-(2'-bromo-[1,1'-biphenyl]-4-yl)-9-phenyl-9H-fluorene to synthesize Compound 434 (yield: 55%).

[0191] m / z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

[0192] <Example>: Fabrication of Organic Light-Emitting Device

[0193] The organic light-emitting element of the present invention was fabricated using the materials tabulated in Table 2 below.

[0194] [Table 2]

[0195]

[0196] [Example 1]

[0197] The glass substrate coated with indium tin oxide (ITO) film with a thickness of 1500 was ultrasonically washed with distilled water. After the distilled water washing was completed, ultrasonic washing and drying were carried out using solvents such as isopropyl alcohol, acetone, and methanol. Next, it was transferred to a plasma cleaner and the above substrate was cleaned with oxygen plasma for 5 minutes. Then, a film was formed on the indium tin oxide (ITO) substrate using a thermal evaporator in the following manner: a hole injection layer HI01 of 600, HATCN of 50, a hole transport layer HT01 of 250, a compound manufactured in Production Example 1 as a light-emitting auxiliary layer of 100. Next, a film of 250 of BH01:BD01 3% doped was formed as a light-emitting layer. Next, after forming a film in the form of ET01:Liq (1:1) of 300 as an electron transport layer, a film was formed in the form of 10 of LiF and 1000 of aluminum (Al). Then, the above device was encapsulated in a glove box to manufacture an organic light-emitting device.

[0198] <Example 2> to <Example 9>

[0199] Manufacture was carried out in the same manner as in Example 1 above, where organic light-emitting devices were manufactured by respectively using the compounds manufactured in Production Examples 2 to 9 to replace the light-emitting auxiliary layer formed by the compound manufactured in Production Example 1.

[0200] <Comparative Example 1> to <Comparative Example 6>

[0201] Manufacture was carried out in the same manner as in Example 1 above, where organic light-emitting devices were manufactured by respectively using Comparative Compounds 1 (Ref.1) to Comparative Compound 6 (Ref.6) shown in Table 3 below to replace the light-emitting auxiliary layer formed by the compound manufactured in Production Example 1.

[0202] [Table 3]

[0203]

[0204] <Performance Evaluation of Organic Light-Emitting Devices>

[0205] Electrons and holes were injected by applying a voltage through a Keithley 2400 source measurement unit, and the brightness when emitting light was measured using a Konica Minolta spectroradiance meter (CS-2000). Thus, the performance of the organic light-emitting devices of the examples and comparative examples, namely the current density and brightness with respect to the applied voltage, was evaluated under atmospheric pressure conditions. The results are shown in Table 4.

[0206] [Table 4]

[0207]

[0208]

[0209] Comparing the examples of the present invention with the comparative examples, it can be found that, compared with Comparative Example 1 and Comparative Example 2, the compounds of the present invention have a structure in which a linking group extended ortho to the 9-position of the fluorene group is bonded to the nitrogen of the arylamine. Therefore, they can have a relatively deep highest occupied molecular orbital (HOMO) while having a relatively high lowest unoccupied molecular orbital (LUMO) and T1.

[0210] In addition, compared with Comparative Example 3 and Comparative Example 4, the compounds of the present invention have a linking group with an extended ortho position adjacent to the amino group, so that the thin film arrangement of the molecules can be more excellent due to a deeper highest occupied molecular orbital (HOMO) and an increase in π-conjugation.

[0211] In addition, compared with Comparative Example 5, the compounds of the present invention have a fluorene group acting as an electron donor. Therefore, they can maintain a relatively fast Hall mobility and a highest occupied molecular orbital (HOMO) suitable for the light-emitting auxiliary layer, so that they can effectively improve the Hall mobility while easily blocking electrons and excitons, thereby ensuring excellent charge balance in the light-emitting layer and suppressing the roll-off phenomenon.

[0212] In summary, compared with the comparative examples, the organic light-emitting device with a lower driving voltage, higher efficiency, and longer service life can be realized through the examples.

Claims

1. A compound represented by the following Chemical Formula 1, characterized in that, <Chemical Formula 1> wherein, in the above Chemical Formula 1, Ar1 is a C6 arylene group, Ar2 is selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, and combinations thereof, L1 is a direct bond, R` and R`` are phenyl groups, and R` and R`` may or may not form a ring by bonding to each other, R is a C1 alkyl group or a C6 aryl group, R1 to R5 are each independently hydrogen or deuterium, l, n, o, and p are each independently an integer from 0 to 4, m is an integer from 0 to 3.

2. The compound according to claim 1, characterized in that, the above Chemical Formula 1 is a compound represented by the following Chemical Formula 2, <Chemical Formula 2> wherein, in the above Chemical Formula 2, the definitions of Ar2, R, R`, R``, R1 to R5, l, n, o, p, and m are the same as those in the above Chemical Formula 1, the definition of R6 is the same as that of R1 above, q is 1, u is 0.

3. The compound according to claim 1, characterized in that, the above Chemical Formula 1 is a compound represented by the following Chemical Formula 3, <Chemical Formula 3> wherein, in the above Chemical Formula 3, the definitions of Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as those in the above Chemical Formula 1, Ar is a C6 aryl group.

4. The compound according to claim 1, characterized in that, the above Chemical Formula 1 is a compound represented by the following Chemical Formula 4, <Chemical Formula 4> wherein, in the above Chemical Formula 4, the definitions of Ar2, R`, R``, R1 to R5, l, n, o, p, and m are the same as those in the above Chemical Formula 1, the definition of R7 is the same as that of R1 above, v is an integer from 0 to 5.

5. The compound according to claim 1, characterized in that, the compound of the above Chemical Formula 1 is any one of the compounds represented by the following chemical formulas, 6. An organic light-emitting device, characterized in that ， it contains the compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, characterized in that, the above compound is contained in any one or more organic layers of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

8. The organic light-emitting device according to claim 6, characterized in that, the above compound is contained in a light-emitting auxiliary layer located between a hole transport layer and a light-emitting layer.

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