Organic compound and organic light-emitting device including same

Abstract

The invention discloses an organic compound, and an organic light emitting diode and an organic light emitting device comprising the same. For example, the organic compound is represented by the following chemical formula. The organic light-emitting diode and the organic light-emitting device each contain the organic compound. # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of and priority to Korean Patent Application No. 10-2023-0150895 filed in Korea on November 3, 2023. Technical Field

[0003] The present application relates to an organic compound, and more particularly, to an organic compound having improved luminous efficiency and lifetime, and also to an organic light-emitting device including the organic compound. Background Art

[0004] Recently, as the demand for small-area flat panel display devices increases, organic light emitting display devices including organic light emitting diodes (OLEDs) have become the subject of recent research and development.

[0005] OLED emits light by injecting electrons from a cathode as an electron injection electrode and holes from an anode as a hole injection electrode into a light-emitting material layer (EML), combining electrons with holes, generating excitons, and converting the excitons from an excited state to a ground state. A flexible substrate (e.g., a plastic substrate) can be used as a bottom substrate for forming an element. In addition, an organic light-emitting display device can operate at a voltage (e.g., below 10V) lower than the operating voltage of other display devices. In addition, an organic light-emitting display device has improved power consumption and color.

[0006] The OLED includes, on a substrate, a first electrode as an anode, a second electrode as a cathode spaced apart from and facing the first electrode, and an organic light emitting layer between the first electrode and the second electrode.

[0007] Although there have been many studies and developments on materials for organic light-emitting layers, OLEDs still have limitations in terms of light-emitting efficiency and lifespan. Summary of the invention

[0008] The present invention is directed to an organic compound and an organic light emitting device that substantially obviates one or more problems associated with limitations and disadvantages of the related art.

[0009] Other features and advantages of the present invention are set forth in the following description and will be apparent from the description or will be clarified through the practice of the present invention. The objects and other advantages of the present invention are realized and achieved by the features described herein and in the accompanying drawings.

[0010] To achieve these and other advantages according to the purpose of embodiments of the present invention, as described herein, one aspect of the present invention is an organic compound represented by Formula 1:

[0011] [Formula 1]

[0012]

[0013] wherein a1 and a2 are each independently an integer of 0 to 4, and a3 and a4 are each independently 0 or 1, X1 and X2 are each independently O or S, Ar1 and Ar2 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S, and R1 and R2 are each independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C60 aryl group, a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S. The group consisting of unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted aryl and substituted or unsubstituted C3 to C60 heteroaryl containing one of N, O and S, and L1 and L2 are each independently selected from the group consisting of substituted or unsubstituted C6 to C60 arylene and substituted or unsubstituted C3 to C60 heteroarylene containing one of N, O and S. It should be understood that when a3 and / or a4 is 0, L1 and / or L2 do not exist, and the central benzene ring is directly connected to the corresponding benzoxazole / benzothiazole group through a single bond.

[0014] In a preferred embodiment, Ar1 and Ar2 are different.

[0015] Another aspect of an embodiment of the present invention is an organic light-emitting device, comprising a substrate; and an organic light-emitting diode located on the substrate, the light-emitting diode comprising a first electrode; a second electrode facing the first electrode; and a first light-emitting component between the first electrode and the second electrode, the first light-emitting component comprising a first light-emitting material layer, a first electron transport layer, and a first hole blocking layer, wherein the first electron transport layer is located between the first light-emitting material layer and the second electrode, and the first hole blocking layer is located between the first light-emitting material layer and the first electron transport layer, and wherein at least one of the first electron transport layer and the first hole blocking layer comprises a first compound of an organic compound represented by Formula 1:

[0016]

[0017] wherein a1 and a2 are each independently an integer of 0 to 4, and a3 and a4 are each independently 0 or 1, X1 and X2 are each independently O or S, Ar1 and Ar2 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S, and R1 and R2 are each independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C60 aryl group, a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S. The invention also includes the following: an unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S, and L1 and L2 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 arylene group and a substituted or unsubstituted C3 to C60 heteroarylene group containing one of N, O and S.

[0018] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention.

[0020] Figure 1 A schematic circuit diagram illustrating an organic light emitting display device according to an exemplary embodiment of the present invention.

[0021] Figure 2 A schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present invention.

[0022] Figure 3 A schematic cross-sectional view showing an OLED according to a second embodiment of the present invention.

[0023] Figure 4 A schematic cross-sectional view showing an OLED according to a third embodiment of the present invention.

[0024] Figure 5 A schematic cross-sectional view showing an organic light emitting display device according to a fourth embodiment of the present invention.

[0025] Figure 6 A schematic cross-sectional view showing an OLED according to a fifth embodiment of the present invention.

[0026] Figure 7 A schematic cross-sectional view showing an OLED according to a sixth embodiment of the present invention. DETAILED DESCRIPTION

[0027] Reference will now be made in detail to some examples and implementations of the present invention which are illustrated in the accompanying drawings. Wherever possible, the same reference numerals will be used throughout the drawings to refer to the same or like parts.

[0028] Advantages and features of the present invention and methods of implementing the same will be described by the following exemplary embodiments described with reference to the accompanying drawings. However, the present invention can be implemented in different forms and should not be construed as being limited to the exemplary embodiments illustrated herein. On the contrary, these exemplary embodiments are provided so that the present invention can be fully thorough and complete, thereby helping those skilled in the art to fully understand the scope of the present invention. In addition, the scope of protection of the present invention is defined by the claims or their equivalents.

[0029] The shapes, sizes, proportions, angles, numbers, etc., illustrated in the drawings to describe the various exemplary embodiments of the present invention are given by way of example only. Therefore, the present invention is not limited to the illustrations in the drawings. The same reference numerals are used throughout the specification to designate the same or similar elements unless otherwise specified.

[0030] In the following description, when detailed descriptions of related known functions or configurations may unnecessarily obscure the gist of the present invention, detailed descriptions of known functions of these configurations may be omitted.

[0031] In this specification, when the terms "comprising", "having", "including", etc. are used, one or more other elements may be added unless terms such as "only" are used. Elements described in the singular are intended to include plural elements and vice versa unless the context clearly indicates otherwise.

[0032] In interpreting an element, the element is to be interpreted as including an error or tolerance range even when an explicit description of such an error or tolerance range is not provided.

[0033] In various embodiments of the present invention, when describing a positional relationship, for example, when using "on", "above", "below", "over", "below", "beside", "adjacent", etc. to describe the positional relationship between two parts, one or more other parts may be located between the two parts, unless more restrictive terms such as "immediately", "directly" or "closely" are used. For example, when one element or layer is disposed "on" another element or layer, a third layer or element may be disposed therebetween.

[0034] When describing a temporal relationship, when the temporal order is described as, for example, "after", "subsequently", "next", or "before", discontinuities may be included unless more restrictive terms such as "directly", "immediately", or the like are used.

[0035] Although the terms "first", "second", etc. may be used herein to describe various elements, the elements are not limited by these terms. These terms are only used to distinguish one element from another element. For example, without departing from the scope of the present invention, the first element may be referred to as the second element, and similarly, the second element may be referred to as the first element.

[0036] Although the terms "first", "second", A, B, (a), (b), etc. may be used herein to describe various elements, the elements should not be interpreted as being limited by these terms because they are not used to define a specific order, priority or quantity of the corresponding elements. These terms are only used to distinguish one element from another.

[0037] The statement that an element or layer is “connected to” another element or layer means that the element or layer may not only be directly connected to the other element or layer but also be indirectly connected or adhered to the other element or layer by having one or more intermediate elements or layers “disposed” or “interposed” between the elements or layers, unless otherwise specified.

[0038] The term "at least one" should be understood to include any and all combinations of more than one of the related listed items. For example, the meaning of "at least one of the first element, the second element, and the third element" includes the combination of all three listed elements, the combination of any two of the three elements, and each individual element, namely the first element, the second element, and the third element.

[0039] As those skilled in the art can fully understand, the features of various embodiments of the present invention can be partially or completely combined or combined with each other, and can be technically operated and driven in various ways. The embodiments of the present invention can be performed independently of each other, or can be performed together in a mutually dependent relationship.

[0040] Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings. When adding reference numerals to the elements of each drawing, similar reference numerals may refer to similar elements even though the same elements are illustrated in other drawings. In addition, for ease of description, the proportion of each element illustrated in the drawings may be different from the actual proportion. Therefore, the illustrated elements are not limited to the specific proportions they are illustrated in the drawings.

[0041] <Organic compounds>

[0042] The organic compound of the present invention is represented by Formula 1.

[0043] [Formula 1]

[0044]

[0045] In Formula 1, a1 and a2 are each independently an integer of 0 to 4, and a3 and a4 are each independently 0 or 1,

[0046] X1 and X2 are each independently O or S,

[0047] Ar1 and Ar2 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S,

[0048] R1 and R2 are each independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S,

[0049] L1 and L2 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 arylene group and a substituted or unsubstituted C3 to C60 heteroarylene group containing one of N, O and S.

[0050] It should be understood that the R group represents substituents permitted by valence. When the group represents no substitution, hydrogen atoms are present as required to satisfy the valence requirements of the compound.

[0051] In the present invention, unless specifically defined, the substituents of the alkyl group, cycloalkyl group, alkoxy group, aryl group, heteroaryl group, arylene group and heteroarylene group may be selected from the group consisting of deuterium (D), halogen, cyano group, hydroxyl group, C1 to C10 alkyl group, C1 to C10 alkoxy group, C3 to C30 cycloalkyl group, C1 to C10 alkylsilyl group, C1 to C10 alkylamine group, C6 to C30 arylsilyl group, C6 to C30 arylamine group, C6 to C30 aryl group and C3 to C30 heteroaryl group. For example, the substituent can be at least one selected from the group consisting of D, F, Br, CN, hydroxyl, methyl, ethyl, propyl, butyl (e.g., tert-butyl), methoxy, ethoxy, propoxy, butoxy (e.g., tert-butoxy), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trimethylsilyl, trimethylamino, triphenylsilyl, triphenylamino, phenyl, biphenyl, naphthyl, anthracenyl, pyridyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0052] In the present invention, in the absence of specific definition, the term "alkyl" means a saturated, linear or branched hydrocarbon chain group with or without a substituent. For example, the C1 to C10 alkyl group may be selected from the group consisting of methyl, ethyl, propyl and butyl, for example, tert-butyl.

[0053] In the present invention, in the absence of specific definition, the term "aryl" refers to a monovalent monocyclic or polycyclic conjugated ring structure. For example, C6 to C60 aryl can be selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentalenyl, indenyl, indenoindenyl, heptalenyl, biphenylene, dicyclopentadienylphenyl, phenalenyl, benzalenyl, dibenzonalenyl, azulene, pyrenyl, fluoranthenyl, triphenylene, The group consisting of phenyl, tetraphenyl, naphthacene, dinaphthophenyl, pentaphenyl, pentacene, fluorenyl, indenofluorenyl and spirofluorenyl.

[0054] In the present invention, in the absence of a specific definition, the term "arylene" refers to a divalent monocyclic or polycyclic conjugated ring structure. For example, the C6 to C60 arylene group can be selected from phenylene, biphenylene, terphenylene, naphthylene, anthracene, pentalene, indenylene, indenylene, heptalene, biphenylene, dicyclopentadienylphenylene, phenalenylene, phenyl and nonalenylene, diphenyl and nonalenylene, azulene, pyrenylene, fluoranthenylene, triphenylene, pyrenylene, fluoranthenylene, pyren ... The present invention also includes the group consisting of phenylene, tetraphenylene, tetraphenylene, dinaphthophenylene, pentphenylene, pentanaphthophenylene, fluorenylene, indenofluorenylene and spirofluorenyl.

[0055] In the present invention, unless otherwise specifically defined, the term "heteroaryl" refers to a 5- to 7-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms such as nitrogen, oxygen or sulfur, and these rings are fused with an aryl, cycloalkyl, heteroaryl or heterocycloalkyl ring. For example, the C3 to C60 heteroaryl group can be selected from pyrrolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indazolyl, indolizinyl, pyrrolizinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, benzofuranocarbazolyl, benzothienylcarbazolyl, quinolyl, isoquinolyl, phthalolyl, quinoxalinyl, cinnolinyl, quinazolinyl, quinazolinyl, purinyl, benzoquinolyl, benzoisoquinolyl, benzoquinazolinyl, benzoquinoxalinyl, The group consisting of quinolinyl, acridinyl, phenanthrolinyl, benzothiophene, phenanthridinyl, pteridinyl, cinnolinyl, naphthylamino, furanyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxinyl, benzofuranyl, dibenzofuranyl, thiopyranyl, xanthyl, chromenyl, isochromenyl, thiazinyl, thienyl, benzothienyl, dibenzothienyl, difuropyrazinyl, benzofuranodibenzofuranyl, benzothienylbenzothienyl, benzothienyldibenzothienyl, benzothienylbenzofuranyl and benzothienyldibenzofuranyl.

[0056] In the present invention, in the absence of specific definition, the term "heteroaryl" refers to the divalent counterpart of the heteroaryl defined above. For example, C3 to C60 heteroaryl can be selected from pyrrolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indazolyl, indolizinyl, pyrrolazinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolecarbazolyl, indenylcarbazolyl, benzofurancarbazolyl, benzothienylcarbazolyl, quinolyl, isoquinolyl, phthalolyl, quinoxalinyl, cinnolinyl, quinazolinyl, quinazolinyl, purinyl, benzoquinolyl, benzoisoquinolyl, benzoquinazolinyl, phenylene. The present invention also includes the group consisting of quinoxalinyl, acridinylene, phenanthrolinyl, benzophenidylene, phenanthridylene, pterygylene, cinnolinylene, naphthylene, furanylene, oxazinylene, oxazolylene, oxadiazolylene, triazolylene, dioxinylene, benzofuranylene, dibenzofuranylene, thiopyranylene, xanthenylene, chromenylene, isochromenylene, thiazinylene, thienylene, benzothienylene, dibenzothienylene, difuropyrazinylene, benzofuranodibenzofuranylene, benzothienylene and benzothienylene dibenzofuranylene.

[0057] In one aspect of the present invention, a1, a2, a3 and a4 may each be 0.

[0058] In one aspect of the present invention, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6 to C60 aryl group, and may be the same or different.

[0059] In one aspect of the present invention, one of Ar1 and Ar2 may be a substituted or unsubstituted C6 to C60 aryl group, and the other of Ar1 and Ar2 may be a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S.

[0060] In one aspect of the present invention, Ar1 and Ar2 may each independently be a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S, and may be the same or different.

[0061] In one aspect of the present invention, Ar1 and Ar2 may be each independently selected from an aryl group represented by Formula 1a-1 and a heteroaryl group represented by Formula 1a-2. In Formulas 1a-1 and 1a-2, the "*" mark indicates a bonding site.

[0062] [Formula 1a-1]

[0063]

[0064] [Formula 1a-2]

[0065]

[0066]

[0067] In one aspect of the present invention, the bonding position of each of the portion including X1 and the portion including X2 can be specified. That is, the organic compound of the present invention represented by Formula 1 can be represented by Formula 1b-1.

[0068] [Formula 1b-1]

[0069]

[0070] In Formula 1b-1, a1, a2, a3, a4, X1, X2, Ar1, Ar2, R1, R2, L1 and L2 are defined the same as in Formula 1.

[0071] In one aspect of the present invention, a3 and a4 may each be 0, and may specify the bonding position of each of the portion including X1 and the portion including X2. That is, the organic compound of the present invention represented by Formula 1 may be represented by Formula 1b-2.

[0072] [Formula 1b-2]

[0073]

[0074] In Formula 1b-2, a1, a2, X1, X2, Ar1, Ar2, R1 and R2 are defined the same as in Formula 1.

[0075] For example, the organic compound of the present invention may be one of the compounds in Formula 2.

[0076] [Formula 2]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] The organic compound of the present invention, which is represented by Formula 1 and can be one of the compounds in Formula 2, has a wide band gap, a low highest occupied molecular orbital (HOMO), and a high triplet energy (T1). Therefore, the stability and carrier mobility of the organic compound are improved. The organic compound is used as at least one of the host of the light-emitting material layer, the hole blocking material of the hole blocking layer, and the electron transport material of the electron transport layer, thereby improving at least one of the luminous efficiency and life of the OLED.

[0108] [synthesis]

[0109] 1. Synthesis of Intermediate A

[0110] [Reaction 1]

[0111]

[0112] In a nitrogen atmosphere, 10g (50mmol) of 5-chlorophenyldiboronic acid and 16.9g (110mmol) of 2-chlorobenzo [d] oxazole were dissolved in 200mL of tetrahydrofuran (THF). 17.3g of potassium carbonate was dissolved in 50mL of distilled water, added to the THF solution and stirred. 1.2g (0.2mmol) of tetrakis (triphenylphosphine) palladium (0) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 9.5g (27mmol) of intermediate A (yield 55%).

[0113] 2. Synthesis of Intermediate B

[0114] [Reaction 2]

[0115]

[0116] In a nitrogen atmosphere, 10 g (50 mmol) of 5-chlorophenyldiboronic acid and 18.6 g (110 mmol) of 2-chlorobenzo [d] thiazole were dissolved in 200 mL of THF. 17.3 g of potassium carbonate was dissolved in 50 mL of distilled water, added to the THF solution and stirred. 1.2 g (0.2 mmol) of tetrakis (triphenylphosphine) palladium (0) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 10.4 g (27 mmol) of intermediate B (yield 55%).

[0117] 3. Synthesis of Intermediate C

[0118] (1) Intermediate Ca

[0119] [Reaction formula 3-1]

[0120]

[0121] In a nitrogen atmosphere, 10 g (31 mmol) of 2-bromo-4-chloro-6-iodo-1,3,5-triazine, 8.7 g (34 mmol) of bisvaleryl diboron (B2(pin)2), 0.5 g (0.5 mmol) of palladium dichloride (Pd(dppf)Cl2) and 6.1 g (62 mmol) of potassium acetate (AcOK) were dissolved in 200 mL of THF and stirred under reflux for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with dichloromethane (MC). The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 8.5 g (28 mmol) of intermediate Ca (yield 90%).

[0122] (2) Intermediate Cb

[0123] [Reaction formula 3-2]

[0124]

[0125] In a nitrogen atmosphere, 8.2 g (27 mmol) of intermediate Ca and 5.1 g (30 mmol) of 2-chlorobenzo [d] thiazole were dissolved in 150 mL of THF. 9.4 g of potassium carbonate was dissolved in 30 mL of distilled water, added to the THF solution and stirred. 0.6 g (1 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 3 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 6.7 g (20 mmol) of intermediate Cb (yield 75%).

[0126] (3) Intermediate Cc

[0127] [Reaction formula 3-3]

[0128]

[0129] In a nitrogen atmosphere, after 6.5g (20mmol) of intermediate Cb, 5.5g (22mmol) of B2 (pin) 2, 0.3g (0.4mmol) of Pd (dppf) Cl2 and 3.9g (40mmol) of potassium acetate (AcOK) were dissolved with 200mL of 1,4-dioxane, the mixture was refluxed and stirred for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and filtered through a silica gel filter. The solid was precipitated with methanol to obtain 6.7g (18mmol) of intermediate Cc (yield 90%).

[0130] (4) Intermediate C

[0131] [Reaction 3-4]

[0132]

[0133] In a nitrogen atmosphere, 6.5 g (17 mmol) of intermediate Cc and 2.9 g (19 mmol) of 2-chlorobenzo [d] oxazole were dissolved in 150 mL of THF. 6.0 g of potassium carbonate was dissolved in 30 mL of distilled water, added to the THF solution and stirred. 0.4 g (0.3 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 3 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.8 g (13 mmol) of intermediate C (yield 75%).

[0134] 4. Synthesis of Intermediate 1

[0135] [Reaction 4]

[0136]

[0137] In a nitrogen atmosphere, 12g (45mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 12.5g (49mmol) of B2(pin)2, 0.7g (1mmol) of Pd(dppf)Cl2 and 8.8g (90mmol) of potassium acetate (AcOK) were dissolved in 150mL of 1,4-dioxane and stirred under reflux for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 6.7g (18mmol) of intermediate 1 (yield 90%).

[0138] 5. Synthesis of Intermediate 2

[0139] (1) Intermediate 2-a

[0140] [Reaction formula 5-1]

[0141]

[0142] In a nitrogen atmosphere, 10 g (38 mmol) of 5'-chloro-(1,1',3',1") terphenyl, 10.6 g (42 mmol) of B2(pin)2, 0.6 g (0.8 mmol) of Pd(dppf)Cl2 and 7.4 g (76 mmol) of potassium acetate (AcOK) were dissolved in 150 mL of 1,4-dioxane and stirred under reflux for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated using methanol to obtain 12.1 g (34 mmol) of intermediate 2-a (yield 90%).

[0143] (2) Intermediate 2-b

[0144] [Reaction formula 5-2]

[0145]

[0146] In a nitrogen atmosphere, 7.0 g (31 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine and 12.1 g (34 mmol) of intermediate 2-a were dissolved in 150 mL of THF. 8.6 g (62 mmol) of potassium carbonate was dissolved in 30 mL of distilled water, added to the THF solution and stirred. 0.7 g (1 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 8.5 g (20 mmol) of intermediate 2-b (yield 65%).

[0147] (3) Intermediate 2

[0148] [Reaction 5-3]

[0149]

[0150] In a nitrogen atmosphere, 11 g (26 mmol) of intermediate 2-b, 7.3 g (29 mmol) of B2 (pin) 2, 0.4 g (1 mmol) of Pd (dppf) Cl2 and 5.1 g (52 mmol) of potassium acetate (AcOK) were dissolved with 150 mL of 1,4-dioxane, and the mixture was refluxed and stirred for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 11.4 g (22 mmol) of intermediate 2 (yield 85%).

[0151] 6. Synthesis of Intermediate 3

[0152] (1) Intermediate 3-a

[0153] [Reaction formula 6-1]

[0154]

[0155] In a nitrogen atmosphere, 21.1 g (126 mmol) of carbazole and THF were added to a two-necked round-bottom flask. 2M n-butyl lithium (2M hexane solution) was slowly added and stirred for 30 minutes. 9.3 g (50 mmol) of 2,4,6-trichlorotriazine dissolved in THF was slowly added and reacted at room temperature for 2 hours. After the reaction was completed, distilled water was added to quench, and the resulting solid was filtered. The filtered material was washed with distilled water, methanol and hexane in turn under a reduced pressure filter and dried to obtain 6.7 g (15 mmol) of intermediate 3-a (yield 30%).

[0156] (2) Intermediate 3

[0157] [Reaction formula 6-2]

[0158]

[0159] In a nitrogen atmosphere, 6.5 g (15 mmol) of intermediate 3-a, 4.1 g (16 mmol) of B2 (pin) 2, 0.2 g (0.3 mmol) of Pd (dppf) Cl2 and 2.9 g (52 mmol) of potassium acetate (AcOK) were dissolved in 60 mL of 1,4-dioxane, and the mixture was stirred and refluxed for 5 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 6.7 g (12 mmol) of intermediate 3 (yield 85%).

[0160] 7. Synthesis of Intermediate 4

[0161] (1) Intermediate 4-a

[0162] [Reaction formula 7-1]

[0163]

[0164] In a nitrogen atmosphere, 6.5 g (21 mmol) of 2-4-dichloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazine and 4.8 g (23 mmol) of dibenzofuran-2-ylboric acid and 0.7 g of tetrabutylammonium bromide (TBAB) were dissolved in 60 mL of toluene. A solution obtained by dissolving 5.4 g (51 mmol) of sodium carbonate in 10 mL of distilled water was added to the toluene reaction solution and heated to 40° C. while maintaining a nitrogen atmosphere. 0.5 g (0.4 mmol) of Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium(0)) was added to the heated mixed solution and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.1 g (11 mmol) of Intermediate 4-a (yield 55%).

[0165] (2) Intermediate 4

[0166] [Reaction 7-2]

[0167]

[0168] In a nitrogen atmosphere, 5.0 g (11 mmol) of intermediate 4-a, 3.1 g (12 mmol) of B2 (pin) 2, 0.2 g (0.2 mmol) of Pd (dppf) Cl2 and 2.2 g (22 mmol) of potassium acetate (AcOK) were dissolved in 50 mL of 1,4-dioxane, and the mixture was stirred and refluxed for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 5.4 g (10 mmol) of intermediate 4 (yield 90%).

[0169] 8. Synthesis of Intermediate 5

[0170] (1) Intermediate 5-a

[0171] [Reaction formula 8-1]

[0172]

[0173] In a nitrogen atmosphere, 8.0 g (35 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine and 11.5 g (39 mmol) of 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were dissolved in 120 mL of THF. 12.2 g (62 mmol) of potassium carbonate was dissolved in 30 mL of distilled water, added to the THF solution and stirred. 0.8 g (1 mmol) of Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium(0)) was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 9.5 g (27 mmol) of Intermediate 5-a (yield 75%).

[0174] (2) Intermediate 5

[0175] [Reaction formula 8-2]

[0176]

[0177] In a nitrogen atmosphere, 11 g (31 mmol) of intermediate 5-a, 8.6 g (34 mmol) of B2 (pin) 2, 0.4 g (0.6 mmol) of Pd (dppf) Cl2 and 6.0 g (61 mmol) of potassium acetate (AcOK) were dissolved in 100 mL of 1,4-dioxane, and the mixture was stirred and refluxed for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 11.7 g (26 mmol) of intermediate 5 (yield 85%).

[0178] 9. Synthesis of Intermediate 6

[0179] (1) Intermediate 6-a

[0180] [Reaction formula 9-1]

[0181]

[0182] In a nitrogen atmosphere and at a temperature of 0°C, 10.0 g (54 mmol) of 2,4,6-trichloro-1,3,5-triazine, 11.5 g (39 mmol) of 9H-carbazole and 5.7 g (60 mmol) of sodium tert-butoxide were dissolved in 200 mL of THT. The mixture was reacted at room temperature for 12 hours. Distilled water was added to the mixture to quench, and the resulting solid was filtered through a vacuum filter. The filtered solid was washed with distilled water and hexane, and then purified using a silica filter. The purified solution was concentrated and precipitated using acetone to obtain 15.5 g (43 mmol) of intermediate 6-a (yield 80%).

[0183] (2) Intermediate 6

[0184] [Reaction formula 9-2]

[0185]

[0186] In a nitrogen atmosphere, 11 g (31 mmol) of intermediate 6-a, 8.6 g (34 mmol) of B2 (pin) 2, 0.5 g (0.6 mmol) of Pd (dppf) Cl2 and 6.1 g (62 mmol) of potassium acetate (AcOK) were dissolved in 100 mL of 1,4-dioxane, and the mixture was stirred and refluxed for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 11.7 g (26 mmol) of intermediate 6 (yield 85%).

[0187] 10. Synthesis of Intermediate 7

[0188] (1) Intermediate 7-a

[0189] [Reaction formula 10-1]

[0190]

[0191] In a nitrogen atmosphere, 10.0 g (33 mmol) of 2-(4-biphenyl)-4,6-dichloro-1,3,5-triazine and 13.0 g (36 mmol) of intermediate 2-a were dissolved in 150 mL of THF. 11.4 g (83 mmol) of potassium carbonate was dissolved in 50 mL of distilled water, added to the THF solution and stirred. 0.8 g (1 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 12.3 g (25 mmol) of intermediate 7-a (yield 75%).

[0192] (2) Intermediate 7

[0193] [Reaction formula 10-2]

[0194]

[0195] In a nitrogen atmosphere, 12g (24mmol) of intermediate 7-a, 6.8g (27mmol) of B2 (pin) 2, 0.4g (0.5mmol) of Pd (dppf) Cl2 and 4.7g (48mmol) of potassium acetate (AcOK) were dissolved in 100mL of 1,4-dioxane, and the mixture was stirred and refluxed for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 12.1g (21mmol) of intermediate 7 (yield 85%).

[0196] 11. Synthesis of Intermediate 8

[0197] (1) Intermediate 8-a

[0198] [Reaction formula 11-1]

[0199]

[0200] In a nitrogen atmosphere, 10.0 g (32 mmol) of 2,4-dichloro-6-(dibenzo[b,d]furan-1-yl)-1,3,5-triazine and 8.8 g (35 mmol) of 4,4,5,5-tetramethyl-2-(naphthalene-2-yl)-1,3,2-dioxaborolane were dissolved in 150 mL of THF. 11.4 g (83 mmol) of potassium carbonate was dissolved in 50 mL of distilled water, added to the THF solution and stirred. 0.8 g (1 mmol) of Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium(0)) was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 12.1 g (24 mmol) of Intermediate 8-a (yield 75%).

[0201] (2) Intermediate 8

[0202] [Reaction formula 11-2]

[0203]

[0204] In a nitrogen atmosphere, 9.5 g (23 mmol) of intermediate 8-a, 6.5 g (26 mmol) of B2 (pin) 2, 0.3 g (0.5 mmol) of Pd (dppf) Cl2 and 4.6 g (47 mmol) of potassium acetate (AcOK) were dissolved in 100 mL of 1,4-dioxane, and the mixture was stirred and refluxed for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 9.9 g (20 mmol) of intermediate 8 (yield 85%).

[0205] 12. Synthesis of Intermediate 9

[0206] (1) Intermediate 9-a

[0207] [Reaction formula 12-1]

[0208]

[0209] In a nitrogen atmosphere, 10.0 g (32 mmol) of 9-(4,6-dichloro-1,3,5-triazine-2-yl)-9H-carbazole and 11.7 g (35 mmol) of 1-methyl-6-(4,4,5,5-tetramethyl)-1,3,2-dioxaborolan-2-yl)-2-phenyl-1H-benzo[d]imidazole were dissolved in 150 mL of THF. 9.2 g (67 mmol) of potassium carbonate was dissolved in 50 mL of distilled water, added to the THF solution and stirred. 0.7 g (0.6 mmol) of Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium(0)) was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate after reduced pressure distillation was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 11.6 g (24 mmol) of Intermediate 9-a (yield 75%).

[0210] (2) Intermediate 9

[0211] [Reaction 12-2]

[0212]

[0213] In a nitrogen atmosphere, 11.5 g (24 mmol) of intermediate 9-a, 6.6 g (26 mmol) of B2 (pin) 2, 0.3 g (0.5 mmol) of Pd (dppf) Cl2 and 4.6 g (47 mmol) of potassium acetate (AcOK) were dissolved in 100 mL of 1,4-dioxane, and the mixture was stirred and refluxed for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 11.6 g (20 mmol) of intermediate 9 (yield 85%).

[0214] 13. Synthesis of Intermediate 10

[0215] (1) Intermediate 10-a

[0216] [Reaction formula 13-1]

[0217]

[0218] In a nitrogen atmosphere, 10.0 g (32 mmol) of 2-4-dichloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazine and 11.6 g (35 mmol) of 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-phenyl-1H-benzo[d]imidazole were dissolved in 150 mL of THF. 9.2 g (66 mmol) of potassium carbonate was dissolved in 50 mL of distilled water, added to the THF solution and stirred. 0.7 g (0.6 mmol) of Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium(0)) was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 11.6 g (24 mmol) of Intermediate 10-a (yield 75%).

[0219] (2) Intermediate 10

[0220] [Reaction 13-2]

[0221]

[0222] In a nitrogen atmosphere, 11.5 g (24 mmol) of intermediate 10-a, 6.6 g (26 mmol) of B2 (pin) 2, 0.3 g (0.5 mmol) of Pd (dppf) Cl2 and 4.6 g (47 mmol) of potassium acetate (AcOK) were dissolved in 100 mL of 1,4-dioxane, and the mixture was stirred and refluxed for 3 hours. The reaction solution was cooled to room temperature, filtered under reduced pressure, and washed with MC. The filtrate was concentrated under reduced pressure and then filtered through a silica gel filter. The solid was precipitated with methanol to obtain 11.6 g (20 mmol) of intermediate 10 (yield 85%).

[0223] 14. Synthesis of Compound 1-1

[0224] [Reaction 14]

[0225]

[0226] In a nitrogen atmosphere, 3.6 g (10 mmol) of intermediate 1 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 3.8 g (7 mmol) of compound 1-1 (yield 70%).

[0227] 15. Synthesis of Compounds 1-10

[0228] [Reaction 15]

[0229]

[0230] In a nitrogen atmosphere, 3.6 g (10 mmol) of intermediate 1 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.0 g (7 mmol) of compound 1-10 (yield 70%).

[0231] 16. Synthesis of Compound 1-57

[0232] [Reaction 16]

[0233]

[0234] In a nitrogen atmosphere, 5.0 g (10 mmol) of intermediate 2 and 3.7 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.8 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.8 g (7 mmol) of compound 1-57 (yield 70%).

[0235] 17. Synthesis of Compound 1-43

[0236] [Reaction 17]

[0237]

[0238] In a nitrogen atmosphere, 5.0 g (10 mmol) of intermediate 2 and 4.1 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.8 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.0 g (7 mmol) of compound 1-43 (yield 70%).

[0239] 18. Synthesis of Compound 3-28

[0240] [Reaction 18]

[0241]

[0242] In a nitrogen atmosphere, 5.5 g (10 mmol) of intermediate 3 and 3.9 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 3.0 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.2 g (7 mmol) of compound 3-28 (yield 70%).

[0243] 19. Synthesis of Compound 3-36

[0244] [Reaction 19]

[0245]

[0246] In a nitrogen atmosphere, 5.4 g (10 mmol) of intermediate 3 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.3 g (7 mmol) of compound 3-36 (yield 70%).

[0247] 20. Synthesis of Compound 3-29

[0248] [Reaction 20]

[0249]

[0250] In a nitrogen atmosphere, 5.4 g (10 mmol) of intermediate 4 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.1 g (7 mmol) of compound 3-29 (yield 70%).

[0251] 21. Synthesis of Compound 3-37

[0252] [Reaction 21]

[0253]

[0254] In a nitrogen atmosphere, 5.4 g (10 mmol) of intermediate 4 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.3 g (7 mmol) of compound 3-37 (yield 70%).

[0255] 22. Synthesis of Compound 2-62

[0256] [Reaction 22]

[0257]

[0258] In a nitrogen atmosphere, 4.5 g (10 mmol) of intermediate 5 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.4 g (7 mmol) of compound 2-62 (yield 70%).

[0259] 23. Synthesis of Compound 3-39

[0260] [Reaction 23]

[0261]

[0262] In a nitrogen atmosphere, 4.5 g (10 mmol) of intermediate 5 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.7 g (7 mmol) of compound 3-39 (yield 70%).

[0263] 24. Synthesis of Compound 2-1

[0264] [Reaction 24]

[0265]

[0266] In a nitrogen atmosphere, 4.5 g (10 mmol) of intermediate 6 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Residual moisture was removed from the organic layer using magnesium sulfate and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.4 g (7 mmol) of compound 2-1 (yield 70%).

[0267] 25. Synthesis of Compound 3-23

[0268] [Reaction 25]

[0269]

[0270] In a nitrogen atmosphere, 4.5 g (10 mmol) of intermediate 6 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.7 g (7 mmol) of compound 3-23 (yield 70%).

[0271] 26. Synthesis of Compounds 1-27

[0272] [Reaction 26]

[0273]

[0274] In a nitrogen atmosphere, 5.9 g (10 mmol) of intermediate 7 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.4 g (7 mmol) of compound 1-27 (yield 70%).

[0275] 27. Compound 3-40

[0276] [Reaction 27]

[0277]

[0278] In a nitrogen atmosphere, 5.9 g (10 mmol) of intermediate 7 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.7 g (7 mmol) of compound 3-40 (yield 70%).

[0279] 28. Synthesis of Compound 1-46

[0280] [Reaction 28]

[0281]

[0282] In a nitrogen atmosphere, 5.9 g (10 mmol) of intermediate 7 and 4.0 g (11 mmol) of intermediate C were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.5 g (7 mmol) of compound 1-46 (yield 70%).

[0283] 29. Compound 2-12

[0284] [Reaction 29]

[0285]

[0286] In a nitrogen atmosphere, 5.0 g (10 mmol) of intermediate 8 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.8 g (7 mmol) of compound 2-12 (yield 70%).

[0287] 30. Synthesis of Compound 3-41

[0288] [Reaction formula 30]

[0289]

[0290] In a nitrogen atmosphere, 5.0 g (10 mmol) of intermediate 8 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.0 g (7 mmol) of compound 3-41 (yield 70%).

[0291] 31. Synthesis of Compound 2-39

[0292] [Reaction 31]

[0293]

[0294] In a nitrogen atmosphere, 5.0 g (10 mmol) of intermediate 8 and 4.0 g (11 mmol) of intermediate C were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 4.9 g (7 mmol) of compound 2-39 (yield 70%).

[0295] 32. Synthesis of Compound 3-4

[0296] [Reaction 32]

[0297]

[0298] In a nitrogen atmosphere, 5.8 g (10 mmol) of intermediate 9 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.4 g (7 mmol) of compound 3-4 (yield 70%).

[0299] 33. Synthesis of Compound 3-42

[0300] [Reaction 33]

[0301]

[0302] In a nitrogen atmosphere, 5.8 g (10 mmol) of intermediate 9 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.6 g (7 mmol) of compound 3-42 (yield 70%).

[0303] 34. Synthesis of Compound 3-43

[0304] [Reaction 34]

[0305]

[0306] In a nitrogen atmosphere, 5.8 g (10 mmol) of intermediate 10 and 3.8 g (11 mmol) of intermediate A were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.4 g (7 mmol) of compound 3-43 (yield 70%).

[0307] 35. Synthesis of Compound 3-38

[0308] [Reaction 35]

[0309]

[0310] In a nitrogen atmosphere, 5.8 g (10 mmol) of intermediate 10 and 4.2 g (11 mmol) of intermediate B were dissolved in 100 mL of 1,4-dioxane. 2.9 g (21 mmol) of potassium carbonate was dissolved in 15 mL of distilled water, added to the THF solution and stirred. 0.2 g (0.2 mmol) of Pd (PPh3) 4 (tetrakis (triphenylphosphine) palladium (0)) was added and refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled under reduced pressure. The filtrate distilled under reduced pressure was extracted with chloroform and water. Magnesium sulfate was used to remove residual moisture from the organic layer and distilled under reduced pressure. The target material was separated from the filtrate by silica gel column chromatography to obtain 5.6 g (7 mmol) of compound 3-38 (yield 70%).

[0311] OLED and Organic Light Emitting Device

[0312] The OLED of the present invention may include the organic compound of the present invention. The OLED may be included in an organic light-emitting display device or an organic light-emitting device. The following description focuses on an example of an organic light-emitting display device including the OLED of the present invention.

[0313] Figure 1 A schematic circuit diagram illustrating an organic light emitting display device according to an exemplary embodiment of the present invention.

[0314] like Figure 1As shown, gate lines GL and data lines DL, which may cross each other to define a pixel region P, and power lines PL may be formed on the organic light display device. A switching thin film transistor (TFT) Ts, a driving thin film transistor (TFT) Td, a storage capacitor Cst, and an OLED D may be formed in the pixel region P. The pixel region P may include a red pixel region, a green pixel region, and a blue pixel region. In addition, the pixel region P may further include a white pixel region.

[0315] The switching thin film transistor Ts may be connected to the gate line GL and the data line DL, and the driving thin film transistor Td and the storage capacitor Cst may be connected between the switching thin film transistor Ts and the power line PL. The OLED D may be connected to the driving thin film transistor Td. When the switching thin film transistor Ts is turned on by a gate signal applied through the gate line GL, a data signal applied through the data line DL may be applied to the gate of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.

[0316] The driving thin film transistor Td can be turned on by a data signal applied to the gate, so that a current proportional to the data signal can be supplied from the power line PL to the OLED D through the driving thin film transistor Td. The OLED D can emit light with a brightness proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst can be charged with a voltage proportional to the data signal, so that the voltage of the gate in the driving thin film transistor Td can be kept constant or similar during one frame. Therefore, the organic light emitting display device can display a desired image.

[0317] Figure 2 A schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present invention.

[0318] like Figure 2 As shown, the organic light-emitting display device 100 may include a substrate 110, a TFT Tr, and an OLED D connected to the TFT Tr. For example, the organic light-emitting device 100 may include a red pixel region, a green pixel region, and a blue pixel region, and the OLED D may be disposed in each of the red, green, and blue pixel regions. The organic light-emitting display device 100 may also include a yellow-green pixel region, and the OLED D may be disposed in the yellow-green pixel region. For example, OLEDs emitting red light, green light, blue light, and yellow-green light may be disposed in the red, green, blue, and yellow-green pixel regions, respectively.

[0319] The substrate 110 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0320] The buffer layer 120 may be formed on the substrate, and the TFT Tr may be formed on the buffer layer 120. The buffer layer 120 may be formed of an inorganic insulating material, such as silicon oxide or silicon nitride. The buffer layer 120 may have a multilayer structure including a first layer of silicon oxide and a second layer of silicon nitride. The buffer layer 120 may be omitted, and the TFT Tr may be disposed on the substrate 110.

[0321] The semiconductor layer 122 may be formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.

[0322] When the semiconductor layer 122 includes an oxide semiconductor material, a light shielding pattern (not shown) may be formed under the semiconductor layer 122. Light toward the semiconductor layer 122 may be shielded or blocked by the light shielding pattern, thereby preventing or reducing thermal degradation of the semiconductor layer 122. On the other hand, when the semiconductor layer 122 includes polycrystalline silicon, impurities may be doped on both sides of the semiconductor layer 122.

[0323] The gate insulating layer 124 may be formed on the semiconductor layer 122. The gate insulating layer 124 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0324] The gate 130 may be formed of a conductive material such as metal, and may be formed on the gate insulating layer 124 to correspond to the center of the semiconductor layer 122 .

[0325] exist Figure 2 In the embodiment, the gate insulating layer 124 may be formed on the entire surface of the substrate 110. Alternatively, the gate insulating layer 124 may have a pattern having the same shape as the gate electrode 130. However, embodiments of the present invention are not limited to these examples.

[0326] The interlayer insulating layer 132 may be formed of an insulating material, and may be formed on the gate electrode 130. The interlayer insulating layer 132 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or a photosensitive acrylic resin.

[0327] The interlayer insulating layer 132 may include first and second contact holes 134 and 136 exposing both sides of the semiconductor layer 122. The first and second contact holes 134 and 136 may not cover portions of the surface of the semiconductor layer 122 closer to both ends than to the center of the semiconductor layer 122. The first and second contact holes 134 and 136 may be located at both sides of the gate 130 to be spaced apart from the gate 130.

[0328] The first and second contact holes 134 and 136 may be formed through the interlayer insulating layer 132 and the gate insulating layer 124. Alternatively, when the gate insulating layer 124 has a pattern of the same shape as the gate 130, the first and second contact holes 134 and 136 may be formed only through the interlayer insulating layer 132. However, embodiments of the present invention are not limited to these examples.

[0329] The source electrode 140 and the drain electrode 142 may be formed of a conductive material such as metal, and may be formed on the interlayer insulating layer 132 .

[0330] The source electrode 140 and the drain electrode 142 may be spaced apart from each other with respect to the gate electrode 130 , and may contact both sides of the semiconductor layer 122 through the first and second contact holes 134 and 136 , respectively.

[0331] The semiconductor layer 122, the gate electrode 130, the source electrode 140, and the drain electrode 142 may constitute a TFT Tr. The TFT Tr may serve as a driving element. For example, the TFT Tr may be connected to ( Figure 1 The driving TFT Td corresponds to the driving TFT Td.

[0332] In the TFT Tr, a gate electrode 130, a source electrode 140, and a drain electrode 142 may be located on the semiconductor layer 122. For example, the TFT Tr may have a coplanar structure.

[0333] Alternatively, in the TFT Tr, the gate electrode may be located below the semiconductor layer, and the source electrode and the drain electrode may be located on the semiconductor layer, so that the TFT Tr may have an inverted staggered structure. In this structure, the semiconductor layer may include amorphous silicon. However, the embodiments of the present invention are not limited to these examples.

[0334] Although not shown, the gate lines and the data lines may cross each other to define a pixel region, and the switching TFT may be connected to the gate lines and the data lines. The switching TFT may be connected to the TFT Tr as a driving element.

[0335] In addition, a power supply line which may be parallel to and spaced apart from one of the gate line and the data line, and a storage capacitor for maintaining a voltage of the gate electrode of the TFT Tr in one frame may also be formed.

[0336] The planarization layer (or passivation layer) 150 may include a drain contact hole 152 exposing the drain electrode 142 of the TFT Tr, and may cover the TFT Tr. The drain contact hole 152 may not cover the drain electrode 142 .

[0337] The first electrode 160 may be connected to the drain electrode 142 of the TFT Tr through the drain contact hole 152 , and may be separately formed in each pixel region and on the planarization layer 150 .

[0338] The first electrode 160 may be an anode and may include a transparent conductive oxide material layer formed of a conductive material such as a transparent conductive oxide (TCO) having a relatively high work function. For example, the transparent conductive oxide material layer of the first electrode 160 may include at least one of indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium copper oxide (ICO), and Al:ZnO (AZO).

[0339] When the organic light emitting display device 100 operates as a bottom emission type, the first electrode 160 may have a single-layer structure of a transparent conductive oxide material layer.

[0340] Alternatively, when the organic light-emitting display device 100 operates as a top emission type, the first electrode 160 may further include a reflective layer and have a double-layer structure or a triple-layer structure. For example, the reflective layer may be formed of silver (Ag) or an aluminum palladium copper (APC) alloy. In the top emission type organic light-emitting display device 100, the first electrode 160 may have a double-layer structure of Ag / ITO or APC / ITO, or a triple-layer structure of ITO / Ag / ITO or ITO / APC / ITO. However, embodiments of the present invention are not limited to these examples.

[0341] The bank layer 166 may be formed on the planarization layer 150 to cover the edge of the first electrode 160. For example, the bank layer 166 may be located at a boundary of the pixel region and may expose the center of the first electrode 160 in the pixel region.

[0342] The organic light emitting layer 162 is disposed on the first electrode 160 and includes the organic compound of the present invention.

[0343] The organic light emitting layer 162 may include a light emitting component including a light emitting material layer (EML) and a functional layer. Alternatively, the organic light emitting layer 162 may include a plurality of light emitting components, and each light emitting component may include an EML and a functional layer. In addition, the organic light emitting layer 162 may further include a charge generation layer between adjacent light emitting components.

[0344] The functional layer may include at least one of an electron transport layer (ETL) and a hole blocking layer (HBL).

[0345] The or each light emitting component may further comprise at least one of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL) and an electron injection layer (EIL).

[0346] The second electrode 164 may be formed over the substrate 110 on which the organic light emitting layer 162 is formed. The second electrode 164 may cover the entire surface of the display area and may be formed of a conductive material having a relatively low work function to act as a cathode. For example, the second electrode 164 may be formed of aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or an alloy thereof, or a combination thereof. In the top emission type organic light emitting display device 100, the second electrode 164 may have a thin profile (small thickness) to provide light transmittance (or semi-light transmittance).

[0347] The first electrode 160 , the organic light emitting layer 162 , and the second electrode 164 may constitute an OLED D.

[0348] An encapsulation layer (eg, an encapsulation film) 170 may be formed on the second electrode 164 to prevent moisture from penetrating into the OLED D. The encapsulation layer 170 may include a first inorganic insulating layer 172, an organic insulating layer 174, and a second inorganic insulating layer 176 stacked in sequence. However, embodiments of the present invention are not limited to these examples. The encapsulation layer 170 may be omitted.

[0349] In the bottom emission type organic light emitting display device 100 , a metal plate may be further disposed on the encapsulation layer 170 .

[0350] The organic light-emitting display device 100 may further include a color filter layer corresponding to the red, green, and blue pixel regions. The color filter layer may include red, green, and blue color filter patterns corresponding to the red, green, and blue pixel regions, respectively. When the organic light-emitting display device 100 includes the color filter layer, the color purity of the organic light-emitting display device 100 may be improved.

[0351] In the bottom emission type organic light emitting display device 100, the color filter layer may be located between the OLED D and the substrate 100, for example, between the interlayer insulating layer 132 and the planarization layer 150. Alternatively, in the top emission type organic light emitting display device 100, the color filter layer may be located above the OLED D, for example, above the second electrode 164 or the encapsulation layer 170.

[0352] The organic light-emitting display device 100 may further include a polarizing plate (not shown) for reducing ambient light reflection. For example, the polarizing plate may be a circular polarizing plate. In a bottom-emission organic light-emitting display device 100, the polarizing plate may be disposed below the substrate 110. In a top-emission organic light-emitting display device 100, the polarizing plate may be disposed on or above the encapsulation layer 170.

[0353] In addition, in the top emission type organic light emitting display device 100, a cover window (not shown) may be attached to the encapsulation layer 170 or the polarizing plate. In this case, the substrate 110 and the cover window may have flexibility such as that a flexible organic light emitting display device may provide.

[0354] In addition, the organic light emitting display device 100 may further include a touch layer or a touch panel. The touch layer or the touch panel may be disposed above the OLED D, for example, between the OLED and the cover window, or disposed below the substrate 100.

[0355] Figure 3 A schematic cross-sectional view showing an OLED according to a second embodiment of the present invention.

[0356] like Figure 3 As shown, the OLED D may include first and second electrodes 160 and 164 facing each other, and an organic light emitting layer 162 therebetween. The organic light emitting layer 162 includes an EML 230 and a charge assisting layer 240 between the second electrode 164 and the EML 230. The charge assisting layer 240 includes at least one of an ETL 242 and an HBL 244. The HBL 244 may be located between the EML 230 and the ETL 244.

[0357] ( Figure 2 The organic light emitting display device 100 may include at least one of a red pixel region, a green pixel region, and a blue pixel region. The OLED D may be located in each of the red, green, and blue pixel regions. The EML 230 in the red pixel region is a red EML, the EML 230 in the green pixel region is a green EML, and the EML 230 in the blue pixel region is a blue EML.

[0358] The first electrode 160 may be an anode that injects holes, and the second electrode 164 may be a cathode that injects electrons. In addition, one of the first and second electrodes 160 and 164 may be a reflective electrode, and the other of the first and second electrodes 160 and 164 may be a transparent (or semi-transparent) electrode.

[0359] For example, the first electrode 160 may include a transparent conductive material layer formed of ITO or IZO. The second electrode 164 may be formed of one of Al, Mg, Ag, AlMg, and MgAg.

[0360] The organic light emitting layer 162 may further include an HTL 220 between the first electrode 160 and the EML 230. In addition, the organic light emitting layer 162 may further include an EBL between the EML 230 and the HBL 220.

[0361] The organic light emitting layer 162 may further include at least one of the HIL 210 between the first electrode 160 and the HTL 220 and the EIL 250 between the second electrode 164 and the charge auxiliary layer 240 .

[0362] The charge auxiliary layer 240 includes the organic compound of the present invention. That is, at least one of the HBL 244 and the ETL 242 may include the organic compound of the present invention.

[0363] For example, the HBL 244 may be formed of only the organic compound of the present invention represented by Formula 1 and have a thickness of 5 to 20 nm, for example, 5 to 10 nm.

[0364] The ETL 242 may include the organic compound of the present invention represented by Formula 1, and may optionally further include the compound of Formula 3 (i.e., quinolyl lithium (Liq)). In this case, in the ETL 242, the weight % ratio of the organic compound of Formula 1 to the compound of Formula 3 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. For example, in the ETL 242, the weight % of the organic compound of Formula 1 and the compound of Formula 3 may be the same.

[0365] [Formula 3]

[0366]

[0367] The thickness of the ETL 242 may be greater than that of the HBL 244. The thickness of the ETL 242 may be 10 to 50 nm, for example, 20 to 40 nm.

[0368] When both the HBL 244 and the ETL 242 contain the organic compound of the present invention, the organic compound in the HBL 244 and the organic compound in the ETL 242 may be the same or different.

[0369] The EML 230 in the green pixel region (ie, green EML) may include the organic compound of the present invention represented by Formula 1. For example, the green EML 230 may include the organic compound of the present invention represented by Formula 1 as a first host, for example, an n-type host.

[0370] Alternatively, the green EML 230 may include the compound in Formula 4 or the compound represented by Formula 5 as a first host, for example, an n-type host.

[0371] [Formula 4]

[0372]

[0373] [Formula 5]

[0374]

[0375] In Formula 5, g1 is an integer from 0 to 4,

[0376] R 51 and R 52 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group,

[0377] R 53 Each is selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group

[0378] X 51 Yes CR 54 ,

[0379] R 54 Select from the free bonding site (ie, X 51 is a carbon atom directly bonded to the triazine moiety), hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group,

[0380] R 51 , R 52 and R 54 At least one of is a substituted or unsubstituted carbazolyl group, and

[0381] L 51 and L 52 Each is independently selected from the group consisting of a substituted or unsubstituted C6 to C60 arylene group.

[0382] In Formula 5, when g1 is 2 or more, 2 or more R 53 The groups may be the same or different.

[0383] In one aspect of the present invention, R 51 , R 52 and R 54 At least one of the groups may be a carbazole group having no substituent or substituted with a C1 to C20 alkyl group.

[0384] In Formula 5, the benzene ring of the benzothiazole part may be bonded to the triazine part. That is, the compound represented by Formula 5 may have a structure represented by Formula 5a.

[0385] [Formula 5a]

[0386]

[0387] In Formula 5a, R 51 , R 52 , R 53 , X 51 , L 51 and L 52 The definition of is the same as that of Formula 5, and g2 is an integer from 0 to 3.

[0388] In Formula 5, the bonding position of the benzothiazole moiety may be specified. That is, the compound represented by Formula 5 may have a structure of one of Formulae 5b to 5e.

[0389] [Formula 5b]

[0390]

[0391] [Formula 5c]

[0392]

[0393] [Formula 5d]

[0394]

[0395] [Formula 5e]

[0396]

[0397] In each of Formulae 5b to 5e, R 51 , R 52 , R 53 , X 51 , L 51 and L 52 The definition of is the same as that of Formula 5, and g2 is an integer from 0 to 3.

[0398] In Formula 5, the thiazole ring of the benzothiazole moiety may be bonded to the triazine moiety. That is, the compound represented by Formula 5 may have a structure represented by Formula 5f.

[0399] [Formula 5f]

[0400]

[0401] In formula 5f, R 51 , R 52 , R 53 , L 51 and L52 The definition of is the same as that of Formula 5, and g3 is an integer from 0 to 4.

[0402] In one aspect of the present invention, R 51 may be a carbazole group having no substituent or substituted with a C1 to C20 alkyl group, and R 52 The group consisting of phenyl, pyrenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl and carbazolyl may be selected. 54 g1 may be hydrogen or a phenyl group having no substituent or substituted with a C1 to C20 alkyl group, and g1 may be 0.

[0403] In one aspect of the present invention, R 52 The group consisting of a phenyl group, a pyrenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a carbazolyl group may be selected, and may have no substituent or be substituted with one of a C1 to C20 alkyl group and a C6 to C60 aryl group.

[0404] For example, the compound represented by Formula 5 may be one of the compounds in Formula 6.

[0405] [Formula 6]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412] The green EML 230 may further include a compound represented by Formula 7 as a second host, for example, a p-type host.

[0413] [Formula 7]

[0414]

[0415] In Formula 7, b1 and b4 are each independently an integer from 0 to 4, b2 and b3 are each independently an integer from 0 to 3,

[0416] R 11 , R 12 , R 13 and R 14each independently selected from the group consisting of deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C60 aryl and substituted or unsubstituted C3 to C60 heteroaryl,

[0417] L 11 and L 12 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C6 to C60 arylene group, and a substituted or unsubstituted C3 to C60 heteroarylene group, and

[0418] Ar 11 and Ar 12 Each is independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group.

[0419] When b1 is 2 or more, more than 2 R 11 The groups are the same or different. When b2 is 2 or more, 2 or more R 12 The groups are the same or different. When b3 is 2 or more, 2 or more R 13 The groups are the same or different. When b4 is 2 or more, 2 or more R 14 The groups may be the same or different.

[0420] In formula 7, L 11 and L 12 can each be a single bond, and Ar 11 and Ar 12 Each may be independently selected from a phenyl group having a substituent or an unsubstituted group. For example, Formula 7 may be represented by Formula 7a.

[0421] [Formula 7a]

[0422]

[0423] In Formula 7a, R 11 , R 12 , R 13 , R 14 , b1, b2, b3 and b4 are defined the same as in Formula 7, Ar 13 and Ar 14 b5 and b6 are each independently selected from a substituted or unsubstituted C6 to C30 aryl group, and b5 and b6 are each independently an integer of 0 to 5.

[0424] For example, in Formula 7a, Ar 13 and Ar 14b5 and b6 may each be 0 or 1. The second host may be one of the compounds in Formula 8.

[0425] [Formula 8]

[0426]

[0427]

[0428]

[0429] In the green pixel region, the EML 230 may include one of the compounds in Formula 9 as a dopant (eg, a light emitting body).

[0430] [Formula 9]

[0431]

[0432] The thickness of the EML 230 may be 10 to 50 nm, for example, 20 to 40 nm.

[0433] In the EML 230, the weight % of each of the first and second hosts may be greater than that of the dopant. The weight % of the first host and the weight % of the second host may be the same or different. In the green EML 230, the weight % ratio of the first host to the second host may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight % of the first host and the weight % of the second host may be the same. For example, in the green EML 230, the weight % of the first host and the second host may be the same, and the content of the dopant may be 5 to 25 weight % based on the total weight of the components in the green EML 230.

[0434] In one aspect of the present invention, HBL 244 may include the organic compound of the present invention represented by Formula 1, and ETL 242 may include at least one of a compound represented by Formula 10 (e.g., a first electron transport material), a compound represented by Formula 11 (e.g., a second electron transport material), and a compound represented by Formula 12 (e.g., a third electron transport material) to replace the organic compound of the present invention represented by Formula 1.

[0435] [Formula 10]

[0436]

[0437] In formula 10, L 21 is selected from the group consisting of a single bond, a substituted or unsubstituted C6 to C60 arylene group, and a substituted or unsubstituted C3 to C60 heteroarylene group,

[0438] Ar 21It is represented by formula 10a or 10b,

[0439] Ar 22 and Ar 23 each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C60 aryl and substituted or unsubstituted C3 to C60 heteroaryl,

[0440] [Formula 10a]

[0441]

[0442] [Formula 10b]

[0443]

[0444] In formula 10a, d1 is an integer from 0 to 4,

[0445] R 21 is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C3 to C60 heteroaryl,

[0446] R 22 each selected from the group consisting of deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group,

[0447] In formula 10b, d2 is an integer from 0 to 4,

[0448] R 23 is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C3 to C60 heteroaryl,

[0449] R 24Each is selected from the group consisting of deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group.

[0450] In each of Formulae 10a and 10b, the mark "*" represents a bonding site.

[0451] In one aspect of the present invention, Ar 22 and Ar 23 Each independently may be a C6 to C60 aryl group (eg, phenyl or naphthyl) having no substituent or substituted with a C1 to C10 alkyl group (eg, tert-butyl group).

[0452] [Formula 11]

[0453]

[0454] In Formula 11, e1, e2, e3, and e4 are each independently an integer of 0 to 4, and e5 is 0 to 1.

[0455] R 31 , R 32 , R 33 and R 34 each independently selected from the group consisting of deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C60 aryl and substituted or unsubstituted C3 to C60 heteroaryl,

[0456] X 31 , X 32 and X 33 Each independently is N or CR 35 , X 31 , X 32 and X 33 At least two of them are N,

[0457] R 35 each selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group,

[0458] Ar 31 and Ar32 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group, and

[0459] L 31 Selected from the group consisting of a substituted or unsubstituted C6 to C60 arylene group and a substituted or unsubstituted C3 to C60 heteroarylene group.

[0460] In one aspect of the invention, e1, e2, e3 and e4 can each be 0 or 1.

[0461] In one aspect of the present invention, R 31 , R 32 , R 33 and R 34 Each may independently be a C6 to C60 aryl group which may have a substituent or may not have a substituent, for example, a phenyl group.

[0462] In one aspect of the present invention, X 31 , X 32 and X 33 Two of them can be N, X 31 , X 32 and X 33 The other one can be CR 35 , and R 35 It may be hydrogen.

[0463] In one aspect of the present invention, Ar 31 and Ar 32 Each may independently be a substituted or unsubstituted C6 to C60 aryl group, for example, a phenyl group or a biphenyl group.

[0464] In one aspect of the present invention, L 31 Each may independently be a C6 to C60 arylene group which may have a substituent or may not have a substituent, for example, a phenylene group.

[0465] [Formula 12]

[0466]

[0467] In Formula 12, f1, f2 and f3 are each independently an integer from 0 to 4, and f4 is an integer from 0 to 3,

[0468] R 41 , R 42 , R 43 and R 44each independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group,

[0469] X 41 O, S or NR 45 ,

[0470] R 45 is a C6 to C60 aryl group which may have a substituent or an unsubstituted group and forms a ring with an adjacent benzene ring, X 42 , X 43 and X 44 Each independently is N or CR 46 , X 42 , X 43 and X 44 At least two of them are N,

[0471] Ar 41 ,Ar 42 , R 46 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group, and

[0472] L 41 Selected from the group consisting of a single bond, a substituted or unsubstituted C6 to C60 arylene group, and a substituted or unsubstituted C3 to C60 heteroarylene group.

[0473] In one aspect of the invention, f1, f2, f3 and f4 may each be zero.

[0474] In one aspect of the present invention, R 45 It may be a phenyl group and form a carbazole with the nitrogen atom and the adjacent benzene ring.

[0475] In one aspect of the present invention, L 41 It may be a single bond or a C6 to C60 arylene group which may have a substituent or an unsubstituted group, for example, a phenylene group.

[0476] In one aspect of the present invention, Ar 41 and Ar 42 Each is independently a substituted or unsubstituted C6 to C60 aryl group, for example, a phenyl group, a naphthyl group, or a naphthylphenyl group.

[0477] In one aspect of the present invention, R 46 It may be hydrogen.

[0478] The first electron transport material of Formula 10 may be one of the compounds of Formula 13.

[0479] [Formula 13]

[0480]

[0481]

[0482] The second electron transport material of Formula 11 may be one of the compounds of Formula 14.

[0483] [Formula 14]

[0484]

[0485] The third electron transport material of Formula 12 may be one of the compounds of Formula 15.

[0486] [Formula 15]

[0487]

[0488]

[0489] In one aspect of the present invention, ETL 242 may include a compound of Formula 16 instead of the organic compound of the present invention represented by Formula 1.

[0490] [Formula 16]

[0491]

[0492] In one aspect of the present invention, ETL 242 may include the organic compound of the present invention represented by Formula 1, and HBL 244 may include the compound of Formula 17 instead of the organic compound of the present invention represented by Formula 1.

[0493] [Formula 17]

[0494]

[0495] The red EML may include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In the red EML, the weight % of the red host may be greater than the red dopant. In the red EML, the content of the red dopant may be 1 to 10 or 1 to 5 weight % based on the total weight of the components in the red EML.

[0496] For example, the red host may be at least one selected from the group consisting of, but not limited to: 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), CBP, 1,3,5-tri(carbazole-9-yl)benzene (TCP), TCTA, 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazole-9-yl)-9,9-spirofluorene (s piro-CBP), DPEPO, 4'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (PCzB-2CN), 3'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN), 3,6-bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1), bis(2-hydroxyphenyl)pyridine)beryllium (Bepp2), bis(10-hydroxybenzo[h]quinoline)beryllium (Bebq2), and 1,3,5-tri(1-pyrenyl)benzene (TPB3).

[0497] The red dopant may be at least one selected from the group consisting of, but not limited to: [bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethyl-3,5-heptanedione)iridium(III), bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III) (Hex-Ir(phq)2(acac)), tris[2-(4-n-hexylphenyl)quinoline]iridium(III) (Hex-Ir(phq)3), tris[2-phenyl-4-methylquinoline]iridium(III) (Ir(Mphq)3), bis(2-phenylquinoline)(2,2,6,6-tetramethyl-3,5-heptanedione)iridium(III) (Ir(dpm)PQ2), bis(phenylisoquinoline)(2,2,6, 6-tetramethyl-3,5-heptanedione)iridium(III) (Ir(dpm)(piq)2), bis[(4-n-hexylphenyl)isoquinolinato](acetylacetonato)iridium(III) (Hex-Ir(piq)2(acac)), tris[2-(4-n-hexylphenyl)quinolinato]iridium(III) (Hex-Ir(piq)3), tris(2-(3-methylphenyl)-7-methyl-quinolinato)iridium (Ir(dmpq)3), bis[2-(2-methylphenyl)-7-methyl-quinolinato](acetylacetonato)iridium(III) (Ir(dmpq)2(acac)) and bis[2-(3,5-dimethylphenyl)-4-methyl-quinolinato](acetylacetonato)iridium(III) (Ir(mphmq)2(acac)).

[0498] The blue EML may include a blue host and a blue dopant. The blue dopant may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In the blue EML, the weight % of the blue host may be greater than that of the blue dopant. In the blue EML, the content of the blue dopant may be 1 to 10 or 1 to 5 weight % based on the total weight of the components in the blue EML.

[0499] For example, the blue host can be independently at least one selected from the group consisting of, but not limited to, mCP, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-carbazole-3-carbonitrile (mCP-CN), mCBP, CBP-CN, 9-(3-(9H-carbazole-9-yl)phenyl)-3-(diphenylphosphino)-9H-carbazole (mCPPO1) 3,5-di(9H-carbazole-9-yl)biphenyl (Ph-mCP), TSPO1, 9-(3'-(9H-carbazole- 9-yl)-[1,1′-biphenyl]-3-yl)-9H-pyrido[2,3-b]indole (CzBPCb), bis(2-methylphenyl)diphenylsilane (UGH-1), 1,4-bis(triphenylsilyl)benzene (UGH-2), 1,3-bis(triphenylsilyl)benzene (UGH-3), 9,9-spirobifluoren-2-yl-diphenyl-phosphine oxide (SPPO1), and 9,9′-(5-(triphenylsilyl)-1,3-phenylene)bis(9H-carbazole) (SimCP).

[0500] The blue dopant may be independently selected from at least one of the following groups, but is not limited thereto: 4,4'-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), 4-(di-p-tolylamino)-4-4'-[(di-p-tolylamino)phenylvinyl]stilbene (DPAVB), 4,4'-bis[4-(diphenylamino)phenylvinyl]biphenyl (BDAVBi), 2,7-bis(4-diphenylamino)phenylvinyl)-9,9-spirofluorene (spiro-DPVBi), [1,4-bis[2-[4-[N,N-di(p-tolyl)amino]phenyl]vinyl]benzene (DSB), 1-4-bis-[4-(N,N-diphenyl)amino]phenylvinyl-benzene (DSA), 2,5,8,11-tetra-tert-butylperylene (TBPe), bis( 2-hydroxyphenyl)-pyridine) beryllium (Bepp2), 9-(9-phenylcarbazole-3-yl)-10-(naphthalene-1-yl) anthracene (PCAN), mer-tri(1-phenyl-3-methylimidazolin-2-yl)-C,C(2)'iridium(III) (mer-Ir(pmi)3), f-tri(1,3-diphenyl-benzimidazolin-2-ylalkyl)-C,C(2)'iridium(III) (f ac-Ir(dpbic)3), bis(3,4,5-trifluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III) (Ir(tfpd)2pic), tris(2-(4,6-difluorophenyl)pyridine))iridium(III) (Ir(Fppy)3), and bis[2-(4,6-difluorophenyl)pyridine-C2,N](picolinate)iridium(III) (FIrpic).

[0501] The thickness of the HTL 220 may be greater than each of the EML 230, the ETL 242, and the HBL 244. The thickness of the HTL 220 may be 80 to 129 nm, for example, 90 to 110 nm.

[0502] The HIL 210 may include at least one compound selected from the group consisting of: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalen-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalen-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazol-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'- Diphenyl-4,4″-diamine (NPB or NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile; HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonic acid (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. The thickness of the HIL 210 may be 1 to 10 nm, for example, 3 to 7 nm.

[0503] HTL220 may include at least one compound selected from the group consisting of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-diphenyl-4,4'-diamine (TPD), NPB (or NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine] (poly-TPD), (poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4'-(N- -(4-sec-butylphenyl)diphenylamine))] (TFB), bis-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), 3,5-bis(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine.

[0504] The EIL 250 may include at least one of an alkali metal such as Li, an alkali metal halide such as LiF, CsF, NaF, or BaF2, and an organic metal compound such as Liq, lithium benzoate, or sodium stearate. The thickness of the EIL 250 may be 1 to 10 nm, for example, 3 to 7 nm.

[0505] The EBL may include at least one compound selected from the group consisting of tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 1,3-bis(carbazol-9-yl)benzene (m CP), 3,3'-bis(N-carbazol-9-yl)-1,1'-biphenyl (mCBP), copper phthalocyanine (CuPc), N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), 3,5-bis(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), and 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene).

[0506] As shown above, in the OLED D, at least one of the ETL 242 and the HBL 244 includes the organic compound of the present invention represented by Formula 1. As a result, the luminous efficiency and lifespan of the OLED D are improved.

[0507] In addition, in the OLED D, the ETL 242 may further include the organic compound of the present invention represented by Formula 1 and the compound in Formula 3, so that the luminous efficiency and lifespan of the OLED D may be further improved.

[0508] In addition, in the OLED D in the green pixel region, the EML 230 , the ETL 242 , and the HBL 244 may include the organic compound of the present invention represented by Formula 1, thereby increasing the manufacturing efficiency (yield) of the OLED and improving the luminous efficiency and lifespan.

[0509] OLED

[0510] An anode (ITO), a HIL (a compound in Formula 18, 5 nm), a HTL (a compound in Formula 19, 100 nm), an EML (30 nm), a HBL (8 nm), an ETL (a compound in Formula 16 and a compound in Formula 3, 30 nm), an EIL (LiF, 5 nm), and a cathode (Al, 100 nm) are sequentially deposited to form a green OLED.

[0511] The EML is formed by using the compound BCZ1 in Formula 8, the compound in Formula 4, and the compound GD1 in Formula 9. The compound BCZ1 in Formula 8 and the compound in Formula 4 are used at the same weight %, and the doping amount of the compound GD1 in Formula 9 is 15 weight %. The compound in Formula 16 and the compound in Formula 3 are used at the same weight %.

[0512] [Formula 18]

[0513]

[0514] [Formula 19]

[0515]

[0516] 1. Comparative Example

[0517] (1) Comparative Example 1 (Ref 1)

[0518] The compound of formula 17 is used to form HBL.

[0519] (2) Comparative Example 2 (Ref2)

[0520] The compound of formula 20 is used to form HBL.

[0521] (3) Comparative Example 3 (Ref3)

[0522] The compound of formula 21 is used to form HBL.

[0523] (4) Comparative Example 4 (Ref4)

[0524] The compound of formula 22 is used to form HBL.

[0525] (5) Comparative Example 5 (Ref5)

[0526] The compound of formula 23 is used to form HBL.

[0527] (6) Comparative Example 6 (Ref6)

[0528] The compound of formula 24 is used to form HBL.

[0529] (7) Comparative Example 7 (Ref7)

[0530] The compound of formula 25 is used to form HBL.

[0531] [Formula 20]

[0532]

[0533] [Formula 21]

[0534]

[0535] [Formula 22]

[0536]

[0537] [Formula 23]

[0538]

[0539] [Equation 24]

[0540]

[0541] [Formula 25]

[0542]

[0543] 2. Example

[0544] (1) Example 1 (Ex1)

[0545] Compound 1-1 in Formula 2 was used for HBL.

[0546] (2) Example 2 (Ex2)

[0547] Compound 1-57 of Formula 2 was used for HBL.

[0548] (3) Example 3 (Ex3)

[0549] Compound 3-28 of Formula 2 was used for HBL.

[0550] (4) Example 4 (Ex4)

[0551] Compound 3-29 of Formula 2 was used for HBL.

[0552] (5) Example 5 (Ex5)

[0553] Compound 3-43 of Formula 2 was used for HBL.

[0554] (6) Example 6 (Ex6)

[0555] Compound 2-62 of Formula 2 was used for HBL.

[0556] (7) Example 7 (Ex7)

[0557] Compound 2-1 in Formula 2 was used for HBL.

[0558] (8) Example 8 (Ex8)

[0559] Compound 1-27 of Formula 2 was used for HBL.

[0560] (9) Example 9 (Ex9)

[0561] Compound 2-12 of Formula 2 was used for HBL.

[0562] (10) Example 10 (Ex10)

[0563] Compound 3-4 in Formula 2 was used for HBL.

[0564] The properties (eg, luminous efficiency and lifetime) of the OLEDs in Comparative Examples 1 to 7 and Examples 1 to 10 were measured and listed in Table 1.

[0565] Table 1

[0566] HBL efficiency life Ref1 Formula 17 100％ 100％ Ref2 Formula 20 100％ 106％ Ref3 Formula 21 101％ 108％ Ref4 Formula 22 101％ 105％ Ref5 Formula 23 101％ 104％ Ref6 Formula 24 100％ 106％ Ref7 Formula 25 101％ 107％ Ex1 Compound 1-1 102％ 114％ Ex2 Compound 1-57 104％ 120％ Ex3 Compound 3-28 102％ 131％ Ex4 Compound 3-29 101％ 130％ Ex5 Compound 3-43 103％ 128％ Ex6 Compound 2-62 102％ 125％ Ex7 Compound 2-1 103％ 124％ Ex8 Compound 1-27 104％ 129％ Ex9 Compound 2-12 103％ 125％ Ex10 Compound 3-4 103％ 130％

[0567] As shown in Table 1, the OLEDs in Ex1 to Ex10 in which the EML includes the example of the organic compound of the present invention have improved luminous efficiency and lifetime compared to the OLEDs in Ref1 to Ref7.

[0568] For example, the compound of Formula 20 includes a single benzoxazole moiety bonded to a phenylene linker at the para position relative to the triazine moiety, while the compound 1-1 of Formula 2 includes two benzoxazole moieties bonded to a phenylene linker at the meta position relative to the triazine moiety. The lifetime of the OLED in Ex1 using the compound 1-1 of Formula 2 is significantly increased compared to the OLED in Ref2 using the compound of Formula 20.

[0569] The compound of Formula 21 comprises a single benzoxazole moiety bonded to a phenylene linker at the para position relative to the triazine moiety, while the compound 3-28 of Formula 2 comprises two benzoxazole moieties bonded to a phenylene linker at the meta position relative to the triazine moiety. The lifetime of the OLED in Ex3 using the compound 3-28 of Formula 2 is significantly increased compared to the OLED in Ref3 using the compound of Formula 21.

[0570] The compound of Formula 23 comprises a single benzoxazole moiety bonded to a phenylene linker at the para position relative to the triazine moiety, while the compound 1-57 of Formula 2 comprises two benzoxazole moieties bonded to a phenylene linker at the meta position relative to the triazine moiety. The lifetime of the OLED in Ex2 using the compound 1-57 of Formula 2 is significantly increased compared to the OLED in Ref5 using the compound of Formula 23.

[0571] The compound of Formula 24 comprises a single benzoxazole moiety bonded to a phenylene linker at the para position relative to the triazine moiety, while the compound 2-62 of Formula 2 comprises two benzoxazole moieties bonded to a phenylene linker at the meta position relative to the triazine moiety. The lifetime of the OLED in Ex6 using the compound 2-62 of Formula 2 is significantly increased compared to the OLED in Ref 6 using the compound of Formula 24.

[0572] The compound of Formula 25 comprises a single benzoxazole moiety bonded to a phenylene linker at the para position relative to the triazine moiety, while the compound of Formula 2, 3-29, comprises two benzoxazole moieties bonded to a phenylene linker at the meta position relative to the triazine moiety. The lifetime of the OLED in Ex4 using the compound of Formula 2, 3-29, significantly increases compared to the OLED in Ref 7 using the compound of Formula 25.

[0573] Figure 4 A schematic cross-sectional view showing an OLED according to a third embodiment of the present invention.

[0574] like Figure 4 As shown, the OLED D may include first and second electrodes 160 and 164 facing each other, and an organic light emitting layer 162 therebetween. The organic light emitting layer 162 may include a first light emitting component 310 and a second light emitting component 330, the first light emitting component 310 includes a first EML 320 and a first charge auxiliary layer 316, and the second light emitting component 330 includes a second light emitting component 340 and a second charge auxiliary layer 334. The first charge auxiliary layer 316 includes at least one of a first ETL 316a and a first HBL 316b, and the second charge auxiliary layer 334 includes at least one of a second ETL 334a and a second HBL 334b. The first HBL 316b may be located between the first EML 320 and the first ETL 316a, and the second HBL 334b ​​may be located between the second EML 340 and the second ETL 334a.

[0575] The organic light emitting layer 162 may further include a CGL 350 between the first and second light emitting parts 310 and 330 .

[0576] ( Figure 2 The organic light emitting display device 100 may include at least one of a red pixel region, a green pixel region, and a blue pixel region. The OLED D may be located in each of the red, green, and blue pixel regions. The first and second EMLs 320 and 340 in the red pixel region are each a red EML, the first and second EMLs 320 and 340 in the green pixel region are each a green EML, and the first and second EMLs 320 and 340 in the blue pixel region are each a blue EML.

[0577] The first electrode 160 may serve as an anode for injecting holes and may be formed of a conductive material having a relatively high work function such as ITO or IZO. The second electrode 164 may serve as a cathode for injecting electrons and may be formed of a conductive material having a relatively low work function such as Al, Mg, or AlMg.

[0578] In the top emission type OLED D, the first electrode 160 may further include a reflective layer to act as a reflective electrode, and the second electrode 164 may have a thin profile to act as a transparent (e.g., semi-transparent) electrode. Alternatively, in the bottom emission type OLED D, the first electrode 160 may act as a transparent electrode, and the second electrode 164 may act as a reflective electrode. However, embodiments of the present invention are not limited to these examples.

[0579] The CGL 350 may be located between the first and second light emitting parts 310 and 330. The first light emitting part 310, the GCL 350, and the second light emitting part 330 may be sequentially stacked on the first electrode 160. For example, the first light emitting part 310 may be located between the first electrode 160 and the GCL 350. The second light emitting part 330 may be located between the second electrode 164 and the CGL 350.

[0580] The first light emitting part 310 may further include a first HTL 314 between the first EML 320 and the electrode 160. In addition, the first light emitting part 310 may further include a HIL 312 between the first HTL 314 and the first electrode 160. In addition, the first light emitting part 310 may further include at least one first EBL between the first EML 320 and the first HTL 314.

[0581] The second light emitting part 310 may further include a second HTL 332 between the second EML 340 and the CGL or between the second EML 340 and the first light emitting part 310. In addition, the second light emitting part 310 may further include an EIL 336 between the second charge assisting layer 334 and the second electrode 164. In addition, the second light emitting part 310 may further include a second EBL between the second EML 340 and the second HTL 332.

[0582] The CGL 350 may be located between the first and second light emitting parts 310 and 330. For example, the first and second light emitting parts 310 and 330 may be connected through the CGL 350. The CGL 350 may be a PN junction CGL including an N-type CGL 352 and a P-type CGL 354.

[0583] The N-type CGL 352 may be located between the first charge assist layer 316 and the second HTL 332. The P-type CGL 354 may be located between the N-type CGL 352 and the second HTL 332.

[0584] The N-type CGL 352 may be an organic layer doped with an alkali metal (e.g., Li, Na, K, and Cs) and / or an alkaline earth metal (e.g., Mg, Sr, Ba, and Ra). For example, the N-type CGL 352 may be formed of an N-type charge generating material including an organic material (e.g., 4,7-diphenyl-1,10-phenanthroline (Bphen) and MTDATA) main body, an alkali metal and / or alkaline earth metal dopant, and the doping amount of the dopant may be 0.01 to 30 wt%.

[0585] The P-type CGL354 can be formed by a P-type charge generating material including an inorganic material (e.g., tungsten oxide (WOx), molybdenum oxide (MoOx), beryllium oxide (Be2O3) or vanadium oxide (V2O5)), an organic material (e.g., NPD, HAT-CN, F4TCNQ, TPD, TNB, TCTA, N,N'-dioctyl-3,4,9,10-perylene diimide (PTCDI-C8) or a combination thereof).

[0586] At least one of the first charge assisting layer 316 and the second charge assisting layer 334 includes the organic compound of the present invention represented by Formula 1. For example, at least one of the first HBL 316b and the first ETL 316a may include the organic compound of the present invention, and at least one of the second HBL 334b ​​and the second ETL 334a may include the organic compound of the present invention.

[0587] In one aspect of the present invention, the first HBL 316b and the second HBL 334b ​​may each contain an organic compound of the present invention. The first HBL 316b and the second HBL 334b ​​may be composed of an organic compound of the present invention. The organic compound in the first HBL 316b and the organic compound in the second HBL 334b ​​may be the same or different.

[0588] The thickness of the first HBL 316 b and the second HBL 334 b may each be 5 to 20 nm, for example, 5 to 10 nm.

[0589] In one aspect of the present invention, the first ETL 316a and the second ETL 334a may each include an organic compound of the present invention. The organic compound in the first ETL 316a and the organic compound in the second ETL 334a may be the same or different.

[0590] In addition, the first ETL 316a and the second ETL 334a may each further include a compound of Formula 3, for example, quinolyl lithium (Liq). In this case, in each of the first ETL 316a and the second ETL 334a, the weight % ratio of the organic compound of Formula 1 to the compound of Formula 3 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. For example, in each of the first ETL 316a and the second ETL 334a, the weight % of the organic compound of Formula 1 and the compound of Formula 3 may be the same.

[0591] The thickness of the first ETL 316a and the thickness of the second ETL 334a may be greater than the first HBL 316b and the second HBL 334b, respectively. The thickness of the first ETL 316a and the second ETL 334a may each be 10 to 50 nm, for example, 20 to 40 nm.

[0592] The first and second EMLs 320 and 340 (i.e., first and second green EMLs) in the green pixel region may each include the organic compound of the present invention represented by Formula 1. For example, the first and second EMLs 320 and 340 may each include the organic compound of the present invention represented by Formula 1 as a first host, for example, an n-type host. The organic compound in the first green EML 320 and the organic compound in the second green EML 340 may be the same or different.

[0593] Alternatively, at least one of the first and second green EMLs 320 and 340 or the first and second green EMLs 320 and 340 may each include the compound in Formula 4 or the compound represented by Formula 5 as a first host, for example, an n-type host.

[0594] The first and second green EMLs 320 and 340 may each include the compound represented by Formula 7 as a second host, for example, a p-type host. In addition, the first and second green EMLs 320 and 340 may each include one of the compounds in Formula 9 as a dopant (eg, a light emitting body).

[0595] The thickness of the first and second green EMLs 320 and 340 may each be 10 to 50 nm, for example, 20 to 40 nm.

[0596] In each of the first and second green EMLs 320 and 340, the weight % of each of the first and second hosts may be greater than that of the dopant. The weight % of the first host and the weight % of the second host may be the same or different. In each of the first and second green EMLs 320 and 340, the weight % ratio of the first host to the second host may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight % of the first host and the weight % of the second host may be the same. For example, in each of the first and second green EMLs 320 and 340, the weight % of the first host and the second host may be the same, and the content of the dopant may be 5 to 25 weight % based on the total weight of the components of each of the first and second green EMLs 320 and 340.

[0597] In one aspect of the present invention, the first and second HBLs 316b and 334b ​​may each contain the organic compound of the present invention represented by Formula 1, and the first and second ETLs 316a and 334a may each contain at least one of a compound represented by Formula 10 (e.g., a first electron transport material), a compound represented by Formula 11 (e.g., a second electron transport material), and a compound represented by Formula 12 (e.g., a third electron transport material) to replace the organic compound of the present invention represented by Formula 1.

[0598] In one aspect of the present invention, the first and second ETLs 316a and 334a may each include the organic compound of the present invention represented by Formula 1, and the first and second HBLs 316b and 334b ​​may each include the compound of Formula 17 instead of the organic compound of the present invention represented by Formula 1.

[0599] In the red pixel region, the first and second EMLs 320 and 340 may each include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In each of the first and second EMLs 320 and 340, the weight % of the red host may be greater than the red dopant. In each of the first and second EMLs 320 and 340, the content of the red dopant may be 1 to 10 or 1 to 5 weight % based on the total weight of the components of each of the first and second EMLs 320 and 340.

[0600] In the blue pixel region, the first and second EMLs 320 and 340 may each include a blue host and a blue dopant. The blue dopant may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In each of the first and second EMLs 320 and 340, the weight % of the blue host may be greater than the blue dopant. In each of the first and second EMLs 320 and 340, the content of the blue dopant may be 1 to 10 or 1 to 5 weight % based on the total weight of the components of each of the first and second EMLs 320 and 340.

[0601] The thickness of the first HTL 314 and the thickness of the second HTL 332 may each be greater than the thickness of each of the first and second EMLs 320 and 340, the thickness of each of the first and second ETLs 316a and 334a, and the thickness of each of the first and second HBLs 316b and 334b. The thickness of the first and second HTLs 314 and 332 may each be 80 to 120 nm, for example, 90 to 110 nm. The first and second HTLs 314 and 332 may each include the above-mentioned hole transport material.

[0602] The HIL 312 may include the above-mentioned hole injection material, and may have a thickness of 1 to 10 nm, for example, 3 to 7 nm.

[0603] The EIL 336 may include the above-described electron injection material, and may have a thickness of 1 to 10 nm, for example, 3 to 7 nm.

[0604] The first and second EBL may each include the above-mentioned electron blocking material.

[0605] As described above, in the OLED D, at least one of the first and second ETLs 316 and 334a and the first and second HBLs 316b and 334b ​​includes the organic compound of the present invention represented by Formula 1. As a result, the light emission efficiency and lifespan of the OLED D are improved.

[0606] In addition, in the OLED D, the first and second ETLs 316 and 334a may each further include the compound of Formula 3 together with the organic compound of the present invention represented by Formula 1, so that the luminous efficiency and lifespan of the OLED D may be further improved.

[0607] In addition, in the OLED D in the green pixel area, the first and second EMLs 320 and 340, the first and second ETLs 316 and 334a, and the first and second HBLs 316b and 334b ​​may include the organic compound of the present invention represented by Formula 1, thereby improving the manufacturing efficiency (yield) of the OLED and improving the luminous efficiency and lifespan.

[0608] Figure 5A schematic cross-sectional view showing an organic light emitting display device according to a fourth embodiment of the present invention.

[0609] like Figure 5 As shown, the organic light-emitting display device 400 may include a first substrate 410 that can define a red pixel area RP, a green pixel area GP and a blue pixel area BP, a second substrate 470 facing the first substrate 410, an OLED D located between the first and second substrates 410 and 470 and providing white emission, and the OLED D, and a color filter layer 480 between the second substrate 470.

[0610] The first and second substrates 410 and 470 may each be a glass substrate or a flexible substrate. For example, the first and second substrates 410 and 470 may each be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0611] The buffer layer 420 may be formed on the substrate. The TFT Tr corresponding to the red, green, and blue pixel regions RP, GP, and BP may be formed on the buffer layer 420. The buffer layer 420 may be formed of an inorganic insulating material, such as silicon oxide or silicon nitride. The buffer layer 420 may have a multilayer structure including a first layer of silicon oxide and a second layer of silicon nitride. The buffer layer 420 may be omitted, and the TFT Tr may be disposed on the substrate 410.

[0612] The semiconductor layer 422 may be formed on the buffer layer 420. The semiconductor layer 422 may include an oxide semiconductor material or polysilicon.

[0613] The gate insulating layer 424 may be formed on the semiconductor layer 422. The gate insulating layer 424 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0614] The gate 430 may be formed of a conductive material such as metal, and may be formed on the gate insulating layer 424 to correspond to the center of the semiconductor layer 422 .

[0615] The interlayer insulating layer 432 may be formed of an insulating material, and may be formed on the gate electrode 430. The interlayer insulating layer 432 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or a photosensitive acrylic resin.

[0616] The interlayer insulating layer 432 may include first and second contact holes 434 and 436 exposing both sides of the semiconductor layer 422. The first and second contact holes 434 and 436 may not cover portions of the surface of the semiconductor layer 422 closer to both ends than to the center of the semiconductor layer 422. The first and second contact holes 434 and 436 may be located at both sides of the gate 430 to be spaced apart from the gate 430.

[0617] The source electrode 440 and the drain electrode 442 may be formed of a conductive material such as metal, and may be formed on the interlayer insulating layer 432 .

[0618] The source electrode 440 and the drain electrode 442 may be spaced apart from each other with respect to the gate electrode 430 , and may contact both sides of the semiconductor layer 422 through the first and second contact holes 434 and 436 , respectively.

[0619] The semiconductor layer 422, the gate electrode 430, the source electrode 440, and the drain electrode 442 may constitute a TFT Tr. The TFT Tr may act as a driving element. For example, the TFT Tr may be connected to ( Figure 1 The driving TFT Td corresponds to the driving TFT Td.

[0620] Although not shown, the gate lines and the data lines may cross each other to define a pixel region, and the switching TFT may be connected to the gate lines and the data lines. The switching TFT may be connected to the TFT Tr as a driving element.

[0621] In addition, a power supply line which may be parallel to and spaced apart from one of the gate line and the data line, and a storage capacitor for maintaining a voltage of the gate electrode of the TFT Tr in one frame may also be formed.

[0622] The planarization layer 450 may include a drain contact hole 452 exposing the drain electrode 442 of the TFT Tr, and may cover the TFT Tr. The drain contact hole 452 may not cover the drain electrode 442 .

[0623] The first electrode 460 may be connected to the drain electrode 442 of the TFT Tr through the drain contact hole 452, and may be separately formed in each pixel region and on the planarization layer 450. The first electrode 460 may be an anode, and may include a transparent conductive oxide material layer formed of a conductive material such as a transparent conductive oxide (TCO) having a relatively high work function.

[0624] For example, the transparent conductive oxide material layer of the first electrode 460 may include at least one of indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium copper oxide (ICO) and Al:ZnO (AZO).

[0625] When the organic light emitting display device 400 operates as a bottom emission type, the first electrode 460 may have a single-layer structure of a transparent conductive oxide material layer.

[0626] The first electrode 460 may also include a reflective layer and have a double-layer structure or a triple-layer structure. For example, the reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In the top-emitting organic light-emitting display device 400, the first electrode 460 may have a double-layer structure of Ag / ITO or APC / ITO, or a triple-layer structure of ITO / Ag / ITO or ITO / APC / ITO. However, the embodiments of the present invention are not limited to these examples.

[0627] The bank layer 466 may be formed on the planarization layer 450 to cover the edge of the first electrode 460. For example, the bank layer 466 may be located at the boundary of the pixel region, and the center of the first electrode 460 may be exposed in the pixel region. Since the OLED D may emit white light in the red, green, and blue pixel regions RP, GP, and BP, the organic light emitting layer 462 may be formed as a common layer in the red, green, and blue pixel regions RP, GP, and BP without separation. The bank layer 466 may be formed to prevent current leakage at the edge of the first electrode 460, and may be omitted.

[0628] The organic light emitting layer 462 is disposed on the first electrode 460 .

[0629] In one aspect of the present invention, the organic light-emitting layer 462 may have a three-layer stacked structure including a first light-emitting component, a second light-emitting component, and a third light-emitting component, wherein the first light-emitting component includes a green EML and a first charge auxiliary layer, the second light-emitting component includes a first blue EML and a second charge auxiliary layer, and the third light-emitting component includes a second blue EML and a third charge auxiliary layer.

[0630] In one aspect of the present invention, the organic light emitting layer 462 may have a double-stacked structure including a first light emitting member including a green EML and a first charge auxiliary layer and a second light emitting member including a blue EML and a second charge auxiliary layer.

[0631] In these configurations, at least one of the first and second charge-assisting layers includes the organic compound of the present invention represented by Formula 1. In addition, the green EML may include the organic compound of the present invention represented by Formula 1.

[0632] The second electrode 464 may be formed over the substrate 410 where the organic light emitting layer 462 may be formed.

[0633] In the organic light emitting display device 400 , since light emitted from the organic light emitting layer 462 may be emitted into the color filter layer 480 through the second electrode 464 , the second electrode 464 may have a thin profile in order to transmit the light.

[0634] The first electrode 460 , the organic light emitting layer 462 , and the second electrode 464 may constitute an OLED D.

[0635] The color filter layer 480 may be located above the OLED D and may include a red filter pattern 482, a green filter pattern 484, and a blue filter pattern 486 corresponding to the red, green, and blue pixel regions RP, GP, and BP, respectively. The red filter pattern 482 may include at least one of a red dye and a red pigment. The green filter pattern 484 may include at least one of a green dye and a green pigment. The blue filter pattern 486 may include at least one of a blue dye and a blue pigment.

[0636] Although not shown, the color filter layer 480 may be attached on the OLED D through an adhesive layer. Alternatively, the color filter layer 480 may be directly formed on the OLED D. However, embodiments of the present invention are not limited to these examples.

[0637] The encapsulation layer may be formed to prevent moisture from penetrating into the OLED D. For example, the encapsulation layer may include a first inorganic insulating layer, an organic insulating layer, and a second inorganic insulating layer sequentially stacked, but the encapsulation layer is not limited thereto. The encapsulation layer may be omitted.

[0638] For example, the color filter layer 480 may be located on the encapsulation layer. In addition, a touch electrode layer including touch electrodes may be located between the color filter layer 480 and the encapsulation layer.

[0639] A polarizing plate for reducing ambient light reflection may be disposed above the top emission type OLED D. For example, the polarizing plate may be a circular polarizing plate.

[0640] exist Figure 5 In the OLED D, the first and second electrodes 460 and 464 may be a reflective electrode and a transparent (or semi-transparent) electrode, respectively. The color filter layer 480 may be disposed above the OLED D. Alternatively, when the first and second electrodes 460 and 464 are transparent (or semi-transparent) electrodes and reflective electrodes, respectively, the color filter layer 480 may be disposed between the OLED D and the first substrate 410. However, embodiments of the present invention are not limited to these examples.

[0641] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 480. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer corresponding to the red, green, and blue pixel regions RP, GP, and BP, respectively. White light from the OLED D may be converted into red light, green light, and blue light through the red, green, and blue conversion layers, respectively. For example, the color conversion layer may include quantum dots. Thus, the color purity of the organic light emitting display device 400 may be further improved.

[0642] Instead of the color filter layer 480, a color conversion layer may be included.

[0643] As described above, in the organic light emitting display device 400, the OLED D in the red, green, and blue pixel regions RP, GP, and BP may emit white light. The white light from the organic light emitting diode D may pass through the red filter layer 482, the green filter layer 484, and the blue filter layer 486. As a result, green light and blue light may be provided by the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, respectively.

[0644] exist Figure 5 In the embodiment of the present invention, the OLED D emitting white light can be used for a display device. Alternatively, the OLED D can be formed on the entire surface of the substrate without at least one of a driving element and a color filter layer, thereby being used for a light-emitting device. A display device and a light-emitting device each including an example of the OLED D of the present invention may be referred to as an organic light-emitting device. However, embodiments of the present invention are not limited to these examples.

[0645] Figure 6 A schematic cross-sectional view showing an OLED according to a fifth embodiment of the present invention.

[0646] like Figure 6As shown, the organic light emitting layer 462 may include a first light emitting component 530, a second light emitting component 540, and a third light emitting component 560, wherein the first light emitting component 530 includes a green EML 510a and a first charge auxiliary layer 520, the second light emitting component 540 includes a first blue EML 546 and a second charge auxiliary layer 550, and the third light emitting component 560 includes a second blue EML 564 and a third charge auxiliary layer 570. The first charge auxiliary layer 520 includes at least one of a first ETL 522 and a first HBL 524, the second charge auxiliary layer 550 includes at least one of a second ETL 552 and a second HBL 554, and the third charge auxiliary layer 570 includes at least one of a third ETL 572 and a third HBL 574. The first HBL 524 may be located between the green EML 510 a and the first ETL 522 , the second HBL 554 may be located between the blue EML 546 and the second ETL 552 , and the third HBL 574 may be located between the second blue EML 564 and the third ETL 572 .

[0647] In addition, the organic light emitting layer 462 may further include a first CGL 580 between the first and second light emitting parts 530 and 540 , and a second CGL 590 between the first and third light emitting parts 530 and 560 .

[0648] ( Figure 5 The organic light emitting display device 400 may include at least one of red, green, and blue pixel regions, and the OLED D may be located in each of the red, green, and blue pixel regions and emit white light.

[0649] The first electrode 460 may serve as an anode for injecting holes and may be formed of a conductive material having a relatively high work function such as ITO or IZO. The second electrode 464 may serve as a cathode for injecting electrons and may be formed of a conductive material having a relatively low work function such as Al, Mg, or AlMg.

[0650] In the top emission type OLED D, the first electrode 460 may further include a reflective layer to act as a reflective electrode, and the second electrode 464 may have a thin profile to act as a transparent (e.g., semi-transparent) electrode. Alternatively, in the bottom emission type OLED D, the first electrode 460 may act as a transparent electrode, and the second electrode 464 may act as a reflective electrode. However, embodiments of the present invention are not limited to these examples.

[0651] The second light emitting part 540 may be located between the first electrode 460 and the first light emitting part 530. The third light emitting part 560 may be located between the first light emitting part 530 and the second electrode 464. The second light emitting part 540 may be located between the first electrode 460 and the first CGL 580. The third light emitting part 560 may be located between the second CGL 590 and the second electrode 464. For example, the second light emitting part 540, the first CGL 580, the first light emitting part 530, the second CGL 590, and the third light emitting part 560 may be sequentially stacked on the first electrode 460.

[0652] The first and second light emitting parts 530 and 540 may be connected by a first CGL 580. The first and third light emitting parts 530 and 560 may be connected by a second CGL 590. The first CGL 580 may be a PN junction CGL including a first N-type CGL 582 and a first P-type CGL 584. The second CGL 590 may be a PN junction CGL including a second N-type CGL 592 and a second P-type CGL 594.

[0653] In the first CGL 580, the first N-type CGL 582 may be located between the first HTL 526 and the second charge assist layer 550. The first P-type CGL 584 may be located between the first N-type CGL 582 and the first HTL 526.

[0654] In the second CGL 580, the second N-type CGL 592 may be located between the third HTL 562 and the first charge assist layer 520. The second P-type CGL 594 may be located between the second N-type CGL 592 and the third HTL 562.

[0655] The first and second N-type CGLs 582 and 592 may each include the above-mentioned N-type charge generation material, and the first and second N-type CGLs 582 and 592 may each include the above-mentioned P-type charge generation material.

[0656] The first light emitting part 530 may further include a red EML 510b. In the first light emitting part 530, the red EML 510b may be disposed under the green EML 510a.

[0657] The first light emitting part 530 may further include a first HTL 526 disposed under the red EML 510 b . In addition, the first light emitting part 530 may further include a first EBL between the red EML 510 b and the first HTL 526 .

[0658] For example, in the first light emitting part 530 , the red EML 510 b may be located between the first HTL 526 and the green EML 510 a. The green EML 510 a may be located between the red EML 510 b and the first charge auxiliary layer 520 .

[0659] The second light emitting part 540 may further include a second HTL 544 disposed under the first blue EML 546. In addition, the second light emitting part 540 may further include a HIL 542 disposed between the first electrode 460 and the second HTL 544. In addition, the second light emitting part 540 may further include a first EBL disposed between the second HTL 544 and the first blue EML 546.

[0660] The third light emitting part 560 may further include a third HTL 562 disposed under the second blue EML 564. In addition, the third light emitting part 560 may further include an EIL 566 disposed between the second electrode 464 and the third charge auxiliary layer 570. In addition, the third light emitting part 560 may further include a second EBL disposed between the third HTL 562 and the second blue EML 564.

[0661] At least one of the first charge assisting layer 520, the second charge assisting layer 550, and the third charge assisting layer 570 includes the organic compound of the present invention represented by Formula 1. For example, at least one of the first HBL 524 and the first ETL 522 may include the organic compound of the present invention. At least one of the second HBL 554 and the second ETL 552 may include the organic compound of the present invention. At least one of the third HBL 574 and the third ETL 572 may include the organic compound of the present invention.

[0662] In one aspect of the present invention, the first HBL 524, the second HBL 554, and the third HBL 574 may each contain an organic compound of the present invention. The first HBL 524, the second HBL 554, and the third HBL 574 may each be composed of an organic compound of the present invention. The organic compound in the first HBL 524, the organic compound in the second HBL 554, and the organic compound in the third HBL 574 may be the same or different.

[0663] The thickness of the first HBL 524 , the second HBL 554 , and the third HBL 574 may each be 5 to 20 nm, for example, 5 to 10 nm.

[0664] In one aspect of the present invention, the first ETL 522, the second ETL 552, and the third ETL 572 may each contain an organic compound of the present invention. The organic compound in the first ETL 522, the organic compound in the second ETL 552, and the organic compound in the third ETL 572 may be the same or different.

[0665] In addition, the first ETL 522, the second ETL 552, and the third ETL 572 may each further include a compound in Formula 3, such as quinolyl lithium (Liq). In this case, in each of the first ETL 522, the second ETL 552, and the third ETL 572, the weight % ratio of the organic compound in Formula 1 to the compound in Formula 3 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. For example, in each of the first ETL 522, the second ETL 552, and the third ETL 572, the weight % of the organic compound in Formula 1 and the compound in Formula 3 may be the same.

[0666] The thickness of the first ETL 522, the second ETL 552, and the third ETL 572 may be respectively greater than the first HBL 524, the second HBL 554, and the third HBL 574. The thickness of the first ETL 522, the second ETL 552, and the third ETL 572 may each be 10 to 50 nm, for example, 20 to 40 nm.

[0667] The green EML 510a may include the organic compound of the present invention represented by Formula 1. For example, the green EML 510a may include the organic compound of the present invention represented by Formula 1 as a first host, for example, an n-type host.

[0668] Alternatively, the green EML 510 a may include the compound in Formula 4 or the compound represented by Formula 5 as a first host, for example, an n-type host.

[0669] The green EML 510a may further include the compound represented by Formula 7 as a second host, for example, a p-type host. In addition, the green EML 510a may further include one of the compounds in Formula 9 as a dopant (for example, a light emitting body).

[0670] The thickness of the green EMLs 510 a may each be 10 to 50 nm, for example, 20 to 40 nm.

[0671] In the green EML 510a, the weight % of each of the first and second hosts may be greater than that of the dopant. The weight % of the first host and the weight % of the second host may be the same or different. In the green EML 510a, the weight % ratio of the first host to the second host may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight % of the first host and the weight % of the second host may be the same. For example, in the green EML 510a, the weight % of the first host and the second host may be the same, and the content of the dopant may be 5 to 25 weight % based on the total weight of the components in the green EML 510a.

[0672] In one aspect of the present invention, the first to third HBLs 522, 552, and 572 may each contain an organic compound of the present invention represented by Formula 1, and the first to third ETLs 524, 554, and 574 may each contain at least one of a compound represented by Formula 10 (e.g., a first electron transport material), a compound represented by Formula 11 (e.g., a second electron transport material), and a compound represented by Formula 12 (e.g., a third electron transport material) to replace the organic compound of the present invention represented by Formula 1.

[0673] In one aspect of the present invention, the first to third ETLs 524, 554 and 574 may each include the organic compound of the present invention represented by Formula 1, and the first to third HBLs 522, 552 and 572 may each include the compound of Formula 17 instead of the organic compound of the present invention represented by Formula 1.

[0674] The red EML 510b may each include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In the red EML 510b, the weight % of the red host may be greater than that of the red dopant. In the red EML 510b, the content of the red dopant may be 1 to 10 or 1 to 5 weight % based on the total weight of the components in the red EML 510b.

[0675] The first light emitting part 530 may further include a yellow-green EML between the red EML 510b and the green EML 510a. The yellow-green EML may include a yellow-green host and a yellow-green dopant. The red dopant, the green dopant, and the yellow-green dopant may each include a phosphorescent compound, a fluorescent compound, and a delayed fluorescent compound.

[0676] For example, the yellow-green host can be selected from the group consisting of, but not limited to, mCP-CN, CBP, mCBP, mCP, DPEPO, 2,8-bis(diphenylphosphino)dibenzothiophene (PPT), TmPyPB, PYD-2Cz, 2,8-bis(9H-carbazole-9-yl)dibenzothiophene (DCzDBT), 3',5'-di(carbazole-9-yl)-[1,1'-biphenyl]-3,5-dicarbonitrile (DCzTPA), 4'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (pCzB-2CN), 3'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN), TSPO1, and 9-(9-phenyl-9H-carbazole-6-yl)-9H-carbazole (CCP).

[0677] For example, the yellow-green dopant may be selected from the group consisting of, but not limited to: 5,6,11,12-tetraphenylnaphthalene (Rubrene), 2,8-di-tert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyl tetracene (TBRb), bis(2-phenylbenzothiazole)(acetylacetonate)iridium(III) (Ir(BT)2(acac)), bis(2-(9,9-diethyl-fluoren-2-yl)-1-phenyl-1H-benzo[d ]imidazole)(acetylacetonate)iridium(III) (Ir(fbi)2(acac)), bis(2-phenylpyridine)(3-(pyridin-2-yl)-2H-chromen-2-one)iridium(III) (fac-Ir(ppy)2Pc), bis(2-(2,4-difluorophenyl)quinoline)(picolinic acid)iridium(III) (FPQIrpic) and bis(4-phenylthienyl[3,2-c]pyridine-N,C2')(acetylacetonate)iridium(III) (PO-01).

[0678] The first blue EML 546 in the second light-emitting component 540 and the second blue EML 564 in the third light-emitting component 560 may each include the above-mentioned blue host and the above-mentioned blue dopant. The blue dopant may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In each of the first and second blue EMLs 546 and 564, the weight % of the blue host may be greater than the blue dopant. In each of the first and second EMLs 546 and 564, the content of the blue dopant based on the total weight of the components of each of the first and second EMLs 546 and 564 may be 1 to 10 or 1 to 5 weight %.

[0679] The thickness of the first HTL 526, the thickness of the second HTL 544, and the thickness of the third HTL 562 may each be greater than the thickness of the green EML 510a, the red EML 510b, the first and second blue EMLs 546 and 564, the first to third ETLs 522, 552, and 572, and the first to third HTLs 526, 544, and 562. The thickness of the first to third HTLs 526, 544, and 562 may each be 80 to 120 nm, for example, 90 to 110 nm. The first to third HTLs 526, 544, and 562 may each include the above-mentioned hole transport material.

[0680] The HIL 542 may include the above-mentioned hole injection material, and may have a thickness of 1 to 10 nm, for example, 3 to 7 nm.

[0681] The EIL 566 may include the above-mentioned electron injection material, and may have a thickness of 1 to 10 nm, for example, 3 to 7 nm.

[0682] The first to third EBLs may each include the above-mentioned electron blocking material.

[0683] As described above, in the OLED D, at least one of the first to third ETLs 522, 552, and 572 and the first to third HBLs 524, 554, and 574 includes the organic compound of the present invention represented by Formula 1. As a result, the luminous efficiency and lifespan of the OLED D are improved.

[0684] In addition, in the OLED D, the first to third ETLs 522, 552, and 572 may each further include the compound of Formula 3 together with the organic compound of the present invention represented by Formula 1, so that the luminous efficiency and lifespan of the OLED D may be further improved.

[0685] In addition, in the OLED D, the first to third ETLs 522, 552, and 572 and the first to third HBLs 524, 554, and 574 may include the organic compound of the present invention represented by Formula 1, thereby increasing the manufacturing efficiency (yield) of the OLED and improving the luminous efficiency and lifespan.

[0686] Figure 7 A schematic cross-sectional view showing an OLED according to a sixth embodiment of the present invention.

[0687] like Figure 7As shown, the organic light emitting layer 462 may include a first light emitting component 630 and a second light emitting component 640, the first light emitting component 630 includes a green EML 610a and a first charge auxiliary layer 620, and the second light emitting component 640 includes a blue EML 646 and a second charge auxiliary layer 650. The first charge auxiliary layer 620 includes at least one of a first ETL 622 and a first HBL 624, and the second charge auxiliary layer 650 includes at least one of a second ETL 652 and a second HBL 654. The first HBL 624 may be located between the green EML 610a and the first ETL 622, and the second HBL 654 may be located between the first blue EML 646 and the second ETL 652.

[0688] In addition, the organic light emitting layer 462 may further include a CGL 660 between the first and second light emitting parts 630 and 640 .

[0689] ( Figure 5 The organic light emitting display device 400 may include at least one of red, green, and blue pixel regions, and the OLED D may be located in each of the red, green, and blue pixel regions and emit white light.

[0690] The first electrode 460 may serve as an anode for injecting holes and may be formed of a conductive material having a relatively high work function such as ITO or IZO. The second electrode 464 may serve as a cathode for injecting electrons and may be formed of a conductive material having a relatively low work function such as Al, Mg, or AlMg.

[0691] In the top emission type OLED D, the first electrode 460 may further include a reflective layer to act as a reflective electrode, and the second electrode 464 may have a thin profile to act as a transparent (e.g., semi-transparent) electrode. Alternatively, in the bottom emission type OLED D, the first electrode 460 may act as a transparent electrode, and the second electrode 464 may act as a reflective electrode. However, embodiments of the present invention are not limited to these examples.

[0692] The first light emitting part 630 may be located between the second electrode 464 and the CGL 660, and the second light emitting part 640 may be located between the first electrode 460 and the CGL 660. For example, the second light emitting part 640, the CGL 660, and the first light emitting part 630 may be sequentially stacked on the first electrode 460.

[0693] The first and second light emitting parts 630 and 640 may be connected through a CGL 660. The CGL 660 may be a PN junction CGL including an N-type CGL 662 and a P-type CGL 664.

[0694] In the CGL 660, an N-type CGL 662 may be located between the first HTL 626 and the second charge assist layer 650. A P-type CGL 664 may be located between the N-type CGL 662 and the first HTL 626.

[0695] The N-type CGL 662 may include the above-described N-type charge generation material, and the P-type CGL 664 may include the above-described P-type charge generation material.

[0696] The first light emitting part 630 may further include a red EML 610b. In the first light emitting part 630, the red EML 610b may be disposed below the green EML 610a.

[0697] The first light emitting part 630 may further include a first HTL 626 disposed under the red EML 610 b. In addition, the first light emitting part 630 may further include a first EBL between the red EML 610 b and the first HTL 626.

[0698] For example, in the first light emitting part 630 , the red EML 610 b may be located between the first HTL 626 and the green EML 610 a. The green EML 610 a may be located between the red EML 610 b and the first charge auxiliary layer 620 .

[0699] The second light emitting part 640 may further include a second HTL 644 disposed under the blue EML 646. In addition, the second light emitting part 640 may further include a HIL 642 disposed between the first electrode 460 and the second HTL 644. In addition, the second light emitting part 640 may further include a first EBL disposed between the second HTL 644 and the blue EML 646.

[0700] At least one of the first charge auxiliary layer 620 and the second charge auxiliary layer 650 includes the organic compound of the present invention represented by Formula 1. For example, at least one of the first HBL 624 and the first ETL 622 may include the organic compound of the present invention. At least one of the second HBL 654 and the second ETL 652 may include the organic compound of the present invention.

[0701] In one aspect of the present invention, the first HBL 624 and the second HBL 654 may each contain an organic compound of the present invention. The first HBL 624 and the second HBL 654 may each consist of an organic compound of the present invention. The organic compound in the first HBL 624 and the organic compound in the second HBL 654 may be the same or different.

[0702] The thickness of the first HBL 624 and the second HBL 654 may each be 5 to 20 nm, for example, 5 to 10 nm.

[0703] In one aspect of the present invention, the first ETL 622 and the second ETL 652 may each contain an organic compound of the present invention. The organic compound in the first ETL 622 and the organic compound in the second ETL 652 may be the same or different.

[0704] In addition, the first ETL 622 and the second ETL 652 may each further include a compound of Formula 3, such as quinolyl lithium (Liq). In this case, in each of the first ETL 622 and the second ETL 652, the weight % ratio of the organic compound of Formula 1 to the compound of Formula 3 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. For example, in each of the first ETL 622 and the second ETL 652, the weight % of the organic compound of Formula 1 and the compound of Formula 3 may be the same.

[0705] The thickness of the first ETL 622 and the thickness of the second ETL 652 may be respectively greater than the first HBL 624 and the second HBL 654. The thickness of the first ETL 622 and the second ETL 652 may each be 10 to 50 nm, for example, 20 to 40 nm.

[0706] The green EML 610a may include the organic compound of the present invention represented by Formula 1. For example, the green EML 610a may include the organic compound of the present invention represented by Formula 1 as a first host, for example, an n-type host.

[0707] Alternatively, the green EML 610 a may include the compound in Formula 4 or the compound represented by Formula 5 as a first host, for example, an n-type host.

[0708] The green EML 610a may further include the compound represented by Formula 7 as a second host, for example, a p-type host. In addition, the green EML 610a may further include one of the compounds in Formula 9 as a dopant (for example, a light emitting body).

[0709] The green EML 610 a may have a thickness of 10 to 50 nm, for example, 20 to 40 nm.

[0710] In the green EML 610a, the weight % of each of the first and second hosts may be greater than the dopant. The weight % of the first host and the weight % of the second host may be the same or different. In the green EML 610a, the weight % ratio of the first host to the second host may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight % of the first host and the weight % of the second host may be the same. For example, in the green EML 610a, the weight % of the first host and the second host may be the same, and the content of the dopant may be 5 to 25 weight % based on the total weight of the components in the green EML 610a.

[0711] In one aspect of the present invention, the first and second HBLs 624 and 654 may each include the organic compound of the present invention represented by Formula 1, and the first and second ETLs 622 and 652 may each include at least one of a compound represented by Formula 10 (e.g., a first electron transport material), a compound represented by Formula 11 (e.g., a second electron transport material), and a compound represented by Formula 12 (e.g., a third electron transport material) to replace the organic compound of the present invention represented by Formula 1.

[0712] In one aspect of the present invention, the first and second ETLs 622 and 652 may each include the organic compound of the present invention represented by Formula 1, and the first and second HBLs 624 and 654 may each include the compound of Formula 17 instead of the organic compound of the present invention represented by Formula 1.

[0713] The red EML 610b may each include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In the red EML 610b, the weight % of the red host may be greater than the red dopant. In the red EML 610b, the content of the red dopant may be 1 to 10 or 1 to 5 weight % based on the total weight of the components in the red EML 610b.

[0714] The first light emitting part 630 may further include a yellow-green EML between the red EML 610b and the green EML 610a. The yellow-green EML may include a yellow-green host and a yellow-green dopant. The red dopant, the green dopant, and the yellow-green dopant may each include a phosphorescent compound, a fluorescent compound, and a delayed fluorescent compound.

[0715] The blue EML 646 in the second light emitting part 640 may include the above-mentioned blue host and the above-mentioned blue dopant. The blue dopant may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In the blue EML 646, the weight % of the blue host may be greater than the blue dopant. In the blue EML 646, the content of the blue dopant may be 1 to 10 or 1 to 5 weight % based on the total weight of the components in the blue EML 646.

[0716] The thickness of the first HTL 626 and the thickness of the second HTL 644 may each be greater than the thickness of the green EML 610a, the red EML 610b, the blue EML 646, the first and second ETLs 622 and 652, and the first and second HBLs 624 and 654. The thickness of the first and second HTLs 626 and 644 may each be 80 to 120 nm, for example, 90 to 110 nm. The first and second HTLs 626 and 644 may each include the above-mentioned hole transport material.

[0717] The HIL 642 may include the above-mentioned hole injection material, and may have a thickness of 1 to 10 nm, for example, 3 to 7 nm.

[0718] The EIL 628 may include the above-mentioned electron injection material, and may have a thickness of 1 to 10 nm, for example, 3 to 7 nm.

[0719] The first and second EBL may each include the above-mentioned electron blocking material.

[0720] As described above, in the OLED D, at least one of the first and second ETLs 622 and 652 and the first and second HBLs 624 and 654 includes the organic compound of the present invention represented by Formula 1. As a result, the light emission efficiency and lifespan of the OLED D are improved.

[0721] In addition, in the OLED D, the first and second ETLs 622 and 652 may each further include the compound of Formula 3 together with the organic compound of the present invention represented by Formula 1, so that the luminous efficiency and lifespan of the OLED D may be further improved.

[0722] In addition, in the OLED D, the first and second ETLs 622 and 652 and the first and second HBLs 624 and 654 may include the organic compound of the present invention represented by Formula 1, thereby increasing the manufacturing efficiency (yield) of the OLED and improving the luminous efficiency and lifespan.

[0723] It is obvious to those skilled in the art that various modifications and changes can be made in the embodiments of the present invention without departing from the spirit and scope of the present invention. Therefore, the modifications and changes are intended to cover the present invention as long as they are within the scope of the appended claims and their equivalents.

Claims

1. An organic compound represented by formula 1: [Formula 1] in, a1 and a2 are each independently an integer of 0 to 4, and a3 and a4 are each independently 0 or 1, X1 and X2 are each independently O or S, Ar1 and Ar2 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S, R1 and R2 are each independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group containing one of N, O and S, and L1 and L2 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 arylene group and a substituted or unsubstituted C3 to C60 heteroarylene group containing one of N, O and S.

2. The organic compound according to claim 1, wherein Ar1 and Ar2 are different.

3. The organic compound according to claim 1 or 2, wherein Ar1 and Ar2 are each independently selected from Formula 1a: [Formula 1a] 4. The organic compound according to any one of claims 1 to 3, wherein Formula 1 is represented by Formula 1b-1: [Formula 1b-1] wherein a1, a2, a3, a4, X1, X2, Ar1, Ar2, R1, R2, L1 and L2 are defined the same as in Formula 1.

5. The organic compound according to any one of claims 1 to 3, wherein Formula 1 is represented by Formula 1b-2: [Formula 1b-2] wherein a1, a2, X1, X2, Ar1, Ar2, R1 and R2 are defined the same as in Formula 1.

6. The organic compound according to claim 1, wherein The organic compound is one of the compounds of Formula 2: [Formula 2] 7. An organic light-emitting device, comprising: a substrate; and an organic light emitting diode located on the substrate, wherein the light emitting diode comprises a first electrode; a second electrode facing the first electrode; and a first light emitting component between the first electrode and the second electrode, wherein the first light emitting component comprises a first light emitting material layer, a first electron transport layer and a first hole blocking layer, in, The first electron transport layer is located between the first light emitting material layer and the second electrode, and the first hole blocking layer is located between the first light emitting material layer and the first electron transport layer, and At least one of the first electron transport layer and the first hole blocking layer comprises a first compound which is the organic compound according to any one of the preceding claims.

8. The organic light-emitting device according to claim 7, wherein: The first electron transport layer includes the first compound and a second compound represented by Formula 3: [Formula 3] 9. The organic light emitting device according to claim 8, wherein: The weight % ratio of the first compound to the second compound is 1:9 to 9:1, 2:8 to 8:2, or 3:7 to 7:

3.

10. The organic light emitting device according to claim 8, wherein: The weight % of the first compound is the same as that of the second compound.

11. The organic light-emitting device according to any one of claims 7 to 10, wherein: The first light emitting material layer, the first electron transport layer, and the first hole blocking layer each include the first compound.

12. The organic light-emitting device according to any one of claims 7 to 11, wherein: The first light emitting material layer includes a first host which is a compound represented by Formula 7: [Formula 7] wherein b1 and b4 are each independently an integer from 0 to 4, b2 and b3 are each independently an integer from 0 to 3, R 11 , R 12 , R 13 and R 14 each independently selected from the group consisting of deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C60 aryl and substituted or unsubstituted C3 to C60 heteroaryl, L 11 and L 12 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C6 to C60 arylene group, and a substituted or unsubstituted C3 to C60 heteroarylene group, and Ar 11 and Ar 12 Each is independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group.

13. The organic light-emitting device according to claim 12, wherein: The first host is one of the compounds of Formula 8: [Formula 8] 14. The organic light-emitting device according to claim 12 or 13, wherein: The first light emitting material layer further includes a second host which is an organic compound represented by Formula 1, wherein the second host is the same as or different from the first compound.

15. The organic light-emitting device according to claim 12 or 13, wherein: The first light emitting material layer further comprises a second host which is an organic compound according to Formula 4: [Formula 4] 16. The organic light-emitting device according to claim 12 or 13, wherein: The first light emitting material layer further comprises a second host which is an organic compound represented by Formula 5: [Formula 5] Wherein, g1 is an integer from 0 to 4, R 51 and R 52 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group, R 53 are each selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group, X 51 Yes CR 54 , R 54 is selected from the group consisting of a bonding site, hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group, R 51 , R 52 and R 54 At least one of is a substituted or unsubstituted carbazolyl group, and L 51 and L 52 Each is independently selected from the group consisting of a single bond, and a substituted or unsubstituted C6 to C60 arylene group.

17. The organic light emitting device according to claim 16, wherein: The second host is an organic compound represented by Formula 5a: [Formula 5a] Among them, R 51 , R 52 , R 53 , X 51 , L 51 and L 52 The definition of is the same as that of Formula 5, and g2 is an integer from 0 to 3.

18. The organic light emitting device according to claim 16, wherein: The second host is an organic compound represented by one of Formulae 5b to 5f: [Formula 5b] [Formula 5c] [Formula 5d] [Formula 5e] [Formula 5f] Wherein, in each of Formulae 5b to 5e, R 51 , R 52 , R 53 , R 54 , L 51 and L 52 The definition of is the same as that of Formula 5, and g2 is an integer from 0 to 3, and in Formula 5f, R 51 , R 52 , R 53 , L 51 and L 52 The definition of is the same as that of Formula 5, and g3 is an integer from 0 to 4, Optionally, wherein R 51 is a carbazole group which is unsubstituted or substituted with a C1 to C20 alkyl group, and R 52 A phenyl group, a pyrenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group are selected from the group consisting of: a phenyl group, a pyrenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group, and have no substituent or are substituted with at least one of a C1 to C20 alkyl group and a C6 to C60 aryl group.

19. The organic light emitting device according to claim 16, wherein: The second host is one of the compounds of Formula 6: [Formula 6] 20. The organic light emitting device according to any one of claims 14 to 19, wherein: The weight % ratio of the first body to the second body is 1:9 to 9:1, 2:8 to 8:2 or 7:3 to 3:7, or wherein, The first body and the second body have the same weight %.

21. The organic light emitting device according to any one of claims 6 to 20, wherein: The organic light emitting diode further includes a second light emitting component, which includes a first blue light emitting material layer, a second electron transport layer and a second hole blocking layer and is located between the first electrode and the first light emitting component.

22. The organic light emitting device according to claim 21, wherein: At least one of the second electron transport layer and the second hole blocking layer includes an organic compound represented by Formula 1, wherein the organic compound is the same as or different from the first compound.

23. The organic light emitting device according to claim 21, wherein: The first light emitting component further includes a red light emitting material layer between the second light emitting component and the first light emitting material layer.

24. The organic light emitting device according to claim 23, wherein: The first light-emitting component further includes a yellow-green light-emitting material between the first light-emitting material layer and the red light-emitting material layer. 25 . The organic light-emitting device according to claim 6 , further comprising color filter layers corresponding to the red pixel region, the green pixel region, and the blue pixel region.

Images