Organic compound, organic light-emitting diode having same, and organic light-emitting device

Abstract

The present disclosure relates to an organic compound, an organic light emitting diode (OLED) having the same, and an organic light emitting device. In particular, an organic compound having the structure of the following Chemical Formula 1 is provided. By applying the organic compound in a light-emitting layer in an organic light-emitting diode (OLED), emission lifetimes of an OLED and an organic light-emitting device (e.g., a display device or a lighting device) including the OLED can be improved. [Chemical Formula 1] # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Korean Patent Application No. 10-2023-0174650 filed in Korea on December 5, 2023, the entire contents of which are hereby expressly incorporated by reference into this application. Technical Field

[0003] The present disclosure relates to organic compounds, and more particularly, to organic compounds having beneficial light-emitting characteristics, and organic light-emitting diodes (OLEDs) and organic light-emitting devices (eg, display devices or lighting devices) including the organic compounds. Background Art

[0004] As a display device that can replace a liquid crystal display device (LCD), a flat panel display device including an organic light emitting diode (OLED) has been studied. The electrode configuration in the OLED can realize a unidirectional or bidirectional image. In addition, the OLED can even be formed on a flexible transparent substrate such as a plastic substrate, so that a flexible or foldable display device can be easily realized using the OLED. In addition, compared with LCD, the OLED can be driven at a lower voltage and the OLED has an advantageous high color purity.

[0005] However, there is still a need to develop OLEDs and devices including the OLEDs with improved luminous efficiency and luminous lifetime. Since fluorescent materials only utilize singlet excitons during the luminescence process, the fluorescent materials of the prior art exhibit low luminous efficiency. Meanwhile, since phosphorescent materials utilize triplet excitons as well as singlet excitons during the luminescence process, they can exhibit high luminous efficiency. However, such phosphorescent materials contain metal complexes that may have a luminous lifetime that is too short for commercial use. Therefore, there is still a need to develop materials with sufficient luminous efficiency and luminous lifetime. Summary of the invention

[0006] Accordingly, some embodiments of the present disclosure are directed to organic compounds, organic light emitting diodes, and organic light emitting devices that substantially obviate one or more of the problems due to limitations and disadvantages of the related art.

[0007] One aspect of the present disclosure provides an organic compound that can be applied to an organic light emitting diode (OLED) having improved driving voltage, luminous efficiency, and / or luminous lifetime.

[0008] Another aspect of the present disclosure provides an organic compound suitable for an OLED.

[0009] Another aspect of the present disclosure provides an OLED and an organic light-emitting device (eg, a display device or a lighting device) having beneficial driving voltage, luminous efficiency, and luminous lifetime.

[0010] Additional features and aspects of the present disclosure will be set forth in the following description, and in part will be apparent from the description, or may be learned by practicing the disclosed concepts provided herein. Other features and aspects of the disclosed concepts may be realized and obtained by structures specifically pointed out in the written description, or derivable therefrom, and in the claims and drawings.

[0011] To achieve these and other aspects of the inventive concept, as embodied and broadly described, in one aspect, the present disclosure provides an organic compound having a structure of the following Chemical Formula 1:

[0012] [Chemical formula 1]

[0013]

[0014] Wherein, in Chemical Formula 1,

[0015] R 1 is protium, deuterium, tritium, unsubstituted or substituted C 1 To C 10 alkyl, or unsubstituted or substituted phenyl, wherein when a1 is 2, 3, 4 or 5, each R 1 are the same as or different from each other, or

[0016] Optionally,

[0017] When a1 is 2, 3, 4 or 5, two adjacent R 1 Further ligation to form unsubstituted or deuterated, C 1 To C 10 A benzene ring substituted with at least one of an alkyl group and a group formed by connecting the above two groups;

[0018] R 2 , R 3 and R 4 are each independently protium, deuterium, tritium, or unsubstituted or substituted C 1 To C 10 Alkyl, wherein when a2 is 2 or 3, each R 2 The same or different from each other, when a3 is 2, 3 or 4, each R 3 are the same as or different from each other, and when a4 is 2, 3 or 4, each R 4 the same as or different from one another;

[0019] R 5 and R 6are each independently phenyl, biphenyl or naphthyl, wherein the phenyl, biphenyl and naphthyl are each independently unsubstituted or substituted with deuterium, C 1 To C 10 Alkyl, and at least one of a group formed by connecting the above two groups;

[0020] a1 is 0, 1, 2, 3, 4 or 5;

[0021] a2 is 0, 1, 2, or 3; and

[0022] a3 and a4 are each independently 0, 1, 2, 3 or 4.

[0023] As an example, the organic compound may have the structure of the following Chemical Formula 2 or Chemical Formula 3:

[0024] [Chemical formula 2]

[0025]

[0026] [Chemical formula 3]

[0027]

[0028] Among them, in Chemical Formula 2 and Chemical Formula 3,

[0029] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1;

[0030] R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C 1 To C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and

[0031] b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

[0032] In one embodiment, the organic compound may have the structure of the following Chemical Formula 4 or Chemical Formula 5:

[0033] [Chemical formula 4]

[0034]

[0035] [Chemical formula 5]

[0036]

[0037] Among them, in Chemical Formula 4 and Chemical Formula 5,

[0038] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1;

[0039] R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C 1 To C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and

[0040] b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

[0041] In one embodiment, in Formula 1, two adjacent R 1 Can be connected to form a benzene ring, R 1 The remaining three in can be protium or deuterium, and R 6 It may be naphthyl.

[0042] In another aspect, the present disclosure provides an organic light emitting diode including: a first electrode; a second electrode facing the first electrode; and a light emitting layer disposed between the first electrode and the second electrode, and the light emitting layer may include the organic compound.

[0043] The light emitting layer may include one or more light emitting material layers, and at least one light emitting material layer may contain the organic compound.

[0044] The at least one light emitting material layer may include a host and a dopant, and the host may include the organic compound.

[0045] The dopant may include at least one of a blue phosphorescent material, a blue fluorescent material, and a blue delayed fluorescent material.

[0046] In one embodiment, the dopant may include a phosphorescent material comprising a platinum organometallic compound.

[0047] In another embodiment, the dopant may comprise a fluorescent material having a polycyclic heteroaromatic ring containing boron as well as nitrogen, oxygen, or sulfur.

[0048] In another embodiment, the dopant may include a first dopant and a second dopant.

[0049] As an example, the first dopant may include at least one of a blue delayed fluorescent material and a blue phosphorescent material and / or the second dopant may include a blue fluorescent material.

[0050] The light emitting layer may include a single light emitting portion or include a plurality of light emitting portions to form a tandem structure.

[0051] In still another aspect, the present disclosure provides an organic light emitting device, such as an organic light emitting display device or an organic light emitting lighting device, which includes a substrate and an organic light emitting diode over the substrate.

[0052] In one or more embodiments, the organic compound may exhibit sufficient performance for use in an organic light emitting diode (OLED). An OLED or organic light emitting device using the organic compound as an organic electroluminescent material may have beneficial luminous efficiency and luminous lifetime.

[0053] 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 inventive concepts as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0054] The accompanying drawings, which are included to provide a further understanding of the disclosure, are incorporated in and constitute a part of this application, illustrate some embodiments of the disclosure and together with the description serve to explain the principle of the disclosure.

[0055] Figure 1 A schematic circuit diagram of an organic light emitting display device according to one or more embodiments of the present disclosure is shown.

[0056] Figure 2 A cross-sectional view of an organic light emitting display device as an example of an organic light emitting device according to an embodiment of the present disclosure is shown.

[0057] Figure 3 A cross-sectional view of an organic light emitting diode having a single light emitting portion according to an embodiment of the present disclosure is shown.

[0058] Figure 4 A cross-sectional view of an organic light emitting diode having a single light emitting portion according to another embodiment of the present disclosure is shown.

[0059] Figure 5 A cross-sectional view of an organic light emitting display device according to another embodiment of the present disclosure is shown.

[0060] Figure 6 A cross-sectional view of an organic light emitting diode having a series structure of two light emitting parts according to another embodiment of the present disclosure is shown.

[0061] Figure 7 A cross-sectional view of an organic light emitting diode having a series structure of three light emitting portions according to another embodiment of the present disclosure is shown. DETAILED DESCRIPTION

[0062] Reference will now be made in detail to some aspects of the present disclosure, some examples of which are illustrated in the accompanying drawings. Whenever possible, the same reference numerals will be used throughout the drawings to refer to the same or like parts.

[0063] All components of each organic light emitting display device according to all embodiments of the present disclosure may be operably coupled and configured.

[0064] [Organic compounds]

[0065] As used herein, the term "organic electroluminescent material" or "electroluminescent material" refers to a material that can be used in an organic light-emitting diode, can include at least one compound, and, if necessary, can be included in any layer constituting the organic light-emitting diode. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (such as a host material and / or a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0066] As used herein, the term "plural hosts" refers to a host material comprising a combination of two or more compounds that may be included in any light-emitting layer constituting an organic light-emitting diode, and may mean both a material before being applied to an organic light-emitting diode (e.g., before deposition) and a material after being applied to an organic light-emitting diode (e.g., after deposition). For example, a plurality of hosts refers to a combination of two or more host materials, and optionally may include conventional materials included in an organic electroluminescent material. The two or more compounds included in the plurality of host materials may be included in one light-emitting layer or different light-emitting layers by a process utilized by conventional means. For example, two or more compounds may be mixed deposited or co-deposited, or deposited separately.

[0067] As used herein, the term "hole transport region" refers to a region in which holes are transported between the first electrode and the light-emitting material layer, and may include, for example, at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescence auxiliary layer, and an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the luminescence auxiliary layer, and the electron blocking layer may each independently be a single layer, or a plurality of layers stacked with two or more layers or three or more layers.

[0068] In one embodiment, the hole transport region may include a first hole transport layer, a second hole transport layer, and optionally a third hole transport layer. The second hole transport layer and the third hole transport layer may each be one or more layers of a plurality of hole transport layers, and may include one or more of a hole transport layer, a light-emitting auxiliary layer, and an electron blocking layer.

[0069] In another embodiment, the first hole transport layer can be disposed between the first electrode and the light emitting material layer, and the second hole transport layer can be disposed between the first hole transport layer and the light emitting material layer. The second hole transport layer can be any layer that acts as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer and / or an electron blocking layer.

[0070] In another embodiment, the hole transport region may include a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer may be disposed between the first electrode and the light emitting material layer, the second hole transport layer may be disposed between the first hole transport layer and the light emitting material layer, and the third hole transport layer may be disposed between the second hole transport layer and the light emitting material layer. The third hole transport layer may be any layer that acts as a hole transport layer, a light emitting auxiliary layer, a hole auxiliary layer, and / or an electron blocking layer.

[0071] As used herein, the term "unsubstituted" means that hydrogen is directly attached to the carbon atom. As used herein, "hydrogen" may refer to protium.

[0072] As used herein, "substituted" means that a hydrogen is replaced by a substituent. A substituent may replace a hydrogen at any position without limitation. When two or more hydrogens in a group are replaced by a substituent, each substituent may be the same or different from each other. The maximum number of substituents of a substituted group may be the total number of valences that may be substituted for the atoms of the group. For example, a substituent may include, but is not limited to, unsubstituted or halogen and / or deuterium substituted C 1 To C 20 Alkyl, unsubstituted or halogen and / or deuterium substituted C 1 To C 20 Alkoxy, halogen, cyano, hydroxyl, carboxyl, carbonyl, amino, C 1 To C 10 Alkylamino, C 6 To C 30 Arylamino, C 3 To C 30 heteroarylamino, nitro, hydrazide, sulfonate, unsubstituted or halogen and / or deuterium-substituted C 1 To C 10 Alkylsilyl, unsubstituted or halogen and / or deuterium substituted C 1 To C 10Alkoxysilyl, unsubstituted or halogen and / or deuterium-substituted C 3 To C 20 Cycloalkylsilyl, unsubstituted or halogen and / or deuterium-substituted C 6 To C 30 Arylsilyl, unsubstituted or halogen and / or deuterium-substituted C 3 To C 30 Heteroarylsilyl, unsubstituted or C 1 To C 20 Alkyl and / or deuterium substituted C 6 To C 30 Aryl, unsubstituted or C 1 To C 20 Alkyl and / or deuterium substituted C 3 To C 30 heteroaryl, or any combination of these groups.

[0073] As an example, the substituents may include, but are not limited to, unsubstituted or substituted methyl, unsubstituted or substituted tert-butyl, unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, unsubstituted or substituted biphenyl, unsubstituted or substituted diphenylfluorenyl, unsubstituted or substituted dimethylfluorenyl, unsubstituted or substituted pyridyl, unsubstituted or substituted dibenzofuranyl, unsubstituted or substituted dibenzothiophenyl, unsubstituted or substituted carbazolyl, and the like.

[0074] As used herein, the term "hetero" in terms such as "heteroalicyclic ring", "heteroaromatic ring", "heterocycloalkyl", "heteroaryl", "heteroaralkyl", "heteroaryloxy", "heteroarylamino", "heteroarylsilyl", "heteroarylgermanyl", "heteroarylene" and the like means that at least one carbon atom (e.g., 1 to 5 carbon atoms) constituting an aliphatic chain, an alicyclic group or an alicyclic ring, or an aromatic group or an aromatic ring is replaced by at least one heteroatom selected from N, O, S and P.

[0075] As used herein, the term “C 1 To C 20The term "alkyl" refers to a linear or branched alkyl group having 1 to 20 carbon atoms. As an example, the carbon number of the alkyl group may be 1 to 15, such as 1 to 10. For example, the alkyl group may include, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 1-methylpentyl, 1-ethylpentyl, 1-methyl ... , 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like. As used herein, C 1 To C 20 The alkylene group may include, but is not limited to, any divalent linking group corresponding to the above alkyl group.

[0076] As used herein, the term “C 3 To C 30 Cycloalkyl" or "C 3 To C 30 "Alicyclic group" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms. As an example, a cycloalkyl group may have 3 to 20, such as 3 to 7, ring carbon atoms. For example, a cycloalkyl group may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.

[0077] As used herein, the term “C 3 To C 30 "Cycloalkenyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms and at least one double bond within the ring. As an example, a cycloalkenyl group may have 3 to 20, such as 3 to 7, ring carbon atoms. For example, cycloalkenyl groups may include, but are not limited to, cyclopropenyl, cyclobutenyl, and cyclopentenyl.

[0078] As used herein, the term “C 3 To C 7 "Heterocycloalkyl" refers to a cycloalkyl group having 3 to 7, for example 3 to 5, ring atoms and at least one heteroatom (for example N, O and S) selected from B, N, O, S, Si and P. For example, heterocycloalkyl may include, but is not limited to, tetrahydrofuranyl, pyrrolidinyl, tetrahydrothiolanyl, tetrahydropyranyl, and the like.

[0079] As used herein, the term “C 6 To C 30"Aryl (or arylene)" means a monocyclic or polycyclic group derived from an aromatic hydrocarbon having 6 to 30 ring carbon atoms or a corresponding divalent linking group or bridging group, and may include a spirocyclic structure. For example, the aryl or arylene group may have 6 to 20, such as 6 to 15, ring carbon atoms.

[0080] For example, C 6 To C 30 The aryl group may include, but is not limited to, non-fused or fused aryl groups such as phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenyl-benzofluorenyl, dibenzofluorenyl, phenanthrenyl, triphenylenyl, phenylphenanthrenyl, anthracenyl, benzanthryl, indenyl, triphenylene, pyrenyl, tetracenyl, Benzo yl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumyl, spiro[fluorene-fluorene]yl (spirobifluorenyl), spiro[fluorene-benzofluorenyl]yl, azulenyl, pentalenyl, indenoindenyl, heptalenyl, indacenyl, phenalenyl, pentaphenyl, indenofluorenyl, etc.

[0081] In another embodiment, C 6 To C 30 The aryl group may include, but is not limited to, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumyl, m-cumyl, p-cumyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl -yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] As used herein, C 6 To C 30 The arylene group may include, but is not limited to, any divalent linking group corresponding to the above aryl group.

[0082] As used herein, the term “C 2 To C 30 The term "heteroaryl (or heteroarylene)" refers to a monocyclic or polycyclic group derived from a heteroaromatic hydrocarbon having 2 to 30 ring atoms and at least one heteroatom selected from B, N, O, S, Si, P, Se and Ge, or a corresponding divalent linking group or bridging group. For example, the heteroaryl group may have 5 to 30 ring atoms and 1 to 4 heteroatoms. The heteroaryl group may have a monocyclic ring or a polycyclic ring fused to at least one 5-membered or 6-membered ring, such as a benzene ring. The heteroaryl group or heteroarylene group may be partially saturated. In addition, the heteroaryl group may include a case where at least one heteroaryl ring is connected to at least one heteroaryl or aryl group by a single bond.

[0083] For example, C 2 To C 30 The heteroaryl group may include, but is not limited to, non-fused or fused heteroaryl groups such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isothiazolyl, Azolyl, Azolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyridinyl, pyrimidinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisothiazolyl, Azolyl, benzo oxazolyl, imidazopyridyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indenocarbazolyl, indolocarbazolyl, phenanthroline, The compounds include oxazinyl, phenanthridinyl, benzodioxolyl, indolizinyl, acridinyl, phenazinyl, phenothiazinyl, silafluorenyl, germafluorenyl and the like.

[0084] In another embodiment, C2 To C 30 The heteroaryl group may include, but is not limited to, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, , 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl , 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4- carbazolyl, 9-carbazolyl, aza-carbazolyl-1-yl, aza-carbazolyl-2-yl, aza-carbazolyl-3-yl, aza-carbazolyl-4-yl, aza-carbazolyl-5-yl, aza-carbazolyl-6-yl, aza-carbazolyl-7-yl, aza-carbazolyl-8-yl, aza-carbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2- Azolyl, 4- Azolyl, 5- Azolyl, 2- Oxazolyl, 5- oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert- As used herein, C 2 To C 30 The heteroarylene group may include, but is not limited to, any divalent linking group corresponding to the above heteroaryl groups.

[0085] In addition, "heteroaryl (or heteroarylene)" can be divided into heteroaryl (or heteroarylene) with electronic characteristics and heteroaryl (or heteroarylene) with hole characteristics. The electronic characteristic heteroaryl (heteroarylene) can be an electron-rich substituent in the core ring. For example, the electronic characteristic heteroaryl can include but is not limited to unsubstituted or substituted pyridyl, unsubstituted or substituted pyrimidinyl, unsubstituted or substituted triazine, unsubstituted or substituted quinazolinyl, unsubstituted or substituted quinoxalinyl, unsubstituted or substituted quinolyl, etc. The hole characteristic heteroaryl (heteroarylene) can be an electron-deficient substituent in the core ring. For example, the hole characteristic heteroaryl can include but is not limited to unsubstituted or substituted carbazolyl, unsubstituted or substituted dibenzofuranyl, unsubstituted or substituted dibenzothiophene, etc.

[0086] As used herein, “C 3 To C 30 Alicyclic ring and C 6 To C 30 The term "aromatic ring fused group" refers to a functional group of a ring system in which an alicyclic ring having 3 to 30, such as 3 to 25 or 3 to 18, ring carbon atoms is fused to an aromatic ring having 6 to 30, such as 6 to 25 or 6 to 18, ring carbon atoms. For example, the fused ring group may include, but is not limited to, a fused ring having at least one benzene ring and at least one cyclohexane ring, or a fused ring having at least one naphthalene ring and at least one cyclopentane ring.3 To C 30 Alicyclic ring and C 6 To C 30 At least one carbon atom in the condensed cyclic group of the aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si and P (eg, N, O and S).

[0087] As used herein, the term "halogen" refers to F, Cl, Br and / or I.

[0088] The terms "ortho-(o-)", "meta-(m-)" and "para-(p-)" refer to the substitution position of all substituents. Ortho refers to the position of the substituent immediately adjacent, for example, in the case of benzene, it refers to the 1st and 2nd positions, and meta refers to the next substitution position after the substitution position immediately adjacent, for example, in the case of benzene, it refers to the 1st and 3rd positions, and para refers to the substitution position after meta, for example, in the case of benzene, it refers to the 1st and 4th positions.

[0089] As used herein, the term "ring formed by connecting adjacent substituents" means an unsubstituted or substituted 2 to 30-membered monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof formed by connecting or fusing two or more adjacent substituents. The ring formed by connecting adjacent substituents may be an unsubstituted or substituted 3 to 26-membered monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. The ring formed by connecting adjacent substituents may include at least one heteroatom selected from B, N, O, S, Si, and P (e.g., N, O, and S). In another embodiment, the ring may have 5 to 20 ring atoms or 5 to 15 ring atoms.

[0090] As used herein, if no substituent is indicated in a chemical formula or chemical structure, it may mean that all positions that may be substituents are hydrogen or deuterium. That is, in the case of deuterium, it is the same type as hydrogen, and some hydrogen atoms may be isotype deuterium. In this case, the deuterium content or deuteration rate may be 0% to 100%. In the case where no substituent is indicated in a chemical formula or chemical structure, the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen. Unless deuterium is explicitly excluded, hydrogen and deuterium may be mixed in the compound.

[0091] As used herein, "combinations thereof" means a combination of one or more elements or components from the corresponding list to form known or chemically stable arrangements that can be envisioned by those skilled in the art from the corresponding list. For example, alkyl and deuterium can be combined to form partially or completely deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents; halogen, alkyl and aryl can be combined to form haloaralkyl. In one embodiment, exemplary combinations of substituents include up to 50 atoms in addition to hydrogen and deuterium, or up to 40 atoms in addition to hydrogen and deuterium, or up to 30 atoms in addition to hydrogen and deuterium. In another embodiment, the combination of substituents can be those that include up to 20 atoms in addition to hydrogen and deuterium.

[0092] As used herein, when there are a plurality of substituents represented by the same symbol in a chemical formula, the substituents represented by the same symbol may be the same as or different from each other.

[0093] The organic compound may be described in detail. In one embodiment, the organic compound may have the structure of the following Chemical Formula 1:

[0094] [Chemical formula 1]

[0095]

[0096] Wherein, in Chemical Formula 1,

[0097] R 1 is protium, deuterium, tritium, unsubstituted or substituted C 1 To C 10 alkyl, or unsubstituted or substituted phenyl, wherein when a1 is 2, 3, 4 or 5, each R 1 are the same as or different from each other, or

[0098] Optionally,

[0099] When a1 is 2, 3, 4 or 5, two adjacent R 1 Further ligation to form unsubstituted or deuterated, C 1 To C 10 A benzene ring substituted with at least one of an alkyl group and a group formed by connecting the above two groups;

[0100] R 2 , R 3 and R 4 are each independently protium, deuterium, tritium, or unsubstituted or substituted C 1 To C 10 Alkyl, wherein when a2 is 2 or 3, each R 2 The same or different from each other, when a3 is 2, 3 or 4, each R 3are the same as or different from each other, and when a4 is 2, 3 or 4, each R 4 the same as or different from one another;

[0101] R 5 and R 6 are each independently phenyl, biphenyl or naphthyl, wherein the phenyl, biphenyl and naphthyl are each independently unsubstituted or substituted with deuterium, C 1 To C 10 Alkyl, and at least one of a group formed by connecting the above two groups;

[0102] a1 is 0, 1, 2, 3, 4 or 5;

[0103] a2 is 0, 1, 2, or 3; and

[0104] a3 and a4 are each independently 0, 1, 2, 3 or 4.

[0105] As an example, R in Chemical Formula 1 5 In one embodiment, R in Chemical Formula 1 5 It may be a phenyl group substituted with at least one deuterium. 5 It may be a phenyl group in which all hydrogens are replaced by deuterium.

[0106] R in Formula 1 2 To R 4 Each can independently be protium or deuterium. For example, R 2 To R 4 Each can be protium or R 2 To R 4 As an example, a2 in Chemical Formula 1 may be 3, and a3 and a4 in Chemical Formula 1 may each independently be 4.

[0107] In another embodiment, the central anthracene ring in the organic compound of Chemical Formula 1 may be directly or indirectly substituted with at least one naphthyl group. As an example, two adjacent R 1 can be connected to form a benzene ring, or R in Formula 1 6 It may be a naphthyl group. The organic compound having such a conformation may have the structure of the following Chemical Formula 2 or Chemical Formula 3:

[0108] [Chemical formula 2]

[0109]

[0110] Among them, in Chemical Formula 2 and Chemical Formula 3,

[0111] R 1 , R2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1;

[0112] R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C 1 To C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and

[0113] b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

[0114] As an example, R in Chemical Formula 2 and / or Chemical Formula 3 11 It can be protium or deuterium. 11 At least a portion of the hydrogen in the reaction mixture may be deuterium.

[0115] In another embodiment, two adjacent R 1 can be fused to a benzene ring to form a 1-naphthyl group, or R in Formula 1 6 It may be 2-naphthyl. The organic compound having such a conformation may have the structure of the following Chemical Formula 4 or Chemical Formula 5:

[0116] [Chemical formula 4]

[0117]

[0118] [Chemical formula 5]

[0119]

[0120] Among them, in Chemical Formula 4 and Chemical Formula 5,

[0121] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1;

[0122] R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C 1 To C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and

[0123] b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

[0124] In another embodiment, two adjacent R 1 can be connected to form a benzene ring, and thus connected to the anthracene ring as a 1-naphthyl group. 1 The other three in the formula may be protium or deuterium, and R in the formula 1 6 It may be a naphthyl group (eg, 2-naphthyl group).

[0125] The organic compound having the structure of Chemical Formulae 1 to 5 may be at least one of the compounds of the following Chemical Formula 6, or may be selected from the group consisting of but not limited to the compounds of the following Chemical Formula 6: [Chemical Formula 6]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] in, express and wherein D represents deuterium.

[0137] The organic compound having the structure of Chemical Formula 1 to 6 has at least one phenyl group connected or substituted to the 9th position of the anthracene ring. In addition, one phenyl group connected to the anthracene ring is substituted by another phenyl group at its ortho position relative to the anthracene ring. The steric hindrance effect of the anthracene skeleton is controlled to reduce the reactivity of the anthracene-containing compound. Therefore, the organic compound having the structure of Chemical Formula 1 to 6 can have a beneficial luminescence lifetime.

[0138] For example, the organic compound having the structure of Chemical Formulae 1 to 6 can be applied to an organic electroluminescent material. In one embodiment, the organic compound can be applied to a host in a light-emitting material layer. In another embodiment, the organic compound having the structure of Chemical Formulae 1 to 6 has an appropriate energy level so that it can be applied to a charge transport layer or a charge blocking layer.

[0139] [Organic light emitting diode and organic light emitting device]

[0140] The organic electroluminescent material to which the organic compound is applied, the organic light emitting diode (OLED) and the organic light emitting device comprising the organic compound will be described. In one embodiment, the organic electroluminescent material can be applied to a light emitting layer, and the light emitting layer includes, for example, a light emitting material layer, a hole transport layer, an electron blocking layer, a hole blocking layer and / or an electron transport layer in an OLED. For example, when the OLED includes two or more hole transport layers, the organic compound can be included in a composition for making a hole transport layer (hole auxiliary layer) adjacent to the light emitting material layer.

[0141] The light-emitting layer may include one or more light-emitting material layers, and at least one light-emitting material layer may contain one or more host materials containing an organic compound having a structure of Chemical Formulae 1 to 6. The light-emitting layer may additionally include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, a hole buffer layer, and an electron buffer layer.

[0142] In one embodiment, the organic light emitting diode may have one light emitting portion, or may have a plurality of light emitting portions to form a series structure. The plurality of light emitting portions may each emit light of the same color or light of different colors.

[0143] As an example, in one or more embodiments of the present disclosure, an organic light emitting diode including an organic compound having a structure of Chemical Formulae 1 to 6 may be applied to an organic light emitting device such as an organic light emitting display device or an organic light emitting lighting device. As an example, an organic light emitting display device will be described.

[0144] Figure 1 1 shows a schematic circuit diagram of an organic light emitting display device according to one or more embodiments of the present disclosure. Figure 1As shown in , in the organic light emitting display device 100, gate lines GL, data lines DL, and power lines PL are provided, each of which crosses each other to define a pixel region P. A switching thin film transistor Ts, a driving thin film transistor Td, a storage capacitor Cst, and an organic light emitting diode D are provided in the pixel region P. The pixel region P may include a first pixel region, a second pixel region, and a third pixel region. However, the embodiments of the present disclosure are not limited to such examples. The organic light emitting display device 100 may include a plurality of such pixel regions P, which may be arranged in a matrix configuration or other configurations.

[0145] The switching thin film transistor Ts is connected to the gate line GL and the data line DL. The driving thin film transistor Td and the storage capacitor Cst are connected between the switching thin film transistor Ts and the power line PL. The organic light emitting diode D is connected to the driving thin film transistor Td. When the switching thin film transistor Ts is turned on by the gate signal applied to the gate line GL, the data signal applied to the data line DL is applied to the gate electrode of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.

[0146] By applying to the gate electrode 130 ( Figure 2 ) turns on the driving thin film transistor Td, so that a current proportional to the data signal is supplied from the power line PL to the organic light emitting diode D through the driving thin film transistor Td. Then, the organic light emitting diode D emits light with a brightness proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst is charged with a voltage proportional to the data signal, so that the voltage of the gate electrode in the driving thin film transistor Td remains constant during one frame. Therefore, the organic light emitting display device can display a desired image.

[0147] Figure 2 A schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present disclosure is shown. Figure 1 The pixel circuit configuration can be used in the present application Figure 2 or other display devices of the diagram.

[0148] like Figure 2 As shown, the organic light emitting display device 100 includes a substrate 102 , a thin film transistor Tr on the substrate 102 , and an organic light emitting diode D connected to the thin film transistor Tr.

[0149] As an example, the substrate 102 may include a red pixel region, a green pixel region, and a blue pixel region, and an organic light emitting diode D may be positioned in each pixel region. The organic light emitting diodes D emitting red light, green light, and blue light, respectively, are positioned in the red pixel region, the green pixel region, and the blue pixel region, respectively.

[0150] The substrate 102 may include, but is not limited to, glass, thin flexible materials, and / or polymer plastics. For example, the flexible material may be selected from, but is not limited to, polyimide (PI), polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), polycarbonate (PC), and / or combinations thereof. The substrate 102 on which thin film transistors Tr and organic light emitting diodes D are disposed forms an array substrate.

[0151] A buffer layer 106 may be provided on the substrate 102. The thin film transistor Tr may be provided on the buffer layer 106. In certain embodiments, the buffer layer 106 may be omitted.

[0152] A semiconductor layer 110 is provided on the buffer layer 106. In one embodiment, the semiconductor layer 110 may include, but is not limited to, oxide semiconductor materials. In this case, a light shielding pattern may be provided below the semiconductor layer 110, and the light shielding pattern may prevent light from incident on the semiconductor layer 110, thereby preventing or reducing the degradation of the semiconductor layer 110 by light. Alternatively, the semiconductor layer 110 may include polysilicon. In this case, the opposite edges of the semiconductor layer 110 may be doped with impurities.

[0153] A gate insulating layer 120 including an insulating material is provided on the semiconductor layer 110. The gate insulating layer 120 may include, but is not limited to, inorganic insulating materials such as silicon oxide (SiO x , where 0 < x ≤ 2) or silicon nitride (SiN x , where 0 < x ≤ 2).

[0154] A gate electrode 130 made of a conductive material such as metal is provided on the gate insulating layer 120 to correspond to the center of the semiconductor layer 110. Although as Figure 2 shown, the gate insulating layer 120 is provided over the entire area of the substrate 102, the gate insulating layer 120 may be patterned in the same manner as the gate electrode 130.

[0155] An interlayer insulating layer 140 including an insulating material is provided on the gate electrode 130 and covers the entire surface of the substrate 102. The interlayer insulating layer 140 may include, but is not limited to, inorganic insulating materials such as silicon oxide (SiO x , where 0 < x ≤ 2) or silicon nitride (SiN x , where 0 < x ≤ 2), or organic insulating materials such as benzocyclobutene or photo-acryl.

[0156] The interlayer insulating layer 140 has a first semiconductor layer contact hole 142 and a second semiconductor layer contact hole 144 that expose a portion of the surface of the semiconductor layer 110 closer to the opposite end than the center or do not cover a portion of the surface of the semiconductor layer 110 closer to the opposite end than the center. The first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are disposed on opposite sides of the gate electrode 130 and are spaced apart from the gate electrode 130. Figure 2 In the embodiment, the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are formed in the gate insulating layer 120 and the interlayer insulating layer 140. Alternatively, in some embodiments, when the gate insulating layer 120 is patterned identically to the gate electrode 130, the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 may be formed only in the interlayer insulating layer 140.

[0157] A source electrode 152 and a drain electrode 154 made of a conductive material such as metal are disposed on the interlayer insulating layer 140. The source electrode 152 and the drain electrode 154 are spaced apart from each other on opposite sides of the gate electrode 130 and contact both sides of the semiconductor layer 110 through the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144, respectively.

[0158] The semiconductor layer 110 , the gate electrode 130 , the source electrode 152 , and the drain electrode 154 constitute a thin film transistor Tr serving as a driving element. Figure 2 The thin film transistor Tr in the embodiment has a coplanar structure in which the gate electrode 130, the source electrode 152 and the drain electrode 154 are arranged on the semiconductor layer 110. Alternatively, the thin film transistor Tr may have an inverted staggered structure in which the gate electrode is arranged below the semiconductor layer and the source electrode and the drain electrode are arranged on the semiconductor layer. In this case, the semiconductor layer may include amorphous silicon.

[0159] A gate line GL and a data line DL that cross each other to define the pixel area P, and a switching thin film transistor Ts connected to the gate line GL and the data line DL may also be formed in the pixel area P. The switching thin film transistor Ts is connected to the thin film transistor Tr that is a driving element. In addition, the power line PL is spaced apart in parallel with the gate line GL or the data line DL. The thin film transistor Tr may further include a storage capacitor Cst configured to keep the voltage of the gate electrode 130 constant for one frame.

[0160] A passivation layer 160 is disposed on the source electrode 152 and the drain electrode 154. The passivation layer 160 covers the thin film transistor Tr on the entire substrate 102. The passivation layer 160 has a flat top surface and a drain contact hole (or contact hole) 162 that exposes the drain electrode 154 of the thin film transistor Tr or does not cover the drain electrode 154 of the thin film transistor Tr. Although the drain contact hole 162 is disposed on the second semiconductor layer contact hole 144, it may be spaced apart from the second semiconductor layer contact hole 144.

[0161] The organic light emitting diode (OLED) D includes a first electrode 210 disposed on the passivation layer 160 and connected to the drain electrode 154 of the thin film transistor Tr. The OLED D also includes a light emitting layer 230 and a second electrode 220 each sequentially disposed on the first electrode 210.

[0162] One of the first electrode 210 and the second electrode 220 may be an anode, and the other of the first electrode 210 and the second electrode 220 may be a cathode. One of the first electrode 210 and the second electrode 220 may be a reflective electrode, and the other of the first electrode 210 and the second electrode 220 may be a transmissive electrode.

[0163] The first electrode 210 is disposed individually in each pixel region P. In one embodiment, the first electrode 210 may be an anode and include a conductive material having a relatively high work function value. For example, the first electrode 210 may include a transparent conductive oxide (TCO).

[0164] In one embodiment, when the organic light-emitting display device 100 is a bottom emission type, the first electrode 210 may have a single-layer structure of TCO. Alternatively, when the organic light-emitting display device 100 is a top emission type, a reflective electrode or a reflective layer may be provided below the first electrode 210. For example, the reflective electrode or the reflective layer may include, but is not limited to, silver (Ag) or aluminum-palladium-copper (APC) alloy. As an example, in a top emission type OLED D, the first electrode 210 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0165] In addition, a bank layer 164 is disposed on the passivation layer 160 to cover the edge of the first electrode 210. The bank layer 164 exposes or does not cover the center of the first electrode 210 corresponding to each pixel area. In some embodiments, the bank layer 164 may be omitted.

[0166] A light emitting layer 230 is disposed on the first electrode 210. In one embodiment, the light emitting layer 230 may have a single-layer structure of a light emitting material layer (EML). Alternatively, the light emitting layer 230 may have a multilayer structure of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an EML, a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL) and / or a charge generation layer (CGL).

[0167] In one embodiment, the light emitting layer 230 may have a single light emitting portion ( Figure 3 and Figure 4 ). Alternatively, the light-emitting layer 230 may have a plurality of light-emitting portions to form a series structure. For example, the light-emitting layer 230 may be applied to an OLED in which a single light-emitting portion is positioned in each of a red pixel region, a green pixel region, and a blue pixel region. Alternatively, the light-emitting layer 230 may be applied to a series-type OLED in which at least two light-emitting portions are stacked.

[0168] The light emitting layer 230 may include an organic compound having the structure of Chemical Formulas 1 to 6. The light emitting lifetime of the OLED D and the organic light emitting display device 100 including the organic compound may be improved.

[0169] A second electrode 220 is disposed on the substrate 102 on which the light emitting layer 230 is disposed. The second electrode 220 may be disposed on the entire display area. The second electrode 220 may include a conductive material having a relatively low work function value compared to the first electrode 210. The second electrode 220 may be a cathode that provides electrons. When the organic light emitting display device 100 is a top emission type, the second electrode 220 is thin so as to have a light transmission (semi-transmission) characteristic.

[0170] In addition, an encapsulation film 170 may be disposed on the second electrode 220 to prevent or reduce external moisture from penetrating into the OLED D. The encapsulation film 170 may have, but is not limited to, a laminated structure of a first inorganic insulating film 172, an organic insulating film 174, and a second inorganic insulating film 176. In some embodiments, the encapsulation film 170 may be omitted.

[0171] A polarizing plate may be attached to the packaging film 170 to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate. When the organic light-emitting display device 100 is a bottom emission type, the polarizing plate may be disposed below the substrate 102. Alternatively, when the organic light-emitting display device 100 is a top emission type, the polarizing plate may be disposed on the packaging film 170. In addition, a cover window may be attached to the packaging film 170 or the polarizing plate. In this case, the substrate 102 and the cover window may have flexible characteristics, so that the organic light-emitting display device 100 may be a flexible display device.

[0172] OLED D is described in more detail. Figure 3 A schematic cross-sectional view of an organic light emitting diode having a single light emitting portion according to an embodiment of the present disclosure is shown. For example, Figure 3 Shows Figure 1 and Figure 2 An example of OLED D in (OLED D1).

[0173] like Figure 3 As shown, an organic light emitting diode (OLED) D1 according to an example of the present disclosure includes a first electrode 210 and a second electrode 220 facing each other and a light emitting layer 230 disposed between the first electrode 210 and the second electrode 220. The organic light emitting display device 100 includes a red pixel region, a green pixel region, and a blue pixel region, and the OLED D1 can be disposed in the red pixel region, the green pixel region, and / or the blue pixel region. As an example, the OLED D1 can be disposed in the blue pixel region.

[0174] In one embodiment, the light emitting layer 230 includes a light emitting material layer (EML) 340 disposed between the first electrode 210 and the second electrode 220. The EML 340 may be a blue light emitting material layer.

[0175] The light emitting layer 230 may include at least one of a hole transport layer (HTL) 320 disposed between the first electrode 210 and the EML 340 and an electron transport layer (ETL) 360 disposed between the second electrode 220 and the EML 340. In certain embodiments, the light emitting layer 230 may also include at least one of a hole injection layer (HIL) 310 disposed between the first electrode 210 and the HTL 320 and an electron injection layer (EIL) 370 disposed between the second electrode 220 and the ETL 360. Alternatively or additionally, the light emitting layer 230 may also include a first exciton blocking layer, i.e., an electron blocking layer (EBL) 330 disposed between the HTL 320 and the EML 340 and / or a second exciton blocking layer, i.e., a hole blocking layer (HBL) 350 disposed between the EML 340 and the ETL 360.

[0176] The first electrode 210 may be an anode that provides holes to the EML 340. The first electrode 210 may include a conductive material having a relatively high work function value, such as a transparent conductive oxide (TCO). As an example, the first electrode 210 may include, but is not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium cerium oxide (ICO), aluminum-doped zinc oxide (AZO), etc.

[0177] The second electrode 220 may be a cathode that provides electrons to the EML 340. The second electrode 220 may include a conductive material having a relatively low work function value, i.e., a highly reflective material. As an example, the second electrode 220 may include, but is not limited to, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloys thereof, and / or combinations thereof, such as aluminum-magnesium alloy (Al-Mg).

[0178] EML340 may include a host 342 and a dopant (luminophore) 344 in which final light emission occurs. EML 340 may emit blue light. Host 342 may be one or more. For example, when EML340 includes two or more hosts, host 342 may include a P-type (hole-type) host having a beneficial hole affinity and / or hole transport properties, and an N-type (electron-type) host having a beneficial electron affinity and / or electron transport affinity. As an example, host 342 may include an anthracene-containing organic compound having a structure of Chemical Formulas 1 to 6.

[0179] The dopant 344 may emit blue light. As an example, the dopant 344 may be a blue phosphorescent material, a blue fluorescent material, or a blue delayed fluorescent material. In one embodiment, the dopant 344 of the blue phosphorescent material may include, but is not limited to, an organic metal compound having a structure of the following chemical formula 7:

[0180] [Chemical formula 7]

[0181]

[0182] Among them, in chemical formula 7,

[0183] R 21 To R 26 are each independently protium, deuterium, tritium, halogen, cyano, unsubstituted or substituted C 1 To C 20 Alkyl, unsubstituted or substituted C 2 To C 20 Alkenyl, unsubstituted or substituted C 2 To C 20 Alkynyl, unsubstituted or substituted C1 To C 20 Alkoxy, amino, unsubstituted or substituted C 1 To C 20 Alkylamino, unsubstituted or substituted C 1 To C 20 Alkylsilyl, unsubstituted or substituted C 3 To C 30 Cycloalkyl, unsubstituted or substituted C 3 To C 30 Heterocycloalkyl, unsubstituted or substituted C 6 To C 30 Aryl, unsubstituted or substituted C 2 To C 30 Heteroaryl, unsubstituted or substituted C 7 To C 30 Arylalkyl, unsubstituted or substituted C 3 To C 30 Heteroaralkyl, unsubstituted or substituted C 6 To C 30 Aryloxy, unsubstituted or substituted C 2 To C 30 Heteroaryloxy, unsubstituted or substituted C 6 To C 30 Arylamino, unsubstituted or substituted C 2 To C 30 Heteroarylamino, unsubstituted or substituted C 6 To C 30 Arylsilyl, unsubstituted or substituted C 2 To C 30 Heteroarylsilyl, unsubstituted or substituted C 1 To C 20 Alkylgermanyl, unsubstituted or substituted C 6 To C 30 Arylgermanyl, unsubstituted or substituted C 2 To C 30 Heteroarylgermanyl, unsubstituted or substituted C 6 To C 30 triarylmethyl, or unsubstituted or substituted C 2 To C 30 triheteroarylmethyl, wherein when c1 is 2, 3 or 4, each R 21 The same or different from each other, when c2 is 2, 3 or 4, each R 22 The same or different from each other, when c3 is 2, each R 23 The same or different from each other, when c4 is 2 or 3, each R 24are the same as or different from each other, and when c5 is 2, each R 25 are the same as or different from each other, or

[0184] Optionally,

[0185] Two adjacent R 21 , two adjacent R 22 , two adjacent R 23 , two adjacent R 24 and / or two adjacent R 25 further connected to form an unsubstituted or substituted benzene ring;

[0186] c1 and c2 are each independently 0, 1, 2, 3 or 4;

[0187] c3 and c5 are each independently 0, 1 or 2; and

[0188] c4 is 0, 1, 2 or 3.

[0189] For example, the dopant 344 of the blue phosphorescent material may be at least one of the compounds of the following Chemical Formula 8, or a compound selected from but not limited to the following Chemical Formula 8:

[0190] [Chemical formula 8]

[0191]

[0192]

[0193]

[0194] In another embodiment, the dopant 344 of the blue fluorescent material may be a polycyclic organic compound having a boron atom and a nitrogen atom. As an example, the dopant 344 of the blue fluorescent material may have the structure of the following chemical formula 9:

[0195] [Chemical formula 9]

[0196]

[0197] Among them, in chemical formula 9,

[0198] Ring A, Ring B and Ring C are each independently unsubstituted or substituted C 6 To C 30 Aromatic ring, or unsubstituted or substituted C 3 To C 30 heteroaromatic ring;

[0199] Y 1 For boron;

[0200] X 1and X 2 Each independently is NR A , O or S;

[0201] R A is protium, deuterium, tritium, halogen, cyano, unsubstituted or substituted C 1 To C 20 Alkyl, unsubstituted or substituted C 2 To C 20 Alkenyl, unsubstituted or substituted C 2 To C 20 Alkynyl, unsubstituted or substituted C 1 To C 20 Alkoxy, amino, unsubstituted or substituted C 1 To C 20 Alkylamino, unsubstituted or substituted C 1 To C 20 Alkylsilyl, unsubstituted or substituted C 3 To C 30 Cycloalkyl, unsubstituted or substituted C 3 To C 30 Heterocycloalkyl, unsubstituted or substituted C 6 To C 30 Aryl, unsubstituted or substituted C 2 To C 30 Heteroaryl, unsubstituted or substituted C 7 To C 30 Arylalkyl, unsubstituted or substituted C 3 To C 30 Heteroaralkyl, unsubstituted or substituted C 6 To C 30 Aryloxy, unsubstituted or substituted C 2 To C 30 Heteroaryloxy, unsubstituted or substituted C 6 To C 30 Arylamino, unsubstituted or substituted C 2 To C 30 heteroarylamino, unsubstituted or substituted triphenylmethyl, unsubstituted or substituted C 6 To C 30 Arylsilyl, unsubstituted or substituted C 2 To C 30 Heteroarylsilyl, unsubstituted or substituted C 1 To C 20 Alkylgermanyl, unsubstituted or substituted C 6 To C 30 Arylgermanyl, unsubstituted or substituted C 2 To C30 Heteroarylgermanyl, or -L 1 -N-(R B )(R C ),or

[0202] Optionally,

[0203] R A is connected to at least one of ring A, ring B and ring C to form an unsubstituted or substituted C 3 To C 30 Alicyclic ring, unsubstituted or substituted C 3 To C 30 Heteroalicyclic ring, unsubstituted or substituted C 6 To C 30 Aromatic ring, or unsubstituted or substituted C 2 To C 30 heteroaromatic ring;

[0204] L 1 is a single bond, unsubstituted or substituted C 6 To C 30 Arylene, unsubstituted or substituted C 2 To C 30 Heteroarylene, unsubstituted or substituted divalent C 1 To C 30 an aliphatic group, or an unsubstituted or substituted C 3 To C 30 Alicyclic ring and unsubstituted or substituted C 6 To C 30 A divalent fused aromatic ring group; and

[0205] R B and R C are each independently unsubstituted or substituted C 1 To C 20 Alkyl, unsubstituted or substituted C 2 To C 20 Alkenyl, unsubstituted or substituted C 6 To C 30 Aryl, or unsubstituted or substituted C 2 To C 30 Heteroaryl.

[0206] For example, Ring A, Ring B, and Ring C in Chemical Formula 9 can each independently be C 6 To C 20 As an example, the dopant 344 of the blue fluorescent material may have the structure of the following Chemical Formula 10:

[0207] [Chemical formula 10]

[0208]

[0209] Among them, in chemical formula 10,

[0210] R 31 To R 35 are each independently protium, deuterium, tritium, halogen, cyano, unsubstituted or substituted C 1 To C 20 Alkyl, unsubstituted or substituted C 2 To C 20 Alkenyl, unsubstituted or substituted C 2 To C 20 Alkynyl, unsubstituted or substituted C 1 To C 20 Alkoxy, amino, unsubstituted or substituted C 1 To C 20 Alkylamino, unsubstituted or substituted C 1 To C 20 Alkylsilyl, unsubstituted or substituted C 3 To C 30 Cycloalkyl, unsubstituted or substituted C 3 To C 30 Heterocycloalkyl, unsubstituted or substituted C 6 To C 30 Aryl, unsubstituted or substituted C 2 To C 30 Heteroaryl, unsubstituted or substituted C 7 To C 30 Arylalkyl, unsubstituted or substituted C 3 To C 30 Heteroaralkyl, unsubstituted or substituted C 6 To C 30 Aryloxy, unsubstituted or substituted C 2 To C 30 Heteroaryloxy, unsubstituted or substituted C 6 To C 30 Arylamino, unsubstituted or substituted C 2 To C 30 Heteroarylamino, unsubstituted or substituted C 6 To C 30 Arylsilyl, unsubstituted or substituted C 2 To C 30 Heteroarylsilyl, unsubstituted or substituted C 1 To C 20 Alkylgermanyl, unsubstituted or substituted C 6 To C 30Arylgermanyl, or unsubstituted or substituted C 2 To C 30 Heteroarylgermanyl, wherein when d1 is 2, 3 or 4, each R 31 The same or different from each other, when d2 is 2, 3 or 4, each R 32 are the same as or different from each other, and when d3 is 2 or 3, each R 33 Same or different from each other,

[0211] Optionally,

[0212] Two adjacent R 31 , two adjacent R 32 and / or two adjacent R 33 Further connected to form unsubstituted or substituted C 3 To C 30 Alicyclic ring, unsubstituted or substituted C 3 To C 30 Heteroalicyclic ring, unsubstituted or substituted C 6 To C 30 Aromatic ring, or unsubstituted or substituted C 2 To C 30 A heteroaromatic ring, or

[0213] R 34 Can be connected to R 31 The benzene ring connected to R 33 At least one of the benzene rings connected, and R 35 Can be connected to R 32 The benzene ring connected to R 33 at least one of the attached benzene rings;

[0214] d1 and d2 are each independently 0, 1, 2, 3 or 4; and

[0215] d3 is 0, 1, 2, or 3.

[0216] As an example, the dopant 344 of the blue fluorescent material may be, but is not limited to, at least one of the compounds of the following Chemical Formula 11, or a compound selected from, but not limited to, the following Chemical Formula 11:

[0217] [Chemical formula 11]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231] In another embodiment, the dopant 344 of the blue delayed fluorescent material may include, but is not limited to, 4,4,6,6-tetrakis(9H-carbazole-9-yl)-[1,1-biphenyl]-3,3-dicarbonitrile (CzBPCN), 4,6-di(carbazole-9-yl)benzene-1,3-dicarbonitrile (DCzIPN), 10-(4-(diphenylphosphoryl)phenyl)-10H-phenanthene, Oxazine (SPXZPO), 10,10'-(4,4'-(phenylphosphoryl)bis(4,1-phenylene))bis(10H-phen Oxazine) (DPXZPO), 10,10',10"-(4,4',4"-phosphoryltri(benzene-4,1-diyl))tri(10H-phen oxazine)(TPXZPO), 9,9'-(5-(4,6-diphenyl-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole)(DcZTrz), 9,9',9",9"'-((6-phenyl-1,3,5-triazine-2,4-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole)(DDczTrz), 10,10'-(4,4'-(4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenylene))bis(10H-phen oxazine)(2PXZ-TAZ), 2,7-bis(9,9-dimethylacridin-10(9H)-yl)-9,9-dimethyl-9H-thioxanthen-10,10-dioxide (DMTDAc), 9,9'-(4,4'-sulfonylbis(4,1-phenylene))bis(3,6-dimethoxy-9H-carbazole)(DMOC-DPS), 10,10'-(4,4'-sulfonylbis(4,1-phenylene))bis(9,9-dimethyl-9,10-dihydroacridinium)(DMAC-DPS), 10-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9, 10-dihydroacridine (DMAC-TRZ), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracen]-10'-one (ACRSA), 3,6-dibenzoyl-4,5-di(1-methyl-9-phenyl-9H-carbazyl)-2-ethynylbenzonitrile (Cz-VPN), 9,9',9"-(5-(4,6-diphenyl-1,3,5-triazine-2-yl)benzene-1,2,3-triyl)tri(9H-carbazole) (TcZTrz), 4,4,6,6-tetrakis(9H-carbazol-9-yl)-[1,1-biphenyl]-3,3-dicarbonitrile (CzBPCN), 2'-(10H-phenoxy)-1,2-diphenyl-2-carbazol-1,2-diphenyl-3,3-dicarbonitrile (CzBPCN), oxazine-10-yl)-[1,1':3',1"-terphenyl]-5'-nitrile (mPTC), bis(4-(9H-3,9'-bicarbazole-9-yl)phenyl)methanone (CC2BP), 9'-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-3,3",6,6"-quadrphenyl-9,3':6',9"-tri-9H-carbazole (BDPCC-TPTA), 9'- [4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9,3':6',9"-tri-9H-carbazole (BCC-TPTA), 9-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)-3',6'-diphenyl-9H-3,9'-bicarbazole (DPCC-TPTA), 10-(4,6-diphenyl-1,3,5-triazine-2-yl)-10H-phenanthene

[0013] The invention relates to 2-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)-9H-carbazole (Cab-Ph-TRZ), 10-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)-10H-spiro[acridine-9,9'-fluorene] (spiroAC-TRZ), 2,4,6-tris(9H-carbazole-9-yl)-3,5-difluorobenzonitrile (3CzFCN), 2,3,4,6-tetrakis(9H-carbazole-9-yl)-5-fluorobenzonitrile (4CzFCN), 5,9-diphenyl-13b-borane-9,13b-dihydro-5H-quinone[2,3,4-kl]acridine (DABNA-1), and / or combinations thereof.

[0232] The content of the body 342 in the EML 340 may be about 50 wt % to about 99 wt %, for example, about 50 wt % to about 95 wt % or about 60 wt % to about 90 wt %, and the content of the dopant 344 in the EML 340 may be about 1 wt % to about 50 wt %, for example, about 5 wt % to about 50 wt % or about 10 wt % to about 40 wt %, but is not limited thereto. When the EML 340 includes both the P-type body and the N-type body, the P-type body and the N-type body may be mixed in a weight ratio of about 4:1 to about 1:4, for example, about 3:1 to about 1:3, but is not limited thereto.

[0233] The HIL 310 is disposed between the first electrode 210 and the HTL 320, and can improve the interface characteristics between the inorganic first electrode 210 and the organic HTL 320. In one embodiment, the hole injection material in the HIL 310 may include, but is not limited to, 4,4'4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tri(4-carbazol-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPB; NPD), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-4,4'-biphenyl diamine (DNTPD), 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), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDA PB), poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N,N'-diphenyl-N,N'-di[4-(N,N'-diphenyl-amino)phenyl]benzidine (NPNPB), the hole injection material of the following Chemical Formula 12, and / or a combination thereof:

[0234] [Chemical formula 12]

[0235]

[0236] In another embodiment, HIL 310 may include a hole injection host of the following hole transport material and a hole injection dopant of the above hole injection material (a P-type dopant, such as HAT-CN, F4-TCNQ, F6-TCNNQ, and / or the material of Chemical Formula 12). In this case, the content of the hole injection dopant in HIL 310 may be, but is not limited to, about 1 wt % to about 10 wt %. In some embodiments, HIL 310 may be omitted according to the characteristics of OLED D1.

[0237] The HTL 320 and the EML 340 are disposed adjacent to each other between the first electrode 210 and the EML 340. In one embodiment, the hole transport material in the HTL 320 may include, but is not limited to, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (NPD), DNTPD, 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-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), di-[4-(N,N-di-p-tolylamino)phenyl] ]cyclohexane (TAPC), 3,5-di(9H-carbazole-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, the hole transport material of the following chemical formula 13, and / or a combination thereof.

[0238] [Chemical formula 13]

[0239]

[0240] In another embodiment, the hole transport material may include an organic compound having the structure of Chemical Formulas 1 to 6.

[0241] The ETL 360 and the EIL 370 may be sequentially laminated between the EML 340 and the second electrode 220. The electron transport material included in the ETL 360 has high electron mobility so as to stably supply electrons to the EML 340 through rapid electron transport.

[0242] The electronic transmission material in ETL 360 may include at least one of the following: Compounds containing oxadiazole, compounds containing triazole, compounds containing phenanthroline, compounds containing benzo Compounds containing azoles, compounds containing benzothiazoles, compounds containing benzimidazoles and compounds containing triazines.

[0243] For example, the electron transport material in ETL360 may include, but is not limited to, tris-(8-hydroxyquinoline aluminum) (Alq 3)、2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4- triazole (PBD), spiro-PBD, 8-hydroxyquinoline lithium (Liq), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H- 1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene-alternate-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ), TSPO1, 2-[4-(9,10-di-2-naphthalene-2-yl-2-anthracen-2-yl)phenyl]-1-phenyl-1H-benzimidazole (ZADN), the electron transport material of the following Chemical Formula 14, and / or a combination thereof:

[0244] [Chemical formula 14]

[0245]

[0246] In another embodiment, the electron transport material may include an organic compound having the structure of Chemical Formulas 1 to 6.

[0247] The EIL 370 is disposed between the second electrode 220 and the ETL 360 and can improve the physical properties of the second electrode 220 and thus can increase the lifespan of the OLED D1. In one embodiment, the electron injection material in the EIL 370 may include, but is not limited to, alkali metal halides or alkaline earth metal halides such as LiF, CsF, NaF, BaF 2 etc., and / or organometallic compounds such as Liq, lithium benzoate, sodium stearate, etc. In certain embodiments, EIL 370 may be omitted.

[0248] In another embodiment, the ETL 360 and the EIL 370 may have a single layer structure. In this case, the above electron transport materials and / or electron injection materials may be mixed with each other. As an example, the ETL / EIL having a single layer structure may include two or more different electron transport materials. For example, the two electron transport materials in the ETL / EIL are mixed in a weight ratio of about 3:7 to about 7:3, but is not limited thereto.

[0249] When holes are transferred to the second electrode 220 and / or electrons are transferred to the first electrode 210 via the EML 340, the OLED D1 may have a short lifespan and reduced light emission efficiency. To prevent these phenomena, the OLED D1 according to this aspect of the disclosure may have at least one exciton blocking layer adjacent to the EML 340.

[0250] As an example, the OLED D1 may include an EBL 330 between the HTL 320 and the EML 340 to control and prevent electron transfer. In one embodiment, the electron blocking material in the EBL 330 may include, but is not limited to, TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, mCP, mCBP, CuPc, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene, and / or a combination thereof. In another embodiment, the electron blocking material may include an organic compound having a structure of Chemical Formulas 1 to 6.

[0251] In addition, the OLED D1 may further include an HBL 350 as a second exciton blocking layer between the EML 340 and the ETL 360 so that holes cannot be transferred from the EML 340 to the ETL 360. In one embodiment, the hole blocking material in the HBL 350 may include, but is not limited to, at least one of the following: Compounds containing oxadiazole, compounds containing triazole, compounds containing phenanthroline, compounds containing benzo Compounds containing azoles, compounds containing benzothiazoles, compounds containing benzimidazoles and compounds containing triazines.

[0252] As an example, the hole blocking material in the HBL 350 may include a material having a relatively low HOMO energy level compared to the light emitting material in the EML 340. For example, the hole blocking material in the HBL 350 may include, but is not limited to, BCP, BAlq, Alq 3, PBD, spiro-PBD, Liq, bis-4,5-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PYMPM), DPEPO, 9-(6-(9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazole, TSPO1, and / or combinations thereof.

[0253] In another embodiment, the hole blocking material may include an organic compound having the structure of Chemical Formulas 1 to 6.

[0254] As described above, the EML 340 includes the host 342 and the dopant 344 , and the host 342 includes the organic compound having the structure of Chemical Formulas 1 to 6. By applying the organic compound having the structure of Chemical Formulas 1 to 6 to the EML 340 , the light emission lifetime of the OLED D1 may be improved.

[0255] The light-emitting material layer may contain a plurality of dopants (luminophores). Figure 4 A cross-sectional view of an organic light emitting diode having a single light emitting portion according to another embodiment of the present disclosure is shown.

[0256] like Figure 4 As shown, the organic light emitting diode D2 includes a first electrode 210, a second electrode 220 facing the first electrode 210, and a light emitting layer 230A disposed between the first electrode 210 and the second electrode 220. Figure 2 ) includes a red pixel region, a green pixel region and a blue pixel region, and the OLED D2 can be positioned in the blue pixel region.

[0257] The light emitting layer 230A includes a light emitting material layer (EML) 340A disposed between the first electrode 210 and the second electrode 220. The light emitting layer 230A may include at least one of a hole transport layer (HTL) 320 disposed between the first electrode 210 and the EML 340A and an electron transport layer (ETL) 360 disposed between the second electrode 220 and the EML 340A. In certain embodiments, the light emitting layer 230A may further include at least one of a hole injection layer (HIL) 310 disposed between the first electrode 210 and the HTL 320 and an electron injection layer (EIL) 370 disposed between the second electrode 220 and the ETL 360. Alternatively, the light emitting layer 230A may further include a first exciton blocking layer, i.e., an electron blocking layer (EBL) 330 disposed between the HTL 320 and the EML 340A and / or a second exciton blocking layer, i.e., a hole blocking layer (HBL) 350 disposed between the EML 340A and the ETL 360.

[0258] The configuration of the first electrode 210, the second electrode 220, and the light emitting layer 230A except the EML 340A may be the same as that of the reference Figure 3 The configurations of the corresponding components are the same.

[0259] The EML 340A includes a host 342 and a plurality of dopants (luminescent bodies) 344 and 346. The host may be one or more and may include an organic compound having a structure of Chemical Formulas 1 to 6.

[0260] In one embodiment, the first dopant 344 may be a blue delayed fluorescent material and / or a blue phosphorescent material. For example, when the first dopant 344 is a blue phosphorescent material, the first dopant 344 may include, but is not limited to, an organic metal compound having a structure of chemical formula 7 to 8. In another embodiment, when the first dopant 344 is a blue delayed fluorescent material, the first dopant 344 may include, but is not limited to, CzBPCN, DCzIPN, SPXZPO, DPXZPO, TPXZPO, DcZTrz, DDczTrz, 2PXZ-TAZ, DMTDAc, DMOC-DPS, DMAC-DPS, DMAC-TRZ, ACRSA, Cz-VPN, TcZTrz, CzBPCN, mPTC, CC2BP, BDPCC-TPTA, BCC-TPTA, DPCC-TPTA, Phen-TRZ, Cab-Ph-TRZ, SpiroAC-TRZ, 3CzFCN, 4CzFCN, DABNA-1, and / or a combination thereof.

[0261] The second dopant 346 may be a blue fluorescent material. For example, the second dopant 346 may include a polycyclic organic compound having a structure of Chemical Formulas 9 to 11 and containing boron and nitrogen.

[0262] The content of the body 342 in the EML 340A may be about 50 wt % to about 99 wt %, for example, about 50 wt % to about 95 wt % or about 60 wt % to about 90 wt %, the content of the first dopant 344 in the EML 340A may be about 3 wt % to about 50 wt %, for example, about 5 wt % to about 30 wt % or about 5 wt % to about 20 wt %, and the content of the second dopant 346 in the EML 340A may be about 0.5 wt % to about 20 wt %, for example, about 1 wt % to about 10 wt % or about 1 wt % to about 5 wt %, but is not limited thereto. When the EML 340A includes both the P-type body and the N-type body, the P-type body and the N-type body may be mixed in a weight ratio of about 4:1 to about 1:4, for example, about 3:1 to about 1:3, but is not limited thereto.

[0263] The EML 340A includes a second dopant 346 of a fluorescent material to maximize the luminescent properties of a first dopant 344 of a delayed fluorescent material or a phosphorescent material. The first dopant 344 of the phosphorescent material and / or the delayed fluorescent material can utilize both singlet exciton energy and triplet exciton energy through an intersystem crossing (ISC) or reverse intersystem crossing (RISC) mechanism.

[0264] When EML340A includes a second dopant 346 of a fluorescent material having an appropriate energy level compared to the energy level of a first dopant 344 of a phosphorescent material and / or a delayed fluorescent material, the second dopant 346 absorbs the exciton energy released from the first dopant 344, and the second dopant 346 can utilize the absorbed energy to generate 100% singlet excitons to maximize its luminous efficiency.

[0265] In one embodiment, the excited singlet exciton energy (including the singlet exciton energy up-converted from the triplet exciton energy and the initial singlet exciton energy) of the first dopant 344 of the delayed fluorescent material in the EML 340A is mainly transferred to the second dopant 346 of the fluorescent material in the same EML 340A through the Forster resonance energy transfer (FRET) mechanism, and the final light emission occurs at the second dopant 346. In another embodiment, the EML 340A includes the first dopant 344 of the phosphorescent material having a beneficial light emission efficiency and the second dopant 346 of the fluorescent material having a beneficial color purity, so that the EML 340A can achieve phosphor-sensitized fluorescence (PSF).

[0266] A compound having an absorption wavelength with a large overlap area relative to the emission wavelength of the first dopant 344 may be selected as the second dopant 346, so that the exciton energy generated at the first dopant 344 can be effectively transferred to the second dopant 346. The final luminescent second dopant 346 has a narrow full-width at half maximum (FWHM), so that the second dopant 346 can exhibit a beneficial color purity.

[0267] The first dopant 344 having delayed fluorescence characteristics and / or phosphorescence characteristics may receive exciton energy from the host 342. The first dopant 344 may generate both singlet exciton energy and triplet exciton energy through ISC or RISC, and may effectively transfer the generated exciton energy to the second dopant 346. The exciton energy generated at the host 342 is transferred to the second dopant 346 having a beneficial color purity via the first dopant 344 having a beneficial luminous efficiency. Therefore, the driving voltage of the OLED D2 may be reduced, and the luminous efficiency, luminous lifetime, and / or color purity of the OLED D2 may be further improved.

[0268] Figure 3 and Figure 4 OLED D1 and OLED D2 each having a single light emitting portion and emitting blue light are shown in FIG. 1 and FIG. 2 . In another embodiment, the organic light emitting display device can realize full colors including white. Figure 5 A schematic cross-sectional view of an organic light emitting display device according to another embodiment of the present disclosure is shown.

[0269] like Figure 5 As shown, the organic light-emitting display device 400 includes: a first substrate 402 that defines each of a red pixel region RP, a green pixel region GP, ​​and a blue pixel region BP; a second substrate 404 facing the first substrate 402; a thin film transistor Tr on the first substrate 402; an OLED D that is disposed between the first substrate 402 and the second substrate 404 and emits white (W) light; and a color filter layer 480 that is disposed between the OLED D and the second substrate 404.

[0270] The first substrate 402 and the second substrate 404 may each include, but are not limited to, glass, flexible materials, and / or polymer plastics. For example, the first substrate 402 and the second substrate 404 may each be made of PI, PES, PEN, PET, PC, and / or a combination thereof. In some embodiments, the second substrate 404 may be omitted. The first substrate 402 on which the thin film transistor Tr and the OLED D are arranged forms an array substrate.

[0271] A buffer layer 406 may be disposed on the first substrate 402. A thin film transistor Tr is disposed on the buffer layer 406 corresponding to each of the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP. In some embodiments, the buffer layer 406 may be omitted.

[0272] A semiconductor layer 410 is disposed on the buffer layer 406. The semiconductor layer 410 may be made of or include an oxide semiconductor material or polysilicon.

[0273] On the semiconductor layer 410, a gate insulating layer 420 is provided which contains an insulating material, for example an inorganic insulating material such as silicon oxide (SiO x , where 0 < x ≤ 2) or silicon nitride (SiN x , where 0 < x ≤ 2).

[0274] Above the gate insulating layer 420, a gate electrode 430 made of a conductive material such as metal is provided to correspond to the center of the semiconductor layer 410. On the gate electrode 430, an interlayer insulating layer 440 is provided which contains an insulating material, for example an inorganic insulating material such as SiO x (where 0 < x ≤ 2) or SiN x (where 0 < x ≤ 2), or an organic insulating material such as benzocyclobutene or photoacrylic.

[0275] The interlayer insulating layer 440 has a first semiconductor layer contact hole 442 and a second semiconductor layer contact hole 444 that expose a part of the semiconductor layer 410's surface closer to the opposite end than the center or do not cover a part of the semiconductor layer 410's surface closer to the opposite end than the center. The first semiconductor layer contact hole 442 and the second semiconductor layer contact hole 444 are provided on opposite sides of the gate electrode 430 and are spaced apart from the gate electrode 430.

[0276] On the interlayer insulating layer 440, a source electrode 452 and a drain electrode 454 made of a conductive material such as metal or containing a conductive material such as metal are provided. The source electrode 452 and the drain electrode 454 are spaced apart from each other with respect to the gate electrode 430. The source electrode 452 and the drain electrode 454 contact both sides of the semiconductor layer 410 through the first semiconductor layer contact hole 442 and the second semiconductor layer contact hole 444 respectively.

[0277] The semiconductor layer 410, the gate electrode 430, the source electrode 452, and the drain electrode 454 constitute a thin film transistor Tr that serves as a driving element.

[0278] Although not shown in Figure 5 , a gate line GL and a data line DL that cross each other to define the pixel region P, and a switching thin film transistor Ts connected to the gate line GL and the data line DL can also be formed in the pixel region P. The switching thin film transistor Ts is connected to the thin film transistor Tr that serves as a driving element. In addition, a power supply line PL is spaced apart parallel to the gate line GL or the data line DL, and the thin film transistor Tr can also include a storage capacitor Cst configured to keep the voltage of the gate electrode 430 constant for one frame.

[0279] A passivation layer 460 is disposed on the source electrode 452 and the drain electrode 454 and covers the thin film transistor Tr over the entire first substrate 402. The passivation layer 460 has a drain contact hole 462 that exposes or does not cover the drain electrode 454 of the thin film transistor Tr.

[0280] The OLED D is positioned on the passivation layer 460. The OLED D includes a first electrode 510 connected to the drain electrode 454 of the thin film transistor Tr, a second electrode 520 facing the first electrode 510, and a light emitting layer 530 disposed between the first electrode 510 and the second electrode 520.

[0281] The first electrode 510 formed for each pixel region RP, GP or BP may be an anode and may include a conductive material having a relatively high work function value. Alternatively, a reflective electrode or a reflective layer may be provided under the first electrode 510. For example, the reflective electrode or the reflective layer may include, but is not limited to, Ag or an APC alloy.

[0282] A bank layer 464 is disposed on the passivation layer 460 to cover the edge of the first electrode 510. The bank layer 464 exposes or does not cover the center of the first electrode 510 corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP. In some embodiments, the bank layer 464 may be omitted.

[0283] A light-emitting layer 530 including a plurality of light-emitting portions is disposed on the first electrode 510. Figure 6 and Figure 7 As shown, the light emitting layer 530 or the light emitting layer 530A may include a plurality of light emitting portions 600, 700, 700A and 800 and at least one charge generation layer 680 and 780. The light emitting portions 600, 700, 700A and 800 each include at least one light emitting material layer and may further include a HIL, HTL, EBL, HBL, ETL and / or EIL.

[0284] The second electrode 520 may be disposed on the first substrate 402 on which the light emitting layer 530 may be disposed. The second electrode 520 may be disposed over the entire display area, may include a conductive material having a relatively low work function value compared to the first electrode 510, and may be a cathode. Since light emitted from the light emitting layer 530 is incident to the color filter layer 480 through the second electrode 520 in the organic light emitting display device 400 according to the second embodiment of the present disclosure, the second electrode 520 has a thin thickness so that the light can be transmitted.

[0285] The color filter layer 480 is disposed on the OLED D and includes a red color filter pattern 482, a green color filter pattern 484, and a blue color filter pattern 486, each of which is disposed corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. Figure 5 , but the color filter layer 480 may be attached to the OLED D through an adhesive layer. Alternatively, the color filter layer 480 may be directly disposed on the OLED D.

[0286] In addition, an encapsulation film 470 may be disposed on the second electrode 520 to prevent or reduce external moisture from penetrating into the OLED D. The encapsulation film 470 may have, but is not limited to, a laminated structure including a first inorganic insulating film, an organic insulating film, and a second inorganic insulating film ( Figure 2 170 in). In addition, a polarizing plate may be attached to the second substrate 404 to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate.

[0287] exist Figure 5 In the embodiment of the present invention, light emitted from the OLED D passes through the second electrode 520 and the color filter layer 480 is disposed on the OLED D. In this case, the organic light emitting display device 400 may be a top emission type. Alternatively, when the organic light emitting display device 400 is a bottom emission type, light emitted from the OLED D passes through the first electrode 510 and the color filter layer 480 may be disposed between the OLED D and the first substrate 402.

[0288] In addition, a color conversion layer may be formed or disposed 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, each of which is disposed corresponding to each pixel (RP, GP, and BP) to convert white (W) light into each of red light, green light, and blue light, respectively. Alternatively, the organic light emitting display device 400 may include a color conversion layer instead of the color filter layer 480.

[0289] As described above, white (W) light emitted from the OLED D passes through the red filter pattern 482, the green filter pattern 484, and the blue filter pattern 486 respectively arranged corresponding to the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, so that red light, green light, and blue light are displayed in the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP.

[0290] An OLED that may be applied to an organic light emitting display device will be described in more detail. Figure 6 A schematic cross-sectional view of an organic light emitting diode having a series structure of two light emitting portions is shown.

[0291] like Figure 6As shown, the OLED D3 according to the embodiment of the present disclosure includes a first electrode 510 and a second electrode 520 facing each other and a light emitting layer 530 disposed between the first electrode 510 and the second electrode 520. The light emitting layer 530 includes a first light emitting portion 600 disposed between the first electrode 510 and the second electrode 520, a second light emitting portion 700 disposed between the first light emitting portion 600 and the second electrode 520, and a charge generation layer (CGL) 680 disposed between the first light emitting portion 600 and the second light emitting portion 700.

[0292] The first electrode 510 may be an anode and may include a conductive material having a relatively high work function value, such as TCO. For example, the first electrode 510 may include, but is not limited to, ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, etc. The second electrode 520 may be a cathode and may include a conductive material having a relatively low work function value. For example, the second electrode 520 may include, but is not limited to, a highly reflective material, such as Al, Mg, Ca, Ag, alloys thereof, and / or combinations thereof, such as Al-Mg.

[0293] The first light emitting portion 600 includes a first EML (EML1) 640. The first light emitting portion 600 may further include at least one of a hole injection layer (HIL) 610 disposed between the first electrode 510 and the EML1 640, a first hole transport layer (HTL1) 620 disposed between the HIL 610 and the EML1 640, and a first electron transport layer (ETL1) 660 disposed between the EML1 640 and the CGL 680. Alternatively or additionally, the first light emitting portion 600 may further include a first electron blocking layer (EBL1) 630 disposed between the HTL1 620 and the EML1 640 and / or a first hole blocking layer (HBL1) 650 disposed between the EML1 640 and the ETL1 660.

[0294] The second light emitting portion 700 includes a second EML (EML2) 740. The second light emitting portion 700 may further include at least one of a second hole transport layer (HTL2) 720 disposed between the CGL 680 and the EML2 740, a second electron transport layer (ETL2) 760 disposed between the second electrode 520 and the EML2 740, and an electron injection layer 770 disposed between the second electrode 520 and the ETL2 760. Alternatively or additionally, the second light emitting portion 700 may further include a second electron blocking layer (EBL2) 730 disposed between the HTL2 720 and the EML2 740 and / or a second hole blocking layer (HBL2) 750 disposed between the EML2 740 and the ETL2 760.

[0295] One of EML1 640 and EML2 740 may include an organic compound having a structure of Chemical Formulas 1 to 6. One of EML1 640 and EML2 740 may emit blue light, and the other of EML1 640 and EML2 740 may emit red to green light, so that OLED D3 may realize white (W) light emission. Hereinafter, OLED D3 in which EML1 640 includes an organic compound having a structure of Chemical Formulas 1 to 6 to emit blue light, and EML2 740 emits red to green light will be described in detail.

[0296] The HIL 610 is disposed between the first electrode 510 and the HTL1 620 and improves the interface characteristics between the inorganic first electrode 510 and the organic HTL1 620. In an exemplary embodiment, the hole injection material in the HIL 610 may include, but is not limited to, MTDATA, NATA, 1T-NATA, 2T-NATA, CuPc, TCTA, NPB (NPD), DNDPT, HAT-CN, F4-TCNQ, F6-TCNNQ, TDAPB, PEDOT / PSS, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, NPNPB, a hole injection material of Chemical Formula 12, and / or a combination thereof. In another embodiment, the HIL 610 may include a hole injection host of a hole transport material and a hole injection dopant of a hole injection material. In certain embodiments, the HIL 610 may be omitted according to the OLED D3 characteristics.

[0297] In one embodiment, the hole transport material in each of HTL1 620 and HTL2 720 may independently include, but is not limited to, TPD, NPB (NPD), DNTPD, CBP, poly-TPD, TFB, TAPC, DCDPA, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, a hole transport material of Chemical Formula 13, and / or a combination thereof. In another embodiment, the hole transport material may include an organic compound having a structure of Chemical Formulas 1 to 6.

[0298] Each of ETL1 660 and ETL2 760 promotes electron transport in each of the first light-emitting portion 600 and the second light-emitting portion 700. As an example, the electron transport material in ETL1 660 and ETL2 760 can independently include at least one of the following: Compounds containing oxadiazole, compounds containing triazole, compounds containing phenanthroline, compounds containing benzo For example, the electron transport materials in ETL1660 and ETL2760 may each include, but are not limited to, Alq 3 , PBD, spiro-PBD, Liq, TPBi, BAlq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ, TSPO1, ZADN, the electron transport material of Chemical Formula 14, and / or a combination thereof. In another embodiment, the electron transport material may include an organic compound having the structure of Chemical Formulas 1 to 6.

[0299] The EIL 770 is disposed between the second electrode 520 and the ETL2 760 and can improve the physical properties of the second electrode 520 and thus can increase the lifespan of the OLED D3. In one embodiment, the electron injection material in the EIL 770 may include, but is not limited to, alkali metal halides or alkaline earth metal halides such as LiF, CsF, NaF, BaF 2 etc., and / or organometallic compounds such as Liq, lithium benzoate, sodium stearate, etc.

[0300] The electron blocking materials in EBL1 630 and EBL2 730 may each independently include, but are not limited to, TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, mCP, mCBP, CuPc, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene, and / or combinations thereof. In another embodiment, the electron blocking material may include an organic compound having a structure of Chemical Formulas 1 to 6.

[0301] The hole blocking materials in HBL1 650 and HBL2 750 may each include, but are not limited to, at least one of the following: Compounds containing oxadiazole, compounds containing triazole, compounds containing phenanthroline, compounds containing benzo For example, the hole blocking materials in HBL1 650 and HBL2 750 may each independently include, but are not limited to, BCP, BAlq, Alq 3 , PBD, spiro-PBD, Liq, B3PYMPM, DPEPO, 9-(6-(9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazole, TSPO1, and / or combinations thereof. In another embodiment, the hole blocking material may include an organic compound having a structure of Chemical Formulas 1 to 6.

[0302] The CGL 680 is disposed between the first light emitting portion 600 and the second light emitting portion 700. The CGL 680 includes an N-type CGL (N-CGL) 685 disposed adjacent to the first light emitting portion 600 and a P-type CGL (P-CGL) 690 disposed adjacent to the second light emitting portion 700. The N-CGL 685 injects electrons into the EML1 640 of the first light emitting portion 600, and the P-CGL 690 injects holes into the EML2 740 of the second light emitting portion 700.

[0303] N-CGL 685 may be an organic layer doped with alkali metals (e.g., Li, Na, K, and Cs) and / or alkaline earth metals (e.g., Mg, Sr, Ba, and Ra). For example, the host in N-CGL 685 may include, but is not limited to, Bphen and MTDATA. The content of the alkali metal or alkaline earth metal in N-CGL 685 may be, but is not limited to, about 0.01 wt % to about 30 wt %.

[0304] P-CGL 690 may include, but is not limited to, tungsten oxide (WO x ), molybdenum oxide (MoO x ), Be 2 O 3 ), vanadium oxide (V 2 O 5 ), and / or inorganic materials selected from NPD, DNTPD, HAT-CN, F4-TCNQ, F6-TCNNQ, TPD, N,N,N',N'-tetranaphthyl-benzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylene dicarboximide (PTCDI-C8), and / or organic materials selected from combinations thereof.

[0305] In one embodiment, EML1 640 may be a blue EML. In this case, EML1 640 may be a blue EML, a sky blue EML, or a dark blue EML. EML1 640 includes a host 642 and a dopant (luminescent body) 644 in which final light emission occurs.

[0306] The host 642 may include an organic compound having a structure of Chemical Formulas 1 to 6. The EML1 640 may include one or more hosts 642 .

[0307] The dopant 644 may include at least one of a blue phosphorescent material, a blue fluorescent material, and a blue delayed fluorescent material. As an example, the dopant 644 of the blue phosphorescent material may include an organic metal compound having a structure of Chemical Formulas 7 to 8. The dopant 644 of the blue fluorescent material may include an organic compound having a structure of Chemical Formulas 9 to 11. The dopant 644 of the blue delayed fluorescent material may be the same as the reference Figure 3 and Figure 4 The same blue delayed fluorescent material.

[0308] In one embodiment, the dopant 644 may be a single dopant. In another embodiment, the dopant 644 may include a first dopant of a delayed fluorescent material and / or a phosphorescent material and a second dopant of a fluorescent material ( Figure 4 ). The contents of the host 642 and dopant 644 in EML1 640 can be compared with those in reference Figure 3 and Figure 4 The contents of the corresponding materials are the same.

[0309] The EML2 740 may include a lower light emitting material layer (lower EML, first layer) 740A disposed between the EBL2 730 and the HBL2 750 and an upper light emitting material layer (upper EML, second layer) 740B disposed between the lower EML 740A and the HBL2 750. One of the first layer 740A and the second layer 740B may emit red light, and the other of the first layer 740A and the second layer 740B may emit green light. Hereinafter, the EML2 740 in which the first layer 740A emits red light and the second layer 740B emits green light will be described in detail.

[0310] The first layer 740A may include a red host and a red dopant (luminescent body). For example, the red host may include a bipolar red host, or include a P-type red host and an N-type red host.

[0311] For example, the P-type red host may include, but is not limited to, an organic compound containing a biscarbazole, an organic compound containing an arylamine or heteroarylamine having at least one fused aromatic and / or fused heteroaromatic moiety, and / or an organic compound containing an arylamine or heteroarylamine having a spirofluorene moiety. As an example, the N-type red host may include, but is not limited to, an organic compound containing an azine, an organic compound containing a benzimidazole, and / or an organic compound containing a quinazoline.

[0312] For example, the red host may include, but is not limited to, mCP-CN, CBP, mCBP, mCP, DPEPO, 2,8-bis(diphenylphosphoryl)dibenzothiophene (PPT), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), 2,6-di(9H-carbazole-9-yl)pyridine (PYD-2Cz), 2,8-di(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, 9-(9-phenyl-9H-carbazole-6-yl)-9H-carbazole (CCP), 4-(3-(triphenylene-2-yl)phenyl )dibenzo[b,d]thiophene, 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(6-(9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazole, 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 1,3,5-tri(carbazole-9-yl)phenyl )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 (spiro-CBP), 3,6-bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1), and / or combinations thereof.

[0313] The red dopant may include at least one of a red phosphorescent material, a red fluorescent material, and a red delayed fluorescent material. For example, the red dopant may include, but is not limited to, bis[2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-dionatoic acid)iridium(III), bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III)(Hex-Ir(phq) 2 (acac)), tris[2-(4-n-hexylphenyl)quinolinol]iridium(III) (Hex-Ir(phq) 3 )、Tris[2-phenyl-4-methylquinoline]iridium(III) (Ir(Mphq) 3 ), bis(2-phenylquinoline)(2,2,6,6-tetramethylheptene-3,5-dionato)iridium(III)(Ir(dpm)PQ 2), bis(phenylisoquinoline)(2,2,6,6-tetramethylheptene-3,5-dionato)iridium(III)(Ir(dpm)(piq) 2 ), bis(1-phenylisoquinoline)(acetylacetonate)iridium(III)(Ir(piq) 2 (acac))、bis[(4-n-hexylphenyl)isoquinolinol](acetylacetonate)iridium(III) (Hex-Ir(piq) 2 (acac)), tris[2-(4-n-hexylphenyl)quinolinol]iridium(III) (Hex-Ir(piq) 3 ), tris(2-(3-methylphenyl)-7-methyl-quinolinol)iridium (Ir(dmpq) 3 ), bis[2-(2-methylphenyl)-7-methyl-quinoline](acetylacetonate)iridium(III) (Ir(dmpq) 2 (acac)), bis[2-(3,5-dimethylphenyl)-4-methyl-quinolinol](acetylacetonate)iridium(III) (Ir(mphmq) 2 (acac)), tris(dibenzoylmethane)mono(1,10-phenanthroline)europium(III) (Eu(dbm) 3 (phen)), and / or combinations thereof.

[0314] As an example, the content of the red host in the first layer 740A may be about 50 wt % to about 99 wt %, such as about 60 wt % to about 99 wt % or about 80 wt % to about 95 wt %, and the content of the red dopant in the first layer 740A may be about 1 wt % to about 50 wt %, such as about 1 wt % to about 40 wt % or about 5 wt % to about 20 wt %, but is not limited thereto. When the first layer 740A includes both the P-type red host and the N-type red host, the P-type red host and the N-type red host may be mixed in a weight ratio of about 4:1 to about 1:4, such as about 3:1 to about 1:3, but is not limited thereto.

[0315] The second layer 740B may include a green host and a green dopant (luminescent body). For example, the green host may include a bipolar green host, or include a P-type green host and an N-type green host. The green host may be the same as the above red host.

[0316] The green dopant may include at least one of a green phosphorescent material, a green fluorescent material, and a green delayed fluorescent material. In one embodiment, the green dopant may include, but is not limited to, [bis(2-phenylpyridine)](pyridyl-2-benzofurano[2,3-b]pyridine)iridium, tris(2-phenylpyridine)iridium(III) (Ir(ppy) 3 ), face-tris(2-phenylpyridine)iridium(III) (face-Ir(ppy) 3), bis(2-phenylpyridine)(acetylacetonate)iridium(III) (Ir(ppy) 2 (acac)), tris[2-(p-tolyl)pyridine]iridium(III) (Ir(mppy) 3 ), bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium(III)(Ir(npy) 2 acac), tris(2-phenyl-3-methyl-pyridine)iridium(Ir(3mppy) 3 ), f-tri(2-(3-p-xylyl)phenyl)pyridineiridium(III) (TEG), and / or combinations thereof.

[0317] In another embodiment, the green dopant having delayed fluorescence characteristics may include, but is not limited to, DMAC-TRZ, DMAC-DPS, ACRSA, Cz-VPN, TcZTrz, 9,9'-(5-(4,6-diphenyl-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole) (DcZTrz), 9,9',9",9"'-((6-phenyl-1,3,5-triazine-2,4-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole) (DDczTrz), CC2BP, BDPCC-TPTA, BCC-TPTA, DMOC-DPS, DPCC-TPTA, Phen-TRZ, Cab-Ph-TRZ, 1,2,3,5-tetrakis(3,6-carbazole-9-yl)-4,6-dicyanobenzene (4CzIPN), 4CzFCN, -4-(2,5-di)(phenyl9H-yl)-carbazole-10H-9-spiro[)aziridine-9, di-9'-carbonitrile tantalum (]2, CzspiroPNA)C, -T1R0-Z(, 4-(and 4, / 6- or di-benzene combination-1.,3,5-triazine

[0318] As an example, the content of the green host in the second layer 740B may be about 50 wt % to about 99 wt %, such as about 60 wt % to about 99 wt % or about 80 wt % to about 95 wt %, and the content of the green dopant in the second layer 740B may be about 1 wt % to about 50 wt %, such as about 1 wt % to about 40 wt % or about 5 wt % to about 20 wt %, but is not limited thereto. When the second layer 740B includes a P-type green host and an N-type green host, the P-type green host and the N-type green host may be mixed in a weight ratio of about 4:1 to about 1:4, such as about 3:1 to about 1:3, but is not limited thereto.

[0319] Optionally, the EML2 740 may further include a third layer ( 740B) disposed between the first layer 740A of the red EML and the second layer 740B of the green EML that may emit yellow-green light. Figure 7 740C in.

[0320] The OLED D3 according to the embodiment has a tandem structure and includes organic compounds having structures of Chemical Formulae 1 to 6. The luminescence lifetime of the OLED D3 including the anthracene-containing organic compound having reduced reactivity may be improved.

[0321] The OLED may have three or more light emitting parts to form a tandem structure. Figure 7 FIG. 2 is a schematic cross-sectional view showing an organic light emitting diode according to still another embodiment of the present disclosure.

[0322] like Figure 7 As shown, the OLED D4 includes a first electrode 510 and a second electrode 520 facing each other and a light emitting layer 530A disposed between the first electrode 510 and the second electrode 520. The light emitting layer 530A includes a first light emitting portion 600 disposed between the first electrode 510 and the second electrode 520, a second light emitting portion 700A disposed between the first light emitting portion 600 and the second electrode 520, a third light emitting portion 800 disposed between the second light emitting portion 700A and the second electrode 520, a first charge generation layer (CGL1) 680 disposed between the first light emitting portion 600 and the second light emitting portion 700A, and a second charge generation layer (CGL2) 780 disposed between the second light emitting portion 700A and the third light emitting portion 800.

[0323] The first light emitting portion 600 includes a first light emitting material layer (EML1) 640. The first light emitting portion 600 may further include at least one of a hole injection layer (HIL) 610 disposed between the first electrode 510 and the EML1 640, a first hole transport layer (HTL1) 620 disposed between the HIL 610 and the EML1 640, and a first electron transport layer (ETL1) 660 disposed between the EML1 640 and the CGL1 680. Alternatively or additionally, the first light emitting portion 600 may further include a first electron blocking layer (EBL1) 630 disposed between the HTL1 620 and the EML1 640 and / or a first hole blocking layer (HBL1) 650 disposed between the EML1 640 and the ETL1 660.

[0324] The second light emitting portion 700A includes a second light emitting material layer (EML2) 740'. The second light emitting portion 700A may also include at least one of a second hole transport layer (HTL2) 720 disposed between CGL1 680 and EML2 740' and a second electron transport layer (ETL2) 760 disposed between EML2 740' and CGL2 780. Alternatively or additionally, the second light emitting portion 700A may also include a second electron blocking layer (EBL2) 730 disposed between HTL2 720 and EML2 740' and / or a second hole blocking layer (HBL2) 750 disposed between EML2 740' and ETL2 760.

[0325] The third light emitting portion 800 includes a third light emitting material layer (EML3) 840. The third light emitting portion 800 may further include at least one of a third hole transport layer (HTL3) 820 disposed between the CGL2 780 and the EML3 840, a third electron transport layer (ETL3) 860 disposed between the second electrode 520 and the EML3 840, and an electron injection layer (EIL) 870 disposed between the second electrode 520 and the ETL3 860. Alternatively or additionally, the third light emitting portion 800 may further include a third electron blocking layer (EBL3) 830 disposed between the HTL3 820 and the EML3 840 and / or a third hole blocking layer (HBL3) 850 disposed between the EML3 840 and the ETL3 860.

[0326] CGL1 680 is disposed between the first light emitting portion 600 and the second light emitting portion 700A, and CGL2 780 is disposed between the second light emitting portion 700A and the third light emitting portion 800. CGL1 680 includes a first N-type charge generation layer (N-CGL1) 685 disposed adjacent to the first light emitting portion 600 and a first P-type charge generation layer (P-CGL1) 690 disposed adjacent to the second light emitting portion 700A. CGL2 780 includes a second N-type charge generation layer (N-CGL2) 785 disposed adjacent to the second light emitting portion 700A and a second P-type charge generation layer (P-CGL2) 790 disposed adjacent to the third light emitting portion 800. N-CGL1 685 and N-CGL2 785 each inject electrons into EML1 640 of the first light emitting portion 600 and EML2 740' of the second light emitting portion 700A, respectively, and P-CGL1 690 and P-CGL2 790 each inject holes into EML2 740' of the second light emitting portion 700A and EML3 840 of the third light emitting portion 800, respectively.

[0327] The materials included in HIL 610, HTL1 to HTL3 620, 720 and 820, EBL1 to EBL3 630, 730 and 830, HBL1 to HBL3 650, 750 and 850, ETL1 to ETL3 660, 760 and 860, EIL 870, CGL1 680 and CGL2 780 can be compared with those in reference Figure 3 and Figure 6 The materials are the same.

[0328] In one embodiment, at least one of EML1 640, EML2 740', and EML3 840 may include an organic compound having a structure of Chemical Formulas 1 to 6. For example, at least one of EML1 640, EML2 740', and EML3 840 may emit blue light, and the rest of EML1 640, EML2 740', and EML3 840 may emit red to green light, so that OLED D4 may achieve white (W) light emission. Hereinafter, OLED D4 in which EML2 740' emits red to green light, and EML1 640 and EML3 840 each emit blue light will be described in detail.

[0329] Each of EML1 640 and EML3 840 may be independently a blue EML. In this case, each of EML1 640 and EML3 840 may be independently a blue EML, a sky blue EML, or a dark blue EML. Each of EML1 640 and EML3 840 may independently include at least one blue host and at least one blue dopant. For example, EML1 640 may include a host 642 and a dopant (luminescent body) 644 in which final light emission occurs, and EML3 840 may include a host 842 and a dopant 844 in which final light emission occurs.

[0330] In one embodiment, the hosts 642 and 842 may each independently include an organic compound having a structure of Chemical Formulae 1 to 6. The hosts 642 and 842 may each be two or more kinds.

[0331] The dopants 644 and 844 may each independently include at least one of a blue phosphorescent material, a blue fluorescent material, and a blue delayed fluorescent material. As an example, the dopant 644 and / or 844 of the blue phosphorescent material may include an organic metal compound having a structure of Chemical Formulas 7 to 8. In another embodiment, the dopant 644 and / or 844 of the blue fluorescent material may include an organic compound having a structure of Chemical Formulas 9 to 11.

[0332] In one embodiment, dopants 644 and 844 can each independently be a single dopant. In another embodiment, dopants 644 and 844 can each independently include a first dopant of a delayed fluorescent material and / or a phosphorescent material and a second dopant of a fluorescent material ( Figure 4 ). The contents of the host 642 or 842 and the dopant 644 or 844 in EML1 640 and EML3 840 may be the same as those in reference Figure 3 and Figure 4 The contents of the corresponding components are the same.

[0333] Alternatively or additionally, the host 642 and / or the dopant 644 in EML1 640 may be the same as or different from the host 842 and / or the dopant 844 in EML3 840 , respectively, in terms of color and / or luminous efficiency.

[0334] The EML2 740′ may include a lower light emitting material layer (first layer) 740A disposed between the EBL2 730 and the HBL2 750, an upper light emitting material layer (second layer) 740B disposed between the first layer 740A and the HBL2 750, and an intermediate light emitting material layer (third layer) 740C disposed between the first layer 740A and the second layer 740B. One of the first layer 740A and the second layer 740B may emit red light, and the other of the first layer 740A and the second layer 740B may emit green light. Hereinafter, the EML2 740′ in which the first layer 740A emits red light and the second layer 740B emits green light will be described in detail.

[0335] The first layer 740A may include a red host and a red dopant. The materials and contents of the red host and the red dopant in the first layer 740A may be the same as those in the reference Figure 6 The second layer 740B may include a green host and a green dopant. The materials and contents of the green host and the green dopant in the second layer 740B may be the same as those in the reference Figure 6 The same.

[0336] The third layer 740C may be a yellow-green EML. The third layer 740C may include a yellow-green host and a yellow-green dopant (luminescent body). For example, the yellow-green host may include a bipolar yellow-green host, or include a P-type yellow-green host and an N-type yellow-green host. For example, the yellow-green host may be the same as the reference Figure 6 The red body and / or green body are the same.

[0337] The yellow-green dopant may include at least one of a yellow-green phosphorescent material, a yellow-green fluorescent material, and a yellow-green delayed fluorescent material. For example, the yellow-green dopant may include, but is 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) (face-Ir(ppy) 2 Pc), bis(2-(2,4-difluorophenyl)quinoline)(picolinic acid)iridium(III) (FPQIrpic), bis(4-phenylthieno[3,2-c]pyrido-N,C2')(acetylacetonate)iridium(III) (PO-01), and / or combinations thereof. In another embodiment, the yellow-green dopant may include an organometallic compound having chemical formulas 7 to 8. In certain embodiments, the third layer 740C may be omitted.

[0338] When the third layer 740C includes at least one yellow-green host, the content of the yellow-green host in the third layer 740C may be about 50 wt % to about 99 wt %, for example, about 60 wt % to about 99 wt % or about 80 wt % to about 95 wt %, and the content of the yellow-green dopant in the third layer 740C may be about 1 wt % to about 50 wt %, for example, about 1 wt % to about 40 wt % or about 5 wt % to about 20 wt %, but is not limited thereto. When the third layer 740C includes a P-type yellow-green host and an N-type yellow-green host, the P-type yellow-green host and the N-type yellow-green host may be mixed in a weight ratio of about 4:1 to about 1:4, for example, about 3:1 to about 1:3, but is not limited thereto.

[0339] The OLED D4 according to the embodiment has a tandem structure and includes organic compounds having structures of Chemical Formulae 1 to 6. The OLED D4 including the organic compounds and three light emitting parts enables its light emission lifetime to be improved, and emits white light.

[0340] exist Figure 7, an OLED D4 having three light-emitting parts is shown. If necessary, the organic light-emitting diode may have four or more light-emitting parts. As an example, when the OLED has four light-emitting parts, two light-emitting parts may emit blue light, another light-emitting part may emit red light, and the remaining light-emitting part may emit green light, so that the OLED can achieve white (W) light emission.

[0341] Synthesis Example 1: Synthesis of Compound C-25

[0342] (1) Synthesis of intermediate 1-1

[0343] [Reaction formula 1-1]

[0344]

[0345] (5-Chloro-2-methoxyphenyl)boronic acid (25 g, 134.12 mmol), bromobenzene (21.05 g, 201.18 mmol), palladium-tetrakis(triphenylphosphine) (Pd(PPh 3 ) 4 , 6.19 g, 5.36 mmol), K 2 CO 3 (37.07 g, 268.24 mmol), toluene (700 ml), distilled water (180 ml) and ethanol (80 ml) were mixed, and then the solution was refluxed at 120° C. for 4 hours under stirring. The solution was cooled to room temperature, distilled water was added to the solution, and the organic layer was extracted with ethyl acetate. MgSO was added to the extracted organic layer to be dried. 4 The organic layer was filtered under reduced pressure. The organic layer was distilled under reduced pressure and purified by column chromatography to obtain Intermediate 1-1 (28 g, 95.46%).

[0346] (2) Synthesis of intermediate 1-2

[0347] [Reaction 1-2]

[0348]

[0349] Intermediate 1-1 (28 g, 128.04 mmol), 2-naphthylboronic acid (26.42 g, 153.6 mmol), palladium (II) acetate (Pd(OAc) 2 , 1.43 g, 6.40 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S phos, 6.30 g, 15.36 mmol), K 3 PO 4(54.35 g, 256.08 mmol), toluene (700 ml), distilled water (150 ml), and isopropanol (80 ml) were mixed, and the solution was refluxed at 120°C for 3 hours. The solution was cooled to room temperature, distilled water was added to the solution, and the organic layer was extracted with ethyl acetate. MgSO was added to the extracted organic layer to be dried. 4 The organic layer was distilled under reduced pressure and purified by column chromatography to obtain Intermediate 1-2 (17.5 g, 44.02%).

[0350] (3) Synthesis of intermediate 1-3

[0351] [Reaction 1-3]

[0352]

[0353] Intermediate 1-2 (17.5 g, 56.37 mmol) was dissolved in dichloromethane (563 ml), and boron tribromide (BBr) was added to the solution at 0 °C. 3 , 1M in dichloromethane, 84.56 ml). After 30 minutes, the solution was stirred at room temperature for 12 hours. The reaction solution was placed in ice water and stirred. The organic layer was extracted with dichloromethane and Na 2 CO 3 To the neutralized organic layer to be dried, MgSO 4 The organic layer was distilled under reduced pressure and purified by column chromatography to obtain Intermediate 1-3 (16.0 g, 95.77%).

[0354] (4) Synthesis of Intermediates 1-4

[0355] [Reaction 1-4]

[0356]

[0357] Intermediate 1-3 (50.0 g, 168.70 mmol) was dissolved in CHCl 3 (1000ml), and 4-dimethylaminopyridine (2.06g, 16.87mmol) was added to the solution. Triethylamine (35.56ml, 253.06mmol) was added to the solution at 0°C, and trifluoromethanesulfonic anhydride (42.2ml, 253.06mmol) was added to the solution after 30 minutes. The temperature of the solution was raised to room temperature, and the solution was stirred for 90 minutes. Distilled water was added to the solution, and the organic layer was extracted with dichloromethane. MgSO was added to the organic layer to be dried. 4The organic layer was distilled under reduced pressure to obtain a solid, and the solid was purified by column chromatography to obtain Intermediate 1-4 (65 g, 89.93%).

[0358] (5) Synthesis of Compound C-25

[0359] [Reaction 1-5]

[0360]

[0361] Intermediate 1-4 (50.0 g, 116.70 mmol), (10-(naphthalen-1-yl)anthracen-9-yl)boronic acid (48.76 g, 140.04 mmol), Pd(OAc) 2 (1.31g, 5.83mmol), S phos (5.75g, 14.0mmol), K 3 PO 4 (49.54 g, 233.41 mmol), toluene (800 ml), distilled water (150 ml) and ethanol (80 ml) were mixed, and the solution was refluxed at 120°C for 2 hours with stirring. The solution was cooled to room temperature, distilled water was added to the solution, and the organic layer was extracted with ethyl acetate. MgSO was added to the organic layer to be dried. 4 The organic layer was filtered under reduced pressure. The organic layer was distilled under reduced pressure and purified by column chromatography to obtain compound C-25 (34.0 g, 49.99%, molecular weight 582.75, melting point 227.5°C).

[0362] Synthesis Example 2: Synthesis of Compound C-100

[0363] (1) Synthesis of intermediate 2-1

[0364] [Reaction formula 2-1]

[0365]

[0366] (5-Chloro-2-methoxyphenyl)boronic acid (55 g, 295 mmol), bromobenzene-D5 (57.4 g, 354 mmol), Pd(PPh 3 ) 4 (13.6 g, 5.36 mmol), K 2 CO 3 (81.5 g, 590 mmol), toluene (1200 ml), distilled water (300 ml) and ethanol (300 ml) were mixed, and then the solution was refluxed at 120° C. for 4 hours under stirring. The solution was cooled to room temperature, distilled water was added to the solution, and the organic layer was extracted with ethyl acetate. MgSO was added to the extracted organic layer to be dried. 4The organic layer was filtered under reduced pressure. The organic layer was distilled under reduced pressure and purified by column chromatography to obtain Intermediate 2-1 (62.8 g, 95.25%).

[0367] (2) Synthesis of intermediate 2-2

[0368] [Reaction formula 2-2]

[0369]

[0370] Intermediate 2-1 (62 g, 281 mmol), 2-naphthylboronic acid (58 g, 337 mmol), Pd(OAc) 2 (3.2g, 14.05mmol), S phos (13.8g, 33.72mmol), K 3 PO 4 (119 g, 562 mmol), toluene (1000 ml), distilled water (300 ml), and isopropanol (150 ml) were mixed, and the solution was refluxed at 120°C for 7 hours. The solution was cooled to room temperature, distilled water was added to the solution, and the organic layer was extracted with ethyl acetate. MgSO was added to the extracted organic layer to be dried. 4 The organic layer was filtered under reduced pressure. The organic layer was distilled under reduced pressure and purified by column chromatography to obtain Intermediate 2-2 (71.1 g, 80.06%).

[0371] (3) Synthesis of intermediate 2-3

[0372] [Reaction 2-3]

[0373]

[0374] Intermediate 2-2 (71.1 g, 225 mmol) was dissolved in dichloromethane (1100 ml), and BBr was added to the solution at 0 °C. 3 (1M in dichloromethane, 300 ml). After 30 minutes, the solution was stirred at room temperature for 5 hours. The reaction solution was placed in ice water and stirred. The reaction solution was slowly added to Na 2 CO 3 The organic layer was extracted with dichloromethane, and MgSO was added to the dried organic layer. 4 The organic layer was distilled under reduced pressure and purified by column chromatography to obtain Intermediate 2-3 (67.6 g, 99.55%).

[0375] (4) Synthesis of Intermediate 2-4

[0376] [Reaction 2-4]

[0377]

[0378] Intermediate 2-3 (67.6 g, 224 mmol) was dissolved in CHCl 3 (1100ml), and 4-dimethylaminopyridine (2.7g, 22.4mmol) was added to the solution. Triethylamine (47ml, 336mmol) was added to the solution at 0°C, and trifluoromethanesulfonic anhydride (56ml, 336mmol) was added to the solution after 30 minutes. After 10 minutes, the temperature of the solution was raised to room temperature, and the solution was stirred for 4 hours. Distilled water was added to the solution, and the organic layer was extracted with dichloromethane. MgSO was added to the organic layer to be dried. 4 The organic layer was filtered under reduced pressure. The organic layer was distilled under reduced pressure to obtain a solid, and the solid was purified by column chromatography to obtain Intermediate 2-4 (65 g, 89.93%).

[0379] (5) Synthesis of Compound C-100

[0380] [Reaction 2-5]

[0381]

[0382] Intermediate 2-4 (50.0 g, 115 mmol), (10-(naphthalen-1-yl)anthracen-9-yl)boronic acid (44 g, 127 mmol), Pd(OAc) 2 (1.31g, 5.75mmol), S phos (5.7g, 13.8mmol), K 3 PO 4 (49 g, 230 mmol), toluene (1100 ml), distilled water (170 ml) and ethanol (115 ml) were mixed, and the solution was refluxed at 120°C for 3 hours under stirring. The solution was cooled to room temperature, distilled water was added to the solution, and the organic layer was extracted with ethyl acetate. MgSO was added to the organic layer to be dried. 4 The organic layer was filtered under reduced pressure. The organic layer was distilled under reduced pressure and purified by column chromatography to obtain compound C-100 (32.0 g, 47.34%, molecular weight 587.75, melting point 162° C.).

[0383] Example 1: Fabrication of OLED

[0384] An organic light-emitting diode in which the light-emitting material layer contains the compound C-25 synthesized in Synthesis Example 1 as a main body is manufactured. The transparent electrode ITO film (10 ohms / square) on the OLED glass substrate is ultrasonically cleaned with acetone and isopropanol and stored in isopropanol. The ITO substrate is transferred to a vacuum chamber for depositing the light-emitting layer and the cathode. Subsequently, the following sequence is used for about 10 -6 Deposition of the light-emitting layer and cathode by evaporation under the support:

[0385] Hole injection layer (HIL, HT-1 (95 wt%), HI (5 wt%), 10 nm thickness); first hole transport layer (HTL1, HT-1, 80 nm thickness); second hole transport layer (HTL2, HT-2, 15 nm thickness); light emitting material layer (EML, compound C-25 (98 wt%), compound FD1 of Chemical Formula 11 (2 wt%), 22.5 nm thickness); electron buffer layer (ET-1, 5 nm thickness); electron transport layer (ETL, EI-1: EI-2 = 2:1, by volume, 25 nm thickness); electron injection layer (EIL, Yb:LiF = 2:1, by volume, 1 nm thickness); cathode (Al, 80 nm thickness).

[0386] The structures of the materials of the hole injection material, the hole transport material, the electron buffer material, and the electron transport material are shown below:

[0387]

[0388] Example 2: Fabrication of OLED

[0389] An OLED was fabricated using the same steps and the same materials as in Example 1, except that Compound C-100 was used instead of Compound C-25 as the host in the EML.

[0390] Comparative Example 1 (Ref. 1): Production of OLED

[0391] An OLED was fabricated using the same steps and the same materials as in Example 1, except that compound H-Ref was used instead of compound C-25 as the host in the EML.

[0392] [Reference compound]

[0393]

[0394] Experimental Example 1: Measurement of the Light Emitting Characteristics of OLED

[0395] Each OLED manufactured in Examples 1 to 2 and Comparative Example 1 was connected to an external power source, and then the luminescent characteristics of all OLEDs were evaluated. In particular, the driving voltage and the time period (T from initial brightness to 95% luminescence by CIE color coordinate standard as luminescent lifetime were measured at a brightness of 1000 nits. 95 ). The measurement results are shown in Table 1 below.

[0396] Table 1: Light-emitting properties of OLEDs

[0397] sample main body Driving voltage(V) <![CDATA[T 95 (Hours)]]> Ex.1 C-25 3.9 54 Ex.2 C-100 3.9 60 Ref.1 H-Ref 3.9 35

[0398] As shown in Table 1, compared with the OLED manufactured in Comparative Example 1, in the OLED manufactured in Examples 1 to 2 in which an anthracene-containing compound with a specific molecular conformation is used as the host in the EML, the luminescence lifetime is significantly improved. Since the anthracene portion in the anthracene-containing host is relatively highly reactive, the luminescence lifetime of the OLED comprising the anthracene-containing host tends to decrease. When the reactivity of the anthracene portion contained in the host decreases, the luminescence lifetime of the OLED can be improved. The phenyl group substituted to one side of the anthracene core includes another phenyl group substituted to the ortho position of the initial phenyl group, so that the steric effect of the anthracene skeleton can be adjusted, and therefore the reactivity of the anthracene core can be reduced. Compared with conventional OLEDs, OLEDs using anthracene-containing compounds with a specific molecular conformation in the light-emitting layer can have a more beneficial luminescence lifetime.

[0399] It will be apparent to those skilled in the art that various modifications and changes can be made in the present disclosure without departing from the scope of the present disclosure. Therefore, the present disclosure is intended to cover modifications and variations of the present disclosure as long as they fall within the scope of the appended claims.

Claims

1. An organic compound having the structure of the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, R 1 is protium, deuterium, tritium, unsubstituted or substituted C1 to C 10 alkyl, or unsubstituted or substituted phenyl, wherein when a1 is 2, 3, 4 or 5, each R 1 are the same as or different from each other, or Optionally, When a1 is 2, 3, 4 or 5, two adjacent R 1 Further ligation to form unsubstituted or deuterated, C1 to C 10 A benzene ring substituted with at least one of an alkyl group and a group formed by connecting the above two groups; R 2 , R 3 and R 4 are each independently protium, deuterium, tritium, or unsubstituted or substituted C1 to C 10 Alkyl, wherein when a2 is 2 or 3, each R 2 The same or different from each other, when a3 is 2, 3 or 4, each R 3 are the same as or different from each other, and when a4 is 2, 3 or 4, each R 4 the same as or different from one another; R 5 and R 6 are each independently phenyl, biphenyl or naphthyl, wherein the phenyl, biphenyl and naphthyl are each independently unsubstituted or substituted with deuterium, C1 to C 10 substituted by at least one of an alkyl group and a group formed by connecting the above two groups; a1 is 0, 1, 2, 3, 4 or 5; a2 is 0, 1, 2, or 3; and a3 and a4 are each independently 0, 1, 2, 3 or 4.

2. The organic compound according to claim 1, wherein the organic compound has a structure of the following Chemical Formula 2 or Chemical Formula 3: [Chemical formula 2] [Chemical formula 3] in, In Chemical Formula 2 and Chemical Formula 3, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1; R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C1 to C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

3. The organic compound according to claim 1, wherein the organic compound has a structure of the following Chemical Formula 4 or Chemical Formula 5: [Chemical formula 4] [Chemical formula 5] in, In Chemical Formula 4 and Chemical Formula 5, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1; R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C1 to C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

4. The organic compound according to claim 1, wherein in Chemical Formula 1, two adjacent R 1 Further connected to form a benzene ring, R 1 The remaining three are hydrogen or deuterium, and R 6 It is naphthyl.

5. The organic compound according to claim 1, wherein two adjacent R 1 Further connected to form a benzene ring, and thereby connected to the anthracene ring as a 1-naphthyl form, and R 6 It is 2-naphthyl.

6. The organic compound according to claim 1, wherein R 5 is phenyl, or a phenyl group in which all hydrogens are replaced by deuterium.

7. The organic compound according to claim 1, wherein the organic compound is at least one of the following: in, express and wherein D represents deuterium.

8. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, The light-emitting layer comprises an organic compound having the structure of the following Chemical Formula 1: [Chemical formula 1] Wherein, in Chemical Formula 1, R 1 is protium, deuterium, tritium, unsubstituted or substituted C1 to C 10 alkyl, or unsubstituted or substituted phenyl, wherein when a1 is 2, 3, 4 or 5, each R 1 are the same as or different from each other, or Optionally, When a1 is 2, 3, 4 or 5, two adjacent R 1 Further ligation to form unsubstituted or deuterated, C1 to C 10 A benzene ring substituted with at least one of an alkyl group and a group formed by connecting the above two groups; R 2 , R 3 and R 4 are each independently protium, deuterium, tritium, or unsubstituted or substituted C1 to C 10 Alkyl, wherein when a2 is 2 or 3, each R 2 The same or different from each other, when a3 is 2, 3 or 4, each R 3 are the same as or different from each other, and when a4 is 2, 3 or 4, each R 4 the same as or different from one another; R 5 and R 6 are each independently phenyl, biphenyl or naphthyl, wherein the phenyl, biphenyl and naphthyl are each independently unsubstituted or substituted with deuterium, C1 to C 10 Alkyl, and at least one of a group formed by connecting the above two groups; a1 is 0, 1, 2, 3, 4 or 5; a2 is 0, 1, 2, or 3; and a3 and a4 are each independently 0, 1, 2, 3 or 4.

9. The organic light emitting diode according to claim 8, wherein the organic compound has a structure of the following Chemical Formula 2 or Chemical Formula 3: [Chemical formula 2] [Chemical formula 3] in, In Chemical Formula 2 and Chemical Formula 3, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1; R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C1 to C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

10. The organic light emitting diode according to claim 8, wherein the organic compound has a structure of the following Chemical Formula 4 or Chemical Formula 5: [Chemical formula 4] [Chemical formula 5] in, In Chemical Formula 4 and Chemical Formula 5, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a1, a2, a3 and a4 are each the same as defined in Chemical Formula 1; R 11 is protium, deuterium, or unsubstituted or deuterium-substituted C1 to C 10 Alkyl, wherein when b1 is 2, 3, 4, 5, 6 or 7, each R 11 be the same as or different from each other; and b1 is 0, 1, 2, 3, 4, 5, 6 or 7.

11. The organic light emitting diode according to claim 8, wherein in Chemical Formula 1, two adjacent R 1 Further connected to form a benzene ring, R 1 The remaining three are hydrogen or deuterium, and R 6 It is naphthyl.

12. The organic light emitting diode according to claim 8, wherein two adjacent R 1 Further connected to form a benzene ring, and thereby connected to the anthracene ring as a 1-naphthyl form, and R 6 It is 2-naphthyl.

13. The organic light emitting diode according to claim 8, wherein R 5 is phenyl, or a phenyl group in which all hydrogens are replaced by deuterium. 14 . The organic light emitting diode according to claim 8 , wherein the light emitting layer comprises one or more light emitting material layers, and wherein at least one light emitting material layer contains the organic compound. 15 . The organic light emitting diode according to claim 14 , wherein the at least one light emitting material layer comprises a host and a dopant, and wherein the host comprises the organic compound. The organic light emitting diode according to claim 15 , wherein the dopant comprises a blue dopant. 17 . The organic light emitting diode according to claim 16 , wherein the blue dopant comprises at least one of a blue phosphorescent material, a blue fluorescent material, and a blue delayed fluorescent material.

18. The organic light emitting diode according to claim 15, wherein the dopant comprises a phosphorescent material having a structure of the following Chemical Formula 7: [Chemical formula 7] in, In Chemical Formula 7, R 21 To R 26 are each independently protium, deuterium, tritium, halogen, cyano, unsubstituted or substituted C1 to C 20 Alkyl, unsubstituted or substituted C2 to C 20 alkenyl, unsubstituted or substituted C2 to C 20 Alkynyl, unsubstituted or substituted C1 to C 20 Alkoxy, amino, unsubstituted or substituted C1 to C 20 Alkylamino, unsubstituted or substituted C1 to C 20 Alkylsilyl, unsubstituted or substituted C3 to C 30 Cycloalkyl, unsubstituted or substituted C3 to C 30 Heterocycloalkyl, unsubstituted or substituted C6 to C 30 Aryl, unsubstituted or substituted C2 to C 30 heteroaryl, unsubstituted or substituted C7 to C 30 Arylalkyl, unsubstituted or substituted C3 to C 30 heteroarylalkyl, unsubstituted or substituted C6 to C 30 Aryloxy, unsubstituted or substituted C2 to C 30 heteroaryloxy, unsubstituted or substituted C6 to C 30 Arylamino, unsubstituted or substituted C2 to C 30 heteroarylamino, unsubstituted or substituted C6 to C 30 Arylsilyl, unsubstituted or substituted C2 to C 30 heteroarylsilyl, unsubstituted or substituted C1 to C 20 Alkylgermanyl, unsubstituted or substituted C6 to C 30 Arylgermanyl, unsubstituted or substituted C2 to C 30 Heteroarylgermanyl, unsubstituted or substituted C6 to C 30 triarylmethyl, or unsubstituted or substituted C2 to C 30 triheteroarylmethyl, wherein when c1 is 2, 3 or 4, each R 21 The same or different from each other, when c2 is 2, 3 or 4, each R 22 The same or different from each other, when c3 is 2, each R 23 The same or different from each other, when c4 is 2 or 3, each R 24 are the same as or different from each other, and when c5 is 2, each R 25 are the same as or different from each other, or Optionally, Two adjacent R 21 , two adjacent R 22 , two adjacent R 23 , two adjacent R 24 and / or two adjacent R 25 further connected to form an unsubstituted or substituted benzene ring; c1 and c2 are each independently 0, 1, 2, 3 or 4; c3 and c5 are each independently 0, 1 or 2; and c4 is 0, 1, 2 or 3.

19. The organic light emitting diode according to claim 15, wherein the dopant comprises a fluorescent material having a structure of the following Chemical Formula 9: [Chemical formula 9] in, In Chemical Formula 9, Ring A, Ring B and Ring C are each independently unsubstituted or substituted C6 to C 30 Aromatic ring, or unsubstituted or substituted C3 to C 30 heteroaromatic ring; Y 1 For boron; X 1 and X 2 Each independently is NR A , O or S; R A is protium, deuterium, tritium, halogen, cyano, unsubstituted or substituted C1 to C 20 Alkyl, unsubstituted or substituted C2 to C 20 alkenyl, unsubstituted or substituted C2 to C 20 Alkynyl, unsubstituted or substituted C1 to C 20 Alkoxy, amino, unsubstituted or substituted C1 to C 20 Alkylamino, unsubstituted or substituted C1 to C 20 Alkylsilyl, unsubstituted or substituted C3 to C 30 Cycloalkyl, unsubstituted or substituted C3 to C 30 Heterocycloalkyl, unsubstituted or substituted C6 to C 30 Aryl, unsubstituted or substituted C2 to C 30 heteroaryl, unsubstituted or substituted C7 to C 30 Arylalkyl, unsubstituted or substituted C3 to C 30 heteroarylalkyl, unsubstituted or substituted C6 to C 30 Aryloxy, unsubstituted or substituted C2 to C 30 heteroaryloxy, unsubstituted or substituted C6 to C 30 Arylamino, unsubstituted or substituted C2 to C 30 heteroarylamino, unsubstituted or substituted triphenylmethyl, unsubstituted or substituted C6 to C 30 Arylsilyl, unsubstituted or substituted C2 to C 30 heteroarylsilyl, unsubstituted or substituted C1 to C 20 Alkylgermanyl, unsubstituted or substituted C6 to C 30 Arylgermanyl, unsubstituted or substituted C2 to C 30 Heteroarylgermanyl, or -L 1 -N-(R B )(R C ),or Optionally, R A is connected to at least one of ring A, ring B and ring C to form an unsubstituted or substituted C3 to C 30 Alicyclic ring, unsubstituted or substituted C3 to C 30 Heteroalicyclic ring, unsubstituted or substituted C6 to C 30 Aromatic ring, or unsubstituted or substituted C2 to C 30 heteroaromatic ring; L 1 is a single bond, unsubstituted or substituted C6 to C 30 Arylene, unsubstituted or substituted C2 to C 30 heteroarylene, unsubstituted or substituted divalent C1 to C 30 an aliphatic group, or an unsubstituted or substituted C3 to C 30 alicyclic ring and unsubstituted or substituted C6 to C 30 A divalent fused aromatic ring group; and R B and R C are each independently unsubstituted or substituted C1 to C 20 Alkyl, unsubstituted or substituted C2 to C 20 alkenyl, unsubstituted or substituted C6 to C 30 Aryl, or unsubstituted or substituted C2 to C 30 Heteroaryl. 20 . The organic light emitting diode according to claim 15 , wherein the dopant comprises a first dopant and a second dopant. 21 . The organic light emitting diode according to claim 20 , wherein the first dopant comprises at least one of a blue delayed fluorescent material and a blue phosphorescent material, and the second dopant comprises a blue fluorescent material.

22. The organic light emitting diode according to claim 8, wherein the light emitting layer comprises: A first light emitting portion disposed between the first electrode and the second electrode and comprising a first light emitting material layer; A second light emitting portion disposed between the first light emitting portion and the second electrode and comprising a second light emitting material layer; as well as a first charge generation layer provided between the first light emitting portion and the second light emitting portion, and At least one of the first light-emitting material layer and the second light-emitting material layer comprises the organic compound. 23 . The organic light emitting diode according to claim 22 , wherein the first light emitting material layer comprises the organic compound. The organic light emitting diode according to claim 22 , wherein the second light emitting material layer emits red to green light.

25. The organic light emitting diode according to claim 22, wherein the light emitting layer further comprises: A third light emitting portion disposed between the second light emitting portion and the second electrode and comprising a third light emitting material layer; as well as A second charge generation layer is provided between the second light emitting portion and the third light emitting portion. 26 . The organic light emitting diode according to claim 25 , wherein at least one of the first light emitting material layer and the third light emitting material layer comprises the organic compound.

27. An organic light-emitting device, comprising: substrate; and An organic light emitting diode according to any one of claims 8 to 26 is disposed over the substrate.

28. An organic compound having the structure of the following Chemical Formula 1: [Chemical formula 1] in, In Chemical Formula 1, R 1 is protium, deuterium or tritium, wherein when a1 is 2, 3, 4 or 5, each R 1 are the same as or different from each other, or Optionally, Two adjacent R 1 The unsubstituted or deuterated, C1 to C 10 an alkyl group, and a benzene ring substituted with at least one of a group formed by connecting the above two groups, and R 1 The remaining three are protium, deuterium or tritium; R 2 , R 3 and R 4 Each independently represents protium, deuterium or tritium, wherein when a2 is 2 or 3, each R 2 The same or different from each other, when a3 is 2, 3 or 4, each R 3 are the same as or different from each other, and when a4 is 2, 3 or 4, each R 4 the same as or different from one another; R 5 is phenyl which is unsubstituted or substituted with at least one deuterium; R 6 is phenyl, biphenyl or naphthyl, wherein the phenyl, biphenyl and naphthyl are each independently unsubstituted or substituted with deuterium, C1 to C 10 substituted by at least one of an alkyl group and a group formed by connecting the above two groups; a1 is 0, 1, 2, 3, 4 or 5; a2 is 0, 1, 2, or 3; and a3 and a4 are each independently 0, 1, 2, 3 or 4.

29. The organic compound according to claim 28, wherein R 5 is phenyl, or a phenyl group in which all hydrogens are replaced by deuterium.

30. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, The light-emitting layer comprises an organic compound having the structure of the following Chemical Formula 1: [Chemical formula 1] Wherein, in Chemical Formula 1, R 1 is protium, deuterium or tritium, wherein when a1 is 2, 3, 4 or 5, each R 1 are the same as or different from each other, or Optionally, Two adjacent R 1 The unsubstituted or deuterated, C1 to C 10 an alkyl group, and a benzene ring substituted with at least one of a group formed by connecting the above two groups, and R 1 The remaining three are protium, deuterium or tritium; R 2 , R 3 and R 4 Each independently represents protium, deuterium or tritium, wherein when a2 is 2 or 3, each R 2 The same or different from each other, when a3 is 2, 3 or 4, each R 3 are the same as or different from each other, and when a4 is 2, 3 or 4, each R 4 the same as or different from one another; R 5 is phenyl which is unsubstituted or substituted with at least one deuterium; R 6 is phenyl, biphenyl or naphthyl, wherein the phenyl, biphenyl and naphthyl are each independently unsubstituted or substituted with deuterium, C1 to C 10 substituted by at least one of an alkyl group and a group formed by connecting the above two groups; a1 is 0, 1, 2, 3, 4 or 5; a2 is 0, 1, 2, or 3; and a3 and a4 are each independently 0, 1, 2, 3 or 4.

31. The organic light emitting diode according to claim 30, wherein R 5 is phenyl, or a phenyl group in which all hydrogens are replaced by deuterium.

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