Composition for organic optoelectronic element, organic optoelectronic element and display device

Abstract

The present invention relates to a composition for an organic optoelectronic element, an organic optoelectronic element, and a display device, the composition comprising: a first compound for an organic optoelectronic element represented by a combination of Chemical Formula 1 and Chemical Formula 2, and a second compound for an organic optoelectronic element represented by a combination of Chemical Formula 3 and Chemical Formula 4. In Chemical Formulas 1 to 4, each substituent is as defined in the specification.

Description

Technical Field

[0001] Disclosed are a composition for an organic optoelectronic element, an organic optoelectronic element and a display device. Background Art

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

[0003] Organic optoelectronic components can be divided into the following categories according to their driving principles. One is a photoelectric component that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, while the other is a light-emitting component that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0004] Examples of organic optoelectronic elements include organic photoelectric elements, organic light emitting diodes, organic solar cells, and organic photoconductors.

[0005] Among these, organic light emitting diodes (OLEDs) have attracted attention in recent years due to an increase in demand for flat panel display devices. An organic light emitting diode is a device that converts electrical energy into light, and an organic material between electrodes greatly affects the performance of the organic light emitting diode. Summary of the invention

[0006] [Technical issues]

[0007] One embodiment provides a composition for an organic optoelectronic element, which can realize an organic optoelectronic element with high efficiency and long lifetime.

[0008] Another embodiment provides an organic optoelectronic element including the composition.

[0009] Another embodiment provides a display device including the organic optoelectronic element.

[0010] [Technical solution]

[0011] According to one embodiment, a composition for an organic optoelectronic device includes a first compound for an organic optoelectronic device represented by a combination of Chemical Formula 1 and Chemical Formula 2 and a second compound for an organic optoelectronic device represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0012]

[0013] In Chemical Formula 1 and Chemical Formula 2,

[0014] Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0015] a 1 * to a 4 The two adjacent * are 1 * and b 2 *connect,

[0016] a 1 * to a 4 *Not with b 1 * and b 2 * The rest of the connection is independent of CL a -R a ,

[0017] L a and L 1 To L 4 are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0018] R a and R 1 To R 4 are independently hydrogen, deuterium, cyano, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0019] R a and R 1 To R 4 At least one of them is a group represented by chemical formula a,

[0020]

[0021] Among them, in chemical formula a,

[0022] L b and L c are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0023] R b and R c are independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0024] * is with L a and L 1 To L 4 The connection point;

[0025]

[0026] Among them, in Chemical Formula 3 and Chemical Formula 4,

[0027] X is O or S,

[0028] c 1 * and c 2 * respectively with d 1 * and d 2 * or d 2 * and d 1 *connect,

[0029] L 5 and L 6 are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0030] R 5 To R 10 are independently hydrogen, deuterium, cyano, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0031] R 5 and R 6 At least one of the is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0032] According to another embodiment, an organic optoelectronic element includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, and the organic layer includes a composition for an organic optoelectronic element.

[0033] According to another embodiment, a display device including an organic optoelectronic element is provided.

[0034] [Beneficial Effects]

[0035] Organic optoelectronic components with high efficiency and long lifetime can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 and Figure 2 are cross-sectional views each showing an organic light emitting diode according to an embodiment.

[0037] <Description of symbols>

[0038] 100, 200: Organic light-emitting diodes

[0039] 105: Organic layer

[0040] 110: cathode

[0041] 120: Anode

[0042] 130: Luminous layer

[0043] 140: Hole auxiliary layer DETAILED DESCRIPTION

[0044] [Best Mode]

[0045] Hereinafter, embodiments of the present invention will be described in detail. However, these embodiments are exemplary, the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0046] In the present specification, if no definition is provided otherwise, "substituted" means that at least one hydrogen of the substituent or the compound is replaced with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl (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 a combination thereof.

[0047] In one example of the present invention, "substituted" means that at least one hydrogen 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 or C2 to C30 heteroaryl. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl or C2 to C30 heteroaryl. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, pyridyl, quinolyl, isoquinolyl, dibenzofuranyl, dibenzothienyl or carbazolyl. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, dibenzofuranyl or dibenzothienyl. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl or dibenzothienyl.

[0048] In the present specification, if no definition is otherwise provided, "hetero" means that one functional group includes one to three hetero atoms selected from N, O, S, P and Si, and the rest are carbon.

[0049] In the present specification, "aryl group" refers to a group including at least one hydrocarbon aromatic portion, and may include a group in which all elements of the hydrocarbon aromatic portion have p orbitals forming conjugation (e.g., phenyl, naphthyl, etc.), a group in which two or more hydrocarbon aromatic portions can be linked by a σ bond (e.g., biphenyl, terphenyl, quaterphenyl, etc.), and a group in which two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring (e.g., fluorenyl, etc.).

[0050] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0051] In the present specification, "heterocyclic group" is a general concept of heteroaryl group, and may include at least one heteroatom selected from N, O, S, P and Si instead of carbon (C) in a cyclic compound such as an aryl group, a cycloalkyl group, a condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0052] For example, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings may be fused. When the heteroaryl is a fused ring, each ring may include 1 to 3 heteroatoms.

[0053] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted The invention may include, but is not limited to, a substituted or unsubstituted triphenylene group (triphenylene group), a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0054] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzophenone, or a substituted or unsubstituted benzophenone. The invention may include, but is not limited to, thiophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but is not limited thereto.

[0055] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0056] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0057] Hereinafter, a composition for an organic optoelectronic element according to one embodiment is described.

[0058] A composition for an organic optoelectronic element according to one embodiment includes a first compound for an organic optoelectronic element having a hole characteristic and a second compound for an organic optoelectronic element having an electron characteristic.

[0059] The first compound for an organic optoelectronic device is represented by a combination of Chemical Formula 1 and Chemical Formula 2.

[0060]

[0061] In Chemical Formula 1 and Chemical Formula 2,

[0062] Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0063] a 1 * to a 4 The two adjacent * are 1 * and b 2 *connect,

[0064] a 1 * to a 4 *Not with b 1 * and b 2 * The rest of the connection is independent of CL a -R a ,

[0065] L a and L 1 To L 4 are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0066] R a and R 1 To R 4 are independently hydrogen, deuterium, cyano, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0067] R a and R 1 To R 4 At least one of them is a group represented by chemical formula a,

[0068]

[0069] Among them, in chemical formula a,

[0070] L b and L c are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0071] R b and R c are independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0072] * is with L a and L 1 To L 4 connection point.

[0073] The first compound for an organic optoelectronic element has a structure in which benzocarbazole is substituted with amine, so that the HOMO electron cloud is extended from the amine to the benzocarbazole, thereby having a high HOMO energy and having excellent hole injection and transport characteristics.

[0074] Furthermore, since benzocarbazole has a relatively higher HOMO energy than bicarbazole and indolecarbazole, a device having a low driving voltage can be realized by applying a structure in which benzocarbazole is substituted with amine.

[0075] In addition, bicarbazole and indolecarbazole have high T1 energy and are not suitable as red hosts, while the structure in which benzocarbazole is substituted with amine has T1 energy suitable as red hosts. Therefore, the device to which the composition according to the present invention is applied can achieve high efficiency / long life characteristics.

[0076] Meanwhile, since it is included together with the second compound for an organic optoelectronic element, it exhibits good interface characteristics as well as hole transporting capability and electron transporting capability, thereby reducing a driving voltage of a device including it.

[0077] For example, R b and R c The groups may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0078] For example, R b and R c The groups may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0079] For example, L b and L c They may independently be a single bond, a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group or a phenanthrylene group.

[0080] For example, L b and L c Each of them may independently be a single bond or a phenylene group.

[0081] For example, Ar may independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0082] For example, Ar can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a combination thereof.

[0083] For example, Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, but is not limited thereto.

[0084] For example, L a and L 1 To L 4 They may independently be a single bond, or a substituted or unsubstituted C6 to C20 arylene group.

[0085] For example, L a and L 1 To L 4 The groups may independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.

[0086] For example, L a and L 1 To L 4 The substituted or unsubstituted m-phenylene, substituted or unsubstituted p-phenylene, substituted or unsubstituted o-phenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted m-terphenylene, substituted or unsubstituted p-terphenylene, or substituted or unsubstituted o-terphenylene. In this article, "substituted" may, for example, mean that at least one hydrogen is replaced by deuterium, C1 to C20 alkyl, C6 to C20 aryl, halogen, cyano, or a combination thereof.

[0087] For example, R a and R 1 To R 4 are independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heterocyclic group, or a group represented by Chemical Formula a.

[0088] For example, R a and R 1 To R 4 They may independently be hydrogen or a group represented by Chemical Formula a, but are not limited thereto.

[0089] As an example, for example, depending on the fusion position of Chemical Formula 1 and Chemical Formula 2, the first compound for an organic optoelectronic element may be represented by one of Chemical Formula 1A to Chemical Formula 1C.

[0090]

[0091] In Chemical Formulae 1A to 1C, Ar, L a and L 1 To L 4 , and R a and R 1 To R 4 Same as above.

[0092] For example, Chemical Formula 1A may be represented by one of Chemical Formulae 1A-1 to 1A-3 depending on the substitution position of the group represented by Chemical Formula a.

[0093]

[0094]

[0095] In Chemical Formulae 1A-1 to 1A-3, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0096] For example, Chemical Formula 1A-1 may be represented by one of Chemical Formulae 1A-1-a to Chemical Formulae 1A-1-d, depending on a specific substitution position of the group represented by Chemical Formula a.

[0097]

[0098] In Chemical Formula 1A-1-a to Chemical Formula 1A-1-d, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0099] In one embodiment, Chemical Formula 1A-1 may be represented by Chemical Formula 1A-1-b or Chemical Formula 1A-1-c.

[0100] For example, depending on the specific substitution position of the group represented by Chemical Formula a, Chemical Formula 1A-2 may be represented by Chemical Formula 1A-2-a or Chemical Formula 1A-2-b.

[0101]

[0102] In the chemical formula 1A-2-a and the chemical formula 1A-2-b, Ar, L a , L b , L c , L 1 To L 4 , R 1 To R 4 , R b and R c Same as above.

[0103] In one embodiment, Chemical Formula 1A-2 may be represented by Chemical Formula 1A-2-a.

[0104] For example, depending on the specific substitution position of the group represented by Chemical Formula a, Chemical Formula 1A-3 may be represented by one of Chemical Formula 1A-3-a to Chemical Formula 1A-3-d.

[0105]

[0106]

[0107] In Chemical Formulas 1A-3-a to 1A-3-d, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0108] In one embodiment, Chemical Formula 1A-3 may be represented by Chemical Formula 1A-3-b or Chemical Formula 1A-3-c.

[0109] For example, Chemical Formula 1B may be represented by one of Chemical Formula 1B-1 to Chemical Formula 1B-3 depending on the substitution position of the group represented by Chemical Formula a.

[0110]

[0111] In Chemical Formula 1B-1 to Chemical Formula 1B-3, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0112] For example, Chemical Formula 1B-1 may be represented by one of Chemical Formulae 1B-1-a to 1B-1-d, depending on a specific substitution position of the group represented by Chemical Formula a.

[0113]

[0114] In Chemical Formula 1B-1-a to Chemical Formula 1B-1-d, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above

[0115] For example, depending on the specific substitution position of the group represented by Chemical Formula a, Chemical Formula 1B-2 may be represented by Chemical Formula 1B-2-a or Chemical Formula 1B-2-b.

[0116]

[0117]

[0118] In the chemical formula 1B-2-a and the chemical formula 1B-2-b, Ar, L a , L b , L c , L 1 To L 4 , R 1 To R 4 , R b and R c Same as above.

[0119] For example, Chemical Formula 1B-3 may be represented by one of Chemical Formulae 1B-3-a to 1B-3-d, depending on a specific substitution position of the group represented by Chemical Formula a.

[0120]

[0121] In the chemical formula 1B-3-a to the chemical formula 1B-3-d, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0122] In one embodiment, Chemical Formula 1B-3 may be represented by Chemical Formula 1B-3-b.

[0123] For example, Chemical Formula 1C may be represented by one of Chemical Formulae 1C-1 to 1C-3 depending on the substitution position of the group represented by Chemical Formula a.

[0124]

[0125] In Chemical Formulae 1C-1 to 1C-3, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0126] For example, Chemical Formula 1C-1 may be represented by one of Chemical Formulae 1C-1-a to 1C-1-d, depending on the specific substitution position of the group represented by Chemical Formula a.

[0127]

[0128]

[0129] In the chemical formula 1C-1-a to the chemical formula 1C-1-d, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0130] In one embodiment, Chemical Formula 1C-1 may be represented by Chemical Formula 1C-1-b.

[0131] For example, depending on the specific substitution position of the group represented by Chemical Formula a, Chemical Formula 1C-2 can be represented by Chemical Formula 1C-2-a or Chemical Formula 1C-2-b.

[0132]

[0133] In the chemical formula 1C-2-a and the chemical formula 1C-2-b, Ar, L a , L b , L c , L 1 To L 4 , R 1 To R 4 , R b and R c Same as above.

[0134] For example, Chemical Formula 1C-3 may be represented by one of Chemical Formulae 1C-3-a to 1C-3-d, depending on the specific substitution position of the group represented by Chemical Formula a.

[0135]

[0136] In the chemical formula 1C-3-a to the chemical formula 1C-3-d, Ar, L a , L b , L c , L 1 To L 4 , R a , R 1 To R 4 , R b and R c Same as above.

[0137] In one embodiment, Chemical Formula 1C-3 is represented by Chemical Formula 1C-3-b.

[0138] In certain embodiments of the present invention, the first compound for an organic optoelectronic device is represented by Chemical Formula 1A, specifically Chemical Formula 1A-1, for example, Chemical Formula 1A-1-b.

[0139] For example, the first compound for an organic optoelectronic element may be one selected from the compounds of Group 1, but is not limited thereto.

[0140] [Group 1]

[0141]

[0142]

[0143]

[0144]

[0145] The second compound for an organic optoelectronic element is represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0146] The second compound for an organic optoelectronic element is a compound having electronic characteristics, and may be included together with the above-mentioned first compound for an organic optoelectronic element to exhibit bipolar characteristics.

[0147]

[0148]

[0149] In Chemical Formula 3 and Chemical Formula 4,

[0150] X is O or S,

[0151] c 1 * and c 2 * respectively with d 1 * and d 2 * or d 2 * and d 1 *connect,

[0152] L 5 and L 6 are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0153] R 5 To R 10 are independently hydrogen, deuterium, cyano, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0154] R 5 and R 6 At least one of the is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0155] The second compound for an organic optoelectronic element is a compound that can receive electrons (i.e., electronic properties) when an electric field is applied. Specifically, it has a core in which a pyrimidine ring and a benzene ring are fused on both sides of a pentagonal ring. For example, when the compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 is used as a host in a light-emitting layer of an organic light-emitting diode, a balance between holes and electrons is achieved by the compound of the first compound for an organic optoelectronic element, resulting in high-efficiency and long-life emission.

[0156] For example, the second compound for an organic optoelectronic element may be represented by Chemical Formula 2-I or Chemical Formula 2-II.

[0157]

[0158] In the chemical formulae 2-I and 2-II, X, L 5 , L 6 and R 5 To R 10 As mentioned above.

[0159] As a specific example, R 5 and R 6 The groups may independently be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0160] For example, R 5 and R 6 The radicals may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolocarbazolyl, or a combination thereof.

[0161] For example, R 5 and R 6 The groups may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof, but are not limited thereto.

[0162] For example, R 7 To R 10 and may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic group.

[0163] As a specific example, R 7 To R 10 and may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0164] More specifically, R 7 To R 10and may independently be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C6 to C12 heterocyclic group.

[0165] In one embodiment, R 7 To R 10 They may independently be hydrogen, but are not limited thereto.

[0166] For example, R 7 To R 10 At least one of them may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group and the rest may be hydrogen, but are not limited thereto.

[0167] In one embodiment, R 7 To R 10 One of them may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl group and the rest may be hydrogen, but are not limited thereto.

[0168] In one embodiment, R 7 and R 9 may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl, and R 8 and R 10 They may independently be hydrogen, but are not limited thereto.

[0169] In one embodiment, R 8 and R 10 may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl, and R 7 and R 9 They may independently be hydrogen, but are not limited thereto.

[0170] The second compound for the organic optoelectronic element may be, for example, one selected from Group 2 compounds, but is not limited thereto.

[0171] [Group 2]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] The first compound for an organic optoelectronic element and the second compound for an organic optoelectronic element may be included in a weight ratio of 1:99 to 99:1. Within this range, the hole transport capability of the first compound for an organic optoelectronic element and the electron transport capability of the second compound for an organic optoelectronic element may be used to adjust the desired weight ratio to achieve bipolar characteristics and thereby improve efficiency and lifespan. Within this range, for example, they may be included in a weight ratio of 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. For example, they may be included in a weight ratio of 50:50 to 60:40, for example, 50:50 or 60:40.

[0202] For example, the composition for an organic optoelectronic element according to one embodiment of the present invention may include a compound represented by Chemical Formula 1A-1-b as a first compound for an organic optoelectronic element and a compound represented by Chemical Formula 2-I as a second compound for an organic optoelectronic element.

[0203] For example, in Chemical Formula 1A-1-b, Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a combination thereof, and L may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a combination thereof. a , L b , L c and L 1 To L 4 R may independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group. a , R 1 , R 2 and R 4 may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and R b and R c may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl,

[0204] In Formula 2-I, X may be O or S, L 5 and L 6 may independently be a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, R 5 and R 6 are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or a combination thereof, and R 7 To R 10 and may independently be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C6 to C12 heterocyclic group.

[0205] The composition for an organic optoelectronic device may further include one or more compounds other than the first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device.

[0206] The composition for an organic optoelectronic element may further include a dopant. For example, the dopant may be a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.

[0207] The dopant is a material mixed in a small amount with the first compound for an organic optoelectronic element and the second compound for an organic optoelectronic element to cause light emission, and generally may be a material that emits light by multiple excitation to a triplet state or higher, such as a metal complex. For example, the dopant may be an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0208] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0209] [Chemical formula Z]

[0210] L 7 MX a

[0211] In the chemical formula Z, M is a metal and L 7 and X a The same or different, and is a ligand that forms a complex with M.

[0212] For example, M can be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 7 and X a This may be, for example, a bidentate ligand.

[0213] The aforementioned composition may be formed by a dry film forming method such as chemical vapor deposition.

[0214] Hereinafter, an organic optoelectronic element is described, which includes the aforementioned compound for an organic optoelectronic element or the composition for an organic optoelectronic element.

[0215] The organic optoelectronic element may be any device that converts electrical energy into optical energy and vice versa without particular limitation, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photoconductor.

[0216] Herein, an organic light emitting diode as one example of an organic optoelectronic element is described with reference to the accompanying drawings.

[0217] Figure 1 and Figure 2 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0218] See also Figure 1 , an organic light emitting diode (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other and an organic layer 105 disposed between the anode (120) and the cathode (110).

[0219] The anode (120) may be made of a conductor with a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode (120) may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO 2 and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDT), polypyrrole, and polyaniline, but not limited thereto.

[0220] The cathode (110) may be made of a conductor with a small work function to facilitate 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 an alloy thereof; a multilayer structure material such as LiF / Al, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca, but is not limited thereto.

[0221] The organic layer (105) includes a light emitting layer (130) including the above composition.

[0222] The light emitting layer (130) may include, for example, the above-described composition.

[0223] The composition may be, for example, a red light-emitting composition.

[0224] For example, the light emitting layer (130) may include the first compound for an organic optoelectronic element and the second compound for an organic optoelectronic element as phosphorescent hosts, respectively.

[0225] See also Figure 2 In addition to the light-emitting layer (130), the organic light-emitting diode (200) further includes a hole auxiliary layer (140). The hole auxiliary layer (140) can further increase hole injection and / or hole mobility and block electrons between the anode (120) and the light-emitting layer (130). For example, the hole auxiliary layer (140) can be a hole transport layer, a hole injection layer and / or an electron blocking layer, and can include at least one layer.

[0226] The hole assisting layer (140) may include, for example, at least one of the Group E compounds.

[0227] Specifically, the hole auxiliary layer (140) may include a hole transport layer between the anode (120) and the light-emitting layer (130), and a hole transport auxiliary layer between the light-emitting layer (130) and the hole transport layer, and at least one of the group E compounds may be included in the hole transport auxiliary layer.

[0228] [Group E]

[0229]

[0230]

[0231] In addition to the above compounds, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having similar structures can also be used for the hole transport auxiliary layer.

[0232] In addition, in an embodiment of the present invention, as Figure 1 or Figure 2In the organic layer (105), the organic light emitting diode may further include an electron transport layer, an electron injection layer and a hole injection layer.

[0233] The organic light emitting diode (100, 200) may be manufactured by forming an anode or a cathode on a substrate, forming an organic layer by a dry film method such as evaporation, sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0234] The organic light emitting diode may be applied to an organic light emitting display device.

[0235] [Invention Mode]

[0236] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the present scope is not limited thereto.

[0237] (Preparation of a First Compound for an Organic Optoelectronic Element)

[0238] Synthesis Example 1: Synthesis of Compound A-2

[0239] [Reaction Scheme 1]

[0240]

[0241] a) Synthesis of intermediate A-2-1

[0242] Phenylhydrazine hydrochloride (70.0 g, 484.1 mmol) and 7-bromo-3,4-dihydro-2H-naphthalene-1-one (108.9 g, 484.1 mmol) were placed in a round-bottom flask and dissolved in ethanol (1200 ml). 60 mL of hydrochloric acid was slowly added dropwise at room temperature and then stirred at 90 ° C for 12 hours. When the reaction was completed, the solvent was removed under reduced pressure and extracted with excess EA. After the organic solvent was removed under reduced pressure, the residue was stirred in a small amount of methanol to obtain 95.2 g (66%) of intermediate A-2-1.

[0243] b) Synthesis of intermediate A-2-2

[0244] Intermediate A-2-1 (95.2 g, 319.3 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (108.7 g, 478.9 mmol) were placed in a round-bottom flask and then dissolved in 600 ml of toluene. The solution was stirred at 80 ° C for 12 hours. When the reaction was completed, after removing the reaction solvent, the residue was treated by column chromatography to obtain 41.3 g (44%) of intermediate A-2-2.

[0245] c) Synthesis of intermediate A-2-3

[0246] Intermediate A-2-2 (41.3 g, 139.0 mmol), iodobenzene (199.2 g, 976.0 mmol), CuI (5.31 g, 28.0 mmol), K 2 CO 3 (28.9 g, 209.0 mmol) and 1,10-phenanthroline (5.03 g, 28.0 mmol) were placed in a round-bottom flask and dissolved in 500 ml of DMF. The solution was stirred at 180 ° C for 12 hours. When the reaction was completed, the reaction solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and then filtered on silica gel. After concentrating the dichloromethane, recrystallization was performed using hexane to obtain 39.0 g (75%) of intermediate A-2-3.

[0247] d) Synthesis of Compound A-2

[0248] Intermediate A-2-3 (23.2 g, 62.5 mmol), bis-biphenyl-4-ylamine (21.1 g, 65.6 mmol), sodium tert-butoxide (NaOtBu) (9.0 g, 93.8 mmol), Pd 2 (dba) 3 (3.4 g, 3.7 mmol) and tri-tert-butylphosphine (P(tBu) 3 ) (4.5 g, 50% in toluene) was placed in xylene (300 mL), and then heated and refluxed for 12 hours under a nitrogen stream. After removing xylene, 200 mL of methanol was added thereto, and the crystallized solid therein was filtered out, dissolved in toluene, filtered with silica gel / diatomaceous earth, and then an appropriate amount of organic solvent was concentrated therefrom to obtain 29 g (76%) of compound A-2.

[0249] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.32 [M+H]

[0250] Synthesis Example 2: Synthesis of Compound A-3

[0251] [Reaction Scheme 2]

[0252]

[0253] a) Synthesis of intermediate A-3-1

[0254] Intermediate A-3-1 was synthesized in the same manner as in a) of Synthesis Example 1 by using 1.0 equivalent of phenylhydrazine hydrochloride and 6-bromo-3,4-dihydro-2H-naphthalen-1-one, respectively.

[0255] b) Synthesis of intermediate A-3-2

[0256] Intermediate A-3-2 was synthesized by the same method as b) of Synthesis Example 1 by using Intermediate A-3-1 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in an equivalent ratio of 1:1.5.

[0257] c) Synthesis of intermediate A-3-3

[0258] Intermediate A-3-3 was synthesized by the same method as in Synthesis Example 1 c) by using Intermediate A-3-2 and iodobenzene in an equivalent ratio of 1:3.

[0259] d) Synthesis of Compound A-3

[0260] Compound A-3 was synthesized by the same method as in d) of Synthesis Example 1 by using intermediate A-3-3 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0261] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.28 [M+H]

[0262] Synthesis Example 3: Synthesis of Compound A-5

[0263] [Reaction Scheme 3]

[0264]

[0265] a) Synthesis of intermediate A-5-1

[0266] Intermediate A-5-1 was synthesized in the same manner as in a) of Synthesis Example 1 by using phenylhydrazine hydrochloride and 3,4-dihydro-2H-naphthalen-1-one in an amount of 1.0 equivalent, respectively.

[0267] b) Synthesis of intermediate A-5-2

[0268] Intermediate A-5-2 was synthesized by the same method as b) of Synthesis Example 1 by using Intermediate A-5-1 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in an equivalent ratio of 1:1.5.

[0269] c) Synthesis of intermediate A-5-3

[0270] Intermediate A-5-3 was synthesized by the same method as in Synthesis Example 1 c) by using Intermediate A-5-2 and iodobenzene in an equivalent ratio of 1:3.

[0271] d) Synthesis of intermediate A-5-4

[0272] Intermediate A-5-3 (23.6 g, 80.6 mmol) was placed in a round-bottom flask and dissolved in 300 mL of dichloromethane. After N-bromosuccinimide (NBS) (14.1 g, 79.0 mmol) was dissolved in 100 mL of DMF, the solution was slowly added thereto in a dropwise manner and then stirred at room temperature for 2 hours. When the reaction was complete, the reaction solvent was removed and the residue was processed by column chromatography to obtain 25 g (83%) of intermediate A-5-4.

[0273] e) Synthesis of Compound A-5

[0274] Compound A-5 was synthesized by the same method as in Synthesis Example 1 (d) by using intermediate A-5-4 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0275] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.33 [M+H]

[0276] Synthesis Example 4: Synthesis of Compound A-7

[0277] [Reaction Scheme 4]

[0278]

[0279] a) Synthesis of intermediate A-7-1

[0280] Intermediate A-7-1 was synthesized in the same manner as in a) of Synthesis Example 1 by using 1.0 equivalent of 4-bromophenylhydrazine hydrochloride and 3,4-dihydro-2H-naphthalen-1-one, respectively.

[0281] b) Synthesis of intermediate A-7-2

[0282] Intermediate A-7-2 was synthesized by the same method as b) of Synthesis Example 1 by using Intermediate A-7-1 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone at an equivalent ratio of 1:1.5.

[0283] c) Synthesis of intermediate A-7-3

[0284] Intermediate A-7-3 was synthesized by the same method as in Synthesis Example 1 c) by using Intermediate A-7-2 and iodobenzene in an equivalent ratio of 1:3.

[0285] d) Synthesis of Compound A-7

[0286] Compound A-7 was synthesized by the same method as d) of Synthesis Example 1 by using intermediate A-7-3 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0287] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.30 [M+H]

[0288] Synthesis Example 5: Synthesis of Compound A-8

[0289] [Reaction Scheme 5]

[0290]

[0291] a) Synthesis of intermediate A-8-1

[0292] Intermediate A-8-1 was synthesized in the same manner as in a) of Synthesis Example 1 by using 1.0 equivalent of 3-bromophenylhydrazine hydrochloride and 3,4-dihydro-2H-naphthalen-1-one, respectively.

[0293] b) Synthesis of intermediate A-8-2

[0294] Intermediate A-8-2 was synthesized by the same method as b) of Synthesis Example 1 by using Intermediate A-8-1 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone at an equivalent ratio of 1:1.5.

[0295] c) Synthesis of intermediate A-8-3

[0296] Intermediate A-8-3 was synthesized by the same method as in Synthesis Example 1 c) by using Intermediate A-8-2 and iodobenzene in an equivalent ratio of 1:3.

[0297] d) Synthesis of Compound A-8

[0298] Compound A-8 was synthesized by the same method as d) of Synthesis Example 1 by using intermediate A-8-3 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0299] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.33 [M+H]

[0300] Synthesis Example 6: Synthesis of Compound A-11

[0301] [Reaction Scheme 6]

[0302]

[0303] a) Synthesis of intermediate A-11-1

[0304] 4-Bromoaniline (50.0 g, 290.7 mmol), 2-naphthaleneboronic acid (59.9 g, 171.9 mmol), K 2 CO 3 (80.4 g, 581.3 mmol) and Pd(PPh3 ) 4 (10.1 g, 8.7 mmol) was placed in a round-bottom flask and dissolved in 800 ml of toluene and 400 ml of distilled water, and then stirred at 80° C. for 12 hours. When the reaction was completed, the aqueous layer was removed therefrom, and the residue was treated by column chromatography to obtain 40.0 g (63%) of Intermediate A-11-1.

[0305] b) Synthesis of intermediate A-11-2

[0306] Intermediate A-11-1 (17.7 g, 80.8 mmol), 4-bromobiphenyl (18.8 g, 80.8 mmol), sodium tert-butoxide (NaOtBu) (11.6 g, 121.1 mmol), Pd 2 (dba) 3 (4.4 g, 4.8 mmol) and tri-tert-butylphosphine (P(tBu) 3 ) (5.9 g, 50% in toluene) was added to xylene (400 mL), and then heated and refluxed under nitrogen flow for 12 hours. After removing xylene, the residue was treated by column chromatography to obtain 20.0 g (67%) of intermediate A-11-2.

[0307] c) Synthesis of Compound A-11

[0308] Compound A-11 was synthesized by the same method as in Synthesis Example 1 (d) by using Intermediate A-11-2 and Intermediate A-2-3 at an equivalent ratio of 1:1.

[0309] LC / MS accurate mass calculated for C50H34N2: 662.27, measured: 662.31 [M+H]

[0310] Synthesis Example 7: Synthesis of Compound A-12

[0311] [Reaction Scheme 7]

[0312]

[0313] Compound A-12 was synthesized by the same method as in Synthesis Example 1 (d) by using Intermediate A-3-3 and Intermediate A-11-2 at an equivalent ratio of 1:1.

[0314] LC / MS accurate mass calculated for C50H34N2: 662.27, measured: 662.30 [M+H]

[0315] Synthesis Example 8: Synthesis of Compound A-29

[0316] [Reaction Scheme 8]

[0317]

[0318] a) Synthesis of intermediate A-29-1

[0319] Aniline (8.3 g, 89.5 mmol), 4-(4-bromo-phenyl)-dibenzofuran (23.1 g, 71.5 mmol), sodium tert-butoxide (NaOtBu) (12.9 g, 134.2 mmol), Pd 2 (dba) 3 (4.9 g, 5.4 mmol) and tri-tert-butylphosphine (P(tBu) 3 ) (6.5 g, 50% in toluene) was added to xylene (400 mL), and then heated and refluxed under a nitrogen stream for 12 hours. After removing xylene, the residue was treated by column chromatography to obtain 20.0 g (67%) of intermediate A-29-1.

[0320] b) Synthesis of Compound A-29

[0321] Compound A-29 was synthesized by the same method as in Synthesis Example 1 (d) by using Intermediate A-29-1 and Intermediate A-2-3 at an equivalent ratio of 1:1.

[0322] LC / MS accurate mass calculated for C46H30N2O: 626.24, measured: 626.28 [M+H]

[0323] Synthesis Example 9: Synthesis of Compound A-38

[0324] [Reaction Scheme 9]

[0325]

[0326] a) Synthetic intermediate A-38-1

[0327] 9,9-dimethyl-9H-fluoren-2-ylamine (17.4 g, 83.0 mmol), 4-bromobiphenyl (15.5 g, 66.4 mmol), sodium tert-butoxide (NaOtBu) (12.0 g, 124.5 mmol), Pd 2 (dba) 3 (4.6 g, 5.0 mmol) and tri-tert-butylphosphine (P(tBu) 3 ) (6.0 g, 50% in toluene) was added to xylene (400 mL), and then heated to reflux for 12 hours under a nitrogen stream. After removing xylene, the residue was treated by column chromatography to obtain 18.0 g (60%) of intermediate A-38-1.

[0328] b) Synthesis of Compound A-38

[0329] Compound A-38 was synthesized by the same method as in Synthesis Example 1 (d) by using Intermediate A-38-1 and Intermediate A-3-3 at an equivalent ratio of 1:1.

[0330] LC / MS accurate mass calculated for C49H36N2: 652.29, measured: 652.33 [M+H]

[0331] Synthesis Example 10: Synthesis of Compound A-51

[0332] [Reaction Scheme 10]

[0333]

[0334] a) Synthesis of intermediate A-51-1

[0335] Intermediate A-3-3 (30.0 g, 80.6 mmol), 4-chlorophenylboronic acid (15.1 g, 96.7 mmol), K 2 CO 3 (22.3 g, 161.2 mmol) and Pd(PPh 3 ) 4 (2.8 g, 2.4 mmol) was placed in a round-bottom flask and dissolved in 200 ml of tetrahydrofuran and 100 ml of distilled water, and then stirred at 80° C. for 12 hours. When the reaction was completed, after removing the water layer therefrom, the residue was treated by column chromatography to obtain 27.0 g (83%) of Intermediate A-51-1.

[0336] b) Synthesis of Compound A-51

[0337] Compound A-51 was synthesized by the same method as in Synthesis Example 1 (d) by using intermediate A-51-1 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0338] LC / MS accurate mass calculated for C52H36N2: 688.29, measured: 688.34 [M+H]

[0339] Synthesis Example 11: Synthesis of Compound A-65

[0340] [Reaction Scheme 11]

[0341]

[0342] a) Synthesis of intermediate A-65-1

[0343] 1,4-dibromo-2-nitrobenzene (30.0 g, 106.8 mmol), 2-naphthaleneboronic acid (18.4 g, 106.8 mmol), K 2 CO 3(29.5 g, 213.6 mmol) and Pd(PPh 3 ) 4 (3.7 g, 3.2 mmol) was placed in a round-bottom flask, dissolved in 300 mL of tetrahydrofuran and 150 mL of distilled water, and then stirred at 80° C. for 12 hours. When the reaction was completed, the aqueous layer was removed therefrom, and the residue was treated by column chromatography to obtain 27.0 g (77%) of Intermediate A-65-1.

[0344] b) Synthetic intermediate A-65-2

[0345] Intermediate A-65-1 (27.0 g, 82.3 mmol) and triphenylphosphine (86.3 g, 329.1 mmol) were placed in a round-bottom flask, dissolved in 300 mL of 1,2-dichlorobenzene, and then stirred at 180° C. for 12 hours. When the reaction was completed, the solvent was removed therefrom, and the residue was treated by column chromatography to obtain 18.0 g (74%) of intermediate A-65-2.

[0346] c) Synthetic intermediate A-65-3

[0347] Intermediate A-65-3 was synthesized by the same method as in Synthesis Example 1 c) by using Intermediate A-65-2 and iodobenzene in an equivalent ratio of 1:3.

[0348] d) Synthesis of Compound A-65

[0349] Compound A-65 was synthesized by the same method as in Synthesis Example 1 (d) by using intermediate A-65-3 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0350] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.30 [M+H]

[0351] Synthesis Example 12: Synthesis of Compound A-72

[0352] [Reaction Scheme 12]

[0353]

[0354] a) Synthesis of intermediate A-72-1

[0355] Intermediate A-72-1 was synthesized in the same manner as in a) of Synthesis Example 1 by using 1.0 equivalent of phenylhydrazine hydrochloride and 6-bromo-3,4-dihydro-1H-naphthalen-2-one, respectively.

[0356] b) Synthetic intermediate A-72-2

[0357] Intermediate A-72-2 was synthesized by the same method as b) of Synthesis Example 1 by using Intermediate A-72-1 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone at an equivalent ratio of 1:1.5.

[0358] c) Synthetic intermediate A-72-3

[0359] Intermediate A-72-3 was synthesized by the same method as in Synthesis Example 1 c) by using Intermediate A-72-2 and iodobenzene in an equivalent ratio of 1:3.

[0360] d) Synthesis of Compound A-72

[0361] Intermediate A-72 was synthesized by the same method as in d) of Synthesis Example 1 by using Intermediate A-72-3 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0362] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.31 [M+H]

[0363] Synthesis Example 13: Synthesis of Compound A-77

[0364] [Reaction Scheme 13]

[0365]

[0366] a) Synthesis of intermediate A-77-1

[0367] Intermediate A-77-1 was synthesized in the same manner as in a) of Synthesis Example 11 by using 1.0 equivalent of 1,4-dibromo-2-nitrobenzene and 1-naphthaleneboronic acid, respectively.

[0368] b) Synthetic intermediate A-77-2

[0369] Intermediate A-77-2 was synthesized by the same method as b) of Synthesis Example 11 by using Intermediate A-77-1 and triphenylphosphine in an equivalent ratio of 1:4.

[0370] c) Synthetic intermediate A-77-3

[0371] Intermediate A-77-3 was synthesized by the same method as in Synthesis Example 1 c) by using Intermediate A-77-2 and iodobenzene in an equivalent ratio of 1:3.

[0372] d) Synthesis of Compound A-77

[0373] Compound A-77 was synthesized by the same method as in Synthesis Example 1 (d) by using intermediate A-77-3 and bis-biphenyl-4-ylamine at an equivalent ratio of 1:1.

[0374] LC / MS accurate mass calculated for C46H32N2: 612.26, measured: 612.29 [M+H]

[0375] Comparative Synthesis Example 1: Synthesis of Comparative Compound V-1

[0376] [Reaction Scheme 14]

[0377]

[0378] The compound biphenylcarbazolyl bromide (12.33 g, 30.95 mmol) was dissolved in 200 mL of toluene under a nitrogen atmosphere, and biphenylcarbazolyl boronic acid (12.37 g, 34.05 mmol) and tetrakis(triphenylphosphine)palladium (1.07 g, 0.93 mmmol) were added thereto, and then stirred. Potassium carbonate saturated in water (12.83 g, 92.86 mmol) was added thereto, and then heated under reflux at 90°C for 12 hours. When the reaction was completed, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), and anhydrous MgSO 4 Treated to remove moisture, filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain compound V-1 (18.7 g, 92%).

[0379] LC / MS accurate mass calculated for C48H32N2: 636.26, measured: 636.30 [M+H]

[0380] Comparative Synthesis Example 2: Synthesis of Comparative Compound V-2

[0381] [Reaction Scheme 15]

[0382]

[0383] In a round-bottom flask, 8 g (31.2 mmol) of intermediate V-2-1 (5,8-dihydro-indolo[2,3-C]carbazole), 20.5 g (73.32 mmol) of 4-iodobiphenyl, 1.19 g (6.24 mmol) of CuI, 1.12 g (6.24 mmol) of 1,10-phenanthroline and 12.9 g (93.6 mmol) of K 2 CO 3 , and 50ml DMF was added thereto, and then stirred and refluxed for 24 hours under a nitrogen atmosphere. When the reaction was completed, distilled water was added thereto, and the crystals precipitated therein were filtered. The solid was dissolved in 250ml xylene, filtered through silica gel, and precipitated into a white solid to obtain 16.2g (yield: 93%) of compound V-2.

[0384] LC / MS accurate mass calculated for C42H28N2: 560.23, measured: 560.27 [M+H]

[0385] (Preparation of the Second Compound for Organic Optoelectronic Component)

[0386] Synthesis Example 14: Synthesis of Compound B-697

[0387] [Reaction Scheme 16]

[0388]

[0389] a) Synthetic intermediate B-697-1

[0390] Intermediate B-697-1 was synthesized in the same manner as in a) of Synthesis Example 11 by using 1.0 equivalent of 2,6-dibromonaphthalene and phenylboric acid, respectively.

[0391] b) Synthetic intermediate B-697-2

[0392] Intermediate B-697-1 (50 g, 177 mmol), bis(pinacol)diboron (67.26 g, 265 mmol), 1,1'-bis(diphenylphosphino)ferrocene (PdCl 2 dppf) (5.77 g, 7 mmol) and potassium acetate (51.99 g, 530 mmol) were placed in a round-bottom flask, 800 mL of toluene was added thereto, and then refluxed and stirred at 130° C. for 12 hours. When the reaction was completed, all the solvent was evaporated therefrom under reduced pressure, and the residue was dissolved in dichloromethane and extracted three times with distilled water. Recrystallization was performed using a mixed solvent of dichloromethane and n-hexane to obtain 46.5 g (79.7%) of intermediate B-697-2.

[0393] c) Synthetic intermediate B-697-3

[0394] Intermediate B-697-3 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of Intermediate B-697-2 and 2,4-dichlorobenzo[4,5]thieno[2,3-d]pyrimidine, and recrystallized from benzene.

[0395] d) Synthesis of Compound B-697

[0396] Compound B-697 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of Intermediate B-697-3 and 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and recrystallized from chlorobenzene.

[0397] LC / MS accurate mass calculated for C38H22N2OS: 554.15, measured: 555.26 [M+H]

[0398] Synthesis Example 15: Synthesis of Compound B-698

[0399] [Reaction Scheme 17]

[0400]

[0401] a) Synthetic intermediate B-698-1

[0402] Intermediate B-698-1 was synthesized in the same manner as in a) of Synthesis Example 11 by using 1.0 equivalent of 2,4-dichlorobenzo[4,5]thieno[2,3-d]pyrimidine and phenylboronic acid, respectively.

[0403] b) Synthesis of Compound B-698

[0404] Compound B-698 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of Intermediate B-698-1 and (4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)boronic acid, and recrystallized using chlorobenzene.

[0405] LC / MS accurate mass calculated for C40H25N3S: 579.18, measured: 580.29 [M+H]

[0406] Synthesis Example 16: Synthesis of Compound B-716

[0407] [Reaction Scheme 18]

[0408]

[0409] a) Synthetic intermediate B-716-1

[0410] Intermediate B-716-1 was synthesized in the same manner as in a) of Synthesis Example 11 by reacting 1.0 equivalent of each of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine and 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and recrystallized using toluene.

[0411] b) Synthetic intermediate B-716-2

[0412] Intermediate B-716-2 was synthesized in the same manner as in a) of Synthesis Example 11 by reacting 1.0 equivalent of each of 3-bromodibenzofuran and 4-chlorophenylboronic acid, and recrystallized using toluene.

[0413] c) Synthetic intermediate B-716-3

[0414] Intermediate B-716-2 (23 g, 83 mmol), bis(pinacol)diboron (31.43 g, 124 mmol), 1,1'-bis(diphenylphosphino)ferrocene (PdCl 2 dppf) (3.37 g, 4 mmol), tricyclohexylphosphine (5.55 g, 20 mmol) and potassium acetate (24.3 g, 248 mmol) were placed in a round-bottom flask, and 400 mL of N, N-dimethylformamide was added thereto, followed by reflux stirring at 160° C. for 12 hours. When the reaction was completed, all the solvent was evaporated therefrom under reduced pressure, the residue was dissolved in dichloromethane, and extracted three times with distilled water. Recrystallization was performed using a mixed solvent of dichloromethane and n-hexane to obtain 24.9 g (81.5%) of intermediate B-716-3.

[0415] d) Synthesis of compound B-716

[0416] Intermediate B-716 was synthesized in the same manner as in a) of Synthesis Example 11 by using 1.0 equivalent of each of Intermediate B-716-1 and Intermediate B-716-3, and recrystallized using dichlorobenzene.

[0417] LC / MS accurate mass calculated for C40H22N2O2S: 594.14, measured: 595.28 [M+H]

[0418] Synthesis Example 17: Synthesis of Compound B-725

[0419] [Reaction Scheme 19]

[0420]

[0421] a) Synthetic intermediate B-725-1

[0422] Intermediate B-725-1 was synthesized in the same manner as in a) of Synthesis Example 11 by reacting 1.0 equivalent of each of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine and 4-biphenylboronic acid, and recrystallized using toluene.

[0423] b) Synthesis of Compound B-725

[0424] Compound B-725 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of Intermediate B-725-1 and (4-(9H-carbazol-9-yl)phenyl)boronic acid, and recrystallized using dichlorobenzene.

[0425] LC / MS accurate mass calculated for C40H25N3S: 579.18, measured: 580.22 [M+H]

[0426] Synthesis Example 18: Synthesis of Compound B-728

[0427] [Reaction Scheme 20]

[0428]

[0429] a) Synthesis of Compound B-728

[0430] Compound B-728 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of Intermediate B-728-1 and (4-(9H-carbazol-9-yl)phenyl)boronic acid, and recrystallized using dichlorobenzene.

[0431] LC / MS accurate mass calculated for C40H23N3OS: 593.16, measured: 594.29 [M+H]

[0432] Synthesis Example 19: Synthesis of Compound B-729

[0433] [Reaction Scheme 21]

[0434]

[0435] a) Synthesis of Compound B-729

[0436] Compound B-729 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of Intermediate B-728-1 and (3-(9H-carbazol-9-yl)phenyl)boronic acid, and recrystallized using dichlorobenzene.

[0437] LC / MS accurate mass calculated for C40H23N3OS: 593.16, measured: 594.27 [M+H]

[0438] Synthesis Example 20: Synthesis of Compound B-735

[0439] [Reaction Scheme 22]

[0440]

[0441] a) Synthetic intermediate B-735-1

[0442] Intermediate B-735-1 was synthesized in the same manner as in a) of Synthesis Example 11 by reacting 1.0 equivalent of each of 2-naphthaleneboric acid and 1-bromo-4-chlorobenzene, and recrystallized using toluene.

[0443] b) Synthetic intermediate B-735-2

[0444] Intermediate B-735-2 was synthesized by reacting Intermediate B-735-1 in the same manner as in Synthesis Example 16 c), and recrystallized using a mixed solvent of dichloromethane and n-hexane.

[0445] c) Synthetic intermediate B-735-3

[0446] Intermediate B-735-3 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine and Intermediate B-735-2, and recrystallized using chlorobenzene.

[0447] d) Synthesis of compound B-735

[0448] Intermediate B-735 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 1.0 equivalent of each of Intermediate B-735-3 and (4-(9H-carbazol-9-yl)phenyl)boronic acid, and recrystallized using dichlorobenzene.

[0449] LC / MS accurate mass calculated for C44H27N3S: 629.19, measured: 630.34 [M+H]

[0450] Synthesis Example 21: Synthesis of Compound B-741

[0451] [Reaction Scheme 23]

[0452]

[0453] a) Synthesis of Compound B-741

[0454] Compound B-741 was synthesized in the same manner as in Synthesis Example 11 a) by reacting intermediate B-735-3 and 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in an amount of 1.0 equivalent each, and recrystallized using dichlorobenzene.

[0455] LC / MS accurate mass calculated for C38H22N2OS: 554.15, measured: 555.27 [M+H]

[0456] Synthesis Example 22: Synthesis of Compound B-744

[0457] [Reaction Scheme 24]

[0458]

[0459] a) Synthesis of Compound B-744

[0460] Compound B-744 was synthesized in the same manner as in Synthesis Example 11 a) by reacting Intermediate B-728-1 and Intermediate B-735-2 in an amount of 1.0 equivalent each, and recrystallized using dichlorobenzene.

[0461] LC / MS accurate mass calculated for C38H22N2OS: 554.15, measured: 555.28 [M+H]

[0462] Synthesis Example 23: Synthesis of Compound B-772

[0463] [Reaction Scheme 25]

[0464]

[0465] a) Synthetic intermediate B-772-1

[0466] Intermediate B-772-1 was synthesized in the same manner as in Synthesis Example 11 a) by reacting 2,4,7-trichlorobenzo[4,5]thieno[3,2-d]pyrimidine and 3-biphenylboronic acid in an amount of 1.0 equivalent each, and recrystallized using chlorobenzene.

[0467] b) Synthetic intermediate B-772-2

[0468] Intermediate B-772-2 was synthesized in the same manner as in Synthesis Example 11 a) by reacting Intermediate B-772-1 and (3-(9H-carbazol-9-yl)phenyl)boronic acid in an amount of 1.0 equivalent each, and recrystallized using chlorobenzene.

[0469] c) Synthesis of Compound B-772

[0470] Intermediate B-772-2 (15.0 g, 24 mmol), phenylboronic acid (3.57 g, 29 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) (0.67 g, 0.7 mmol) and cesium carbonate (11.9 g, 37 mmol) were placed in a round-bottom flask, 100 mL of 1,4-dioxane was added thereto, and 50% tri-tert-butylphosphine solution (1.4 mL, 3 mmol) was slowly added thereto in a dropwise manner, and then refluxed and stirred at 100 ° C for 12 hours. When the reaction was completed, all the solvent was evaporated therefrom under reduced pressure. The product thus obtained was boiled and dissolved in dichlorobenzene, and then filtered and recrystallized on silica gel to obtain compound B-772 (5.8 g, 68%).

[0471] LC / MS accurate mass calculated for C46H29N3S: 655.21, measured: 656.35 [M+H]

[0472] Synthesis Example 24: Synthesis of Compound B-846

[0473] [Reaction Scheme 26]

[0474]

[0475] a) Synthetic intermediate B-846-1

[0476] Intermediate B-846-1 was synthesized in the same manner as in a) of Synthesis Example 11 by reacting 1.0 equivalent of each of Intermediate B-772-1 and phenylboronic acid, and recrystallized using chlorobenzene.

[0477] b) Synthesis of Compound B-846

[0478] Compound B-846 was synthesized by reacting 1.0 equivalent of each of Intermediate B-846-1 and 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in the same manner as in Synthesis Example 23 c), and recrystallized using dichlorobenzene.

[0479] LC / MS accurate mass calculated for C40H24N2OS: 580.16, measured: 581.23 [M+H]

[0480] (Manufacturing of organic light-emitting diodes)

[0481] Example 1

[0482] Use distilled water and ultrasonic cleaning to clean the coating with a thickness of ITO (indium tin oxide) glass substrate. After washing with distilled water, the glass substrate is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., and dried, then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then moved to a vacuum depositor. The obtained ITO transparent electrode is used as an anode, and compound A is vacuum deposited on the ITO substrate to form A thick hole injection layer is deposited on the injection layer. thick compound B, then deposited Thick compound C is deposited on the hole transport layer to form a hole transport layer. Compound C-1 was added to form a hole transport auxiliary layer. Compounds A-2 and B-716 were used as the main body on the hole transport auxiliary layer and doped with 2 wt% [Ir(piq) 2 acac] as a dopant, formed by vacuum deposition Herein, compound A-2 and compound B-716 are used in a weight ratio of 5:5, and the ratios are described for the following examples, respectively. Subsequently, on the light-emitting layer, compound D and Liq are simultaneously vacuum deposited in a weight ratio of 1:1 to form A thick electron transport layer is formed, and on the electron transport layer, vacuum deposited Thick and harmonious Thick Liq and Al to make organic light-emitting diodes.

[0483] The organic light emitting diode has five organic thin layers, and specifically has the following structure.

[0484] ITO / Compound A / Compound B / Compound C / Compound C-1 / EML[Compound A-2:B-716:[Ir(piq) 2 acac](2wt%)] / Compound D:Liq / Liq / Al

[0485] Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazole-3-yl)biphenyl-4,4'-diamine

[0486] Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),

[0487] Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0488] Compound C-1: N,N-di([[1,1'-biphenyl]-4-yl]-7,7-dimethyl-7H-fluoro[4,3-b]benzofuran-10-amine

[0489] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazine-2-yl)phenyl)quinoline

[0490] Examples 2 to 14

[0491] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to the composition shown in Table 1.

[0492] Comparative Examples 1 and 2

[0493] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to the composition shown in Table 1.

[0494] evaluate

[0495] The power efficiency of the organic light emitting diodes according to Examples 1 to 14 and Comparative Examples 1 and 2 was evaluated.

[0496] The specific measurement method is as follows, and the results are shown in Table 1.

[0497] (1) Measuring the change in current density based on the change in voltage

[0498] While increasing the voltage from 0 V to 10 V, the current value flowing in the obtained organic light emitting diode with respect to the unit device was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to obtain the result.

[0499] (2) Measuring brightness changes based on voltage changes

[0500] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0501] (3) Measuring power efficiency

[0502] Using the current density and voltage from items (1) and (2), calculate the 2 ) under power efficiency (cd / A).

[0503] (4) Measurement life

[0504] By converting the brightness (cd / m 2 ) maintained at 9000cd / m 2 At the same time, the time when the current efficiency (cd / A) drops to 97% is measured to obtain the results.

[0505] (5) Measure the driving voltage

[0506] A current-voltage meter (Keithley 2400) was used at 15 mA / cm 2 Measure the driving voltage of each diode.

[0507] [Table 1]

[0508]

[0509] Referring to Table 1, compared with the organic light emitting diodes according to Comparative Examples 1 and 2, the driving voltage, efficiency, and lifespan of the organic light emitting diodes according to Examples 1 to 14 are significantly improved.

[0510] While the invention has been described in connection with what are presently considered to be practical embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A composition for an organic optoelectronic component, comprising A first compound for an organic optoelectronic device represented by Chemical Formula 1A-1, and a second compound for an organic optoelectronic device represented by Chemical Formula 2-I: [Chemical Formula 1A-1] in, In Chemical Formula 1A-1, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, L a and L 1 To L 4 All are single bonds, R a , R 1 , R 2 and R 4 are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, or a combination thereof, L b and L c are independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and R b and R c are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene or substituted or unsubstituted dibenzofuranyl, [Chemical Formula 2-I] Wherein, in Chemical Formula 2-1, X is S, L 5 and L 6 are independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 5 and R 6 are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted carbazolyl, R 7 To R 10 One of is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C12 heterocyclic group, R 7 To R 10 The remaining three of are independently hydrogen, deuterium or substituted or unsubstituted C1 to C10 alkyl, and "Substituted" means that at least one hydrogen of the substituted group is replaced with deuterium or a C1 to C5 alkyl group.

2. The composition for an organic optoelectronic device according to claim 1, wherein The first compound for an organic optoelectronic device is represented by Chemical Formula 1A-1-b: [Chemical formula 1A-1-b] Wherein, in Chemical Formula 1A-1-b, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, L a and L 1 To L 4 All are single bonds, L b and L c are independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, R a , R 1 , R 2 and R 4 are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, or a combination thereof, and R b and R c and independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene or substituted or unsubstituted dibenzofuranyl.

3. The composition for an organic optoelectronic device according to claim 1, wherein R 7 To R 10 One of is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, R 7 To R 10 The remaining three of are independently hydrogen, deuterium or substituted or unsubstituted C1 to C10 alkyl, and "Substituted" means that at least one hydrogen of the substituted group is replaced with deuterium or a C1 to C5 alkyl group. 4 . The composition for an organic optoelectronic device according to claim 1 , further comprising a dopant.

5. An organic optoelectronic component, comprising: The anode and cathode face each other, at least one organic layer between the anode and the cathode, The organic layer comprises the composition for an organic optoelectronic element according to any one of claims 1 to 4.

6. The organic optoelectronic component according to claim 5, wherein The organic layer includes a light-emitting layer, and The light-emitting layer includes the composition for an organic optoelectronic element.

7. The organic optoelectronic device according to claim 6, wherein: The first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device are respectively included as phosphorescent hosts of the light-emitting layer.

8. The organic optoelectronic device according to claim 7, wherein: The composition for an organic optoelectronic element is a composition that emits red light. 9 . A display device comprising the organic optoelectronic element according to claim 5 .

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