Organic optoelectronic compound, organic optoelectronic composition, organic optoelectronic element and display device

Abstract

This invention relates to an organic optoelectronic element compound represented by Chemical Formula 1, an organic optoelectronic element composition comprising the compound, an organic optoelectronic element, and a display device. Detailed description of Chemical Formula 1 is as defined in the specification.

Description

Technical Field

[0001] A compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device are disclosed. Background Technology

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

[0003] Based on their operating principles, organic optoelectronic devices can be broadly classified into two types. One type is a photoelectronic device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other type is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to the electrodes.

[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 gained attention due to the increasing demand for flat panel displays. OLEDs are devices that convert electrical energy into light, and the organic materials between the electrodes have a significant impact on their performance. Summary of the Invention

[0006] Technical issues

[0007] One embodiment provides a compound for use in organic optoelectronic devices, the compound being capable of achieving high-efficiency and long-life organic optoelectronic devices.

[0008] Another embodiment provides a composition for an organic optoelectronic device comprising the compound.

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

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

[0011] Technical solution

[0012] According to one embodiment, a compound represented by chemical formula 1 for use in organic optoelectronic devices is provided.

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] X is O or S.

[0017] L 1 To L 3 Independently, it is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0018] R 1 and R 2 Independently, it is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.

[0019] R 3 and R 4 Independently, it is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0020] R 5 To R 8 It is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

[0021] According to another embodiment, a composition for an organic optoelectronic device comprises a first compound for an organic optoelectronic device and a second compound for an organic optoelectronic device.

[0022] The first compound for use in organic optoelectronic devices is the compound described above for use in organic optoelectronic devices, and the second compound for use in organic optoelectronic devices can be represented by chemical formula 2.

[0023] [Chemical Formula 2]

[0024]

[0025] In chemical formula 2,

[0026] Y 1 For O, S, NL a -R a CR b R c or SiR d R e ,

[0027] L a It is a single bond, or a substituted or unsubstituted C6 to C12 arylene.

[0028] R a The substituted or unsubstituted C6 to C20 aryl group, or the substituted or unsubstituted C2 to C30 heterocyclic group,

[0029] R b R c R d and R e Independently, it is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.

[0030] R 9 and R 10 Independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0031] A is any ring selected from group I.

[0032] [Group I]

[0033]

[0034] In group I,

[0035] * indicates a connection point.

[0036] Y 2 For O or S,

[0037] R 11 To R 22 Independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0038] R a and R 9 To R 22 At least one of them is a group represented by chemical formula a.

[0039] [Chemical formula a]

[0040]

[0041] In chemical formula a,

[0042] Z 1 To Z 3 Independently N or CR f ,

[0043] R f It is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

[0044] Z 1 To Z 3 At least two of them are N.

[0045] L 4 To L6 Independently, it is a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0046] R 23 and R 24 Independently, it is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0047] * indicates a connection point.

[0048] According to another embodiment, the organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer contains a compound for the organic optoelectronic device.

[0049] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0050] Beneficial effects

[0051] It can realize high-efficiency and long-life organic optoelectronic devices. Attached Figure Description

[0052] Figure 1 and Figure 2 Cross-sectional views of organic light-emitting diodes according to embodiments are shown for each.

[0053] <Symbol Explanation>

[0054] 100, 200: Organic Light Emitting Diodes

[0055] 105: Organic layer

[0056] 110: Cathode

[0057] 120: Anode

[0058] 130: Emissive layer

[0059] 140: Hole auxiliary layer Detailed Implementation

[0060] Best mode

[0061] Embodiments of the present invention are 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.

[0062] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by: deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl (silyl, methylsilyl), 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.

[0063] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by 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, C2 to C30 heteroaryl, or cyano. In another embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In yet another embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In yet another embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0064] As used herein, unless otherwise defined, “heterogeneous” means a functional group containing 1 to 3 heteroatoms selected from N, O, S, P and Si, with the remainder being carbon.

[0065] As used herein, “aryl” refers to a group comprising at least one hydrocarbon aromatic moiety, and may include groups in which all elements of the hydrocarbon aromatic moiety have conjugated p orbitals (e.g., phenyl, naphthyl, etc.), groups in which two or more hydrocarbon aromatic moiety are linked by σ bonds (e.g., biphenyl, terphenyl, tetraphenyl, etc.), and groups in which two or more hydrocarbon aromatic moiety are directly or indirectly fused to provide a non-aromatic fused ring (e.g., fluorene, etc.).

[0066] Aryl groups can contain monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0067] As used herein, "heterocyclic group" is a general concept of heteroaryl and may contain at least one heteroatom selected from N, O, S, P, and Si replacing a carbon (C) in a cyclic compound (e.g., aryl, cycloalkyl, their fused rings, or combinations thereof). When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0068] For example, "heteroaryl" refers to an aryl group containing 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 contains two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring can contain 1 to 3 heteroatoms.

[0069] More specifically, the substituted or unsubstituted C6 to C30 aryl group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted o-terphenyl, or a substituted or unsubstituted terphenyl. The group includes, but is not limited to, triphenylene group (substituted or unsubstituted), perylene group (substituted or unsubstituted), fluorenyl group (substituted or unsubstituted), indole group (substituted or unsubstituted), furanyl group (substituted or unsubstituted), or combinations thereof.

[0070] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted pyrazol group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophene group, or a substituted or unsubstituted C2 to C30 heterocyclic group. The following are not limited to: substituted benzimidazolyl, 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 benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl or combinations thereof.

[0071] In this specification, hole characteristics refer to the ability to contribute electrons to form holes when an electric field is applied, and holes formed in the anode can be easily injected into and transported in the light-emitting layer due to the conductivity characteristics of the highest occupied molecular orbital (HOMO) energy level.

[0072] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to their conductivity based on the lowest unoccupied molecular orbital (LUMO) energy level.

[0073] The following describes a compound for use in an organic optoelectronic device according to an embodiment.

[0074] The compound for organic optoelectronic devices according to the embodiments is represented by chemical formula 1.

[0075] [Chemical Formula 1]

[0076]

[0077] In chemical formula 1,

[0078] X is O or S.

[0079] L 1 To L 3 Independently, it is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0080] R 1 and R 2 Independently, it is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.

[0081] R 3 and R 4 Independently, it is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0082] R 5 To R 8 It is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

[0083] The compound represented by Formula 1 has the following structure, in which benzofuran (or benzothiophene) is further fused with dibenzosilole in the core, and the core is substituted with at least one substituted or unsubstituted amino group.

[0084] Dibenzothiophene exhibits rapid hole transport characteristics, but due to its deep HOMO level, it is impossible to ensure sufficient hole transport capacity to achieve charge balance. However, in this invention, benzofuran (or benzothiophene) is further fused, and thus the compound has a shallow HOMO level. Therefore, optimized hole transport capacity can be ensured, and by substituting it with an amino group, it can have a T1 energy suitable for use as a host, and thus, devices incorporating it can achieve low drive and high efficiency.

[0085] Specifically, when dibenzothiophene is fused at positions 3 and 4, hole mobility increases to accelerate the driving voltage, the hole-electron balance can be adjusted, and the glass transition temperature can be increased to achieve excellent membrane properties during device fabrication.

[0086] When the amino group is substituted in the direction of further fusion of benzofuran (or benzothiophene) into the phenyl portion of dibenzothiophene in the core of dibenzothiophene, the glass transition temperature can be increased, thereby further improving thermal stability and membrane properties, thus exhibiting excellent device performance.

[0087] Depending on the substitution position of the substituted or unsubstituted amino group, chemical formula 1 can be represented by any of the following, for example, chemical formulas 1-1 to 1-4.

[0088]

[0089]

[0090] In chemical formulas 1-1 to 1-4

[0091] X, L 1 To L 3 and R 1 To R 8 Same as described above.

[0092] According to the implementation method, chemical formula 1 can be represented by chemical formula 1-2.

[0093] For example, L of chemical formula 1 1 It can be a single bond, and L 2 and L 3 It can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0094] As a specific example, L 2 and L 3 It can be a single bond, a substituted or unsubstituted p-phenylene, or a substituted or unsubstituted m-phenylene.

[0095] For example, R 1 and R 2It can be independently an unsubstituted methyl, an unsubstituted ethyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted biphenyl.

[0096] For example, R 3 and R 4 It can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted [unspecified compound]. The group includes fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthiophenyl, substituted or unsubstituted benzooxazolyl.

[0097] As a specific example, R 3 and R 4 It can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl.

[0098] For example, R 5 To R 8 It can be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0099] As a specific example, R 5 To R 8 It can be hydrogen, deuterium, or phenyl independently.

[0100] For example, a compound represented by chemical formula 1 for an organic optoelectronic device may be one of the compounds selected from group 1, but is not limited to this.

[0101] [Group 1]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] According to another embodiment, the composition for an organic optoelectronic device includes a first compound for an organic optoelectronic device and a second compound for an organic optoelectronic device, wherein the first compound for an organic optoelectronic device may be the aforementioned compound for an organic optoelectronic device, and the second compound for an organic optoelectronic device may be represented by chemical formula 2.

[0114] [Chemical Formula 2]

[0115]

[0116] In chemical formula 2,

[0117] Y 1 For O, S, NL a -R a CR b R c or SiR d R e ,

[0118] L a It is a single bond, or a substituted or unsubstituted C6 to C12 arylene.

[0119] R a The substituted or unsubstituted C6 to C20 aryl group, or the substituted or unsubstituted C2 to C30 heterocyclic group,

[0120] R b R c R d and R e Independently, it is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.

[0121] R 9 and R 10 Independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0122] A is any one of the rings selected from group I.

[0123] [Group I]

[0124]

[0125] In group I,

[0126] * indicates a connection point.

[0127] Y 2 For O or S,

[0128] R 11 To R 22 Independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0129] R a and R 9 To R 22 At least one of them is a group represented by chemical formula a.

[0130] [Chemical formula a]

[0131]

[0132] In chemical formula a,

[0133] Z 1 To Z 3 Independently N or CR f ,

[0134] R f It is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

[0135] Z 1 To Z 3 At least two of them are N.

[0136] L 4 To L 6 Independently, it is a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0137] R 23 and R 24 Independently, it is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0138] * indicates a connection point.

[0139] The second compound for organic optoelectronic devices can be used together with the first compound for organic optoelectronic devices in the light-emitting layer to increase charge mobility and stability, thereby improving luminous efficiency and lifetime characteristics.

[0140] For example, chemical formula 2 can be represented by one of chemical formulas 2-I to 2-X.

[0141]

[0142]

[0143]

[0144] In chemical formulas 2-I to 2-X

[0145] Y 1 Y 2 R 9 To R 18 R 20 To R 24 L 4 To L 6 and Z 1 To Z 3 Same as above.

[0146] As a specific example, chemical formula 2-I can be represented by chemical formula 2-Ia or chemical formula 2-Ib.

[0147]

[0148] As a specific example, chemical formula 2-III can be represented by chemical formula 2-IIIa.

[0149] [Chemical Formula 2-IIIa]

[0150]

[0151] As a specific example, chemical formula 2-IV can be represented by chemical formula 2-IVa.

[0152] [Chemical formula 2-IVa]

[0153]

[0154] As a specific example, chemical formula 2-V can be represented by chemical formula 2-Va.

[0155] [Chemical formula 2-Va]

[0156]

[0157] As a specific example, chemical formula 2-VI can be represented by chemical formula 2-VIa or chemical formula 2-VIb.

[0158]

[0159] As a specific example, chemical formula 2-VII can be represented by chemical formula 2-VIIa.

[0160] [Chemical Formula 2-VIIa]

[0161]

[0162] As a specific example, chemical formula 2-VIII can be represented by chemical formula 2-VIIIa or chemical formula 2-VIIIb.

[0163]

[0164] In the above chemical formula, each substituent is as described above.

[0165] As a more specific example, the second compound used in organic optoelectronic devices can be represented by one of chemical formulas 2-I, 2-III, and 2-VI.

[0166] For example, a second compound used in an organic optoelectronic device may be represented by one of the chemical formulas 2-Ia, 2-IIIa, 2-VIa, and 2-VIb.

[0167] In exemplary embodiments, in chemical formulas 2-Ia, 2-IIIa, 2-VIa, and 2-VIb, Y 1 It can be O or S, R 9 To R 15 It can be independently hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, L 4 To L 6 It can be independently a single bond, or a substituted or unsubstituted C6 to C12 arylene, and R 23 and R 24 It can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.

[0168] For example, the second compound used in an organic optoelectronic device may be one of the compounds listed in Group 2, but is not limited to that.

[0169] [Group 2]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] As a more specific example, the compounds for organic optoelectronic devices according to the present invention can be represented by chemical formulas 1-2, and

[0177] In chemical formulas 1-2, X can be O or S, L 1 It can be a single bond, L 2 and L 3 It can be a single-bonded, substituted, or unsubstituted phenylene, R 1 and R 2 It can be independently methyl, R 3 and R 4 It can independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophene, and R 5 To R 8 It can be hydrogen independently.

[0178] In addition to the compounds mentioned above for use in organic optoelectronic devices, one or more compounds may also be included.

[0179] For example, it may be a composition comprising the aforementioned first compound for organic optoelectronic devices and the second compound for organic optoelectronic devices.

[0180] The compound and the second compound for an organic optoelectronic device can be contained in a weight ratio of 1:99 to 99:1. Within this range, bipolar characteristics can be achieved by adjusting the appropriate weight ratio using the hole transport capability of the first compound and the electron transport capability of the second compound, thereby improving efficiency and lifetime. Within this range, for example, the compound can be contained in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50). As specific examples, the compound can be contained in a weight ratio of 30:70, 40:60, or 50:50.

[0181] For example, it may further contain dopants.

[0182] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.

[0183] A dopant is a material that is mixed in small amounts with a compound or composition used in an organic optoelectronic device to induce luminescence, and can generally be a material that emits light by being excited to the triplet state or more multiple times, such as a metal complex. The dopant can be, for example, an inorganic compound, an organic compound, or an organic-inorganic compound, and one or more of these types can be used.

[0184] Examples of dopants may be phosphorescent dopants, and examples of phosphorescent dopants may be organometallic compounds comprising Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0185] [Chemical Formula Z]

[0186] L 7 MX 1

[0187] In the chemical formula Z, M represents a metal, and L... 7 With X 1 They may be the same or different from each other, and are ligands that form complexes with M.

[0188] 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 7 and X 1 It could be, for example, a bidentate ligand.

[0189] The aforementioned compounds and compositions for organic optoelectronic devices can be formed by, for example, dry film formation methods such as chemical vapor deposition.

[0190] The following describes an organic optoelectronic device comprising the above-mentioned compound for organic optoelectronic devices.

[0191] Organic optoelectronic devices can be any device that converts electrical energy into light energy or light energy into electrical energy without particular limitation, and can be, for example, organic optoelectronic devices, organic light-emitting diodes, organic solar cells, and organic photoconductor drums.

[0192] In this paper, an organic light-emitting diode (OLED) is illustrated as an example of an organic optoelectronic device with reference to the figures.

[0193] Figure 1 and Figure 2 A cross-sectional view of an organic light-emitting diode according to an embodiment is shown.

[0194] Reference Figure 1The organic light-emitting diode (100) according to the embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) located between the anode (120) and the cathode (110).

[0195] The anode (120) 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. For example, the anode (120) may be a metal, such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; a metal oxide, such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metal and oxide, 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.

[0196] The cathode (110) may be made of a conductor with a small work function to aid electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode (110) 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 material, such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0197] The organic layer (105) may contain the aforementioned compounds used in organic optoelectronic devices.

[0198] The organic layer (105) may include a light-emitting layer (130), and the light-emitting layer (130) may contain the aforementioned compound for organic optoelectronic devices.

[0199] The composition for organic optoelectronic devices that further includes dopants can be, for example, a red light emitting composition.

[0200] The light-emitting layer (130) may contain, for example, the compounds described above for organic optoelectronic devices.

[0201] In addition to the light-emitting layer, the organic layer may further include an auxiliary layer.

[0202] The auxiliary layer can be, for example, a hole auxiliary layer (140).

[0203] Reference Figure 2The organic light-emitting diode (200) further includes a hole auxiliary layer (140) in addition to the light-emitting layer (130). The hole auxiliary layer (140) further increases hole injection and / or hole mobility and blocks electrons between the anode (120) and the light-emitting layer (130).

[0204] The hole-assisted layer (140) may contain at least one compound, for example, group E.

[0205] Specifically, the hole auxiliary layer (140) may include a hole transport layer located between the anode (120) and the light-emitting layer (130), and a hole transport auxiliary layer located between the light-emitting layer (130) and the hole transport layer, and the hole transport auxiliary layer may contain at least one compound of group E.

[0206] [Group E]

[0207]

[0208]

[0209]

[0210] In addition to the compounds mentioned above, known compounds and similar compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A may also be used in the hole transport auxiliary layer.

[0211] In the implementation method, Figure 1 or Figure 2 In the organic light-emitting diode, an electron transport layer, an electron injection layer, or a hole injection layer may be further included as an organic layer (105).

[0212] Organic light-emitting diodes (100) and (200) can be manufactured by forming an anode or cathode on a substrate; forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating; and forming a cathode or anode on the organic layer.

[0213] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0214] Invention Model

[0215] The embodiments are described in more detail below with reference to examples. However, these examples are exemplary, and the scope of the invention is not limited thereto.

[0216] Unless otherwise noted, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods.

[0217] (Preparation of compounds for organic optoelectronic devices)

[0218] The compounds presented as more specific examples of compounds of the present invention are synthesized through the following steps.

[0219] Synthesis Example 1: Synthesis of compound A-1

[0220] [Reaction Scheme 1]

[0221]

[0222] Step 1: Synthesize Int-3

[0223] Int-2 (100 g, 275.33 mmol) was dissolved in 1.0 L of tetrahydrofuran (THF), and Int-1 (62.79 g, 275.33 mmol) and tetrakis(triphenylphosphine)palladium (9.54 g, 8.26 mmol) were added, followed by stirring. Then, potassium carbonate saturated in 500 mL of water (95.13 g, 688.34 mmol) was added, and the mixture was heated to reflux at 80 °C for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove water, and then filtered and concentrated under reduced pressure. The residue was separated and purified by rapid column chromatography to obtain 71.88 g (73%) of Int-3.

[0224] Step 2: Synthesize Int-4

[0225] Int-3 (71.88 g, 192.35 mmol) was dissolved in 670 mL of tetrahydrofuran (THF), and the internal temperature was then lowered to -78 °C. n-BuLi (104.5 g, 261.24 mmol) was then slowly added dropwise to this solution while maintaining the internal temperature at -78 °C, and the mixture was stirred at this temperature for 1 hour.

[0226] Subsequently, dichlorodimethylsilane (30.64 ml, 281.39 mmol) was added at -78 °C, and the mixture was stirred at room temperature for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove water, filtered under reduced pressure, and concentrated. The residue was separated and purified by rapid column chromatography to obtain 33.86 g (50%) of Int-4.

[0227] Step 3: Synthesize Int-5

[0228] Int-4 (33.80 g, 100.33 mmol) was dissolved in 300 mL of trifluorotoluene, and di-tert-butyl peroxide (56.42 g, 300.99 mmol) was slowly added dropwise. The mixture was heated under reflux at an internal temperature of 120 °C for 48 hours. When the reaction was complete, the reaction solution was cooled to room temperature, and 200 mL of water was added, followed by stirring for 1 hour. The result was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove water, filtered under reduced pressure, and concentrated. The residue was separated and purified by rapid column chromatography to obtain 20.16 g (60%) of Int-5.

[0229] Step 4: Synthesize compound A-1

[0230] 2.82 g (8.42 mmol) Int-5, 2.62 g (8.42 mmol) Int-6, 2.42 g (25.26 mmol) sodium tert-butoxide, and 0.34 g (0.84 mmol) tri-tert-butylphosphine were dissolved in 50 mL xylene, and 0.38 g (0.42 mmol) Pd2(dba)3 was added. The mixture was then refluxed and stirred under nitrogen atmosphere for 12 hours. When the reaction was complete, the mixture was extracted with xylene and distilled water, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography using n-hexane / dichloromethane (2:1 v / v) to obtain 3.7 g (yield: 74%) of compound A-1.

[0231] Calculated C₄₂H₃₁NOSi: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73. Measured: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73.

[0232] Synthesis Example 2: Synthesis of compound B-1

[0233] [Reaction Scheme 2]

[0234]

[0235] Except that Int-7 was used instead of Int-1 as shown in reaction scheme 2, compound B-1 was synthesized according to the same method as in synthesis example 1.

[0236] Calculated C42H31NSSi: C, 82.72; H, 5.12; N, 2.30; S, 5.26; Si, 4.61; Measured: C, 82.71; H, 5.12; N, 2.30; S, 5.26; Si, 4.61

[0237] Synthetic Examples 3 to 19

[0238] Except that Int A from Table 1 was used instead of Int-5 in Synthesis Example 1 or Synthesis Example 2, and Int B from Table 1 was used instead of Int-6, the compounds were synthesized according to the same method as in Synthesis Example 1 or Synthesis Example 2.

[0239] [Table 1]

[0240]

[0241]

[0242]

[0243] Comparative Synthesis Example 1: Preparation of Comparative Compound 1

[0244] [Reaction Scheme 3]

[0245]

[0246] 5.0 g (15.68 mmol) of intermediate M-3, 5.04 g (15.68 mmol) of intermediate A, 4.52 g (47.95 mmol) of sodium tert-butoxide, and 0.1 g (0.47 mmol) of tri-tert-butylphosphine were dissolved in 200 mL of toluene, and 0.27 g (0.47 mmol) of Pd(dba)2 was added. The mixture was then refluxed and stirred for 12 hours under a nitrogen atmosphere. When the reaction was complete, the mixture was extracted with toluene and distilled water, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (2:1 v / v) to obtain 7.8 g (yield: 82.3%) of comparative compound 1 as a white solid.

[0247] Calculated C₄⁵H₃⁻NO: C, 89.52; H, 5.51; N, 2.32; O, 2.65; Measured: C, 89.53; H, 5.50; N, 2.32; O, 2.65

[0248] Comparative Synthesis Example 2: Preparation of Comparative Compound 2

[0249] [Reaction Scheme 4]

[0250]

[0251] 5.0 g (15.68 mmol) of intermediate M-3, 4.63 g (15.68 mmol) of intermediate B, 4.52 g (47.95 mmol) of sodium tert-butoxide, and 0.1 g (0.47 mmol) of tri-tert-butylphosphine were dissolved in 200 mL of toluene. 0.27 g (0.47 mmol) of Pd(dba)2 was added, and the mixture was refluxed and stirred for 12 hours under a nitrogen atmosphere. When the reaction was complete, the mixture was extracted with toluene and distilled water, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography using n-hexane / dichloromethane (2:1 v / v) to obtain 7.3 g (yield: 80.5%) of comparative compound 2 as a white solid.

[0252] Calculated C43H31NO: C, 89.40; H, 5.41; N, 2.42; O, 2.77; Measured: C, 89.40; H, 5.41; N, 2.42; O, 2.77

[0253] Synthesis Example 20: Synthesis of compound C-3

[0254] [Reaction Scheme 5]

[0255]

[0256]

[0257] Step 1: Synthesize Int-22

[0258] In a round-bottom flask, 22.6 g (100 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine was added to 200 mL of tetrahydrofuran, 100 mL of distilled water, and 0.9 equivalents of dibenzofuran-3-boric acid (CAS No.: 395087-89-5). Then, 0.03 equivalents of tetra(triphenylphosphine)palladium and 2 equivalents of potassium carbonate were added, and the mixture was heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The obtained solid was washed with water and hexane, and recrystallized from the solid with 200 mL of toluene to obtain 21.4 g (yield: 60%) of Int-22.

[0259] Step 2: Synthesize Int-23

[0260] In a round-bottom flask, 50.0 g (261.16 mmol) of 1-bromo-4-chlorobenzene, 44.9 g (261.16 mmol) of 2-naphthoboric acid, 9.1 g (7.83 mmol) of tetraphenylphosphine palladium, and 71.2 g (522.33 mmol) of potassium carbonate were dissolved in 1000 mL of tetrahydrofuran and 500 mL of distilled water, and then heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The obtained solid was washed with water and hexane, and then recrystallized from 200 mL of toluene to obtain 55.0 g (yield: 88%) of Int-23.

[0261] Step 3: Synthesize Int-24

[0262] In a round-bottom flask, 100.0 g (418.92 mmol) of Int-23 was dissolved in 1000 mL of DMF, and 17.1 g (20.95 mmol) of dichlorodiphenylphosphine ferrocene palladium, 127.7 g (502.70 mmol) of dipinallodiborone and 123.3 g (1256.76 mmol) of potassium acetate were added. The mixture was then heated under reflux for 12 hours under a nitrogen atmosphere. The reaction solution was cooled and then added dropwise to 2 L of water to recover the solid. The obtained solid was dissolved in boiling toluene, filtered through silica gel, and the resulting filtrate was concentrated. The concentrated solid was stirred with a small amount of hexane and filtered to obtain 28.5 g (yield: 70%) of Int-24.

[0263] Step 4: Synthesize compound C-3

[0264] In a round-bottom flask, 10.0 g (27.95 mmol) of intermediate 24, 11.1 g (33.54 mmol) of intermediate 22, 1.0 g (0.84 mmol) of tetraphenylphosphine palladium, and 7.7 g (55.90 mmol) of potassium carbonate were dissolved in 150 mL of tetrahydrofuran and 75 mL of distilled water, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The obtained solid was washed with water and methanol, and then recrystallized from 200 mL of toluene to obtain 13.4 g (yield: 91%) of compound C-3.

[0265] Calculated C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured: C, 84.55; H, 4.41; N, 8.00; O, 3.03

[0266] Synthesis Example 21: Synthesis of compound C-71

[0267] [Reaction Scheme 6]

[0268]

[0269] Step 1: Synthesize Int-25

[0270] Int-25 was synthesized using 1.0 equivalents of 2,4-dichloro-6-phenyl-1,3,5-triazine and 1-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxacyclopentaborane-2-yl)-dibenzofuran, respectively, according to the same method as that used for Int-22 in Synthesis Example 20.

[0271] Step 2: Synthesize compound C-71

[0272] Except for the use of Int-25 and Int-24 in amounts of 1.0 equivalent each, compound C-71 was synthesized according to the same method as in step four of synthesis example 20.

[0273] Calculated C43H27N3O: C, 85.83; H, 4.52; N, 6.98; O, 2.66; Measured: C, 85.83; H, 4.52; N, 6.98; O, 2.66

[0274] Synthesis Example 22: Synthesis of compound C-61

[0275] [Reaction Scheme 7]

[0276]

[0277] Step 1: Synthesize Int-26

[0278] In a round-bottom flask, 21.95 g (135.53 mmol) of 2-benzofuranylboronic acid, 26.77 g (121.98 mmol) of 2-bromo-5-chlorobenzaldehyde, 2.74 g (12.20 mmol) of Pd(OAc)₂ and 25.86 g (243.96 mmol) of Na₂CO₃ were suspended in 200 mL of acetone / 220 mL of distilled water for 12 hours at room temperature. When the reaction was complete, the product was concentrated, and the organic layer obtained by extraction with dichloromethane was subjected to silica gel column chromatography to obtain 21.4 g (yield: 68%) of Int-26.

[0279] Step 2: Synthesize Int-27

[0280] 20.4 g (79.47 mmol) of Int-26 and 29.97 g (87.42 mmol) of (methoxymethyl)triphenylphosphonium chloride were suspended in 400 mL of THF, and 10.70 g (95.37 mmol) of potassium tert-butoxide was added. The mixture was then stirred at room temperature for 12 hours. When the reaction was complete, 400 mL of distilled water was added for extraction. The organic layer was concentrated and then re-extracted with dichloromethane. Magnesium sulfate was added and the mixture was stirred for 30 minutes. The resulting filtrate was then concentrated. 100 mL of dichloromethane and 10 mL of methanesulfonic acid were added to the concentrated filtrate, and the mixture was stirred for 1 hour.

[0281] When the reaction was complete, the resulting solid was filtered and dried with distilled water and methanol to obtain 21.4 g (yield: 65%) Int-27.

[0282] Step 3: Synthesize Int-28

[0283] 12.55 g (49.66 mmol) Int-27, 2.43 g (2.98 mmol) Pd(dppf)Cl2, 15.13 g (59.60 mmol) bis(pinacol)diboron, 14.62 g (148.99 mmol) KOAc and 3.34 g (11.92 mmol) P(Cy)3 were suspended in 200 mL of DMF and then refluxed with stirring for 12 hours. When the reaction was complete, 200 mL of distilled water was added, and the solids produced were filtered. The organic layer extracted with dichloromethane was subjected to column chromatography with hexane:EA = 4:1 (v / v) to obtain 13 g (yield: 76%) Int-28.

[0284] Step 4: Synthesize compound C-61

[0285] Compound C-61 was synthesized using 1.0 equivalents of Int-28 and Int-29, respectively, according to the same method as in step four of Synthesis Example 20.

[0286] Calculated C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured: C, 84.55; H, 4.41; N, 7.99; O, 3.04

[0287] Synthesis Example 23: Synthesis of compound C-17

[0288] [Reaction Scheme 8]

[0289]

[0290] Compound C-17 was synthesized using 1.0 equivalents of Int-30 and Int-31, respectively, according to the same method as in step four of Synthesis Example 20.

[0291] Calculated C₄¹H₂₅N₃O: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Measured: C, 85.53; H, 4.38; N, 7.30; O, 2.77

[0292] Synthesis Example 24: Synthesis of compound C-37

[0293] [Reaction Scheme 9]

[0294]

[0295] Compound C-37 was synthesized using 1.0 equivalents of Int-30 and Int-29, respectively, according to the same method as in step four of Synthesis Example 20.

[0296] Calculated C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured: C, 84.57; H, 4.40; N, 7.99; O, 3.03

[0297] Synthetic Examples 25 to 27

[0298] Except that Int C from Table 2 was used instead of Int-28 in Synthesis Example 22 and Int D from Table 2 was used instead of Int-29, the compounds were synthesized according to the same method as in step four of Synthesis Example 20.

[0299] [Table 2]

[0300]

[0301] (Manufacturing Organic Light Emitting Diodes: A Single Entity)

[0302] Example 1

[0303] The ITO (indium tin oxide) coated glass substrate was washed with distilled water and ultrasonically. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, or methanol and then dried. The glass substrate was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum depositor. Using the obtained ITO transparent electrode as the anode, compound A, doped with 1% NDP-9 (available from Novaled), was vacuum deposited on the ITO substrate to form a 1400 Å thick hole transport layer, and compound B was deposited on the hole transport layer to a thickness of 600 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, a 400 Å thick light-emitting layer was formed by vacuum deposition using compound A-1 obtained in Synthesis Example 1 as the host and 2 wt% [Ir(piq)2acac] as the dopant. Subsequently, compound C was deposited on the light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, and compound D and LiQ were simultaneously vacuum-deposited at a 1:1 weight ratio to form an electron transport layer with a thickness of 300 Å. On the electron transport layer, LiQ and Al were sequentially vacuum-deposited to thicknesses of 15 Å and 1200 Å, respectively, thereby fabricating an organic light-emitting diode.

[0304] ITO / Compound A (1% NDP-9 doped, 1400 Å) / Compound B (600 Å) / EML[Compound A-1:[Ir(piq)2acac](2wt%) (400 Å) / Compound C (50 Å) / Compound D:Liq (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0305] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0306] Compound B: N,N-bis([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluorene[4,3-b]benzofuran-10-amine

[0307] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluorene-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0308] Compound D: 8-(4-(4,6-bis(naphthyl-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0309] Examples 2 to 19, Comparative Examples 1 and 2

[0310] Apart from the changes to the main body as shown in Table 3, diodes of Examples 2 to 19 and Comparative Examples 1 and 2 were manufactured according to the same method as in Example 1.

[0311] (Manufacturing Organic Light Emitting Diodes: Hybrid Body)

[0312] Example 20

[0313] The ITO (indium tin oxide) coated glass substrate was washed with distilled water and ultrasonically. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, or methanol and then dried. The glass substrate was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum depositor. Using the obtained ITO transparent electrode as the anode, compound A, doped with 1% NDP-9 (available from Novaled), was vacuum deposited on the ITO substrate to form a 1400 Å thick hole transport layer. Compound B was deposited on the hole transport layer to a thickness of 600 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound A-1 obtained in Synthesis Example 1 and compound C-17 obtained in Synthesis Example 23 were used as the host and 2 wt% [Ir(piq)2acac] as the dopant to form a 400 Å thick light-emitting layer by vacuum deposition. In this paper, compound A-1 and compound C-17 were used in a 5:5 weight ratio. Subsequently, compound C was deposited on the light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, and compound D and LiQ were simultaneously vacuum-deposited at a 1:1 weight ratio to form an electron transport layer with a thickness of 300 Å. On the electron transport layer, LiQ and Al were sequentially vacuum-deposited to thicknesses of 15 Å and 1200 Å, respectively, thereby fabricating an organic light-emitting diode.

[0314] ITO / compound A (1% NDP-9 doped, 1400 Å) / compound B (600 Å) / EML [98 wt% mixture of compound A-1 and compound C-17 in a 5:5 weight ratio, and 2 wt% [Ir(piq)2acac] (400 Å) / compound C (50 Å) / compound D:Liq (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0315] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0316] Compound B: N,N-bis([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluorene[4,3-b]benzofuran-10-amine

[0317] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluorene-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0318] Compound D: 8-(4-(4,6-bis(naphthyl-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0319] Examples 21 to 42, Comparative Examples 3 and 4

[0320] Except for the main body changes shown in Table 4, diodes of Examples 21 to 42, Comparative Examples 3 and 4 were manufactured using the same method as in Example 1.

[0321] Assessment: Effect on increasing lifespan

[0322] (1) Measure the change in current density based on voltage change.

[0323] While increasing the voltage from 0V to 10V using a current-voltmeter (Keithley 2400), the current flowing in the cell device of the obtained organic light-emitting diode is measured, and the measured current value is divided by the area to provide the result.

[0324] (2) Measure the brightness change based on voltage changes

[0325] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a luminance meter (Minolta Cs-1000A).

[0326] (3) Measure luminous efficiency

[0327] The same current density (10 mA / cm²) was calculated using the brightness and current density measured in (1) and (2). 2 The luminous efficiency (cd / A) of .

[0328] (4) Measuring lifespan

[0329] In terms of brightness (cd / m 2 Maintain at 5,000 cd / m 2 Meanwhile, the results were obtained by measuring the time it took for the current efficiency (cd / A) to drop to 90%.

[0330] (5) Measure the driving voltage

[0331] Using a current-voltmeter (Keithley 2400) at 15mA / cm 2 Measure the drive voltage of each diode.

[0332] (6) Calculate the T90 lifetime ratio (%)

[0333] Using the T90(h) of Comparative Example 2 in Table 3 or Comparative Example 4 in Table 4 as reference values, the relative comparison value of each T90(h) value is calculated and shown in Table 3 and Table 4.

[0334] (7) Calculate the driving voltage ratio (%)

[0335] Using the driving voltage of Comparative Example 2 in Table 3 or Comparative Example 4 in Table 4 as reference values, the relative comparison value of each driving voltage is calculated and shown in Table 3 and Table 4.

[0336] (8) Calculate the luminous efficiency ratio (%)

[0337] Using the luminous efficacy (cd / A) of Comparative Example 2 in Table 3 or Comparative Example 4 in Table 4 as reference values, the relative comparison values ​​of each luminous efficacy (cd / A) were calculated and are shown in Tables 3 and 4.

[0338] [Table 3]

[0339]

[0340]

[0341] [Table 4]

[0342]

[0343] Referring to Tables 3 and 4, compared with the comparative compounds, the compounds according to the present invention exhibit significantly improved driving voltage, efficiency, and lifetime.

[0344] Although the invention has been described in conjunction with 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.

Claims

1. A composition for use in an organic optoelectronic device, comprising: A first compound for use in an organic optoelectronic device, the first compound for use in an organic optoelectronic device being represented by chemical formula 1, and A second compound for use in an organic optoelectronic device, wherein the second compound for use in an organic optoelectronic device is represented by one of chemical formulas 2-I, 2-III, and 2-VI: [Chemical Formula 1] in, In chemical formula 1, X is O or S. L 1 It is a single key. L 2 and L 3 Independently, it is a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. R 1 and R 2 Independently, it is a substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted biphenyl. R 3 and R 4 Independently, it is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophene. R 5 To R 8 It is independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C30 alkyl group; [Chemical Formula 2-I] [Chemical Formula 2-III] [Chemical Formula 2-VI] In chemical formulas 2-I, 2-III, and 2-VI Y 1 For O or S, R 9 To R 15 Independently, it is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl. Z 1 To Z 3 Both are N, L 4 To L 6 Independently, it can be a single bond or a substituted or unsubstituted C6 to C12 arylene group. R 23 and R 24 Independently, it is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl group, and "Substitution" means that at least one hydrogen atom of a substituent is replaced by a deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano group.

2. The composition according to claim 1, wherein, The first compound for organic optoelectronic devices is represented by one of chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] Among them, in chemical formulas 1-1 to 1-4, X, L 1 To L 3 and R 1 To R 8 The limitation is the same as that defined in claim 1.

3. The composition according to claim 1, wherein, R in chemical formula 1 1 and R 2 It is independently an unsubstituted methyl or an unsubstituted ethyl.

4. The composition according to claim 1, wherein the first compound for the organic optoelectronic device is one of the compounds in group 1: [Group 1] 。 5. The composition according to claim 1, wherein, The second compound for organic optoelectronic devices is represented by one of the following chemical formulas: 2-Ia, 2-IIIa, 2-VIa, and 2-VIb. [Chemical Formula 2-Ia] [Chemical Formula 2-IIIa] [Chemical Formula 2-VIa] [Chemical Formula 2-VIb] Among them, in chemical formulas 2-Ia, 2-IIIa, 2-VIa, and 2-VIb, Y 1 R 9 To R 15 L 4 To L 6 Z 1 To Z 3 R 23 and R 24 As defined in claim 1.

6. An organic optoelectronic device, comprising: The anode and cathode facing each other; and At least one organic layer between the anode and the cathode in, The organic layer comprises the composition for an organic optoelectronic device according to any one of claims 1 to 5.

7. The organic optoelectronic device according to claim 6, wherein... The organic layer includes a light-emitting layer, and The light-emitting layer comprises the composition for organic optoelectronic devices.

8. A display device comprising the organic optoelectronic device of claim 6.

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