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

Abstract

The present invention relates to: a composition for an organic optoelectronic diode, the composition comprising a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formula 2 and chemical formula 3; and an organic optoelectronic diode and a display device which comprise same. The details of chemical formula 1 to chemical formula 3 are the same as those defined in the specification.

Description

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

[0001] The present invention relates to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.

[0002] Organic optoelectronic diodes are devices that can convert electrical energy and light energy to each other.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One type is a photoelectric device, in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy. The other type is a light-emitting device, in which light energy is generated from electrical energy by supplying voltage or current to an electrode.

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

[0005] Among these, organic light-emitting diodes (OLEDs) have recently attracted significant attention due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is significantly influenced by the organic materials located between the electrodes.

[0006] One embodiment provides a composition for an organic optoelectronic device capable of implementing a high-efficiency and long-life organic optoelectronic device.

[0007] Another embodiment provides an organic optoelectronic device comprising the composition for the organic optoelectronic device.

[0008] Another embodiment provides a display device including the organic optoelectronic device.

[0009] According to one embodiment, a composition for an organic optoelectronic device is provided, comprising a first compound represented by the following chemical formula 1, and a second compound represented by a combination of the following chemical formulas 2 and 3.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] R 1 Inland R 6 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0014] R 7 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group,

[0015] L 1 and L 2 are each 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,

[0016] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0017] m1, m4, m6 and m7 are each independently an integer from 1 to 4,

[0018] m2, m3, and m5 are each independently an integer from 1 to 3;

[0019] [Chemical Formula 2] [Chemical Formula 3]

[0020]

[0021] In the above chemical formulas 2 and 3,

[0022] Ar 3 Inland Ar 5 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0023] Among a1* to a4* of chemical formula 2, two adjacent ones are connecting points that are connected to * of chemical formula 3, and among a1* to a4* of chemical formula 2, the remaining two that are not connected to * of chemical formula 3 are each independently CL a -R a And,

[0024] Z 1 Inland Z 3 are each independently N or CL b -R b And,

[0025] Z 1 Inland Z 3 At least two of them are N,

[0026] L a , L b and L 3 Inland L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0027] R a , R b , R 8 and R 9 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0028] m8 and m9 are each independently one of the integers 1 to 4.

[0029] According to another embodiment, an organic optoelectronic device is provided, comprising an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the composition for an organic optoelectronic device.

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

[0031] It can realize low-power, high-efficiency, and long-life organic optoelectronic devices.

[0032] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0033] <Explanation of symbols>

[0034] 100: Organic light-emitting diode

[0035] 105: Organic layer

[0036] 110: Cathode

[0037] 120: Bipolar

[0038] 130: Emissive layer

[0039] 140: Hole transport region

[0040] 150: Electron transport region

[0041]

[0042] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention. The present invention is defined solely by the scope of the claims set forth below.

[0043] As used herein, “substituted” means that at least one hydrogen in a substituent or compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof, unless otherwise defined.

[0044] In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is replaced with a deuterium group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0045] As used herein, “unsubstituted” means that a hydrogen atom remains a hydrogen atom without being replaced by another substituent.

[0046] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0047] In this specification, unless otherwise defined, “hetero” means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon.

[0048] In this specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, a naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

[0049] Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0050] In this specification, "heterocyclic group" is a superordinate concept including a heteroaryl group, and means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms.

[0051] For example, a "heteroaryl group" means an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected via a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0052] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, 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 naphthacenyl 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 chrysenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0053] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl 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 benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthfuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0054] In this specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has a conductive characteristic along the HOMO level, which means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement in the light-emitting layer.

[0055] In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conductive properties along the LUMO level, which means the property of facilitating the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

[0056] Hereinafter, a composition for an organic optoelectronic device according to an embodiment is described.

[0057] A composition for an organic optoelectronic device according to one embodiment comprises a first compound and a second compound.

[0058] The first compound is represented by the following chemical formula 1, and the second compound is represented by a combination of the following chemical formulas 2 and 3.

[0059] [Chemical Formula 1]

[0060]

[0061] In the above chemical formula 1,

[0062] R 1 Inland R 6 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0063] R 7 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group,

[0064] L 1 and L 2 are each 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,

[0065] Ar 1 and Ar 2are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0066] m1, m4, m6 and m7 are each independently an integer from 1 to 4,

[0067] m2, m3, and m5 are each independently an integer from 1 to 3;

[0068] [Chemical Formula 2] [Chemical Formula 3]

[0069]

[0070] In the above chemical formulas 2 and 3,

[0071] Ar 3 Inland Ar 5 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0072] Among a1* to a4* of chemical formula 2, two adjacent ones are connecting points that are connected to * of chemical formula 3, and among a1* to a4* of chemical formula 2, the remaining two that are not connected to * of chemical formula 3 are each independently CL a -R a And,

[0073] Z 1 Inland Z 3 are each independently N or CL b -R b And,

[0074] Z 1 Inland Z 3 At least two of them are N,

[0075] L a , L b and L 3 Inland L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0076] R a , R b , R8 and R 9 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0077] m8 and m9 are each independently one of the integers 1 to 4.

[0078] The compound represented by Chemical Formula 1 can have a shallower HOMO energy level by substituting carbazole in the N-direction of bicarbazole, and Chemical Formula 1 can have a faster hole mobility by having three carbazoles in total.

[0079] In particular, carbazole substituted in the N-direction of bicarbazole increases steric hindrance by including ortho-phenylene as a linking group, and thus the efficiency of an organic light-emitting device to which it is applied can be further improved.

[0080] In addition, when using a second compound represented by a combination of Chemical Formula 2 and Chemical Formula 3, hole injection can be facilitated more smoothly, and the balance of electrons and holes can be well maintained to implement stable device characteristics. In particular, when introducing the first compound and the second compound having similar deposition temperatures together, it can have the advantage of not significantly changing the device characteristics during the deposition process.

[0081] If the above m1 is 2 or more, each R 1 may be identical or different.

[0082] If the above m2 is 2 or more, each R 2 may be identical or different.

[0083] If the above m3 is 2 or more, each R 3 may be identical or different.

[0084] If the above m4 is 2 or more, each R 4 may be identical or different.

[0085] If the above m5 is 2 or more, each R 5 may be identical or different.

[0086] If the above m6 is 2 or more, each R 6 may be identical or different.

[0087] If the above m7 is 2 or more, each R 7 may be identical or different.

[0088] For example, the first compound can be expressed by any one of the following chemical formulas 1-1 to 1-8.

[0089] [Chemical Formula 1-1]

[0090]

[0091] [Chemical Formula 1-2]

[0092]

[0093] [Chemical Formula 1-3]

[0094]

[0095] [Chemical Formula 1-4]

[0096]

[0097] [Chemical Formula 1-5]

[0098]

[0099] [Chemical Formula 1-6]

[0100]

[0101] [Chemical Formula 1-7]

[0102]

[0103] [Chemical Formula 1-8]

[0104]

[0105] In the above chemical formulas 1-1 to 1-8,

[0106] R 1 Inland R 7 , L 1 and L 2 , Ar 1 and Ar 2 , and m1 to m7 are as defined in chemical formula 1.

[0107] As a specific example, the first compound can be expressed by the chemical formula 1-1 or chemical formula 1-7.

[0108] For example, the above Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0109] In one embodiment, the Ar 1 and Ar 2 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0110] For example, the above L 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted phenylene group.

[0111] In a specific embodiment, L of the chemical formula 1 1 -Ar 1 and L 2 -Ar 2 Each of the substituents may be independently selected from among the substituents listed in Group I below.

[0112] [Group Ⅰ]

[0113]

[0114] In the above group Ⅰ,

[0115] R 14 Inland R 16 , R 16a , R 16b , R 16c , R 16d , R 16e , and R 16f are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,

[0116] m14 is an integer between 1 and 5,

[0117] m15 is an integer between 1 and 4,

[0118] m16 is an integer between 1 and 3,

[0119] * is a connection point.

[0120] If the above m14 is 2 or more, each R 14 may be identical or different.

[0121] If the above m15 is 2 or more, each R 15 may be identical or different.

[0122] If the above m16 is 2 or more, each R 16 may be identical or different.

[0123] For example, the above R 1 Inland R 6 may each independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0124] For example, the above R 1 Inland R 6Each of may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0125] For example, the above R 7 may be hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0126] For example, the first compound may be, but is not limited to, one selected from the compounds listed in Group 1 below.

[0127] [Group 1]

[0128] [A-1] [A-2] [A-3] [A-4]

[0129]

[0130] [A-5] [A-6] [A-7] [A-8]

[0131]

[0132] [A-9] [A-10] [A-11] [A-12]

[0133]

[0134] [A-13] [A-14] [A-15] [A-16]

[0135]

[0136] [A-17] [A-18] [A-19] [A-20]

[0137]

[0138] [A-21] [A-22] [A-23] [A-24]

[0139]

[0140] [A-25] [A-26] [A-27] [A-28]

[0141]

[0142] [A-29] [A-30] [A-31] [A-32]

[0143]

[0144] [A-33] [A-34] [A-35] [A-36]

[0145]

[0146] [A-37] [A-38] [A-39] [A-40]

[0147]

[0148] For example, the second compound can be expressed by any one of the following chemical formulas 2A to 2F.

[0149] [Chemical Formula 2A] [Chemical Formula 2B]

[0150]

[0151] [Chemical Formula 2C] [Chemical Formula 2D]

[0152]

[0153] [Chemical Formula 2E] [Chemical Formula 2F]

[0154]

[0155] In the above chemical formulas 2A to 2F,

[0156] Z 1 Inland Z 3 , R 8 , R 9 , L 3 Inland L 6 , Ar 3 Inland Ar 5 , m8 and m9 are as defined in Chemical Formula 2 and Chemical Formula 3,

[0157] R a1 Inland R a4 Silver R 8 and R 9 is the same as the definition of

[0158] La1 Inland L a4 Silver L 3 Inland L 6 It is the same as the definition of .

[0159] As a specific example, the second compound can be represented by any one of Chemical Formula 2A, Chemical Formula 2B, and Chemical Formula 2D.

[0160] As a more specific example, the second compound can be represented by chemical formula 2B or chemical formula 2D.

[0161] In one embodiment, the second compound may be represented by chemical formula 2B.

[0162] If the above m8 is 2 or more, each R 8 may be identical or different.

[0163] If the above m9 is 2 or more, each R 9 may be identical or different.

[0164] For example, the above Ar 3 It 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 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 substituted or unsubstituted dibenzosilolyl group.

[0165] For example, the above Ar 4 and Ar 5 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl 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 substituted or unsubstituted dibenzosilolyl group.

[0166] As a specific example, the above Ar 4 and Ar 5 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted fluorenyl group.

[0167] For example, the above L 4 Inland L 6 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0168] Above L 5 -Ar 4 and L 6 -Ar 5 Each can be independently selected from the substituents listed in Group II below.

[0169] [Group II]

[0170]

[0171] In the above group II,

[0172] R 17 Inland R 20 , R 19a , R 19b , R 19c , R 19d , R 19e , and R 19f are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,

[0173] m17 is an integer between 1 and 5,

[0174] m18 is one of the integers 1 to 4,

[0175] m19 is an integer between 1 and 3,

[0176] m20 is an integer of 1 or 2,

[0177] * is a connection point.

[0178] If the above m17 is 2 or more, each R 17 may be identical or different.

[0179] If the above m18 is 2 or more, each R 18 may be identical or different.

[0180] If the above m19 is 2 or more, each R 19 may be identical or different.

[0181] If the above m20 is 2 or more, each R 20 may be identical or different.

[0182] For example, the above R 8 and R 9 may each independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0183] For example, the above R 8 and R 9 Each of may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0184] For example, the above R a1 Inland R a4 may each independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0185] For example, the above R a1 Inland R a4Each of may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0186] For example, the second compound may be, but is not limited to, one selected from the compounds listed in Group 2 below.

[0187] [Group 2]

[0188] [B-1] [B-2] [B-3] [B-4] [B-5]

[0189]

[0190] [B-6] [B-7] [B-8] [B-9] [B-10]

[0191]

[0192] [B-11] [B-12] [B-13] [B-14] [B-15]

[0193]

[0194] [B-16] [B-17] [B-18] [B-19] [B-20]

[0195]

[0196] [B-21] [B-22] [B-23] [B-24] [B-25]

[0197]

[0198] [B-26] [B-27] [B-28] [B-29] [B-30]

[0199]

[0200] [B-31] [B-32] [B-33] [B-34] [B-35]

[0201]

[0202] [B-36] [B-37] [B-38] [B-39] [B-40]

[0203]

[0204] [B-41] [B-42] [B-43] [B-44] [B-45]

[0205]

[0206] [B-46] [B-47] [B-48] [B-49] [B-50]

[0207]

[0208] [B-51] [B-52] [B-53] [B-54] [B-55]

[0209]

[0210] [B-56] [B-57] [B-58] [B-59] [B-60]

[0211]

[0212] [B-61] [B-62] [B-63] [B-64] [B-65]

[0213]

[0214] [B-66] [B-67] [B-68] [B-69] [B-70]

[0215]

[0216] [B-71] [B-72] [B-73] [B-74] [B-75]

[0217]

[0218] [B-76] [B-77] [B-78] [B-79] [B-80]

[0219]

[0220] [B-81] [B-82] [B-83] [B-84] [B-85]

[0221]

[0222] [B-86] [B-87] [B-88] [B-89] [B-90]

[0223]

[0224] [B-91] [B-92] [B-93] [B-94] [B-95]

[0225]

[0226] [B-96] [B-97] [B-98] [B-99] [B-100]

[0227]

[0228] [B-101] [B-102] [B-103] [B-104] [B-105]

[0229]

[0230] [B-106] [B-107] [B-108] [B-109] [B-110]

[0231]

[0232] [B-111] [B-112] [B-113] [B-114] [B-115]

[0233]

[0234] [B-116] [B-117] [B-118] [B-119] [B-120]

[0235]

[0236] [B-121] [B-122] [B-123] [B-124] [B-125]

[0237]

[0238] [B-126] [B-127] [B-128] [B-129] [B-130]

[0239]

[0240] [B-131] [B-132] [B-133] [B-134] [B-135]

[0241]

[0242] [B-136] [B-137] [B-138] [B-139] [B-140]

[0243]

[0244] [B-141] [B-142] [B-143] [B-144] [B-145]

[0245]

[0246] [B-146] [B-147] [B-148] [B-149] [B-150]

[0247]

[0248] [B-151] [B-152] [B-153] [B-154] [B-155]

[0249]

[0250] [B-156] [B-157] [B-158] [B-159] [B-160]

[0251]

[0252] [B-161] [B-162] [B-163] [B-164] [B-165]

[0253]

[0254] [B-166] [B-167] [B-168] [B-169] [B-170]

[0255]

[0256] [B-171] [B-172] [B-173] [B-174] [B-175]

[0257]

[0258] [B-176] [B-177] [B-178] [B-179] [B-180]

[0259]

[0260] [B-181] [B-182] [B-183] [B-184] [B-185]

[0261]

[0262] [B-186] [B-187] [B-188] [B-189] [B-190]

[0263]

[0264] [B-191] [B-192] [B-193] [B-194] [B-195]

[0265]

[0266] [B-196] [B-197] [B-198] [B-199] [B-200]

[0267]

[0268] [B-201] [B-202] [B-203] [B-204] [B-205]

[0269]

[0270] [B-206] [B-207] [B-208] [B-209] [B-210]

[0271]

[0272] [B-211] [B-212] [B-213] [B-214] [B-215]

[0273]

[0274] [B-216] [B-217] [B-218] [B-219] [B-220]

[0275]

[0276] [B-221] [B-222] [B-223] [B-224] [B-225]

[0277]

[0278] [B-226] [B-227] [B-228] [B-229] [B-230]

[0279]

[0280] [B-231] [B-232] [B-233] [B-234] [B-235]

[0281]

[0282] [B-236] [B-237] [B-238] [B-239]

[0283]

[0284] [B-240] [B-241] [B-242] [B-243]

[0285]

[0286] [B-244] [B-245] [B-246] [B-247]

[0287]

[0288] [B-248] [B-249] [B-250] [B-251]

[0289]

[0290] [B-252] [B-253] [B-254] [B-255]

[0291]

[0292] [B-256] [B-257] [B-258] [B-259]

[0293]

[0294] [B-260] [B-261] [B-262] [B-263]

[0295]

[0296] [B-264] [B-265] [B-266] [B-267]

[0297]

[0298] [B-268] [B-269] [B-270] [B-271]

[0299]

[0300] [B-272] [B-273] [B-274] [B-275]

[0301]

[0302] [B-276] [B-277] [B-278] [B-279]

[0303]

[0304] [B-280] [B-281] [B-282] [B-283]

[0305] .

[0306] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included in the above range, the electron transport ability of the first compound and the hole transport ability of the second compound can be used to achieve an appropriate weight ratio to implement bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, the weight ratio may be included in a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 80:20, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, the weight ratio may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0307] In addition to the first compound and the second compound described above, one or more compounds may be further included.

[0308] The composition for the organic optoelectronic device described above may be a composition further including a dopant.

[0309] The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0310] A dopant is a substance that causes light emission when mixed in a trace amount in a composition for an organic optoelectronic device. Generally, a substance such as a metal complex that emits light by multiple excitation that excites to a triplet state or higher can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may be included in one or more types.

[0311] An example of a dopant is a phosphorescent dopant, and examples of a phosphorescent dopant include an organometallic compound containing 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 following chemical formula Z, but is not limited thereto.

[0312] [Chemical formula Z]

[0313] L 7 MX

[0314] In the above chemical formula Z, M is a metal, and L 7 and X are ligands that are the same or different and form a complex with M.

[0315] The above M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and the above L 7 and X may be, for example, a bidentate ligand.

[0316] L 7 Examples of ligands represented by and X may be selected from, but are not limited to, the chemical formulas listed in Group A below.

[0317] [Group A]

[0318]

[0319] In the above group A,

[0320] R 300 Inland R302 are each independently a C1 to C30 alkyl group substituted or unsubstituted with hydrogen, deuterium, halogen, a C6 to C30 aryl group substituted or unsubstituted with C1 to C30 alkyl, or halogen,

[0321] R 303 Inland R 324 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0322] The dopant according to one embodiment may be an iridium complex, for example, represented by the following chemical formula 4-1 or chemical formula 4-2.

[0323] [Chemical Formula 4-1]

[0324]

[0325] In the above chemical formula 4-1,

[0326] R 101 Inland R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0327] The above R 132Inland R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0328] R 101 Inland R 116 At least one of them is a functional group represented by the following chemical formula V-1,

[0329] L 100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0330] m21 and m22 are independently any integer from 0 to 3, and m21 + m22 is any integer from 1 to 3,

[0331] [Chemical Formula V-1]

[0332]

[0333] In the above chemical formula V-1,

[0334] R 135 Inland R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0335] * indicates a part connected to a carbon atom.

[0336] [Chemical Formula 4-2]

[0337]

[0338] In the above chemical formula 4-2,

[0339] R 101 Inland R 117 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 And,

[0340] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0341] L 100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0342] n1 and n2 are independently any integers from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0343] In another embodiment, the dopant may be a platinum complex, for example represented by the chemical formula Z-1.

[0344] [Chemical Formula Z-1]

[0345]

[0346] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0347] R A , R B , R C , and R D each independently represents monosubstitution, disubstitution, trisubstitution, tetrasubstitution, or no substitution;

[0348] L B , L C , and L D are independently selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0349] If nA is 1, L Eis selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist;

[0350] R A , R B , R C , R D , R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are randomly connected to form a ring; X B , X C , X D , and X E are independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 represent oxygen or direct bonds, respectively.

[0351] The above platinum complex can be represented, for example, by the following chemical formula 5-1 or chemical formula 5-2.

[0352] [Chemical Formula 5-1]

[0353]

[0354] [Chemical Formula 5-2]

[0355]

[0356] In the above chemical formulas 5-1 and 5-2,

[0357] X 100 Silver O, S and NR 132 Selected from among,

[0358] R 118 Inland R 132 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or - SiR 133 R 134 R 135 And,

[0359] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0360] R 118 Inland R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl group,

[0361] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group.

[0362] An organic optoelectronic device using the composition for an organic optoelectronic device described above is described below.

[0363] Organic optoelectronic devices are not particularly limited as long as they can convert electrical energy and light energy to each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0364] Here, an organic light-emitting device, which is an example of an organic optoelectronic device, is described with reference to drawings.

[0365] Fig. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0366] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) positioned between the anode (120) and the cathode (110).

[0367] The anode (120) can be made of a conductor having a high work function, for example, to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode (120) may be, but is not limited to, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an 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) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0368] The cathode (110) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide, and / or a conductive polymer. The cathode (110) may be made of, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0369] The organic layer (105) may include the composition for the organic optoelectronic device described above.

[0370] The above organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) may include the composition for an organic optoelectronic device described above.

[0371] The composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light-emitting composition.

[0372] The light-emitting layer (130) may include, for example, the composition for an organic optoelectronic device described above as a phosphorescent host.

[0373] The organic layer may further include a charge transport region in addition to the light-emitting layer.

[0374] The above charge transport region may be, for example, a hole transport region (140).

[0375] The above hole transport region (140) can further increase hole injection and / or hole mobility between the anode (120) and the light-emitting layer (130) and block electrons.

[0376] Specifically, the hole transport region (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.

[0377] The composition for the organic optoelectronic device described above is included in the light-emitting layer, and at least one of the compounds listed in Group B below may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0378] [Group B]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411] Here, Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted.

[0412] In addition to the above-described compound, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure thereto may also be used in the above-described hole transport region (140).

[0413] Additionally, the charge transport region may be, for example, an electron transport region (150).

[0414] The above electron transport region (150) can further increase electron injection and / or electron mobility between the cathode (110) and the light-emitting layer (130) and block holes.

[0415] Specifically, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light-emitting layer (130), and an electron transport auxiliary layer between the light-emitting layer (130) and the electron transport layer, and at least one of the compounds listed in Group C below may be included in at least one layer of the electron transport layer and the electron transport auxiliary layer.

[0416] [Group C]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431] One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

[0432] Another embodiment may be an organic light-emitting device including an emission layer and a hole transport region as the organic layer.

[0433] Another embodiment may be an organic light-emitting device including an emission layer and an electron transport region as the organic layer.

[0434] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to a light-emitting layer (130) as an organic layer (105), as shown in FIG. 1.

[0435] Meanwhile, the organic light-emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light-emitting layer as the aforementioned organic layer.

[0436] An organic light-emitting device (100) can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film forming method such as evaporation, sputtering, plasma plating, and ion plating, and then forming a cathode or anode thereon.

[0437] The above-described organic light-emitting device can be applied to an organic light-emitting display device.

[0438] The implementation examples described above are described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0439] The starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry or P&H Tech, or synthesized using known methods, unless otherwise specified.

[0440]

[0441] (Synthesis of the first compound)

[0442] Synthesis Example 1: Synthesis of Compound A-4

[0443] [Reaction Formula 1]

[0444]

[0445] Step 1: Synthesis of intermediate A-4-1

[0446] 9-phenyl-9H,9'H-3,3'-bicarbazole (50 g, 122.4 mmol), 1-bromo-2-fluorobenzene (22.5 g, 128.5 mmol), and potassium phosphate (77.9 g, 367.2 mmol) were dissolved in 600 mL of dimethylsulfoxide and stirred under reflux at 180 °C for 12 hours. After the reaction was completed, the residue was purified by column chromatography (dichloromethane: n-hexane) to obtain 46.9 g (yield: 68.0%) of intermediate A-4-1.

[0447] Step 2: Synthesis of compound A-4

[0448] Intermediate A-1 (10.0 g, 17.7 mmol), (9-phenyl-9H-carbazol-2-yl)boronic acid (5.4 g, 18.6 mmol), tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol), and potassium carbonate (7.4 g, 53.2 mmol) were dissolved in 90 mL of a mixed solvent of tetrahydrofuran: distilled water = 2:1 by volume, and stirred under reflux at 80 °C for 12 hours. After the reaction was completed, the residue was purified by column chromatography (dichloromethane: n-hexane) to obtain 9.7 g (yield: 75.2%) of compound A-4.

[0449]

[0450] Synthesis examples 2 and 3

[0451] The final compound was synthesized through the two-step reaction (Suzuki rxn) of Synthesis Example 1 using reactants 1 and 2 as starting materials.

[0452] Synthesis Example Reactant 1 Reactant 2 Product Yield Synthesis Example 2 80.1% synthetic example 3 55.4%

[0453] Comparative Synthesis Example 1: Synthesis of Compound C-1

[0454] [Reaction Formula 2]

[0455]

[0456] Step 1: Synthesis of intermediate C-1-1

[0457] Using 1-bromo-2-nitrobenzene and 2-fluorophenylboronic acid as starting materials, the synthesis was carried out in the same manner as step 2 of Synthesis Example 1, and 45.2 g (yield: 77.6%) of intermediate C-1-1 was obtained.

[0458] Step 2: Synthesis of intermediate C-1-2

[0459] Intermediate C-1-1 (45.0 g, 207.2 mmol) and triphenylphosphine (163.0 g, 621.5 mmol) were added to 1 L of 1,2-dichlorobenzene, heated under a nitrogen stream, and refluxed for 12 hours. Upon completion of the reaction, the solvent was removed, and the mixture was purified by column chromatography (dichloromethane: n-hexane) to obtain 22.9 g (yield: 59.8%) of intermediate C-1-2.

[0460] Step 3: Synthesis of intermediate C-1-3

[0461] Intermediate C-1-2 (22.9 g, 123.7 mmol), copper iodide (4.7 g, 24.7 mmol), potassium carbonate (25.6 g, 185.5 mmol), and 1,10-phenanthroline (2.7 g, 14.8 mmol) were added to 600 mL of N,N-dimethylformamide, heated under a nitrogen stream, and stirred at reflux for 12 hours. After the reaction was completed, the solvent was removed, and the residue was purified by column chromatography (dichloromethane: n-hexane) to obtain 25.7 g (yield: 79.5%) of intermediate C-1-3.

[0462] Step 4: Synthesis of compound C-1

[0463] Using intermediate C-1-3 and 9-phenyl-9H,9'H-3,3'-bicarbazole as starting materials and changing the solvent to N-Methyl-2-pyrrolidone, the synthesis was carried out in the same manner as the synthesis of intermediate A-4-1 in Synthesis Example 1, to obtain 5.8 g (yield: 63.7%) of compound C-1.

[0464]

[0465] Comparative Synthesis Example 2: Synthesis of Compound C-2

[0466] [Reaction Formula 3]

[0467]

[0468] 9-phenyl-9H,9'H-3,3'-bicarbazole (10.0 g, 24.5 mmol), bromobenzene (4.2 g, 26.9 mmol), sodium t-butoxide (3.5 g, 36.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.1 g, 1.2 mmol), and tri-tert-butylphosphine solution (0.7 g, 3.7 mmol) were added to 120 mL of xylene, heated under a nitrogen stream, and refluxed for 12 h. After removing the solvent, the residue was purified by column chromatography (dichloromethane: n-hexane) to obtain 9.0 g (yield: 75.5%) of compound C-2.

[0469]

[0470] Comparative Synthesis Example 3: Synthesis of Compound C-3

[0471] [Reaction Formula 4]

[0472]

[0473] Using 9-phenyl-9H,9'H-3,3'-bicarbazole and 4-(4-bromophenyl)dibenzo[b,d]furan as starting materials, the synthesis was carried out in the same manner as the synthesis method of compound C-2 in Comparative Synthesis Example 2, and 3.7 g (yield: 52.3%) of compound C-3 was obtained.

[0474]

[0475] (Synthesis of the second compound)

[0476] Synthesis Example 4: Synthesis of Compound B-42

[0477] [Reaction Formula 5]

[0478]

[0479] Step 1: Synthesis of intermediate B-42-1

[0480] Using 11,12-dihydroindolo[2,3-a]carbazole and 3-bromobiphenyl as starting materials, synthesis was carried out in the same manner as the synthesis of compound C-2 in Comparative Synthesis Example 2, to obtain 22.5 g (yield: 42.3%) of intermediate B-42-1.

[0481] Step 2: Synthesis of compound B-42

[0482] Intermediate B-42-1 (10 g, 24.5 mmol) was dissolved in 120 mL of N,N-dimethylformamide, sodium hydride (0.9 g, 36.7 mmol) was slowly added, and the mixture was stirred for 30 minutes. 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (8.8 g, 25.7 mmol) was slowly added, and the mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the resulting product was recrystallized from a dichloromethane: n-hexane mixture to obtain 12.3 g (yield: 70.2%) of compound B-42.

[0483]

[0484] Synthesis Example 5: Synthesis of Compound B-76

[0485] [Reaction Formula 6]

[0486]

[0487] Step 1: Synthesis of intermediate B-76-1

[0488] Using 11,12-dihydroindolo[2,3-a]carbazole and 1-fluorodibenzofuran as starting materials, synthesis was carried out in the same manner as the synthesis of compound C-1 in Comparative Synthesis Example 1, and 16.4 g (yield: 79.2%) of intermediate B-76-1 was obtained.

[0489] Step 2: Synthesis of compound B-76

[0490] Using intermediate B-76-1 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine as starting materials, the synthesis was carried out in the same manner as the synthesis of compound C-2 in Comparative Synthesis Example 2, and 5.2 g (yield: 45.1%) of compound B-76 was obtained.

[0491]

[0492] (Fabrication of organic light-emitting devices)

[0493] Example 1

[0494] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was ultrasonically washed in distilled water. After washing with distilled water, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a 100Å thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness of 1350Å to form a hole transport layer. Compound B was deposited on the hole transport layer to a thickness of 350Å to form a hole transport auxiliary layer. Compound A-4 obtained in Synthesis Example 1 and Compound B-42 obtained in Synthesis Example 4 were simultaneously used as hosts on the hole transport auxiliary layer, and PhGD was doped at 10 wt% as a dopant to form a 330 Å thick light-emitting layer by vacuum deposition. Subsequently, Compound C was deposited at a thickness of 50 Å on the light-emitting layer to form an electron transport auxiliary layer, and Compound D and LiQ were simultaneously vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer at a thickness of 300 Å. LiQ at 15 Å and Al at 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0495] It was fabricated with the structure of ITO / compound A (3% NDP-9 doping, 100Å) / compound A (1350Å) / compound B (350Å) / EML [90 wt% of host (compound A-4:compound B-42 = 4:6 w / w): 10 wt% of PhGD] (330Å) / compound C (50Å) / compound D:LiQ (300Å) / LiQ (15Å) / Al (1200Å).

[0496] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0497] Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0498] Compound C: 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0499] Compound D: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0500] [PhGD]

[0501]

[0502]

[0503] Examples 2 to 6 and Comparative Examples 1 to 6

[0504] Devices of Examples 2 to 6 and Comparative Examples 1 to 6 were manufactured in the same manner as in Example 1, except that the host was changed as described in Table 2 below.

[0505]

[0506] Example 7 and Comparative Example 7

[0507] Devices of Example 7 and Comparative Example 7 were manufactured in the same manner as in Example 1, except that the host was changed as described in Table 2 below and the mixing ratio of the first host and the second host was changed to 3:7.

[0508]

[0509] Example 8 and Comparative Example 8

[0510] Devices of Example 8 and Comparative Example 8 were manufactured in the same manner as in Example 1, except that the host was changed as described in Table 2 below and the mixing ratio of the first host and the second host was changed to 2:8.

[0511]

[0512] evaluation

[0513] (1) Measurement of changes in current density according to voltage changes

[0514] For the manufactured organic light-emitting device, the current flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

[0515] (2) Measurement of luminance change according to voltage change

[0516] For the manufactured organic light-emitting device, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the results were obtained.

[0517] (3) Measurement of luminous efficiency

[0518] Using the luminance and current density measured from (1) and (2) above, the same current density (10 mA / cm 2 ) was calculated for luminous efficacy (cd / A).

[0519] The relative values ​​based on the luminous efficiency of Comparative Example 1 are shown in Table 2 below.

[0520] (4) Life span measurement

[0521] The initial luminance (cd / m) of the manufactured organic light-emitting device was measured using a polaronics lifetime measurement system. 2 ) to 24,000cd / m 2 The luminance was measured over time by emitting light, and the point at which the luminance decreased by 95% of the initial luminance was measured as the T95 lifespan.

[0522] The relative values ​​based on the T95 life of Comparative Example 1 are shown in Table 2 below.

[0523] First hostSecond hostLuminous efficiency(%)Lifespan T95(%)Example 1A-4B-42104190Example 2A-5B-42104220Example 3A-6B-42106150Example 4A-4B-76106180Example 5A-5B-76106220Example 6A-6B-76107145Example 7A-6B-42105170Example 8A-6B-42102160Comparative example 1C-1B-42100100Comparative example 2C-1B-7610190Comparative example 3C-2B-42102130Comparative example 4C-2B-76102120Comparative example 5C-3B-4210280Comparative example 6C-3B-7610270Comparative example 7C-1B-4298110Comparative example 8C-1B-429690

[0524] Referring to Table 2, it can be confirmed that the organic light-emitting device to which the compound according to the embodiment of the present invention is applied has significantly improved efficiency and lifespan characteristics compared to the organic light-emitting device according to the comparative example.

[0525] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. A first compound represented by the following chemical formula 1, and A second compound represented by a combination of the following chemical formulas 2 and 3 Composition for organic optoelectronic devices comprising: [Chemical Formula 1] In the above chemical formula 1, R 1 Inland R 6 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R 7 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, L 1 and L 2 are each 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, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m1, m4, m6 and m7 are each independently an integer from 1 to 4, m2, m3, and m5 are each independently an integer from 1 to 3; [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, Ar 3 Inland Ar 5 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Among a1* to a4* of chemical formula 2, two adjacent ones are connecting points that are connected to * of chemical formula 3, and among a1* to a4* of chemical formula 2, the remaining two that are not connected to * of chemical formula 3 are each independently CL a -R a And, Z 1 Inland Z 3 are each independently N or CL b -R b And, Z 1 Inland Z 3 At least two of them are N, L a , L b and L 3 Inland L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a , R b , R 8 and R 9 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m8 and m9 are each independently one of the integers 1 to 4.

2. In paragraph 1, The above first compound is a composition for an organic optoelectronic device represented by any one of the following chemical formulas 1-1 to 1-8: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] In the above chemical formulas 1-1 to 1-8, R 1 Inland R 7 , L 1 and L 2 , Ar 1 and Ar 2 , and m1 to m7 are as defined in chemical formula 1.

3. In paragraph 1, Ar of the above chemical formula 1 1 and Ar 2 A composition for an organic optoelectronic device, wherein each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

4. In paragraph 1, L of the above chemical formula 1 1 -Ar 1 and L 2 -Ar 2 A composition for an organic optoelectronic device, wherein each independently represents one of the substituents listed in Group Ⅰ below: [Group Ⅰ] In the above group Ⅰ, R 14 Inland R 16 , R 16a , R 16b , R 16c , R 16d , R 16e , and R 16f are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, m14 is an integer between 1 and 5, m15 is an integer between 1 and 4, m16 is an integer between 1 and 3, * is a connection point.

5. In paragraph 1, The above first compound is a compound for an organic optoelectronic device selected from the compounds listed in Group 1 below: [Group 1] [A-1] [A-2] [A-3] [A-4] [A-5] [A-6] [A-7] [A-8] [A-9] [A-10] [A-11] [A-12] [A-13] [A-14] [A-15] [A-16] [A-17] [A-18] [A-19] [A-20] [A-21] [A-22] [A-23] [A-24] [A-25] [A-26] [A-27] [A-28] [A-29] [A-30] [A-31] [A-32] [A-33] [A-34] [A-35] [A-36] [A-37] [A-38] [A-39] [A-40] .

6. In paragraph 1, The second compound is a composition for an organic optoelectronic device represented by any one of the following chemical formulas 2A to 2F: [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] [Chemical Formula 2D] [Chemical Formula 2E] [Chemical Formula 2F] In the above chemical formulas 2A to 2F, Z 1 Inland Z 3 , R 8 , R 9 , L 3 Inland L 6 , Ar 3 Inland Ar 5 , m8 and m9 are as defined in Chemical Formula 2 and Chemical Formula 3, R a1 Inland R a4 Silver R 8 and R 9 is the same as the definition of L a1 Inland L a4 Silver L 3 Inland L 6 It is the same as the definition of .

7. In paragraph 1, The above Ar 3 is 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 substituted or unsubstituted dibenzosilolyl group, The above Ar 4 and Ar 5 A composition for an organic optoelectronic device, wherein each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl 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 substituted or unsubstituted dibenzosilolyl group.

8. In paragraph 1, Above L 5 -Ar 4 and L 6 -Ar 5 A composition for an organic optoelectronic device, wherein each of the substituents is independently selected from the substituents listed in Group II below: [Group II] In the above group II, R 17 Inland R 20 , R 19a , R 19b , R 19c , R 19d , R 19e , and R 19f are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, m17 is an integer between 1 and 5, m18 is one of the integers 1 to 4, m19 is an integer between 1 and 3, m20 is an integer of 1 or 2, * is a connection point.

9. In paragraph 1, The second compound is a compound for an organic optoelectronic device selected from the compounds listed in Group 2 below: [Group 2] [B-1] [B-2] [B-3] [B-4] [B-5] [B-6] [B-7] [B-8] [B-9] [B-10] [B-11] [B-12] [B-13] [B-14] [B-15] [B-16] [B-17] [B-18] [B-19] [B-20] [B-21] [B-22] [B-23] [B-24] [B-25] [B-26] [B-27] [B-28] [B-29] [B-30] [B-31] [B-32] [B-33] [B-34] [B-35] [B-36] [B-37] [B-38] [B-39] [B-40] [B-41] [B-42] [B-43] [B-44] [B-45] [B-46] [B-47] [B-48] [B-49] [B-50] [B-51] [B-52] [B-53] [B-54] [B-55] [B-56] [B-57] [B-58] [B-59] [B-60] [B-61] [B-62] [B-63] [B-64] [B-65] [B-66] [B-67] [B-68] [B-69] [B-70] [B-71] [B-72] [B-73] [B-74] [B-75] [B-76] [B-77] [B-78] [B-79] [B-80] [B-81] [B-82] [B-83] [B-84] [B-85] [B-86] [B-87] [B-88] [B-89] [B-90] [B-91] [B-92] [B-93] [B-94] [B-95] [B-96] [B-97] [B-98] [B-99] [B-100] [B-101] [B-102] [B-103] [B-104] [B-105] [B-106] [B-107] [B-108] [B-109] [B-110] [B-111] [B-112] [B-113] [B-114] [B-115] [B-116] [B-117] [B-118] [B-119] [B-120] [B-121] [B-122] [B-123] [B-124] [B-125] [B-126] [B-127] [B-128] [B-129] [B-130] [B-131] [B-132] [B-133] [B-134] [B-135] [B-136] [B-137] [B-138] [B-139] [B-140] [B-141] [B-142] [B-143] [B-144] [B-145] [B-146] [B-147] [B-148] [B-149] [B-150] [B-151] [B-152] [B-153] [B-154] [B-155] [B-156] [B-157] [B-158] [B-159] [B-160] [B-161] [B-162] [B-163] [B-164] [B-165] [B-166] [B-167] [B-168] [B-169] [B-170] [B-171] [B-172] [B-173] [B-174] [B-175] [B-176] [B-177] [B-178] [B-179] [B-180] [B-181] [B-182] [B-183] [B-184] [B-185] [B-186] [B-187] [B-188] [B-189] [B-190] [B-191] [B-192] [B-193] [B-194] [B-195] [B-196] [B-197] [B-198] [B-199] [B-200] [B-201] [B-202] [B-203] [B-204] [B-205] [B-206] [B-207] [B-208] [B-209] [B-210] [B-211] [B-212] [B-213] [B-214] [B-215] [B-216] [B-217] [B-218] [B-219] [B-220] [B-221] [B-222] [B-223] [B-224] [B-225] [B-226] [B-227] [B-228] [B-229] [B-230] [B-231] [B-232] [B-233] [B-234] [B-235] [B-236] [B-237] [B-238] [B-239] [B-240] [B-241] [B-242] [B-243] [B-244] [B-245] [B-246] [B-247] [B-248] [B-249] [B-250] [B-251] [B-252] [B-253] [B-254] [B-255] [B-256] [B-257] [B-258] [B-259] [B-260] [B-261] [B-262] [B-263] [B-264] [B-265] [B-266] [B-267] [B-268] [B-269] [B-270] [B-271] [B-272] [B-273] [B-274] [B-275] [B-276] [B-277] [B-278] [B-279] [B-280] [B-281] [B-282] [B-283] .

10. Positive and negative poles facing each other, comprising at least one organic layer positioned between the anode and the cathode, An organic optoelectronic device comprising a composition for an organic optoelectronic device according to any one of claims 1 to 9, wherein the organic layer comprises:

11. In paragraph 10, The above organic layer includes a light-emitting layer, An organic optoelectronic device, wherein the light-emitting layer comprises the composition for an organic optoelectronic device.

12. A display device comprising an organic optoelectronic device according to Article 10.

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