Organic compounds, compositions, organic optoelectronic devices and display devices

Abstract

The present application relates to an organic compound represented by Chemical Formula 1, a composition comprising the same, an organic optoelectric device, and a display device.

Description

Technical Field

[0001] This invention discloses an organic compound, a composition, an organic optoelectronic device, and a display device. Background Technology

[0002] Organic optoelectronic devices (organic photodiodes) are devices that convert electrical energy into light energy, and vice versa.

[0003] Based on their driving principles, organic optoelectronic devices can be classified as follows: One type is the photodiode, in which light energy generates excitons, which are split into electrons and holes and transferred to different electrodes to generate electrical energy; the other type is the light-emitting diode, in which voltage or current is supplied to the electrodes to generate light energy from electrical energy.

[0004] Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting diodes, organic solar cells, and organic photoconductor drums.

[0005] Organic light-emitting diodes (OLEDs) have recently garnered significant attention due to the increasing demand for flat panel displays. OLEDs convert electrical energy into light by applying current to organic light-emitting materials, and their performance can be influenced by the organic materials positioned between the electrodes. Summary of the Invention

[0006] [Technical Issues]

[0007] One embodiment provides an organic compound capable of realizing organic optoelectronic devices with high efficiency and long lifespan.

[0008] Another embodiment provides a composition capable of realizing an organic optoelectronic device with high efficiency and long lifespan.

[0009] Another embodiment provides an organic optoelectronic device comprising the organic compound or composition.

[0010] Another embodiment provides a display device including the organic optoelectronic device.

[0011] [Technical Solution]

[0012] According to one embodiment, an organic compound represented by chemical formula 1 is provided.

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] X 1 and X 2 Independently O or S,

[0017] Ar 1 and Ar 2 Independently, it is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof.

[0018] L 1 It is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof, and

[0019] R 1 To R 6 It is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclic, cyano, or combinations thereof.

[0020] According to another embodiment, a composition includes a first organic compound and a second organic compound including a carbazole moiety, wherein the first organic compound is the same as the second organic compound, and the second organic compound is represented by chemical formula 4.

[0021] [Chemical Formula 4]

[0022]

[0023] In chemical formula 4,

[0024] Y 1 It is a single-bonded, substituted or unsubstituted C6 to C30 arylene group, or a divalent or unsubstituted C2 to C30 heterocyclic group.

[0025] A 1 It is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0026] R 9 Land R 14 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group,

[0027] R 9 and R 10 They exist independently or are connected to form a ring, and

[0028] R 11 To R 14 Independent existence or R 11 To R 14 Adjacent groups in the compound connect to each other to form a ring.

[0029] According to another embodiment, an organic optoelectronic device includes an anode and a cathode facing each other and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the organic compound or the composition.

[0030] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0031] [Beneficial Effects]

[0032] It can realize organic optoelectronic devices with high efficiency and long life. Attached Figure Description

[0033] Figure 1 and Figure 2 This is a cross-sectional view showing an organic light-emitting diode according to an embodiment. Detailed Implementation

[0034] Embodiments of the present invention will be described in detail below. However, these embodiments are exemplary, and the present invention is not limited thereto, and is defined by the scope of the claims.

[0035] In this specification, unless otherwise defined, “substitution” means a group that replaces at least one hydrogen a group with a deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or combinations thereof.

[0036] In examples of the present invention, "substitution" refers to a group that replaces at least one hydrogen a group containing deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. Furthermore, in specific examples of the present invention, "substitution" refers to a group that replaces at least one hydrogen a group containing deuterium, C1 to C20 alkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. Additionally, in specific examples of the present invention, "substitution" refers to a group that replaces at least one hydrogen a group containing deuterium, C1 to C5 alkyl, C6 to C18 aryl, pyridyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophenyl, or carbazoleyl. Furthermore, in specific embodiments of the present invention, "substitution" refers to a group that replaces at least one hydrogen atom with a group containing deuterium, C1 to C5 alkyl, C6 to C18 aryl, dibenzofuranyl, or dibenzothiophene. Additionally, in specific embodiments of the present invention, "substitution" refers to a group that replaces at least one hydrogen atom with a group containing deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl, or dibenzothiophene.

[0037] In this specification, unless otherwise defined, "heterogeneous" means that a functional group includes 1 to 3 heteroatoms selected from N, O, S, P and Si, with the remainder being carbon.

[0038] In this specification, "aryl" refers to a group comprising at least one aromatic hydrocarbon moiety, wherein all elements of the aromatic hydrocarbon moiety have conjugated p-orbitals, such as phenyl, naphthyl, etc. Two or more aromatic hydrocarbon moiety portions may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., or two or more aromatic hydrocarbon moiety portions may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl. Aryl groups may include monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0039] In this specification, "heterocyclic group" is a general concept of heteroaryl and may include at least one heteroatom selected from N, O, S, P, and Si in cyclic compounds such as aryl, cycloalkyl, fused rings, or combinations thereof, instead of carbon (C). When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0040] For example, "heteroaryl" refers to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by σ bonds, or when a heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0041] Specific examples of heterocyclic groups may include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, etc.

[0042] More specifically, the substituted or unsubstituted C6 to C30 aryl and / or substituted or unsubstituted C2 to C30 heterocyclic groups can be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted trefoil, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted indole, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiophene Azolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzooxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiaphenyl, or combinations thereof, but not limited thereto.

[0043] In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected and transported to the light-emitting layer.

[0044] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected and transported to the light-emitting layer.

[0045] The organic compounds according to embodiments are described below.

[0046] An organic compound according to one embodiment is represented by chemical formula 1.

[0047] [Chemical Formula 1]

[0048]

[0049] In chemical formula 1,

[0050] X 1 and X 2 Independently O or S,

[0051] Ar 1 and Ar 2 Independently, it is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof.

[0052] L 1 It is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof.

[0053] R 1 To R 6 It is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclic, cyano, or combinations thereof.

[0054] The organic compound represented by Formula 1 can exhibit rapid electron transport properties through a fused ring comprising a substituted pyrimidine ring and benzofuran or benzothiophene, and can exhibit even faster electron transport properties by further incorporating a dibenzofuran group or a dibenzothiophene group onto the fused ring of benzofuran or benzothiophene. Therefore, when this organic compound is applied to a device, a device with low driving voltage and high efficiency can be realized.

[0055] Furthermore, the organic compound represented by Formula 1 has a relatively high glass transition temperature. Therefore, when this organic compound is applied to a device, its degradation during processing or operation can be reduced or prevented, thereby improving the device's thermal stability and lifespan. For example, this organic compound may have a glass transition temperature of approximately 50°C to 300°C.

[0056] For example, X of chemical formula 1 1 and X 2 They can be the same or different. For example, X 1 and X 2 Can be the same and X 1 and X 2 Each can be O or X 1 and X 2 Each of them can be S. For example, X 1 and X 2 They can be different from each other and X 1 It can be S and X 2It can be O or X 1 It can be O and X 2 It can be S.

[0057] For example, Ar of chemical formula 1 1 and Ar 2 It can be independently a substituted or unsubstituted C6 to C30 aryl group, such as a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracene, or a substituted or unsubstituted triphenylene. “Substitution” means replacing at least one hydrogen atom with a deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyano group.

[0058] For example, L 1 It can be a single bond or a substituted or unsubstituted C6 to C30 aryl group. For example, L 1 It can be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted anthracene. For example, L 1 It can be a single bond or a substituted or unsubstituted phenylene group. “Substitution” means replacing at least one hydrogen group with a deuterium, C1 to C20 alkyl, C6 to C12 aryl or cyano group.

[0059] For example, R 1 To R 6 It can be hydrogen, cyano, C1 to C20 alkyl, C6 to C30 aryl, or a C6 to C30 aryl group substituted with a cyano group.

[0060] For example, R 1 To R 6 It can be independently hydrogen, cyano, C1 to C4 alkyl, C6 to C12 aryl, or a C6 to C12 aryl group substituted with a cyano group.

[0061] For example, the organic compound can be represented by any of the chemical formulas 2 to 5, but is not limited thereto.

[0062]

[0063] In chemical formulas 2 to 5, X 1 X 2 Ar 1 Ar 2 and R 1 To R 6 Same as above.

[0064] For example, the organic compound can be represented by any one of the chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, but is not limited thereto.

[0065]

[0066]

[0067]

[0068] In chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, X 1 X 2 Ar 1 Ar 2 and R 1 To R 6 Same as above.

[0069] For example, in chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, L 1 It can be a single bond or a substituted or unsubstituted phenylene.

[0070] For example, in chemical formulas 2a to 2d, 3a to 3d, 4a to 4d, and 5a to 5d, L 1 It can be a single key.

[0071] For example, the organic compound may be selected from, but is not limited to, the compounds listed in Group 1.

[0072] [Group 1]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] The aforementioned organic compounds can be used alone or in combination with other organic compounds in organic optoelectronic devices. When used together with other organic compounds, they can be applied as a composition.

[0089] The composition according to one embodiment is described below.

[0090] A composition according to one embodiment may include the aforementioned organic compound (hereinafter referred to as the "first organic compound") and an organic compound having cavitation properties (hereinafter referred to as the "second organic compound").

[0091] The second organic compound may include, for example, a carbazole moiety and may be, for example, a substituted or unsubstituted carbazole compound, a substituted or unsubstituted biscarbazole compound, or a substituted or unsubstituted indolocarbazole compound, but is not limited thereto.

[0092] For example, the second organic compound may include, for example, a carbazole moiety represented by chemical formula 4.

[0093] [Chemical Formula 4]

[0094]

[0095] In chemical formula 4,

[0096] Y 1 It is a single-bonded, substituted or unsubstituted C6 to C30 arylene or a divalent substituted or unsubstituted C2 to C30 heterocyclic group.

[0097] A 1 It is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0098] R 9 To R 14 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group,

[0099] R 9 and R 10 They exist independently or are connected to form a ring, and

[0100] R 11 To R 14 Independent existence or R 11 To R14 Adjacent groups in the ring connect with each other to form a ring.

[0101] For example, in the definition of Formula 4, "substitution" means replacing at least one hydrogen group with a group that is deuterium, C1 to C10 alkyl, C6 to C12 aryl or C2 to C10 heteroaryl, such as replacing at least one hydrogen group with a group that is deuterium, phenyl, o-biphenyl, meta-biphenyl, p-biphenyl, terphenyl, naphthyl, dibenzofuranyl or dibenzothiophene.

[0102] For example, the second organic compound can be a compound represented by chemical formula 4A.

[0103] [Chemical Formula 4A]

[0104]

[0105] In chemical formula 4A,

[0106] Y 1 and Y 2 It can be independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0107] A 1 and A 2 It can be independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0108] R 9 To R 11 and R 15 To R 17 It can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0109] m can be an integer from 0 to 2.

[0110] For example, Y of chemical formula 4A 1 and Y 2 It can be a single bond, a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene, such as a single bond, meta-phenylene, para-phenylene, meta-biphenylene or para-biphenylene.

[0111] For example, the A in chemical formula 4A 1 and A 2 It can be independently a substituted or unsubstituted C6 to C30 aryl group, and for example, the aryl group can be phenyl, biphenyl, terphenyl, or naphthyl. Furthermore, A in formula 4A... 1 and A 2It can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, or a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted fluorenyl, or a combination thereof, for example, A of formula 4A. 1 and A 2 It can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted carbazolyl.

[0112] For example, R in chemical formula 4A 9 To R 11 and R 15 To R 17 It can be hydrogen, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C2 to C30 heterocyclic groups, and for example, they can all be hydrogen.

[0113] For example, m in chemical formula 4A can be 0 or 1; for example, m can be 0.

[0114] For example, the bonding positions of the two carbazole groups in chemical formula 4A can be 2,3-bond, 3,3-bond, or 2,2-bond, such as 3,3-bond.

[0115] For example, a compound represented by chemical formula 4A can be represented by chemical formula 4A-1.

[0116] [Chemical Formula 4A-1]

[0117]

[0118] In chemical formula 4A-1, Y 1 Y 2 A 1 A 2 R 9 To R 11 and R 15 To R 17 Same as above.

[0119] For example, a compound represented by chemical formula 4A could be one in which one of the carbazole nuclei listed in group 2 is combined with a substituent (*-Y) listed in group 3. 1 -A 1 and *-Y 2 -A 2 Compounds in combination, but not limited to those in combination.

[0120] [Group 2]

[0121]

[0122] [Group 3]

[0123]

[0124] In groups 2 and 3, * represents a connection point.

[0125] For example, the compound represented by formula 4A can be one of the compounds listed in group 4, but is not limited thereto.

[0126] [Group 4]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] For example, the second organic compound can be an indolocarbazole compound represented by a combination of chemical formulas 4B-1 and 4B-2.

[0133]

[0134] In chemical formulas 4B-1 and 4B-2,

[0135] Y 1 and Y 3 It can be independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0136] A 1 and A 3 It can be independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0137] The two adjacent * of formula 4B-1 combine with the two * of chemical formula 4B-2,

[0138] The remaining two asterisks in chemical formula 4B-1 are independently CR. 11 , where R 11 They are the same or different from each other, and

[0139] R 9 To R 11 R 18 and R 19It can be hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic or a combination thereof.

[0140] For example, Y in chemical formulas 4B-1 and 4B-2 1 and Y 3 It can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0141] For example, A in chemical formulas 4B-1 and 4B-2 1 and A 3 The aryl group can be substituted or unsubstituted, ranging from C6 to C30. For example, the aryl group can be phenyl, biphenyl, naphthyl, terphenyl, or anthracene, and more preferably biphenyl, naphthyl, terphenyl, or phenyl. Furthermore, A of chemical formulas 4B-1 and 4B-2... 1 and A 3 It can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted fluorenyl, or a combination thereof.

[0142] For example, an indole-carbazole compound represented by a combination of chemical formulas 4B-1 and 4B-2 can be represented by one of chemical formulas 4B-a and 4B-e.

[0143]

[0144]

[0145] In chemical formulas 4B-a to 4B-e, Y 1 Y 3 A 1 A 3 R 9 To R 11 R 18 and R 19 Same as above.

[0146] For example, an indole-carbazole compound represented by a combination of chemical formulas 4B-1 and 4B-2 can be chemical formula 4B-c or 4B-d.

[0147] For example, an indole-carbazole compound represented by a combination of chemical formulas 4B-1 and 4B-2 can be chemical formula 4B-c.

[0148] For example, a compound represented by a combination of chemical formulas 4B-1 and 4B-2 can be one of the compounds in group 5, but is not limited thereto.

[0149] [Group 5]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155] The first organic compound and the second organic compound can be combined in various ways to include various components. The composition can include the first organic compound and the second organic compound in a weight ratio of about 1:99 to 99:1, such as about 10:90 to 90:10, about 20:80 to 80:20, about 30:70 to 70:30, about 40:60 to 60:40, or about 50:50.

[0156] The composition may further include one or more organic compounds in addition to the first organic compound and the second organic compound.

[0157] The composition may further comprise a dopant. The dopant may be a red, green, or blue dopant. The dopant is a material that emits light in small amounts and is typically a material such as a metal complex that emits light by being excited to a triplet or more multiple states. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and may be included in one or more of these types. Based on the total amount of the composition, the included dopant may be from about 0.1% to 20% by weight.

[0158] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0159] [Chemical Formula Z]

[0160] L2MX

[0161] In the chemical formula Z, M is a metal, and L and X are the same or different and are ligands that form complexes with M.

[0162] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, and L and X can be, for example, bidentate ligands.

[0163] An organic optoelectronic device comprising the above-described organic compounds or compositions is described below.

[0164] The organic optoelectronic device can be, for example, an organic light-emitting diode (OLED), an organic optoelectronic device, or an organic solar cell. The organic optoelectronic device can be, for example, an organic light-emitting diode (OLED).

[0165] The organic optoelectronic device includes an anode and a cathode facing each other, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the aforementioned organic compound or composition.

[0166] The organic layer may include an active layer such as a light-emitting layer or a light-absorbing layer, and the aforementioned organic compound or composition may be included in the active layer.

[0167] The organic layer may include an auxiliary layer disposed between the anode and the active layer and / or between the cathode and the active layer, and the aforementioned organic compound or composition may be included in the auxiliary layer.

[0168] Figure 1 This is a cross-sectional view showing an example of an organic light-emitting diode (OLED) as an example of an organic optoelectronic device.

[0169] See Figure 1 An organic light-emitting diode 100 according to one embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 disposed between the anode 110 and the cathode 120.

[0170] The anode 110 may be made of a conductor with a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 110 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metals and oxides such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0171] The cathode 120 may be made of a conductor with a low work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 120 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or alloys thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0172] The organic layer 105 may include the above-described organic compounds or compositions.

[0173] The organic layer 105 may include the light-emitting layer 130.

[0174] The light-emitting layer 130 may include the aforementioned organic compound or composition as a host. The light-emitting layer 130 may further include another organic compound as a host. The light-emitting layer 130 may further include a dopant, and the dopant may be, for example, a phosphorescent dopant.

[0175] The organic layer 105 may further include an auxiliary layer (not shown) disposed between the anode 110 and the light-emitting layer 130 and / or between the cathode 120 and the light-emitting layer 130. The auxiliary layer may be a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, or a combination thereof. The auxiliary layer may include the aforementioned organic compounds or compositions.

[0176] Figure 2 This is a cross-sectional view of an organic light-emitting diode according to another embodiment.

[0177] See Figure 2 The organic light-emitting diode 200 according to this embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 disposed between the anode 110 and the cathode 120.

[0178] The organic layer 105 includes an electron auxiliary layer 140 disposed between the light-emitting layer 230 and the cathode 120. The electron auxiliary layer 140 may be, for example, an electron injection layer, an electron transport layer, and / or a hole blocking layer, and may facilitate the injection and transport of electrons between the cathode 120 and the light-emitting layer 230.

[0179] For example, the aforementioned organic compound or composition may be included in the light-emitting layer 230. The light-emitting layer 230 may further comprise another organic compound as a host. The light-emitting layer 230 may further include a dopant, and the dopant may be, for example, a phosphorescent dopant.

[0180] For example, the aforementioned organic compound may be included in the electronic auxiliary layer 140. The electronic auxiliary layer 140 may include the aforementioned organic compound alone, may include a mixture of at least two types of the aforementioned organic compounds, or may include a mixture of the aforementioned organic compound and another organic compound.

[0181] exist Figure 2 In this process, the organic layer 105 may further include at least one hole auxiliary layer (not shown) disposed between the anode 110 and the light-emitting layer 230.

[0182] This organic light-emitting diode can be used in organic light-emitting display devices.

[0183] [Implementation Methods of the Invention]

[0184] The embodiments described below will be described in more detail with reference to examples. However, these embodiments are exemplary and the scope is not limited thereto.

[0185] In the following text, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich Co., Ltd. or TCI Inc. (unless otherwise commented) or synthesized by known methods.

[0186] (Preparation of compounds for organic optoelectronic devices)

[0187] The compound, which is a specific example of the present invention, is synthesized through the following steps.

[0188] (First compound for organic optoelectronic devices)

[0189] Synthesis of intermediates

[0190] Synthesis Example 1: Synthesis of Intermediate A

[0191] [Reaction Scheme 1]

[0192]

[0193] Synthesis of intermediate A-1

[0194] 100 g (0.64 mol) of 4-chloro-2-fluorobenzyl nitrile, 70.0 mL (0.77 mol) of methyl mercaptoacetate, and 1.2 L of N,N-dimethylformamide were placed in a 3 L round-bottom flask, and the internal temperature was lowered to -5 °C. Sodium tert-butoxide (93.67 g, 0.96 mol) was slowly added to the flask, while maintaining the internal temperature below 0 °C. The reaction mixture was stirred at room temperature for 2 hours, and then slowly added dropwise to cold water. The resulting solid was stirred at room temperature, filtered, and dried to obtain intermediate A-1 (142.9 g, 92%).

[0195] Synthesis of intermediate A-2

[0196] In a 2L round-bottom flask, a mixture of intermediate A-1 (140.0 g, 0.58 mol) and urea (173.9 g, 2.90 mol) was stirred at 200 °C for 2 hours. The reaction mixture was cooled to room temperature and poured into a sodium hydroxide solution. After filtration and removal of impurities, the reactants were acidified (HCl, 2N) to obtain a precipitate. The precipitate was dried to give intermediate A-2 (114.17 g, 78%).

[0197] Synthesis of intermediate A

[0198] In a 2000 mL round-bottom flask, a mixture of intermediate A-2 (114 g, 0.45 mol) and chloride oxide (1000 mL) was refluxed and stirred for 8 hours. The reaction mixture was cooled to room temperature and then poured into ice / water while being rapidly cooled, resulting in a precipitate. The resulting reaction mixture was filtered to obtain intermediate A (122.8 g, 94%, white solid). The elemental analysis results of intermediate A are as follows.

[0199] Calculated C 10 H3Cl3N2S: C, 41.48; H, 1.04; Cl, ​​36.73; N, 9.67; S, 11.07; Detected: C, 41.48; H, 1.04; Cl, ​​36.73; N, 9.67; S, 11.07

[0200] Synthesis Example 2: Synthesis of intermediates B, C, and D

[0201] [Reaction Scheme 2]

[0202]

[0203] Intermediates B, C, and D were synthesized in the same manner as in Synthesis Example 1, except that the starting materials were changed according to reaction scheme 2.

[0204] Synthesis Example 3: Synthesis of Intermediate E

[0205] [Reaction Scheme 3]

[0206]

[0207] Synthesis of intermediate E-1

[0208] 100 g (0.65 mol) of 4-chloro-2-hydroxybenzyl nitrile, 130.5 g (0.78 mol) of ethyl bromoacetate, and 1.3 L of N,N-dimethylformamide were placed in a 3 L round-bottom flask, and the internal temperature was lowered to -5 °C. Then, 93.88 g (0.98 mol) of sodium tert-butoxide was slowly added, with the internal temperature controlled not to exceed 0 °C. The reaction mixture was stirred at room temperature for 2 hours, and then slowly added dropwise to cold water. The resulting solid was stirred at room temperature, then filtered and dried to obtain intermediate E-1 (132.2 g, 90%).

[0209] Synthesis of intermediate E-2 and intermediate E

[0210] Intermediate E was synthesized in the same manner as intermediates A-2 and A in Synthesis Example 1.

[0211] Synthesis Example 4: Synthesis of intermediates F, G and H

[0212] [Reaction Scheme 4]

[0213]

[0214] Intermediates F, G, and H were synthesized in the same manner as in Synthesis Example 3, except that the starting materials were changed according to reaction scheme 4.

[0215] Synthesis Example 5: Synthesis of Intermediate I

[0216] [Reaction Scheme 5]

[0217]

[0218] Synthesis of intermediate I-1

[0219] 200.0 g (0.8 mol) of 4-bromo-9H-carbazole, 248.7 g (1.2 mol) of iodobenzene, 168.5 g (1.2 mol) of potassium carbonate, 31.0 g (0.2 mol) of copper iodide (I), and 29.3 g (0.2 mol) of 1,10-phenanthroline as intermediates were added to 2.5 L of N,N-dimethylformamide in a 5 L flask, and then refluxed under a nitrogen stream for 24 hours. The resulting mixture was added to 4 L of distilled water, and the crystallized solid was filtered and washed with water, methanol, and hexane. The obtained solid was extracted with water and dichloromethane, and the resulting organic layer was treated with magnesium sulfate to remove water. The mixture was then concentrated and purified by column chromatography to give intermediate I-1 as a white solid (216.2 g, yield 83%).

[0220] Calculated C 27 H 18ClN3: C, 67.10; H, 3.75; Br, 24.80; N, 4.35; Detected: CC, 67.12; H, 3.77; Br, 24.78; N, 4.33

[0221] Synthesis of intermediate I-2

[0222] Intermediate I-1 (216.0 g, 0.7 mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane) (212.8 g, 0.8 mol), potassium acetate (KOAc, 197.4 g, 2.0 mol), 1,1'-bis(diphenylphosphine)ferrocene-palladium(II) dichloride (21.9 g, 0.03 mol), and tricyclohexylphosphine (45.1 g, 0.2 mol) were added to 3 L of N,N-dimethylformamide in a 5 L flask, and then stirred at 130 °C for 12 hours. After the reaction was complete, the reaction solution was extracted with water and EA, and the resulting organic layer was treated with magnesium sulfate to remove water. The solution was then concentrated and purified by column chromatography to give intermediate I-2 as a white solid (205.5 g, 83% yield).

[0223] Calculated C 26 H 25 BN2O2: C, 78.06; H, 6.55; B, 2.93; N, 3.79; O, 8.67; Detected: C, 78.08; H, 6.57; B, 2.91; N, 3.77; O, 8.67

[0224] Synthesis of intermediate I-3

[0225] In a 5-liter flask, 150.0 g (0.4 mol) of intermediate I-2, 164.1 g (0.8 mol) of intermediate 1-bromo-2-nitrobenzene, 278.1 g (2.01 mol) of potassium carbonate, and 23.5 g (0.02 mol) of tetrakis(triphenylphosphine)palladium(O) were added to 2 L of 1,4-dioxane and 1 L of water. The mixture was then heated at 90 °C for 16 hours under a nitrogen atmosphere. After removing the reaction solvent, the residue was dissolved in dichloromethane, filtered through silica gel / diatomaceous earth to remove an appropriate amount of organic solvent, and recrystallized from methanol to give intermediate I-3 as a yellow solid (86.3 g, yield 58%).

[0226] Calculated C 18 H 12 N₂O₂: C, 79.11; H, 4.43; N, 7.69; O, 8.78; Detected: C, 79.13; H, 4.45; N, 7.67; O, 8.76

[0227] Synthesis of Intermediate I

[0228] In a 1000 mL flask, intermediate I-3 (86.0 g, 0.23 mol) and triphenylphosphine (309.5 g, 1.18 mol) were added to 600 mL of dichlorobenzene. After purging with nitrogen, the mixture was stirred at 160 °C for 12 hours. When the reaction was complete, the solvent was removed, and the product was purified by column chromatography using hexane to obtain intermediate I as a yellow solid (57.3 g, 73% yield).

[0229] Calculated C 18 H 12 N2: C, 86.72; H, 4.85; N, 8.43; Detected: C, 86.70; H, 4.83; N, 8.47

[0230] Synthesis of the final compound

[0231] Synthesis example 6

[0232] [Reaction Scheme 6]

[0233]

[0234] Synthesis of intermediate 1-1

[0235] In a 250 mL flask, intermediate A (10.0 g, 34.1 mmol), 3-biphenylboronic acid (7.83 g, 34.53 mmol), potassium carbonate (11.93 g, 86.33 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.04 mmol) were added to 80 mL of 1,4-dioxane and 40 mL of water, and then heated at 70 °C for 12 hours under a nitrogen atmosphere. The organic layer was separated and added to 240 mL of methanol. The crystalline solid was filtered, dissolved in monochlorobenzene, filtered with silica gel / diatomaceous earth to remove the appropriate amount of organic solvent, and recrystallized from monochlorobenzene to give intermediate 1-1 (10.83 g, 77% yield).

[0236] Synthesis of intermediates 1-2

[0237] In a 250 mL flask, intermediate 1-1 (10.5 g, 25.78 mmol), phenylboronic acid (3.14 g, 25.78 mmol), potassium carbonate (8.91 g, 64.45 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.89 g, 0.77 mmol) were added to 70 mL of 1,4-dioxane and 35 mL of water, and then heated at 70 °C for 12 hours under a nitrogen atmosphere. The organic layer was separated and added to 210 mL of methanol. The crystallized solid was filtered, dissolved in monochlorobenzene, filtered with silica gel / diatomaceous earth to remove the appropriate amount of organic solvent, and recrystallized from monochlorobenzene to give intermediate 1-2 (8.44 g, 79% yield).

[0238] Synthesis of Compound 2

[0239] In a 100 mL flask, intermediates 1-2 (4.0 g, 8.92 mmol), 3-dibenzofuranboronic acid (2.27 g, 10.70 mmol), 0.15 g (0.27 mmol) tris(dibenzylacetone)dipalladium, 0.33 g (50% toluene solution) tri-tert-butylphosphine, and cesium carbonate (5.81 g, 17.84 mmol) were added to 60 mL of 1,4-dioxane, and the mixture was heated at 110 °C for 12 hours under a nitrogen atmosphere. The organic layer was added to 120 mL of methanol, and the crystalline solid was filtered, dissolved in monochlorobenzene, filtered with silica gel / diatomaceous earth to remove the appropriate amount of organic solvent, and recrystallized from monochlorobenzene to obtain compound 2 (4.10 g, 79% yield).

[0240] Calculated C 40 H 24 N2OS: C, 82.73; H, 4.17; N, 4.82; O, 2.76; S, 5.52; Detected: C, 82.73; H, 4.17; N, 4.82; O, 2.76; S, 5.52

[0241] Synthetic Examples 7 to 33

[0242] Except for using the compounds shown in Table 1 as starting materials, the following final compounds were synthesized in the same manner as in Synthesis Example 6.

[0243] [Table 1]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249] (The second compound used in organic optoelectronic devices)

[0250] Synthesis Example 34

[0251] [Reaction Scheme 8]

[0252]

[0253] Synthesis of intermediate B2

[0254] In a 1000 mL round-bottom flask, 39.99 g (156.01 mmol) of indolocarbazole, 26.94 g (171.61 mmol) of bromobenzene, 22.49 g (234.01 mmol) of sodium tert-butoxide, 4.28 g (4.68 mmol) of tris(dibenzylacetone)dipalladium, and 2.9 mL (50% methyl methacrylate solution) of tritert-butylphosphine were mixed with 500 mL of xylene and refluxed under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol, and the crystalline solid was filtered, dissolved in dichlorobenzene, filtered with silica gel / diatomaceous earth to remove a certain amount of organic solvent, and recrystallized from methanol to obtain intermediate B2 (23.01 g, yield 44%).

[0255] Calculated C 24 H 16 N2: C, 86.72; H, 4.85; N, 8.43; Detected: C, 86.72; H, 4.85; N, 8.43

[0256] Synthesis of compound F-21

[0257] In a 500 mL round-bottom flask, 22.93 g (69.03 mmol) of intermediate B2, 11.38 g (72.49 mmol) of bromobenzene, 4.26 g (75.94 mmol) of potassium hydroxide, 13.14 g (69.03 mmol) of copper iodide, and 6.22 g (34.52 mmol) of 1,10-phenanthroline were added to 230 mL of DMF, and the mixture was heated under reflux for 15 hours under a nitrogen atmosphere. The resulting mixture was added to 1000 mL of methanol, and the crystalline solid was filtered off, dissolved in dichlorobenzene, filtered with silica gel / diatomaceous earth to remove appropriate amounts of organic solvent, and recrystallized from methanol to give compound F-21 (12.04 g, 43% yield).

[0258] Calculated C 30 H 20N2: C, 88.21; H, 4.93; N, 6.86; Detected: C, 88.21; H, 4.93; N, 6.86

[0259] Synthetic Examples 35 to 47

[0260] Except for using the compounds shown in Table 2 as starting materials, the following final compounds were synthesized in the same manner as in Synthesis Example 34.

[0261] [Table 2]

[0262]

[0263]

[0264]

[0265] Manufacturing of Organic Light Emitting Diode I

[0266] Example 1

[0267] The glass substrate with the ITO electrode formed on it was cut into 50mm×50mm×0.5mm pieces, ultrasonically cleaned for 15 minutes each in acetone, isopropanol and pure water, and then subjected to 30 minutes of UV ozone cleaning.

[0268] m-MTDATA Vacuum deposition rate is used to deposit ITO electrodes to form A thick hole injection layer, and then on this hole injection layer... Vacuum deposition of α-NPB at a deposition rate to form A thick hole transport layer. Subsequently, respectively with... and The deposition rate allows Ir(ppy)3 (doper 1) and compound 2 (host) to be co-deposited onto the hole transport layer, forming... A thick luminescent layer. BAlq is then used... The deposition rate is high enough for vacuum deposition onto the luminescent layer to form... A thick hole-blocking layer is formed, and Alq3 is vacuum-deposited on this hole-blocking layer to create... A thick electron transport layer. LiF(II) is then sequentially deposited on this electron transport layer under vacuum. Thick electron injection layer) and Al ( (Thick cathode) is used to manufacture organic light-emitting diodes.

[0269] Examples 2 to 25

[0270] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 was used instead of compound 2 as the host of the light-emitting layer.

[0271] Comparative Examples 1 to 5

[0272] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that comparative compounds 18, 40, 48, 155 or 189 were used instead of compound 2 as the host of the light-emitting layer.

[0273] Comparative compounds 18, 40, 48, 155, or 189 were prepared by the methods disclosed in Japanese Patent No. 564848 or Japanese Patent Publication No. 2015-134745.

[0274]

[0275] Evaluation Example I

[0276] The driving voltage, efficiency, and luminance of each organic light-emitting diode according to Examples 1 to 25 and Comparative Examples 1 to 5 were measured using a luminance meter powered by a current and voltmeter (Kethley SMU 236) and a PR650 spectral scanning source measurement unit (Photo Research Inc.).

[0277] The specific measurement method is as follows.

[0278] (1) Measuring current density change based on voltage change

[0279] Using a current-voltmeter (Keithley 2400), the current flowing through the unit device of the obtained organic light-emitting diode was measured while the voltage was increased from 0V to 10V. The measured current value was then divided by the area to obtain the result.

[0280] (2) Measuring brightness changes based on voltage changes

[0281] The brightness was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0V to 10V.

[0282] (3) Measurement of luminous efficiency

[0283] Using the brightness, current density, and voltage (V) of items (1) and (2), the calculation was performed at the same current density (10 mA / cm²). 2 Current efficiency (cd / A) at )

[0284] (4) Lifetime measurement

[0285] T95 Lifetime is used to evaluate the time (in hours) required for an organic light-emitting diode to reach 95% of its initial brightness relative to 100% initial brightness.

[0286] The results are shown in Table 3.

[0287] [Table 3]

[0288]

[0289]

[0290] Referring to Table 3, compared with the organic light-emitting diodes according to Comparative Examples 1 to 5, the organic light-emitting diodes according to Examples 1 to 25 exhibit equal or lower driving voltages, higher efficiency, and / or longer lifetimes. Therefore, the host material in the emitting layer of the organic light-emitting diodes used in Examples 1 to 25, as a phosphorescent host material, possesses excellent charge transport characteristics. Furthermore, since its absorption spectrum overlaps with the emission wavelength region of the dopant, performance improvements (such as increased efficiency and equal or better driving voltage reduction) and its potential as an OLED material are maximized. Most importantly, its lifetime is significantly improved.

[0291] Conversely, the comparative compound 18 used as the host in the organic light-emitting diode of Comparative Example 1 exhibits extremely weak electron transport capability and may not be able to achieve a balance between hole and electron transport. Therefore, the organic light-emitting diode of Comparative Example 1, which uses it as the host of the light-emitting layer, has insufficient current efficiency. Furthermore, since the comparative compounds 18, 40, 48, and 156 used as the host in the organic light-emitting diodes of Comparative Examples 2 to 5 have a structure in which the carbon adjacent to the N of pyridine, pyrimidine, and quinoxaline in the fused ring is not substituted, i.e., the structure has CH, when applied to the light-emitting layer of the organic light-emitting diode, their thermal and electrical stability is weak. Therefore, the organic light-emitting diodes of the Comparative Examples, which use them as the host of the light-emitting layer, exhibit significantly reduced lifetime characteristics.

[0292] Manufacturing of Organic Light Emitting Diode II

[0293] Example 26

[0294] Organic light-emitting diodes were fabricated using compound 3 obtained in Synthesis Example 7 as the host and (piq)2Ir(acac)(doper 2) as the dopant.

[0295] As for the anode, use -Thick ITO, and as for the cathode, use - Thick aluminum. Specifically, a method for manufacturing organic light-emitting diodes is described, using a thin layer with a resistance of 15 Ω / cm. 2The ITO glass substrate was cut into 50mm×50mm×0.7mm sizes, ultrasonically cleaned in acetone, isopropanol and pure water for 15 minutes each, and then UV ozone cleaned for 30 minutes to manufacture the anode.

[0296] On the substrate, at 650×10 -7 Under a vacuum of Pa, N4,N4'-di(naphthyl-1-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine (NPB) (80 nm) was formed by deposition at a deposition rate of 0.1 to 0.3 nm / s. A thick hole transport layer was then formed. Subsequently, under the same vacuum deposition conditions, compound 3 of synthesis example 7 was used, and phosphorescent dopant (piq)2Ir(acac) was simultaneously deposited to form... A thick luminescent layer. In this paper, by adjusting the deposition rate, the deposition amount of phosphorescent dopant was 3 wt%, based on a total luminescent layer weight of 100 wt%.

[0297] On the luminescent layer, bis(2-methyl-8-quinolinate)-4-(phenylphenol)aluminum (BAlq) was formed by depositing it under the same vacuum deposition conditions. A thick hole-blocking layer. Subsequently, Alq3 was deposited under the same vacuum deposition conditions to form... A thick electron transport layer. An organic light-emitting diode (OLED) is fabricated by sequentially depositing LiF and Al onto the electron transport layer to form a cathode.

[0298] The structure of the organic light-emitting diode is ITO / NPB (80nm) / EML (compound 3 (97wt%) + (piq)2Ir(acac)(3wt%), 30nm) / Balq (5nm) / Alq3 (20nm) / LiF (1nm) / Al (100nm).

[0299] Examples 27 to 35

[0300] Organic light-emitting diodes were manufactured in the same manner as in Example 26, except that compounds 9, 17, 18, 19, 23, 41, 97, 131 and 256 were used instead of compound 3 as the main body when forming the light-emitting layer.

[0301] Comparative Examples 6 to 13

[0302] Organic light-emitting diodes were manufactured in the same manner as in Example 52, except that comparative compounds 18, 40, 48, 155, 156, 189, 327 and 328 were used instead of compound 3.

[0303] Comparative compounds 18, 40, 48, 155, or 189 were prepared by the methods disclosed in Japanese Patent No. 564848 or Japanese Patent Publication No. 2015-134745.

[0304]

[0305] Evaluation Example II

[0306] The luminous efficiency and lifetime characteristics of each organic light-emitting diode according to Examples 26 to 35 and Comparative Examples 6 to 13 were evaluated.

[0307] The specific measurement methods are as follows, and the results are shown in Table 4.

[0308] (1) Measuring current density change based on voltage change

[0309] Using a current-voltmeter (Keithley 2400), the current flowing through the unit device of the obtained organic light-emitting diode was measured while the voltage was increased from 0V to 10V. The measured current value was then divided by the area to obtain the result.

[0310] (2) Measuring brightness changes based on voltage changes

[0311] The brightness was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0V to 10V.

[0312] (3) Measurement of luminous efficiency

[0313] Using the brightness, current density, and voltage (V) of items (1) and (2), the calculation was performed at the same current density (10 mA / cm²). 2 Current efficiency (cd / A) at )

[0314] (4) Lifetime measurement

[0315] In terms of brightness (cd / m 2 Maintain at 5000 cd / m 2 Simultaneously, the time required until the current efficiency (cd / A) drops to 90% is measured to obtain the lifetime.

[0316] (5) Roll-off

[0317] The maximum value was calculated to be – 5000 cd / m 2 The value below / maximum value, calculate the decrease in numerical efficiency of (3) as a percentage (%).

[0318] [Table 4]

[0319]

[0320] Referring to Table 4, compared with the organic light-emitting diodes of Comparative Examples 6 to 13, the organic light-emitting diodes of Examples 26 to 35 have a longer lifespan with the same or lower driving voltage and the same or better luminous efficiency.

[0321] Therefore, the host material used in the emitting layer of the organic light-emitting diodes in Examples 26 to 35 has excellent charge transport characteristics as a phosphorescent host material. At the same time, since its absorption spectrum has an overlapping emission wavelength region with the absorption spectrum of the dopant, performance improvements (such as increased efficiency and reduced driving voltage, and especially long lifetime) and its ability as an OLED material are maximized.

[0322] Manufacturing of Organic Light Emitting Diode III

[0323] Examples 36 to 60 and Comparative Examples 14 to 21

[0324] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that the first and second substrates shown in Table 6 were used instead of compound 2 as the substrate of the light-emitting layer. In this paper, the dopant:first substrate:second substrate was co-deposited in a weight ratio of 10:45:45.

[0325] Evaluation Example III

[0326] The drive voltage, efficiency, luminance, and lifetime of each organic light-emitting diode (OLED) in Examples 36 to 60 and Comparative Examples 14 to 21 were measured using a luminance meter powered by a current-voltage meter (Kethley SMU 236) and a PR650 spectral scanning source measurement unit (Photo Research Inc.). The results are shown in Table 5. 95 Lifetime is used to evaluate the time (in hours) required for an organic light-emitting diode to reach 95% of its initial brightness relative to 100% initial brightness.

[0327] [Table 5]

[0328]

[0329] Referring to Table 5, compared with the organic light-emitting diodes of Comparative Examples 14 to 21, the organic light-emitting diodes of Examples 36 to 60 have improved efficiency / superior long lifespan at the same or lower driving voltage.

[0330] Manufacturing of Organic Light Emitting Diode IV

[0331] Examples 61 to 75 and Comparative Examples 22 to 25

[0332] An organic light-emitting diode was fabricated in the same manner as in Example 26, except that the first and second substrates shown in Table 7 were used instead of compound 2 as the substrate of the light-emitting layer. In this document, the dopant:first substrate:second substrate was co-deposited in a weight ratio of 3:48.5:48.5.

[0333] Evaluation Example IV

[0334] The driving voltage, efficiency, luminance, and lifetime of each organic light-emitting diode of Examples 61 to 75 and Comparative Examples 22 to 25 were measured using a luminance meter powered by a current and voltmeter (Kethley SMU 236) and a PR650 spectral scanning source measurement unit (Photo Research Inc.).

[0335] The results are shown in Table 6.

[0336] [Table 6]

[0337]

[0338] Referring to Table 6, the organic light-emitting diodes of Examples 61 to 75 have a longer lifespan compared to the organic light-emitting diodes of Comparative Examples 22 to 25.

[0339] Although the invention has been described in conjunction with exemplary embodiments now considered practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. Therefore, the foregoing embodiments should be understood as exemplary and not as limiting the invention in any way.

[0340] The scope of this invention is not limited thereto, but all modifications and improvements made by those skilled in the art using the basic concept of the invention as defined in the appended claims are also within the scope of this invention.

Claims

1. An organic compound represented by one of chemical formulas 2 to 4: [Chemical Formula 2][Chemical Formula 3] [Chemical Formula 4] in, In chemical formulas 2 to 4, X 1 and X 2 Independently O or S, Ar 1 and Ar 2 Independently, it is a substituted or unsubstituted C6 to C30 aryl group, wherein "substituted" means that at least one hydrogen atom of the group is replaced by a deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyano group. L 1 It is a single-bonded or unsubstituted phenylene, and R 1 To R 6 It is independently hydrogen, cyano, C1 to C4 alkyl, C6 to C12 aryl, or C6 to C12 aryl substituted with cyano.

2. The organic compound according to claim 1, wherein Ar 1 and Ar 2 Independently, it is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl or a substituted or unsubstituted anthraquinone, or a substituted or unsubstituted triphenylene.

3. The organic compound according to claim 1, wherein the organic compound is selected from the compounds listed in Group 1. [Group 1] 。 4. A composition comprising: The first organic compound, wherein the first organic compound is the organic compound according to claim 1, and The second organic compound, which contains a carbazole moiety, is represented by chemical formula 4: [Chemical Formula 4] in, In chemical formula 4, Y 1 It is a single-bonded, substituted or unsubstituted C6 to C30 arylene group, or a divalent or unsubstituted C2 to C30 heterocyclic group. A 1 For substituted or unsubstituted C6 to C30 aryl groups or substituted or unsubstituted C2 to C30 heterocyclic groups, R 9 To R 14 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and R 11 To R 14 Independent existence or R 11 To R 14 Adjacent groups in the ring connect with each other to form a ring.

5. The composition according to claim 4, wherein the second organic compound is represented by chemical formula 4A or a combination of chemical formulas 4B-1 and 4B-2: [Chemical Formula 4A] [Chemical Formula 4B-1] [Chemical Formula 4B-2] in, In chemical formula 4A, chemical formula 4B-1, or chemical formula 4B-2 Y 1 To Y 3 Independently, it is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. A 1 To A 3 Independently, it can be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. Two adjacent ones in Equation 4B-1 Two with chemical formula 4B-2 Combine, The remaining two in chemical formula 4B-1 Independent for CR 11 , where R 11 Whether they are the same or different, R 9 To R 11 and R 15 To R 19 Independently, it is hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and m is an integer between 0 and 2.

6. The composition according to claim 5, wherein A of chemical formula 4A, chemical formula 4B-1 and chemical formula 4B-2 1 To A 3 Independently, it is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted fluorenyl, or a combination thereof.

7. The composition according to claim 5, wherein The second organic compound is represented by the chemical formula 4A-1, 4B-c, or 4B-d: [Chemical Formula 4A-1] [Chemical Formula 4B-c] [Chemical Formula 4B-d] in, In chemical formulas 4A-1, 4B-c, and 4B-d, Y 1 To Y 3 Independently, it is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. A 1 To A 3 Independently, it is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, or a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted fluorene, or a combination thereof, and R 9 To R 11 and R 15 To R 19 It is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic or a combination thereof.

8. An organic optoelectronic device comprising: The anode and cathode facing each other, and An organic layer disposed between the anode and the cathode The organic layer comprises the organic compound of claim 1 or the composition of claim 4.

9. The organic optoelectronic device according to claim 8, wherein... The organic layer includes a light-emitting layer. The organic compound or the composition is included as a main component in the luminescent layer.

10. The organic optoelectronic device according to claim 8, wherein... The organic layer comprises: Emissive layer, and An electronic auxiliary layer disposed between the cathode and the light-emitting layer The electronic auxiliary layer comprises the organic compound of claim 1.

11. A display device comprising the organic optoelectronic device of claim 8.

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