Compound and organic light-emitting device containing the same

Abstract

The present invention relates to a novel compound and an organic light-emitting device comprising the same. The novel compound according to one example of the present invention is suitable for an organic light-emitting device and can ensure high efficiency, long life, low driving voltage and driving stability of the organic light-emitting device.

Description

Technical Field

[0001] The present invention relates to novel compounds and organic light-emitting devices comprising the same. Background Art

[0002] In an organic light-emitting diode, the materials used as the organic layer can be roughly classified into luminescent materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. according to their functions. In addition, the above-mentioned luminescent materials can be classified into high molecular weight and low molecular weight according to molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons according to the luminescence mechanism. The luminescent materials can be classified into blue, green, red luminescent materials and yellow and orange luminescent materials required to reflect better natural colors according to the luminescent color. In addition, in order to increase the color purity and increase the luminous efficiency through energy transfer, the main body / dopant class can be used as a luminescent substance. The principle is that if a dopant with a small energy band gap and excellent luminous efficiency is mixed in a small amount in the luminescent layer compared to the main body that mainly constitutes the luminescent layer, the excitons generated in the main body are transported to the dopant, thereby emitting light with high efficiency. At this time, the wavelength of the main body moves to the wavelength band of the dopant, so that the desired wavelength of light can be obtained according to the type of dopant and main body used.

[0003] As substances used in such organic light-emitting devices, various compounds are well known. However, in the case of organic light-emitting devices using the well-known substances, the development of new materials continues to be required due to high driving voltage, low efficiency and short life. Therefore, efforts are continuously made to develop organic light-emitting devices with low voltage driving, high brightness and long life using substances with excellent characteristics.

[0004] Prior art literature

[0005] Patent Literature

[0006] Korean Publication Patent 10-2015-0086721 Summary of the invention

[0007] The present invention provides novel organic compounds and organic light-emitting devices comprising the same.

[0008] However, the problems to be solved by the present invention are not limited to the problems described above, and ordinary technicians in the technical field to which the present invention belongs can clearly understand other problems not described according to the following records.

[0009] One 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,

[0013] Ar1 to Ar3 are each independently substituted or unsubstituted C6 to C 50 aryl, or substituted or unsubstituted C5~C 50 wherein at least one of Ar1 to Ar3 is a substituted or unsubstituted C 10 ~C 50 An aryl group or the following chemical formula 1-1,

[0014] Chemical formula 1-1

[0015]

[0016] X is O, S, CRR` or NAr, and the above Ar is substituted or unsubstituted C6~C 50 aryl, or substituted or unsubstituted C5~C 50 wherein R and R' are independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C1~C 30 Alkoxy, or substituted or unsubstituted C1~C 30 The thioether group

[0017] R1 to R6 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C1~C 30 sulfide group, or substituted or unsubstituted C6~C 30 The adjacent multiple R3, R4, R5, and R6 may form a ring or not,

[0018] L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6-C 30 arylene, or substituted or unsubstituted C5~C 30 Heteroarylene,

[0019] l, m and o are each independently 0 or an integer from 1 to 3, and n and p are each independently 0 or an integer from 1 to 4.

[0020] A second embodiment of the present invention provides an organic light-emitting device including an organic material layer containing the compound of the present invention between a first electrode and a second electrode.

[0021] According to a diamine compound of one example of the present invention, as a substituent of the diamine, the diamine comprises dibenzothiophene and one or more three-ring condensed rings, and has two nitrogen atoms of the diamine bonded to a phenylene linking group at the ortho or meta position, thereby forming a deep highest occupied molecular orbital (HOMO) energy level and a high lowest unoccupied molecular orbital (LUMO) energy level that is easy to block electrons, maintaining a high T1, and having excellent electron and exciton blocking effects, thereby realizing a low-voltage and high-efficiency organic light-emitting device.

[0022] Furthermore, the diamine compound according to one embodiment of the present invention has a three-ring condensed ring (dibenzofuran, dibenzothiophene, carbazole or fluorene) with excellent electron resistance, thereby improving durability and increasing the life of the organic light-emitting device.

[0023] Furthermore, the diamine compound according to one example of the present invention has an aryl or heteroaryl group having 10 or more carbon atoms as a substituent, thereby increasing π-conjugation, facilitating molecular arrangement, improving hole mobility, and suppressing the roll-off phenomenon, thereby achieving a long-life organic light-emitting device.

[0024] Furthermore, the diamine compound according to one example of the present invention has a high Tg due to dibenzothiophene and a three-ring condensed ring, and thus the recrystallization of the thin film is prevented, thereby ensuring the driving stability of the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 A schematic diagram showing an organic light emitting device according to an example of the present invention.

[0026] Description of Reference Numerals

[0027] 100: Substrate

[0028] 200: Hole injection layer

[0029] 300: Hole transport layer

[0030] 400: Luminous layer

[0031] 500: Electron transport layer

[0032] 600: Electron injection layer

[0033] 1000: Anode

[0034] 2000: Cathode DETAILED DESCRIPTION

[0035] Hereinafter, examples and embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art can easily implement the present invention.

[0036] However, the present invention can be implemented in many different forms and is not limited to the examples and embodiments described herein. In addition, in the drawings, in order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are marked with similar reference numerals throughout the specification.

[0037] Throughout the specification of the present invention, when one component is located “on” another component, it includes not only the case where one component is in contact with the other component, but also the case where other components exist between the two components.

[0038] Throughout the present specification, when a part "includes" a structural element, unless there is a special record to the contrary, it means that other structural elements may also be included, rather than excluding other structural elements. The terms "about", "substantially", etc. used throughout the present specification are used with their numerical values ​​or close to their numerical values ​​when the mentioned meanings indicate inherent preparation and material tolerances, so as to prevent unscrupulous infringers from improperly using the disclosure that mentions accurate or absolute numerical values ​​to help understand the present invention. The terms "(of) step" or "step of" used throughout the present specification do not mean "step for" .

[0039] Throughout the specification of the present invention, the term "combination thereof" contained in the expression of Markush form means a mixture or combination of one or more selected from the group consisting of multiple structural elements recorded in the expression of Markush form, and means including one or more selected from the group consisting of the above-mentioned multiple structural elements.

[0040] Throughout the present specification, the description "A and / or B" means "A or B, or A and B".

[0041] Throughout the present specification, the term "aryl" means a group containing C 5-30 Aromatic hydrocarbon ring groups, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthryl, triphenylalkenyl, phenylalkenyl, Benzotriphenylbenzene, fluoranthene, benzofluorenyl, benzotriphenylene, benzo Aromatic rings such as phenylene, anthracene, stilbene, and pyrene; "heteroaryl" refers to a C 3-30The aromatic ring includes, for example, a pyrrolinyl group, a pyrazinyl group, a pyridyl group, an indolyl group, an isoindolyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzophenylthio group, a dibenzophenylthio group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a carbazolyl group, a phenanthrylidinyl group, an acridinyl group, a phenanthrolinyl group, a thienyl group, and a heterocyclic group formed by a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, an acridinium ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazide ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, and a dibenzothiophene ring.

[0042] In the present specification, the term "substituted or unsubstituted" may mean a substituted or unsubstituted substituted group selected from deuterium, halogen, amino, nitrile, nitro or C1-C 20 Alkyl, C2~C 20 Alkenyl, C1~C 20 Alkoxy, C3~C 20 Cycloalkyl, C3~C 20 Heterocycloalkyl, C6~C 30 The aromatic group and C3~C 30 One or more groups in the group consisting of heteroaryl groups may be substituted or unsubstituted.

[0043] Furthermore, throughout the specification of the present invention, the same reference numerals may have the same meaning unless otherwise specified.

[0044] Throughout the present specification, the term "fluorene" may include fluorenes in which the hydrogen bonded to the carbon at position 9 is replaced or unsubstituted by a C 1-20 Alkyl, substituted or unsubstituted C 5-30 aryl, or substituted or unsubstituted C 3-30 The case of heteroaryl substitution.

[0045] A first embodiment of the present invention provides a compound represented by the following Chemical Formula 1.

[0046] Chemical formula 1

[0047]

[0048] In the above chemical formula 1,

[0049] Ar1 to Ar3 are each independently substituted or unsubstituted C6 to C 50 aryl, or substituted or unsubstituted C5~C 50wherein at least one of Ar1 to Ar3 is a substituted or unsubstituted C 10 ~C 50 An aryl group or the following chemical formula 1-1,

[0050] Chemical formula 1-1

[0051]

[0052] X is O, S, CRR` or NAr, and the above Ar is substituted or unsubstituted C6~C 50 aryl, or substituted or unsubstituted C5~C 50 wherein R and R' are independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C1~C 30 Alkoxy, or substituted or unsubstituted C1~C 30 The thioether group

[0053] R1 to R6 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C1~C 30 sulfide group, or substituted or unsubstituted C6~C 30 The adjacent multiple R3, R4, R5, and R6 may form a ring or not,

[0054] L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6-C 30 arylene, or substituted or unsubstituted C5~C 30 Heteroarylene,

[0055] l, m and o are each independently 0 or an integer from 1 to 3, and n and p are each independently 0 or an integer from 1 to 4.

[0056] In one embodiment of the present invention, when one of the above Ar1 to Ar3 is the above Chemical Formula 1-1, at least one of the remaining Ar1 to Ar3 may be a substituted or unsubstituted C 10 ~C 50 Although not limited thereto, C 10 ~C 50The aryl group may be selected from the group consisting of naphthyl, biphenyl, terphenyl, quaterphenyl, phenanthryl, triphenylene, and combinations thereof.

[0057] Furthermore, when two or more of Ar1 to Ar3 are represented by the chemical formula 1-1, the remaining Ar1, Ar2 or Ar3 may be substituted or unsubstituted C6 to C 50 aryl, or substituted or unsubstituted C5~C 50 The heteroaryl group.

[0058] According to a diamine compound of one example of the present invention, as a substituent of the diamine, the diamine comprises dibenzothiophene and one or more three-ring condensed rings, and has two nitrogen atoms of the diamine bonded to a phenylene linking group at the ortho or meta position, thereby forming a deep highest occupied molecular orbital (HOMO) energy level and a high lowest unoccupied molecular orbital (LUMO) energy level that is easy to block electrons, maintaining a high T1, and having excellent electron and exciton blocking effects, thereby realizing a low-voltage and high-efficiency organic light-emitting device.

[0059] Furthermore, the diamine compound according to one embodiment of the present invention has a three-ring condensed ring (dibenzofuran, dibenzothiophene, carbazole or fluorene) with excellent electron resistance, thereby improving durability and increasing the life of the organic light-emitting device.

[0060] Furthermore, the diamine compound according to one example of the present invention has an aryl or heteroaryl group having 10 or more carbon atoms as a substituent, thereby increasing π-conjugation, facilitating molecular arrangement, improving hole mobility, and suppressing the roll-off phenomenon, thereby achieving a long-life organic light-emitting device.

[0061] Furthermore, the diamine compound according to one example of the present invention has a high Tg due to dibenzothiophene and a three-ring condensed ring, and thus the recrystallization of the thin film is prevented, thereby ensuring the driving stability of the organic light-emitting device.

[0062] In one embodiment of the present invention, the L2 may be bonded to the meta position of the phenylene group relative to the NAr1Ar2.

[0063] In one embodiment of the present invention, the compound can be represented by the following Chemical Formula 2 or the following Chemical Formula 3.

[0064] Chemical formula 2

[0065]

[0066] Chemical formula 3

[0067]

[0068] In the above Chemical Formula 2 or Chemical Formula 3,

[0069] R7 and R8 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C1~C 30 sulfide group, or substituted or unsubstituted C6~C 30 The aromatic group,

[0070] q and r are each independently 0 or an integer from 1 to 4.

[0071] The compound represented by the above chemical formula 2 is a case where Ar1 in the above chemical formula 1 is a case where L1 and L2 are embodied by substituted or unsubstituted phenylene groups, and the compound represented by the above chemical formula 3 is a case where Ar3 in the above chemical formula 1 is a case where L1 and L2 are embodied by substituted or unsubstituted phenylene groups. In this case, a high T1 can be formed, thereby effectively blocking excitons.

[0072] In one embodiment of the present invention, the compound can be represented by one of the following Chemical Formulas 4 to 7.

[0073] Chemical formula 4

[0074]

[0075] Chemical formula 5

[0076]

[0077] Chemical formula 6

[0078]

[0079] Chemical formula 7

[0080]

[0081] The compound represented by the above chemical formula 4 is the case where Ar1 in the above chemical formula 1 is the chemical formula 1-1 and L1 and L2 are directly bonded, the compound represented by the above chemical formula 5 is the case where Ar3 in the above chemical formula 1 is the chemical formula 1-1 and L1 and L2 are directly bonded, the compound represented by the above chemical formula 6 is the case where Ar1 and Ar2 in the above chemical formula 1 are the chemical formula 1-1 and L1 and L2 are directly bonded, and the compound represented by the above chemical formula 7 is the case where Ar1 to Ar3 in the above chemical formula 1 are the chemical formula 1-1 and L1 and L2 are directly bonded. In this case, there is fast hole mobility, thereby effectively improving the driving voltage.

[0082] In one embodiment of the present invention, the compound can be represented by one of the following Chemical Formulas 8 to 10.

[0083] Chemical formula 8

[0084]

[0085] Chemical formula 9

[0086]

[0087] Chemical formula 10

[0088]

[0089] In the above Chemical Formulas 8 to 10,

[0090] R7 and R8 are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C1~C 30 sulfide group, or substituted or unsubstituted C6~C 30 The aromatic group.

[0091] The compound represented by the above chemical formula 8 is a case where Ar1 in the above chemical formula 1 is a case where L1 is a substituted or unsubstituted phenylene group, and L2 is a direct bond. The compound represented by the above chemical formula 9 is a case where Ar1 in the above chemical formula 1 is a case where L1 is a direct bond, and L2 is a substituted or unsubstituted phenylene group. The compound represented by the above chemical formula 10 is a case where Ar1 in the above chemical formula 1 is a case where L1 and L2 are substituted or unsubstituted phenylene groups. In this case, the HOMO is deep, and thus the efficiency can be effectively improved.

[0092] In one example of the present invention, the compound can be represented by one of the following Chemical Formulas 11 to 13.

[0093] Chemical formula 11

[0094]

[0095] Chemical formula 12

[0096]

[0097] Chemical formula 13

[0098]

[0099] In the above chemical formula 13,

[0100] R2 is substituted or unsubstituted C6~C 30 The aromatic group.

[0101] The compound represented by the above chemical formula 11 is a case where Ar1 in the above chemical formula 1 is a case where L1 and L2 are directly bonded, R1 and R2 are hydrogen, and two nitrogens are bonded to the meta position of the phenylene group, the compound represented by the above chemical formula 12 is a case where Ar1 in the above chemical formula 1 is a case where L1 and L2 are directly bonded, R1 and R2 are hydrogen, and two nitrogens are bonded to the ortho position of the phenylene group, and the compound represented by the above chemical formula 13 is a case where Ar1 in the above chemical formula 1 is a case where L1 and L2 are directly bonded, R1 is hydrogen, R2 is a substituted or unsubstituted aryl group, and two nitrogens are bonded to the meta position of the phenylene group. In this case, the linking group is minimized to form a high LUMO and T1, thereby effectively blocking the movement of unnecessary electrons.

[0102] According to one example of the present invention, in the above Chemical Formulas 1 to 13, the two nitrogen atoms of the diamine are independently bonded to the second or third position of the three-ring condensed ring containing X, or may be bonded to the second or third position of the three-ring condensed ring containing S (dibenzothiophene).

[0103] Furthermore, the connection position numbers of the three-ring condensed ring including the above X or S can be as follows.

[0104]

[0105] According to one embodiment of the present invention, one of the two nitrogen atoms of the diamine can be bonded to the second or third position of the three-ring condensed ring containing X, and the other nitrogen atom can be bonded to the second or third position of the three-ring condensed ring containing S (dibenzothiophene).

[0106] According to an example of the present invention, in the above Chemical Formula 1-1, X may be O. In this case, the bulkiness is minimized and a lower driving voltage may be achieved.

[0107] Furthermore, according to an example of the present invention, in the above Chemical Formula 1-1, X may be S. In this case, the electron donor function is prominent, thereby effectively improving efficiency and lifespan.

[0108] According to an example of the present invention, the above R1 to R8 can be independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and combinations thereof, and specifically can be hydrogen, phenyl or biphenyl.

[0109] Furthermore, according to an embodiment of the present invention, at least one of Ar1 to Ar3 can be selected from the group consisting of naphthyl, biphenyl, terphenyl, quaterphenyl, phenanthryl, triphenylene and combinations thereof, and specifically, can be naphthyl, biphenyl or terphenyl.

[0110] According to an example of the present invention, the compound represented by the above Chemical Formula 1 may be one of the following compounds, but may not be limited thereto.

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] The second embodiment of the present invention provides an organic light-emitting device including the compound represented by the above Chemical Formula 1. The organic light-emitting device may include one or more organic layers including the compound of the present invention between the first electrode and the second electrode.

[0135] In one embodiment of the present invention, the organic layer may be a hole injection layer, a hole transport layer, and a luminescent auxiliary layer, but may not be limited thereto. Furthermore, when the compound of the present invention forms an organic layer, it may be used alone or together with a known compound. In the present invention, the luminescent auxiliary layer refers to a layer formed between the hole transport layer and the luminescent layer, and may also be referred to as the second hole transport layer or the third hole transport layer, etc., depending on the number of hole transport layers.

[0136] In one embodiment of the present invention, the light-emitting auxiliary layer may include the compound of the present invention.

[0137] The above-mentioned 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 a first electrode (anode) and a second electrode (cathode).

[0138] For example, the organic light emitting device may be Figure 1 The organic light-emitting device can be stacked in order from bottom to top: anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / luminescent layer 400 / electron transport layer 500 / electron injection layer 600 / cathode (electron injection electrode 2000).

[0139] exist Figure 1 In the embodiment, the substrate 100 may be a substrate for an organic light-emitting device, and in particular, may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.

[0140] The hole injection electrode 1000 is used as an anode for injecting holes into the organic light emitting device. In order to inject holes, 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.

[0141] The hole injection layer material is deposited on the anode electrode by vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc., thereby forming the hole injection layer 200. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the desired hole injection layer, etc., but generally, the deposition temperature is 50-500°C, 10 -8 Up to 10 -3 torr (torr) vacuum degree, 0.01 to / sec deposition rate, The layer thickness is appropriately selected within the range of 10 to 5 μm.

[0142] Next, a hole transport layer material is deposited on the hole injection layer 200 by vacuum deposition, spin coating, casting, LB method, etc., thereby forming the hole transport layer 300. When the hole transport layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferred to select conditions within the same range as those for forming the hole injection layer.

[0143] The hole transport layer 300 may use the compound of the present invention. As described above, the compound of the present invention may be used alone or together with a known compound. In addition, the hole transport layer 300 of one embodiment of the present invention may be more than one layer, and may include a hole transport layer formed only of a known substance. In addition, according to one embodiment of the present invention, a light-emitting auxiliary layer may be formed on the hole transport layer 300.

[0144] The light-emitting layer material is deposited on the hole transport layer 300 or the light-emitting auxiliary layer by vacuum deposition, spin coating, casting, LB method, etc., thereby forming the light-emitting layer 400. In the case of forming the light-emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferred to select conditions within the same range as those for forming the hole injection layer. In addition, the light-emitting layer material can use a known compound as a host or a dopant.

[0145] Furthermore, in the light-emitting layer, when used together with a phosphorescent dopant, in order to prevent triplet excitons or holes from diffusing to the electron transport layer, a hole suppression material (HBL) may be stacked by vacuum deposition or spin coating. The hole suppression material that can be used at this time is not particularly limited, but any substance can be selected from the known substances used as hole suppression materials. For example, oxadiazole derivatives or triazole derivatives, phenanthroline derivatives or hole suppression materials described in Japanese Patent Laid-Open No. 11-329734 (A1) may be cited. Typically, Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenyl phenolate), phenanthroline (phenanthroline) compounds (such as BCP (BassoCoupoline) of Universal Display (UDC) Company) and the like may be used.

[0146] The electron transport layer 500 is formed on the light emitting layer 400 formed as above. At this time, the electron transport layer can be formed by vacuum deposition, spin coating, casting, etc. Moreover, the deposition conditions of the electron transport layer vary depending on the compound used, but generally, it is preferred to select conditions within the same range as those for forming the hole injection layer.

[0147] Afterwards, an electron injection layer material may be deposited on the electron transport layer 500 to form the electron injection layer 600. At this time, the electron transport layer may be formed using conventional electron injection layer materials by vacuum deposition, spin coating, casting, and the like.

[0148] The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the organic light emitting device may use the compound of the present invention or the following substances, or the compound of the present invention and known substances may be used together.

[0149]

[0150] A cathode 2000 for injecting electrons is formed on the electron injection layer 600 by vacuum deposition or sputtering. Various metals can be used as the cathode, and specific examples include aluminum, gold, silver, and the like.

[0151] The organic light-emitting device of the present invention can not only adopt an organic light-emitting device with an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode structure, but can also adopt the structure of an organic light-emitting device with multiple structures. As needed, one or two intermediate layers can be formed.

[0152] As described above, the thickness of each organic layer formed according to the present invention can be adjusted to a desired extent, preferably, specifically, 1 to 1000 nm, more specifically, 5 to 200 nm.

[0153] In addition, in the present invention, the organic layer including the compound represented by the above Chemical Formula 1 can adjust the thickness of the organic layer in molecular units, and thus has advantages of uniform surface and excellent morphological stability.

[0154] The organic light-emitting compound of this embodiment can be applied to the contents described in the first embodiment of the present invention, but may not be limited thereto.

[0155] Hereinafter, the present invention will be described in more detail by way of examples, but the scope of the present invention is not limited to these examples.

[0156] Example

[0157] Synthesis of the compound represented by Chemical Formula 1

[0158] The compound represented by Chemical Formula 1 may be synthesized through the following reaction, but is not limited thereto.

[0159]

[0160] Synthesis of intermediate IM

[0161] In order to synthesize the target compound, the intermediate IM can be synthesized by the following reaction depending on the type of the three-ring condensed ring, but is not limited thereto.

[0162]

[0163]

[0164] Synthesis of intermediate IM1

[0165] Intermediate IM1 was synthesized as follows.

[0166]

[0167] In a round-bottom flask, 10.0 g of 2-bromodibenzo[b,d]thiophene, 7.1 g of [1,1'-biphenyl]-4-amine, 5.5 g of t-BuONa, 1.4 g of Pd2(dba)3, and 1.7 ml of (t-Bu)3P were dissolved in 250 ml of toluene and refluxed. After confirming the reaction by thin layer chromatography (TLC), water was added to terminate the reaction. The organic layer was extracted with methylcellulose (MC), filtered under reduced pressure, and then column purified and recrystallized to obtain 10.0 g (yield 75%) of IM1.

[0168] Synthesis of Intermediate IM2 to Intermediate IM8

[0169] As shown in Table 1 below, the starting materials were changed and the following IM2 to IM7 were synthesized in the same manner as the above IM1.

[0170]

[0171] Table 1

[0172]

[0173] Synthesis of compounds

[0174] Using the above intermediates IM1 to IM7, the target compound was synthesized as follows.

[0175] Synthesis of compound 1

[0176]

[0177] In a round-bottom flask, 5.0 g of IM1, 5.6 g of 1-bromo-3-iodobenzene, 2.0 g of t-BuONa, 0.5 g of Pd2(dba)3, and 0.8 ml of (t-Bu)3P were dissolved in 160 ml of toluene and refluxed. The reaction was confirmed by thin-layer chromatography and water was added to terminate the reaction. The organic layer was extracted with methylcellulose and filtered under reduced pressure, followed by column purification and recrystallization to obtain 4.2 g (yield 58%) of IM1-1.

[0178] In a round-bottom flask, 2.0 g of the above IM1, 1.5 g of IM2, 0.6 g of t-BuONa, 0.15 g of Pd2(dba)3, and 0.2 ml of (t-Bu)3P were dissolved in 50 ml of toluene and refluxed. The reaction was confirmed by thin layer chromatography, and water was added to terminate the reaction. The organic layer was extracted with methylcellulose, filtered under reduced pressure, and then column purified and recrystallized to obtain 2.1 g (yield 70%) of compound 1.

[0179] m / z: 760.25 (100.0%), 761.26 (58.9%), 762.26 (18.1%), 762.25 (4.5%), 763.26 (3.5%), 763.25 (2.7%), 761.25 (1.5%)

[0180] Synthesis of compound 2

[0181]

[0182] In a round-bottom flask, 2.0 g of IM1, 0.7 g of 1,3-dibromobenzene, 0.8 g of t-BuONa, 0.2 g of Pd2(dba)3, and 0.1 ml of (t-Bu)3P were dissolved in 50 ml of toluene and refluxed. The reaction was confirmed by thin layer chromatography, and water was added to terminate the reaction. The organic layer was extracted with methylcellulose, filtered under reduced pressure, and then column purified and recrystallized to obtain 3.2 g (yield 72%) of compound 2.

[0183] m / z: 776.23 (100.0%), 777.24 (58.8%), 778.24 (17.0%), 778.23 (10.4%), 779.23 (5.4%), 779.24 (3.6%), 777.23 (2.3%), 780.23 (1.6%)

[0184] Synthesis of compound 3

[0185]

[0186] Compound 3 was synthesized by using IM3 instead of IM2 in the same manner as compound 1. (Yield 69%)

[0187] m / z: 852.26 (100.0%), 853.27 (65.4%), 854.27 (22.1%), 854.26 (9.5%), 855.26 (6.0%), 855.27 (4.9%), 853.26 (2.3%), 856.27 (2.0%)

[0188] Synthesis of compound 4

[0189]

[0190] Compound 4 was synthesized by using IM4 instead of IM1 and IM3 instead of IM2 in the same manner as compound 1. (Yield 70%)

[0191] m / z: 826.25 (100.0%), 827.25 (64.8%), 828.25 (20.8%), 828.24 (9.1%), 829.25 (6.2%), 829.26 (4.0%), 830.25 (1.9%)

[0192] Synthesis of compound 5

[0193]

[0194] Compound 5 was synthesized by using IM3 instead of IM1 in the same manner as compound 2. (Yield 73%)

[0195] m / z: 928.29 (100.0%), 929.30 (71.9%), 930.30 (26.6%), 930.29 (9.6%), 93 1.29(6.6%), 931.30(6.4%), 932.30(2.4%), 929.29(2.3%), 932.31(1.0%)

[0196] Synthesis of compound 6

[0197]

[0198] Compound 6 was synthesized by using IM3 instead of IM1 and IM5 instead of IM2 in the same manner as compound 1. (Yield: 66%)

[0199] m / z: 928.29 (100.0%), 929.30 (71.9%), 930.30 (26.6%), 930.29 (9.6%), 93 1.29(6.6%), 931.30(6.4%), 932.30(2.4%), 929.29(2.3%), 932.31(1.0%)

[0200] Synthesis of compound 7

[0201]

[0202] Compound 7 was synthesized by using IM5 instead of IM1 in the same manner as compound 2. (Yield 70%)

[0203] m / z: 928.29 (100.0%), 929.30 (71.9%), 930.30 (26.6%), 930.29 (9.6%), 93 1.29(6.6%), 931.30(6.4%), 932.30(2.4%), 929.29(2.3%), 932.31(1.0%)

[0204] Synthesis of compound 8

[0205]

[0206] In a round-bottom flask, 1.0 g of 2-bromodibenzo[b,d]thiophene, 0.7 g of benzene-1,3-diamine, 0.5 g of t-BuONa, 0.15 g of Pd2(dba)3, and 0.05 ml of (t-Bu)3P were dissolved in 30 ml of toluene and refluxed. The reaction was confirmed by thin layer chromatography and water was added to terminate the reaction. The organic layer was extracted with methylcellulose and filtered under reduced pressure, followed by column purification and recrystallization to obtain 2.1 g (yield 65%) of compound 8.

[0207] m / z: 836.14 (100.0%), 837.15 (58.8%), 838.15 (19.3%), 838.14 (18.1%), 83 9.14(11.1%), 837.14(3.9%), 839.15(3.9%), 840.15(3.2%), 840.14(1.6%)

[0208] Synthesis of compound 9

[0209]

[0210] Compound 9 was synthesized by using IM6 instead of IM2 in the same manner as compound 1. (Yield 70%)

[0211] m / z: 776.23 (100.0%), 777.24 (58.8%), 778.24 (17.0%), 778.23 (10.4%), 779.23 (5.4%), 779.24 (3.6%), 777.23 (2.3%), 780.23 (1.6%)

[0212] Synthesis of compound 10

[0213]

[0214] Compound 10 was synthesized by using IM7 instead of IM2 in the same manner as compound 1. (Yield 71%)

[0215] m / z: 776.23 (100.0%), 777.24 (58.8%), 778.24 (17.0%), 778.23 (10.4%), 779.23 (5.4%), 779.24 (3.6%), 777.23 (2.3%), 780.23 (1.6%)

[0216] Synthesis of compound 11

[0217]

[0218] Compound 11 was synthesized by using IM7 instead of IM1 in the same manner as compound 2. (Yield: 30%)

[0219] m / z: 776.23 (100.0%), 777.24 (58.8%), 778.24 (17.0%), 778.23 (10.4%), 779.23 (5.4%), 779.24 (3.6%), 777.23 (2.3%), 780.23 (1.6%)

[0220] Synthesis of compound 12

[0221]

[0222] Compound 12 was synthesized in the same manner as compound 2 by using 1,2-dibromobenzene instead of 1,3-dibromobenzene. (Yield 45%)

[0223] m / z: 776.23 (100.0%), 777.24 (58.8%), 778.24 (17.0%), 778.23 (10.4%), 779.23 (5.4%), 779.24 (3.6%), 777.23 (2.3%), 780.23 (1.6%)

[0224] Synthesis of compound 13

[0225]

[0226] Compound 13 was synthesized in the same manner as compound 2 by using 3,5-dibromo-1,1'-biphenyl instead of 1,3-dibromobenzene. (Yield: 67%)

[0227] m / z: 852.26 (100.0%), 853.27 (65.4%), 854.27 (22.1%), 854.26 (9.5%), 855.26 (6.0%), 855.27 (4.9%), 853.26 (2.3%), 856.27 (2.0%)

[0228] Synthesis of compound 14

[0229]

[0230] Compound 14 was synthesized in the same manner as compound 2 by using 3,4'-dibromo-1,1'-biphenyl instead of 1,3-dibromobenzene. (Yield: 67%)

[0231] m / z: 852.26 (100.0%), 853.27 (65.4%), 854.27 (22.1%), 854.26 (9.5%), 855.26 (6.0%), 855.27 (4.9%), 853.26 (2.3%), 856.27 (2.0%)

[0232] Synthesis of compound 15

[0233]

[0234] Compound 15 was synthesized in the same manner as compound 2 by using 4,4"-dibromo-1,1':3',1"-terphenyl instead of 1,3-dibromobenzene. (Yield: 65%)

[0235] m / z: 928.29 (100.0%), 929.30 (71.9%), 930.30 (26.6%), 930.29 (9.6%), 93 1.29(6.6%), 931.30(6.4%), 932.30(2.4%), 929.29(2.3%), 932.31(1.0%)

[0236] Preparation of organic light-emitting devices

[0237] Example 1

[0238] Ultrasonication of distilled water The glass substrate coated with indium tin oxide (ITO) to a thickness of 10000 was washed. After the distilled water washing was completed, ultrasonic washing was performed using a solvent such as isopropyl alcohol, acetone, and methanol. After drying, the substrate was transferred to a plasma cleaning machine, and then the substrate was cleaned using oxygen plasma for 5 minutes. Then, a thermal evaporator was used on the top of the indium tin oxide substrate as a hole injection layer. HI01 was used to make the film. HATCN was used to form a film as a hole transport layer. HT01 is used to make a film, and as a light-emitting auxiliary layer After the film is formed by compound 1, 3% RH01:RD01 is doped as the above-mentioned light-emitting layer to Next, as an electron transport layer, After the film was made by mixing ET01 and Liq (1:1), LiF A film was formed by using aluminum (Al) and the device was encapsulated in a glove box to prepare an organic light-emitting device.

[0239] Example 2 to Example 15

[0240] An organic light-emitting device was prepared by using Compounds 2 to 15 instead of Compound 1 in the same manner as in Example 1.

[0241] Comparative Examples 1 to 7

[0242] Ref. 1 to Ref. 7 were used instead of Compound 1 in the same manner as in Example 1 to prepare an organic light emitting device.

[0243]

[0244] Performance evaluation of organic light-emitting devices

[0245] A voltage was applied using a Keithley 2400 source measurement unit to inject electrons and holes, and a Konica Minolta spectroradiometer (CS-2000) was used to measure the brightness of the light. The current density and brightness for the applied voltage were measured under atmospheric pressure to evaluate the performance of the organic light-emitting devices of the embodiments and comparative examples. The results are shown in the following Table 2.

[0246] Table 2

[0247] Op.V <![CDATA[mA / cm 2 ]]> Cd / A CIEx CIE LT99 Example 1 3.9 10 34.5 0.683 0.316 153 Example 2 4.1 10 37.0 0.685 0.315 178 Example 3 4.1 10 37.3 0.685 0.315 180 Example 4 4.1 10 36.8 0.684 0.315 174 Example 5 4.1 10 37.5 0.685 0.315 172 Example 6 4.1 10 38.1 0.685 0.315 174 Example 7 4.2 10 38.5 0.685 0.315 172 Example 8 4.1 10 37.2 0.685 0.315 172 Example 9 4.2 10 36.1 0.683 0.316 167 Example 10 4.1 10 37.3 0.685 0.315 175 Embodiment 11 4.1 10 37.8 0.683 0.316 177 Example 12 4.0 10 37.2 0.684 0.315 175 Embodiment 13 4.2 10 39.8 0.685 0.315 185 Embodiment 14 4.2 10 40.1 0.685 0.315 177 Embodiment 15 4.2 10 40.5 0.684 0.315 175 Comparative Example 1 5.0 10 22.7 0.679 0.322 58 Comparative Example 2 4.7 10 26.0 0.680 0.320 90 Comparative Example 3 4.6 10 24.5 0.677 0.325 75 Comparative Example 4 4.3 10 30.2 0.683 0.317 108 Comparative Example 5 4.4 10 30.0 0.684 0.315 110 Comparative Example 6 4.5 10 28.7 0.683 0.316 100 Comparative Example 7 4.3 10 29.7 0.685 0.315 122

[0248] As shown in Table 2, it was confirmed that Examples 1 to 15 using the compounds of the present invention as the luminescence-assisting layer had improved efficiency and lifetime compared to Comparative Examples 1 to 7 and exhibited lower driving voltage.

[0249] More specifically, compared with Comparative Examples 1 and 2, the embodiments of the present invention have a dibenzothiophene substituent with a diamine directly bonded to nitrogen, which can have fast hole mobility and thus present a low driving voltage.

[0250] Furthermore, compared to Comparative Example 3, in the examples of the present invention, the two nitrogen atoms of the diamine are bonded to the meta or ortho position of the phenylene linker, forming a deep HOMO energy level while having a high LUMO energy level and a high T1, thereby exhibiting high efficiency.

[0251] Furthermore, compared to Comparative Examples 4 to 6, in the embodiments of the present invention, the diamine has dibenzothiophene and an aromatic group having more than 10 carbon atoms as substituents, or has dibenzothiophene and two or more three-ring condensed rings, thereby increasing π-conjugation and inducing effective π stacking between molecules, thereby improving the molecular arrangement, improving the hole mobility, and exhibiting low driving voltage by suppressing the roll-off phenomenon, and exhibiting high efficiency and long life characteristics.

[0252] Furthermore, compared to Comparative Example 7, in the examples of the present invention, the diamine has dibenzothiophene, forming a deeper HOMO energy level while inducing molecular distortion, thereby exhibiting high efficiency and long life characteristics.

[0253] The above description of the present invention is for illustrative purposes, and a person skilled in the art of the present invention can understand that the present invention can be easily deformed in other specific ways without changing the technical concept or essential features of the present invention. Therefore, it should be understood that the multiple embodiments described above are illustrative in all aspects, rather than restrictive. For example, each structural element described in a single type can be implemented in a dispersed manner, and similarly, multiple structural elements described as dispersed can also be implemented in a combined manner.

[0254] The scope of the present invention is indicated by the attached claims for protection, rather than the above detailed description. The meaning and scope of the claims for protection and all changes or modifications derived from their equivalent concepts should be interpreted as being included in the scope of the present invention.

Claims

1. A compound, characterized in that It is represented by the following chemical formula 1, Chemical formula 1 In the chemical formula 1, Ar2 to Ar3 are each independently a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted quaterphenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzothienyl, or a substituted or unsubstituted dibenzofuranyl, Ar1 is a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzofuranyl group, At least one of Ar2 and Ar3 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, or a group of Formula 1-1, Chemical formula 1-1 X is O or S, R1 is hydrogen or deutrium, R2 is hydrogen, phenyl or biphenyl, R3 and R4 are independently hydrogen, deuterium, phenyl or biphenyl, R5 and R6 are independently hydrogen, phenyl or biphenyl, L1 and L2 are each independently a direct bond or a phenylene group, Substituted or unsubstituted is defined as C6~C 30 Aryl substituted or unsubstituted, l, m, o, n and p are each independently 1 or 0.

2. The compound according to claim 1, characterized in that The L2 is bonded to the meta position of the phenylene group relative to the NAr1Ar2.

3. The compound according to claim 1, characterized in that The compound is represented by the following chemical formula 2, Chemical formula 2 In the chemical formula 2, R7 and R8 are each independently hydrogen, q and r are each independently 0 or 1.

4. The compound according to claim 1, characterized in that The compound is represented by one of the following Chemical Formula 4, Chemical Formula 6 and Chemical Formula 7, Chemical formula 4 Chemical formula 6 Chemical formula 7 5. The compound according to claim 1, characterized in that The compound is represented by one of the following Chemical Formulas 8 to 10, Chemical formula 8 Chemical formula 9 Chemical formula 10 In the chemical formula 8 to the chemical formula 10, R7 and R8 are each independently hydrogen.

6. The compound according to claim 1, characterized in that The compound is represented by one of the following Chemical Formulas 11 to 13, Chemical formula 11 Chemical formula 12 Chemical formula 13 In the chemical formula 13, R2 is phenyl or biphenyl.

7. The compound according to claim 1, characterized in that The two nitrogen atoms of the diamine are independently bonded to the second or third position of a three-ring condensed ring containing X, or bonded to the second or third position of a dibenzothiophene which is a three-ring condensed ring containing S.

8. The compound according to any one of claims 1 to 6, characterized in that The X is O.

9. The compound according to any one of claims 1 to 6, characterized in that The X is S.

10. The compound according to any one of claims 1 to 6, characterized in that At least one of Ar2 to Ar3 is selected from the group consisting of naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, and combinations thereof.

11. The compound according to claim 1, characterized in that The compound is one of the following compounds, 12. An organic light-emitting device, characterized in that: An organic layer containing the compound according to any one of claims 1 to 11 is included between the first electrode and the second electrode.

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

14. The organic light emitting device according to claim 13, characterized in that: The organic layer is a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer.

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