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

Abstract

Disclosed are a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device, wherein the organic optoelectronic device comprises the composition. The composition includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2. Details of Chemical Formula 1 and Chemical Formula 2 are defined in the specification.

Description

[0001] Citation of Related Applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10-2021-0026317, filed with the Korean Intellectual Property Office on February 26, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Disclosed are a composition for an organic optoelectronic device (organic optoelectronic device, organic optoelectronic device, organic optoelectronic device, organic optoelectronic device), an organic optoelectronic device, and a display device (display device, display device). Background Art

[0004] An organic optoelectronic device (organic photodiode) is a device capable of converting electrical energy and light energy into each other.

[0005] According to the operating principle, organic optoelectronic devices can be roughly divided into two types. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to the electrodes.

[0006] Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting diodes, organic solar cells, and organic photoreceptors.

[0007] Among them, due to the increasing demand for flat panel display devices, organic light-emitting diodes (OLEDs) have attracted much attention in recent years. An organic light-emitting diode is a device that converts electrical energy into light, and the performance of an organic light-emitting diode is greatly affected by the organic materials between the electrodes. Summary of the Invention

[0008] One embodiment provides a composition for an organic optoelectronic device, which can realize an organic optoelectronic device with high efficiency and long life.

[0009] Another embodiment provides an organic optoelectronic device including a composition for an organic optoelectronic device.

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

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

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] n1 and n2 are each independently an integer from 0 to 2,

[0016] n3 is an integer of 0 or 1,

[0017] * is a connecting point,

[0018] R a 、R b 、R c 、R d 、R e 、R f and R 1 to R 3 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 - C30 alkyl group, a substituted or unsubstituted C2 - C30 alkenyl group, a substituted or unsubstituted C2 - C30 alkynyl group, a substituted or unsubstituted C6 - C30 aryl group, or a substituted or unsubstituted C2 - C30 heterocyclic group, and

[0019] R a 、R b 、R c 、R d 、R e 、R f and R 1 to R 3 at least one of them is a group represented by Chemical Formula a,

[0020] [Chemical Formula a]

[0021]

[0022] wherein, in Chemical Formula a,

[0023] L 1 to L 3 are each independently a single bond, or a substituted or unsubstituted C6 - C30 arylene group, and

[0024] Ar 1 to Ar 2 are each independently a substituted or unsubstituted C6 - C30 aryl group, or a substituted or unsubstituted C2 - C30 heterocyclic group;

[0025] [Chemical Formula 2]

[0026]

[0027] wherein, in Chemical Formula 2,

[0028] X 1 is O, S, N-L a -R a’ , CR b’ R c’ , or SiR d’ R e’ ,

[0029] L a is a single bond, or a substituted or unsubstituted C6-C12 arylene group,

[0030] R a’ is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group,

[0031] R b’ , R c’ , R d’ and R e’ are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group,

[0032] R 4 and R 5 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0033] A is any one of the rings selected from Group I,

[0034] [Group I]

[0035]

[0036] wherein, in Group I,

[0037] * is a connection point,

[0038] X 2 is O or S,

[0039] R 6 to R 17 are each independently hydrogen, deuterium, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0040] R a’ and R 4 to R 17 at least one of which is a group represented by Chemical Formula b,

[0041] [Chemical Formula b]

[0042]

[0043] Among them, in Chemical Formula b,

[0044] Z 1 to Z 3 are each independently N or CR f’ ,

[0045] Z 1 to Z 3 at least two of which are N,

[0046] R f’ is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group,

[0047] L 4 to L 6 are each independently a single bond, or a substituted or unsubstituted C6-C30 arylene group,

[0048] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0049] * is a connection point.

[0050] According to another embodiment, the organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer contains a composition for the organic optoelectronic device.

[0051] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0052] An organic optoelectronic device with high efficiency and long life can be achieved. Description of the Drawings

[0053] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0054] <Description of the Reference Numerals>

[0055] 100: Organic light-emitting diode

[0056] 105: Organic layer

[0057] 110: Cathode

[0058] 120: Anode

[0059] 130: Light-emitting layer

[0060] 140: hole transport region

[0061] 150: electron transport region Detailed Description of the Invention

[0062] In the following, embodiments of the present invention are 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.

[0063] In the present specification, unless otherwise defined, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C30 amine group, a nitro group, a substituted or unsubstituted C1-C40 silyl group, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C1-C20 alkoxy group, a C1-C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0064] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, or a cyano group. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a C1-C20 alkyl group, a C6-C30 aryl group, or a cyano group. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a C1-C5 alkyl group, a C6-C18 aryl group, or a cyano group. In a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or a compound is replaced by deuterium, 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.

[0065] In the present specification, unless otherwise defined, "hetero" means that a functional group includes one to three heteroatoms selected from N, O, S, P, and Si and the remainder is carbon.

[0066] In this specification, "aryl" refers to a group that includes at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p orbitals, such as phenyl, naphthyl, etc. Two or more hydrocarbon aromatic moieties can be connected by a σ bond and can be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0067] An aryl can include monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0068] In this specification, "heterocyclic group" is a general concept of heteroaryl, and can include at least one heteroatom selected from N, O, S, P, and Si in place of carbon (C) in a cyclic compound such as aryl, cycloalkyl, their fused rings, or a combination thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group can include one or more heteroatoms.

[0069] For example, "heteroaryl" refers to an aryl that includes at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryls are directly connected by a σ bond, or when the heteroaryl includes two or more rings, two or more rings can be fused. When the heteroaryl is a fused ring, each ring can include one to three heteroatoms.

[0070] More specifically, the substituted or unsubstituted C6-C30 aryl can be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted group, substituted or unsubstituted triphenylene group (benzophenanthrenyl), substituted or unsubstituted perylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, substituted or unsubstituted furyl, or a combination thereof, but not limited thereto.

[0071] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted thienyl 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 benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted 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 benzothiazinyl 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 dibenzothienyl group, or a combination thereof, but not limited thereto.

[0072] In the present specification, the hole property refers to the ability to contribute electrons to form holes when an electric field is applied, and according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode due to the conductive property can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0073] In addition, the electron property refers to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode due to the conductive property can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0074] Hereinafter, a composition for an organic optoelectronic device according to an embodiment is described.

[0075] A composition for an organic optoelectronic device according to an embodiment includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.

[0076] [Chemical Formula 1]

[0077]

[0078] In Chemical Formula 1,

[0079] n1 and n2 are each independently an integer from 0 to 2,

[0080] n3 is an integer of 0 or 1,

[0081] * is a connection point,

[0082] Ra , R b , R c , R d , R e , R f and R 1 to R 3 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group, and

[0083] R a , R b , R c , R d , R e , R f and R 1 to R 3 at least one of which is a group represented by Chemical Formula a,

[0084] [Chemical Formula a]

[0085]

[0086] wherein, in Chemical Formula a,

[0087] L 1 to L 3 are each independently a single bond, or substituted or unsubstituted C6-C30 arylene, and

[0088] Ar 1 and Ar 2 are each independently substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group;

[0089] [Chemical Formula 2]

[0090]

[0091] wherein, in Chemical Formula 2,

[0092] X 1 is O, S, N-L a -R a’ , CR b’ R c’ , or SiR d’ R e’ ,

[0093] L a is a single bond, or substituted or unsubstituted C6-C12 arylene,

[0094] R a’ is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group,

[0095] R b’ 、R c’ 、R d’ and R e’ are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group,

[0096] R 4 and R 5 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0097] A is any one of the rings selected from Group I,

[0098] [Group I]

[0099]

[0100] wherein, in Group I,

[0101] * is a connection point,

[0102] X 2 is O or S,

[0103] R 6 to R 17 are each independently hydrogen, deuterium, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0104] R a’ and R 4 to R 17 at least one of them is a group represented by Chemical Formula b,

[0105] [Chemical Formula b]

[0106]

[0107] wherein, in Chemical Formula b,

[0108] Z 1 to Z 3 are each independently N or CR f’ ,

[0109] Z 1 to Z 3 at least two of them are N,

[0110] Rf’ is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group,

[0111] L 4 to L 6 each independently is a single bond, or a substituted or unsubstituted C6-C30 arylene group,

[0112] Ar 3 and Ar 4 each independently is a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0113] * is a connection point.

[0114] The structure of the first compound represented by Chemical Formula 1 includes a nucleus in which two carbazoles are fused while sharing a nitrogen atom (N); and at least one amino group substituted in the nucleus.

[0115] By including a fused nucleus sharing a nitrogen atom (N), when the first compound forms an exciplex with a second compound having a structure substituted with a nitrogen-containing 6-membered ring, the HOMO energy level can be lowered and the energy gap can be increased, thereby achieving high performance of the organic optoelectronic device containing it.

[0116] Meanwhile, the second compound has a structure substituted with a nitrogen-containing 6-membered ring.

[0117] Since the second compound effectively expands the LUMO energy band by being substituted with a nitrogen-containing 6-membered ring, when used together with the aforementioned first compound in the light-emitting layer, the balance of holes and electrons can be increased to improve the light-emitting efficiency and lifetime characteristics of the device containing it, and the driving voltage can be reduced.

[0118] According to the substitution position of the amino group, the first compound can be represented by one of Chemical Formulas 1A to 1C.

[0119] [Chemical Formula 1A]

[0120]

[0121] [Chemical Formula 1B]

[0122]

[0123] [Chemical Formula 1C]

[0124]

[0125] In Chemical Formulas 1A to 1C,

[0126] R a, R b , R c , R d , R e , R f and R 1 to R 3 each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 - C30 alkyl, substituted or unsubstituted C2 - C30 alkenyl, substituted or unsubstituted C2 - C30 alkynyl, substituted or unsubstituted C6 - C30 aryl, or substituted or unsubstituted C2 - C30 heterocyclic group, and

[0127] L 1 to L 3 , Ar 1 , and Ar 2 is the same as above.

[0128] For example, each of n1 to n3 in Chemical Formula 1 can be 0, and

[0129] For example, Chemical Formula 1 can be represented by one of Chemical Formulas 1A - 1 to 1A - 4, Chemical Formulas 1B - 1 to 1B - 3, and Chemical Formulas 1C - 1 to 1C - 4.

[0130]

[0131]

[0132] Among Chemical Formulas 1A - 1 to 1A - 4, Chemical Formulas 1B - 1 to 1B - 3, and Chemical Formulas 1C - 1 to 1C - 4,

[0133] R 1 to R 3 , L 1 to L 3 , Ar 1 , and Ar 2 is the same as above.

[0134] For example, Chemical Formula 1 can be represented by Chemical Formula 1B or Chemical Formula 1C.

[0135] As a specific example, Chemical Formula 1B can be represented by Chemical Formula 1B - 1, and Chemical Formula 1C can be represented by one of Chemical Formulas 1C - 1 to 1C - 4 above.

[0136] For example, n1 + n2 + n3 in Chemical Formula 1 can be greater than or equal to 1.

[0137] That is to say, at least one benzene can be further fused to provide at least one of substituted or unsubstituted naphthalene and substituted or unsubstituted phenanthrene, and

[0138] For example, Chemical Formula 1 can be represented by one of Chemical Formulae 1A-I to 1A-V, Chemical Formulae 1B-I to 1B-VII, and Chemical Formulae 1C-I to 1C-VIII.

[0139]

[0140]

[0141]

[0142] Among Chemical Formulae 1A-I to 1A-V, Chemical Formulae 1B-I to 1B-VII, and Chemical Formulae 1C-I to 1C-VIII,

[0143] R a 、R b 、R c 、R d 、R c1 、R c2 、R d1 、R d2 、R e 、R f and R 1 to R 3 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0144] L 1 to L 3 、Ar 1 、and Ar 2 are the same as those above.

[0145] According to the specific substitution positions of the amino groups, Chemical Formula 1A-I to Chemical Formula 1A-V, Chemical Formula 1B-I to Chemical Formula 1B-VII, and Chemical Formula 1C-I to Chemical Formula 1C-VIII can be represented by Chemical Formula 1A-I-1 to Chemical Formula 1A-I-4, Chemical Formula 1A-II-1 to Chemical Formula 1A-II-4, Chemical Formula 1A-III-1 to Chemical Formula 1A-III-4, Chemical Formula 1A-IV-1 to Chemical Formula 1A-IV-4, Chemical Formula 1A-V-1 to Chemical Formula 1A-V-4, Chemical Formula 1B-I-1 to Chemical Formula 1B-I-3, Chemical Formula 1B-II-1 to Chemical Formula 1B-II-3, Chemical Formula 1B-III-1 to Chemical Formula 1B-III-3, Chemical Formula 1B-IV-1 to Chemical Formula 1B-IV-3, Chemical Formula 1B-V-1 to Chemical Formula 1B-V-3, Chemical Formula 1B-VI-1 to Chemical Formula 1B-VI-3, Chemical Formula 1B-VII-1 to Chemical Formula 1B-VII-3, Chemical Formula 1C-I-1 to Chemical Formula 1C-I-4, Chemical Formula 1C-II-1 to Chemical Formula 1C-II-4, Chemical Formula 1C-III-1 to Chemical Formula 1C-III-4, Chemical Formula 1C-IV-1 to Chemical Formula 1C-IV-4, Chemical Formula 1C-V-1 to Chemical Formula 1C-V-4, Chemical Formula 1C-VI-1 to Chemical Formula 1C-VI-4, Chemical Formula 1C-VII-1 to Chemical Formula 1C-VII-4, and Chemical Formula 1C-VIII-1 to Chemical Formula 1C-VIII-4.

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] In Chemical Formula 1B-I-1, Chemical Formula 1B-III-1, Chemical Formula 1B-IV-1, Chemical Formula 1B-V-1, Chemical Formula 1B-VII-1, Chemical Formula 1C-I-2, Chemical Formula 1C-I-3, Chemical Formula 1C-II-2, Chemical Formula 1C-III-2, Chemical Formula 1C-V-2, Chemical Formula 1C-VI-1, Chemical Formula 1C-VII-2, and Chemical Formula 1C-VIII-2,

[0152] R a 、R b 、R c 、R d 、R c1 、R c2 、Rd1 , R d2 , R e , R f and R 1 to R 3 , L 1 to L 3 , Ar 1 , and Ar 2 is the same as above.

[0153] As a specific example, Chemical Formula 1 can be represented by one of Chemical Formula 1B-I, Chemical Formula 1B-III, Chemical Formula 1B-IV, Chemical Formula 1B-V, Chemical Formula 1B-VII, Chemical Formula 1C-I, Chemical Formula 1C-II, Chemical Formula 1C-III, Chemical Formula 1C-V, Chemical Formula 1C-VI, Chemical Formula 1C-VII, and Chemical Formula 1C-VIII.

[0154] In one embodiment, Chemical Formula 1 can be represented by one of Chemical Formula 1B-I-1, Chemical Formula 1B-III-1, Chemical Formula 1B-IV-1, Chemical Formula 1B-V-1, Chemical Formula 1B-VII-1, Chemical Formula 1C-I-2, Chemical Formula 1C-I-3, Chemical Formula 1C-II-2, Chemical Formula 1C-III-2, Chemical Formula 1C-V-2, Chemical Formula 1C-VI-1, Chemical Formula 1C-VII-2, and Chemical Formula 1C-VIII-2.

[0155] In one embodiment, L 1 to L 3 can each independently be a single bond, or a substituted or unsubstituted C6 to C12 arylene group.

[0156] In a particular embodiment, L 3 can be a single bond, and L 1 and L 2 can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0157] In one embodiment, Ar 1 and Ar 2 can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

[0158] In a particular embodiment, *-L 1 -Ar 1 and *-L2 -Ar 2 may each independently be a substituent selected from Group II.

[0159] [Group II]

[0160]

[0161] In Group II, * is the point of attachment.

[0162] In a more specific embodiment, Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted anthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl, and

[0163] Ar 1 and Ar 2 at least one of which may be a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted anthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

[0164] For example, the first compound may be one of the compounds selected from Group 1.

[0165] [Group 1]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] Meanwhile, Ring A of the second compound may be selected from the rings of Group I, and for example, Chemical Formula 2 may be represented by one of Chemical Formulas 2A to 2J.

[0173]

[0174]

[0175] In Chemical Formulas 2A to 2J,

[0176] X 1 、X 2 、Z 1 to Z 3 、R 4 to R 13 、R 15 to R 17 、L 4 to L 6 、Ar 3 、and Ar 4 are the same as above.

[0177] The second compound according to one embodiment can be represented by one of Chemical Formulas 2A, 2C, and 2F.

[0178] The second compound according to a specific embodiment can be represented by one of Chemical Formulas 2A-1, 2A-3, 2C-1, 2F-1, and 2F-3.

[0179]

[0180]

[0181] In Chemical Formulas 2A-1, 2A-3, 2C-1, 2F-1, and 2F-3,

[0182] X 1 、Z 1 to Z 3 、R 4 to R 10 、L 4 to L 6 、Ar 3 、and Ar 4 are the same as above.

[0183] In one embodiment, Ar 3 and Ar 4 can 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 naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group (benzophenanthryl group), a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0184] In one embodiment, L 4 to L 6It may be each independently a single bond, or a substituted or unsubstituted phenylene group.

[0185] In one embodiment, R 4 to R 17 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group.

[0186] As a specific example, R 4 to R 17 may each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0187] For example, X 1 may be O, S, CR b’ R c’ , or SiR d’ R e’ , and R b’ , R c’ , R d’ , and R e’ may each independently be a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C20 aryl group.

[0188] As a specific example, R b’ , R c’ , R d’ , and R e’ may each independently be methyl, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0189] For example, the second compound may be one selected from the compounds in Group 2.

[0190] [Group 2]

[0191]

[0192]

[0193]

[0194]

[0195] The composition for an organic optoelectronic device according to a more specific embodiment of the present invention may include a first compound represented by one of Chemical Formula 1C-3, Chemical Formula 1B-I-1, and Chemical Formula 1C-I-2, and a second compound represented by one of Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3.

[0196] For example, the first compound and the second compound may be included in a weight ratio of 1:99 to 99:1. Within this range, the hole-transporting ability of the first compound and the electron-transporting ability of the second compound can be used to adjust the desired weight ratio to achieve bipolar characteristics and thereby improve efficiency and lifetime. Within this range, they may be included, for example, in a weight ratio of about 90:10 to 10:90, about 80:20 to 10:90, about 70:30 to 10:90, or about 60:40 to 10:90. For example, they may be included in a weight ratio of 60:40 to 20:80, and for example, they may be included in a weight ratio of 60:40 to 30:70.

[0197] According to a more specific embodiment, they may be included in a weight ratio of about 60:40 to about 40:60.

[0198] In an embodiment of the present invention, the first compound and the second compound may each be included as a host of the light-emitting layer, for example, a phosphorescent host.

[0199] The aforementioned composition for an organic optoelectronic device may be formed into a film by a dry film-forming method such as chemical vapor deposition (CVD).

[0200] Hereinafter, an organic optoelectronic device including the aforementioned composition for an organic optoelectronic device is described.

[0201] Without particular limitation, the organic optoelectronic device may be any device that converts electrical energy into light energy and vice versa, and may be, for example, an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, and an organic photosensitive drum.

[0202] Herein, an organic light-emitting diode as an example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0203] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0204] Reference Figure 1 , an organic light-emitting diode 100 according to an 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.

[0205] The anode 120 can be made of a conductor with a large work function to assist hole injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 can be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc. or their alloys; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; 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-(ethylenedioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but not limited thereto.

[0206] The cathode 110 can be made of a conductor with a small work function to assist electron injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 can be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc. or their alloys; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but not limited thereto.

[0207] The organic layer 105 can include the aforementioned composition for an organic optoelectronic device.

[0208] The organic layer 105 can include a light-emitting layer 130, and the light-emitting layer 130 can include the aforementioned composition for an organic optoelectronic device.

[0209] The light-emitting layer 130 can include, for example, a composition for an organic optoelectronic device as a phosphorescent host.

[0210] In addition to the aforementioned host, the light-emitting layer can further include one or more compounds.

[0211] The light-emitting layer can further include a dopant. The dopant can be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and can be, for example, a red phosphorescent dopant.

[0212] For example, the composition for an organic optoelectronic device that further contains a dopant can be a composition that emits red light.

[0213] The dopant is a material that is mixed in a small amount with a compound or composition for an organic optoelectronic device to cause luminescence, and can generally be a material such as a metal complex that emits light through multiple excitations to a triplet state or a higher multiplicity state. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof can be used.

[0214] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[0215] [Chemical Formula Z]

[0216] L 7 MX 3

[0217] In Chemical Formula Z, M is a metal, and L 7 and X 3 are the same or different and are ligands for forming a coordination compound with M.

[0218] M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 7 and X 3 may be, for example, bidentate ligands.

[0219] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0220] The charge transport region may be, for example, a hole transport region 140.

[0221] The hole transport region 140 may further increase the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0222] 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, and at least one of the compounds of Group A may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0223] [Group A]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229] In the hole transport region 140, in addition to the aforementioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds similar thereto can be used.

[0230] In addition, the charge transport region may be, for example, the electron transport region 150.

[0231] The electron transport region 150 can further increase the electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0232] 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 in Group B may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0233] [Group B]

[0234]

[0235]

[0236]

[0237] One embodiment may provide an organic light-emitting diode including a light-emitting layer as an organic layer.

[0238] Another embodiment may provide an organic light-emitting diode including a light-emitting layer and a hole transport region as organic layers.

[0239] Another embodiment may provide an organic light-emitting diode including a light-emitting layer and an electron transport region as organic layers.

[0240] As Figure 1 shown, in addition to the light-emitting layer 130 as the organic layer 105, the organic light-emitting diode according to one embodiment of the present invention may further include a hole transport region 140 and an electron transport region 150.

[0241] On the other hand, in addition to the light-emitting layer as the above-mentioned organic layer, the organic light-emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc.

[0242] The organic light-emitting diode 100 can be manufactured by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0243] Organic light-emitting diodes can be applied to organic light-emitting display devices.

[0244] Hereinafter, the embodiments will be described in more detail with reference to examples. However, these examples are exemplary, and the scope of the present invention is not limited thereto.

[0245] Hereinafter, unless otherwise specifically noted, starting materials and reactants used in the examples and synthesis examples are purchased from Sigma-Aldrich Co., Ltd., TCI Inc., Tokyo chemical industry, or P&H tech, or synthesized by known methods.

[0246] (Preparation of Compounds for Organic Optoelectronic Devices)

[0247] Compounds presented as more specific examples of the compounds of the present invention are synthesized through the following steps.

[0248] Synthesis of the First Compound

[0249] Synthesis Example 1: Synthesis of Compound A-5

[0250] [Reaction Scheme 1]

[0251]

[0252] a) Synthesis of Intermediate A-5-1

[0253] Carbazole (50.0 g, 299.0 mmol), 1-bromo-4-chloro-2-fluorobenzene (75.2 g, 358.8 mmol), and K2CO3 (124.0 g, 897.1 mmol) were dissolved in 1500 mL of N-methyl-2-pyrrolidone (NMP), and then stirred and refluxed at 160 °C for 12 hours. When the reaction was completed, after removing the NMP using a rotary evaporator, the residue was extracted twice with a mixed solvent of dichloromethane and distilled water. The organic layer therefrom was filtered through silica gel and then purified by slurrying in methanol to obtain 95.6 g (89.6%) of Intermediate A-5-1.

[0254] b) Synthesis of Intermediate A-5-2

[0255] Intermediate A-5-1 (90.0 g, 252.3 mmol), palladium(II) acetate (2.8 g, 12.6 mmol), tricyclohexylphosphine tetrafluoroborate (14.6 g, 37.9 mmol) and K2CO3 (69.8 g, 504.7 mmol) were dissolved in 1200 mL of dimethylacetamide, and then stirred and refluxed at 160 °C for 12 hours. When the reaction was completed, the solvent was removed completely using a rotary evaporator. The residue was extracted twice with a mixed solvent of dichloromethane and distilled water, and the organic layer was dried. The dried organic layer was recrystallized with a mixed solvent of dichloromethane and n-hexane to obtain 58.6 g (84.2%) of Intermediate A-5-2.

[0256] c) Synthesis of Compound A-5

[0257] Intermediate A-5-2 (10.0 g, 36.3 mmol), N-(4-(naphthalen-2-yl)phenyl)naphthalen-1-amine (13.8 g, 39.9 mmol), Pd2(dba)3 (1.7 g, 1.8 mmol) and NaO(t-Bu) (5.2 g, 54.4 mmol) were dissolved in 200 mL of xylene, and then a solution of P(t-Bu)3 (1.1 g, 5.4 mmol) was slowly added dropwise thereto, and then stirred and refluxed at 130 °C for 12 hours. When the reaction was completed, the resulting product was purified by column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 15.2 g (71.7%) of Compound A-5. For LC / MS of C44H28N2, calculated exact mass: 584.23, measured: 585.26 [M+H]

[0258] Synthesis Example 2: Synthesis of Compound A-31

[0259] [Reaction Scheme 2]

[0260]

[0261] a) Synthesis of Compound A-31

[0262] Except for using Intermediate A-5-2 and 4-(naphthalen-2-yl)-N-phenylaniline as starting materials and purifying by column chromatography using a mixed solvent of dichloromethane and n-hexane, 14.7 g (70.6%) of Compound A-31 was obtained in the same manner as the synthesis method of Compound A-5 according to Synthesis Example 1. For LC / MS of C40H26N2, calculated exact mass: 534.21, measured: 535.31 [M+H]

[0263] Synthesis Example 3: Synthesis of Compound A-34

[0264] [Reaction Scheme 3]

[0265]

[0266] a) Synthesis of Compound A-34

[0267] Except for using intermediate A-5-2 and N-phenylnaphtho[1,2-b]benzofuran-9-amine as starting materials and purifying by column chromatography using a mixed solvent of dichloromethane and n-hexane, 19.2 g (96.9%) of compound A-34 was obtained in the same manner as the synthesis method of compound A-5 according to Synthesis Example 1. For LC / MS of C40H24N2O, calculated exact mass: 548.19, measured: 549.41 [M+H]

[0268] Synthesis Example 4: Synthesis of Compound A-35

[0269] [Reaction Scheme 4]

[0270]

[0271] a) Synthesis of Compound A-35

[0272] Except for using intermediate A-5-2 and 4-(phenanthren-9-yl)-N-phenylaniline as starting materials and purifying by column chromatography using a mixed solvent of dichloromethane and n-hexane, 16.5 g (75.2%) of compound A-35 was obtained in the same manner as the synthesis method of compound A-5 according to Synthesis Example 1. For LC / MS of C44H28N2, calculated exact mass: 584.23, measured: 585.43 [M+H]

[0273] Synthesis Example 5: Synthesis of Compound A-49

[0274] [Reaction Scheme 5]

[0275]

[0276] a) Synthesis of Compound A-49

[0277] Except for using intermediate A-5-2 and N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine as starting materials and purifying by column chromatography using a mixed solvent of dichloromethane and n-hexane, 15.2 g (71.2%) of compound A-49 was obtained in the same manner as the synthesis method of compound A-5 according to Synthesis Example 1. For LC / MS of C46H30N2: calculated exact mass: 610.24, measured: 611.34 [M+H]

[0278] Synthesis Example 6: Synthesis of Compound A-55

[0279] [Reaction Scheme 6]

[0280]

[0281] a) Synthesis of Compound A-55

[0282] Except for using intermediate A-5-2 and N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine as starting materials and purifying by column chromatography using a mixed solvent of dichloromethane and n-hexane, 15.3 g (71.4%) of compound A-55 was obtained in the same manner as the synthesis method of compound A-5 according to Synthesis Example 1. LC / MS for C46H30N2: Calculated exact mass: 610.24, Measured: 611.22 [M+H]

[0283] Synthesis Example 7: Synthesis of Compound A-58

[0284] [Reaction Scheme 7]

[0285]

[0286] a) Synthesis of Compound A-58

[0287] Except for using intermediate A-5-2 and N-([1,1'-biphenyl]-2-yl)naphtho[1,2-b]benzofuran-9-amine as starting materials and purifying by column chromatography using a mixed solvent of dichloromethane and n-hexane, 18.9 g (82.1%) of compound A-58 was obtained in the same manner as the synthesis method of compound A-5 according to Synthesis Example 1. LC / MS for C46H28N2O: Calculated exact mass: 624.22, Measured: 625.19 [M+H]

[0288] Synthesis Example 8: Synthesis of Compound A-60

[0289] [Reaction Scheme 8]

[0290]

[0291] a) Synthesis of Compound A-60

[0292] Except that intermediate A-5-2 and N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-2-amine are used as starting materials and purified by column chromatography using a mixed solvent of dichloromethane and n-hexane, 18.9 g (82.1%) of compound A-60 is obtained in the same manner as the synthesis method of compound A-5 according to Synthesis Example 1. LC / MS for C46H28N2O: Calculated exact mass: 624.22, Measured: 625.19 [M+H]

[0293] Synthesis Example 9: Synthesis of Compound A-98

[0294] [Reaction Scheme 9]

[0295]

[0296] a) Synthesis of Intermediate A-98-1

[0297] Except that 11H-benzo[a]carbazole and 1-bromo-4-chloro-2-fluorobenzene are used as starting materials and then purified, 49.2 g (88.5%) of intermediate A-98-1 is obtained in the same manner as the synthesis method of intermediate A-5-1 according to Synthesis Example 1.

[0298] b) Synthesis of Intermediate A-98-2

[0299] Except that intermediate A-98-2 is used as a starting material and then purified, 36.2 g (96.2%) of intermediate A-98-2 is obtained in the same manner as the synthesis method of intermediate A-5-2 according to Synthesis Example 1.

[0300] c) Synthesis of Compound A-98

[0301] Except that intermediate A-98-2 and 4-(naphthalen-2-yl)-N-phenylaniline are used as starting materials and a mixed solvent of n-hexane and dichloromethane is used for recrystallization, 17.6 g (77.5%) of compound A-98 is obtained in the same manner as the synthesis method of compound A-5 according to Synthesis Example 1. LC / MS for C44H28N2: Calculated exact mass: 584.23, Measured: 585.41 [M+H]

[0302] Synthesis Example 10: Synthesis of Compound A-105

[0303] [Reaction Scheme 10]

[0304]

[0305] a) Synthesis of Intermediate A-105-1

[0306] 2-Naphthaleneboronic acid (120.0 g, 697.7 mmol), 1,4-dichloro-2-nitrobenzene (140.7 g, 732.6 mmol), Pd(PPh3)4 (40.3 g, 34.9 mmol) and K2CO3 (289.3 g, 2093.1 mmol) were dissolved in 3 L of a mixed solvent of tetrahydrofuran:distilled water = 2:1 (v / v), and then stirred and refluxed at 80 °C. When the reaction was completed, after removing the aqueous layer, the organic layer therein was concentrated using a rotary evaporator. The concentrated product was purified by recrystallization with a mixed solvent of dichloromethane and n-hexane to obtain 175.6 g (88.7%) of Intermediate A-105-1.

[0307] b) Synthesis of Intermediate A-105-2

[0308] Intermediate A-105-1 (175.6 g, 599.2 mmol) and triphenylphosphine (471.5 g, 1797.6 mmol) were dissolved in 3 L of 1,2-dichlorobenzene, and then stirred and refluxed at 200 °C. When the reaction was completed, the organic layer therefrom was concentrated using a rotary evaporator. The concentrated organic layer was purified by column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 97.0 g (64.3%) of Intermediate A-105-2.

[0309] c) Synthesis of Intermediate A-105-3

[0310] Except for using Intermediate A-105-2 and 1,2-dibromobenzene as starting materials and using a mixed solvent of n-hexane and dichloromethane for recrystallization, 54.2 g (40.2%) of Intermediate A-105-3 was obtained in the same manner as in the method for synthesizing Compound A-5 in Synthesis Example 1.

[0311] d) Synthesis of Intermediate A-105-4

[0312] Except for using Intermediate A-105-3 as a starting material and using a mixed solvent of n-hexane and dichloromethane for recrystallization, 50.7 g (95.4%) of Intermediate A-105-4 was obtained in the same manner as in the method for synthesizing Intermediate A-5-2 in Synthesis Example 1.

[0313] e) Synthesis of Compound A-105

[0314] Except for using intermediate A-105-4 and 4-(naphthalen-2-yl)-N-phenylaniline as starting materials and performing recrystallization using a mixed solvent of n-hexane and dichloromethane, 21.2 g (77.6%) of compound A-105 was obtained in the same manner as in the method for synthesizing compound A-5 in Synthesis Example 1. LC / MS for C44H28N2: Calculated exact mass: 584.23, measured: 585.25 [M+H]

[0315] Comparative Synthesis Examples 1 to 8: Synthesis of Compounds HT-1 to HT-8

[0316] Using intermediate A and intermediate B in Table 1 as starting materials, compounds HT-1 to HT-8 were synthesized in the same manner as in the synthesis of compound A-5 in Synthesis Example 1.

[0317] (Table 1)

[0318]

[0319] <Intermediate A>

[0320]

[0321] <Intermediate B>

[0322]

[0323] <Final Product>

[0324]

[0325] However, intermediate A-6 in Comparative Synthesis Example 7 and intermediate A-7 in Comparative Synthesis Example 8 were synthesized by the following synthesis examples.

[0326] Comparative Synthesis Example 7: Synthesis of Intermediate A-6

[0327] [Reaction Scheme 11]

[0328]

[0329] a) Synthesis of Intermediate A-6-1

[0330] 5,12-Diphenyl-5,12-dihydroindolo[3,2-a]carbazole (50.0 g, 122 mmol) and N-bromosuccinimide (19.6 g, 110 mmol) were dissolved in 250 mL of N,N-dimethylformamide and then stirred at room temperature. When the reaction was complete, after concentrating the organic solvent using a rotary evaporator, a mixed solvent of dichloromethane and n-hexane was used for recrystallization to obtain 49.6 g (83.1%) of intermediate A-6-1.

[0331] b) Synthesis of Intermediate A-6-2

[0332] Dissolve Intermediate A-6-1 (49.6 g, 101.8 mmol), bis(pinacolato)diboron (33.6 g, 132.3 mmol), PdCl2(dppf) (4.2 g, 5.1 mmol), and KOAc (30.0 g, 305.3 mmol) in 500 mL of toluene, and then stir and reflux at 110 °C. When the reaction is complete, use a mixed solvent of n-hexane and dichloromethane for recrystallization to obtain 37.1 g (68.2%) of Intermediate A-6-2.

[0333] c) Synthesis of Intermediate A-6-3

[0334] Except for using Intermediate A-6-2 and 1-bromo-2-nitrobenzene as starting materials and using a mixed solvent of n-hexane and dichloromethane for recrystallization, Intermediate A-6-3 (16.4 g, 55.2%) is obtained in the same manner as the method for synthesizing Intermediate A-105-1 according to Synthesis Example 10.

[0335] d) Synthesis of Intermediate A-6

[0336] Except for using Intermediate A-6-3 as a starting material and using a mixed solvent of n-hexane and dichloromethane for recrystallization, Intermediate A-6 (9.7 g, 56.5%) is obtained in the same manner as the method for synthesizing Intermediate A-105-2 according to Synthesis Example 10.

[0337] Comparative Synthesis Example 8: Synthesis of Intermediate A-7

[0338] [Reaction Scheme 12]

[0339]

[0340] Using 11,12-diphenyl-11,12-dihydroindolo[2,3-a]carbazole as a starting material, Intermediate A-7 is synthesized in the same manner as the synthesis of Intermediate A-6.

[0341] Synthesis of the Second Compound

[0342] Synthesis Example 11: Synthesis of Compound B-3

[0343] [Reaction Scheme 13]

[0344]

[0345] a) Synthesis of Intermediate B-3-1

[0346] In the same manner as in the synthesis of Intermediate A-105-1 in Synthesis Example 10, 47.2 g (46.2%) of Intermediate B-3-1 was obtained by using 2,4-dichloro-6-phenyl-1,3,5-triazine and dibenzo[b,d]furan-3-ylboronic acid as starting materials for synthesis and performing recrystallization with a mixed solvent of n-hexane and dichloromethane.

[0347] b) Synthesis of Compound B-3

[0348] In the same manner as in the synthesis of Intermediate A-105-1 in Synthesis Example 10, 12.1 g (66.9%) of Compound B-3 was obtained by using Intermediate B-3-1 and (4-(naphthalen-2-yl)phenyl)boronic acid as starting materials for synthesis and performing recrystallization with toluene. LC / MS for C37H23N3O: Calculated exact mass: 525.18, Measured: 526.19 [M+H]

[0349] Synthesis Examples 12 to 17

[0350] Intermediate C and Intermediate D in Table 2 were synthesized in the same manner as in the synthesis method of Intermediate A-105-1 in Synthesis Example 10.

[0351] (Table 2)

[0352]

[0353]

[0354] <Intermediate C>

[0355]

[0356] <Intermediate D>

[0357]

[0358] (Manufacture of Organic Light-Emitting Diode)

[0359] Example 1

[0360] The glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonically. After washing with distilled water, the glass substrate was ultrasonically washed with solvents such as isopropyl alcohol, acetone, methanol, etc. and dried, then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred to a vacuum evaporator. The obtained ITO transparent electrode was used as the anode, and Compound A doped with 1% NDP-9 (available from Novaled) was vacuum-deposited on the ITO substrate to form a thick hole injection layer, and Compound A was deposited on the hole injection layer to form A thick hole transport layer. Compound B is deposited on the hole transport layer to form a thick hole transport auxiliary layer. On the hole transport auxiliary layer, by simultaneously vacuum depositing Compound A-5 obtained in Synthesis Example 1 and Compound B-17 obtained in Synthesis Example 13 as hosts and doping 2 wt% of Ir(piq)2acac as a dopant, a thick light-emitting layer is formed. Herein, Compound A-5 and Compound B-17 are used in a weight ratio of 5:5. Subsequently, Compound C is deposited on the light-emitting layer to form a thick electron transport auxiliary layer, and simultaneously vacuum depositing Compound D and LiQ in a weight ratio of 1:1 to form a thick electron transport layer. LiQ and Al are successively vacuum deposited on the electron transport layer to form a cathode, thereby fabricating an organic light-emitting diode.

[0361] ITO / Compound A (doped with 1% NDP-9, ) / Compound A / Compound B / EML [host 98 wt% (Compound A-5:Compound B-17 = 5:5), 2 wt% (Ir(piq)2acac)] / Compound C / Compound D:LiQ / LiQ / Al

[0362] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0363] Compound B: N,N-bis([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran-10-amine

[0364] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0365] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0366] Examples 2 to 25 and Comparative Examples 1 to 8

[0367] Except for changing the main body as shown in Table 3, the diodes of Examples 2 to 25 and Comparative Examples 1 to 8 were manufactured in the same manner as in Example 1.

[0368] Evaluation:

[0369] The characteristics of the organic light-emitting diodes according to Examples 1 to 25 and Comparative Examples 1 to 8 were evaluated, and the results are shown in Table 3. The specific measurement methods are as follows.

[0370] (1) Measurement of the change in current density according to voltage change

[0371] While increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), the current value flowing through the unit device in the obtained organic light-emitting diode was measured, and the measured current value was divided by the area to provide the result.

[0372] (2) Measurement of the change in luminance according to voltage change

[0373] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, the luminance was measured by using a luminance meter (Minolta Cs-1000A).

[0374] (3) Measurement of luminous efficiency

[0375] By using the luminance and current density from items (1) and (2), the luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated.

[0376] (4) Measurement of lifetime

[0377] By measuring the time when the current efficiency (cd / A) decreased to 90% while maintaining the luminance (cd / m 2 ) at 5,000 cd / m 2 .

[0378] (5) Calculation of luminous efficiency ratio (%)

[0379] The relative comparison value with the luminous efficiency measurement value of Comparative Example 1 is shown in Table 3.

[0380] (6) Calculation of lifetime ratio (%)

[0381] The relative comparison value with the T90 (h) lifetime measurement value of Comparative Example 1 is shown in Table 3.

[0382] (Table 3)

[0383]

[0384]

[0385] Referring to Table 3, the compounds according to the present invention exhibit significantly improved efficiency and lifetime as compared to the comparative compounds.

[0386] Although the present invention has been described in connection with presently considered practical embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, 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 device, comprising a first compound represented by one of Chemical Formula 1A to Chemical Formula 1C and a second compound represented by Chemical Formula 2: [Chemical Formula 1A] [Chemical Formula 1B] [Chemical Formula 1C] In Chemical Formula 1A to Chemical Formula 1C, n1 and n2 are each independently an integer from 0 to 2, n3 is an integer of 0 or 1, n1 + n2 + n3 is greater than or equal to 1, * is a connection point, R a 、R b 、R c 、R d 、R e 、R f and R 1 to R 3 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, L 1 to L 3 each independently is a single bond, or a substituted or unsubstituted C6 to C30 arylene group, and Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group; [Chemical Formula 2] Among them, In Chemical Formula 2, X 1 is O, S, N-L a -R a’ , CR b’ R c’ , or SiR d’ R e’ , L a is a single bond, or a substituted or unsubstituted C6-C12 arylene group, R a’ is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, R b’ 、R c’ 、R d’ and R e’ each independently is a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, R 4 and R 5 each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group, and A is any one of the rings selected from Group I, [Group I] wherein, in Group I, * is a connection point, X 2 is O or S, R 6 to R 17 each independently is hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and R a’ and R 4 to R 17 at least one of which is a group represented by Chemical Formula b, [Chemical Formula b] wherein, in Chemical Formula b, Z 1 from Z to Z 3 each independently is N or CR f’ , Z 1 to Z 3 at least two of which are N, R f’ is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group L 4 to L 6 each independently is a single bond, or a substituted or unsubstituted C6 to C30 arylene group Ar 3 and Ar 4 each independently is a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and * is a connection point.

2. The composition for an organic optoelectronic device according to claim 1, wherein Chemical Formula 1A is represented by one of Chemical Formula 1A-I to Chemical Formula 1A-V, Chemical Formula 1B is represented by one of Chemical Formula 1B-I to Chemical Formula 1B-VII, and Chemical Formula 1C is represented by one of Chemical Formula 1C-I to Chemical Formula 1C-VIII: wherein, in Chemical Formula 1A-I to Chemical Formula 1A-V, Chemical Formula 1B-I to Chemical Formula 1B-VII, and Chemical Formula 1C-I to Chemical Formula 1C-VIII, R a 、R b 、R c 、R d 、R c1 、R c2 、R d1 、R d2 、R e 、R f and R 1 to R 3 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and L 1 to L 3 、Ar 1 and Ar 2 are defined in claim 1.

3. The composition for an organic optoelectronic device according to claim 1, wherein, Chemical Formula 1B is represented by one of Chemical Formula 1B-I-1, Chemical Formula 1B-III-1, Chemical Formula 1B-IV-1, Chemical Formula 1B-V-1, Chemical Formula 1B-VII-1, Chemical Formula 1C is represented by one of Chemical Formula 1C-I-2, Chemical Formula 1C-I-3, Chemical Formula 1C-II-2, Chemical Formula 1C-III-2, Chemical Formula 1C-V-2, Chemical Formula 1C-VI-1, Chemical Formula 1C-VII-2, and Chemical Formula 1C-VIII-2: wherein, in Chemical Formula 1B-I-1, Chemical Formula 1B-III-1, Chemical Formula 1B-IV-1, Chemical Formula 1B-V-1, Chemical Formula 1B-VII-1, Chemical Formula 1C-I-2, Chemical Formula 1C-I-3, Chemical Formula 1C-II-2, Chemical Formula 1C-III-2, Chemical Formula 1C-V-2, Chemical Formula 1C-VI-1, Chemical Formula 1C-VII-2, and Chemical Formula 1C-VIII-2, R a 、R b 、R c 、R d 、R c1 、R c2 、R d1 、R d2 、R e 、R f and R 1 to R 3 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and L 1 to L 3 、Ar 1 and Ar 2 are defined in claim 1.

4. The composition for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted anthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

5. The composition for an organic optoelectronic device according to claim 1, wherein, *-L 1 -Ar 1 and *-L 2 -Ar 2 each independently is one of the substituents of Group II: [Group II] wherein, in Group II, * is a connection point.

6. The composition for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted anthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl, and Ar 1 and Ar 2 at least one of which is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

7. The composition for an organic optoelectronic device according to claim 1, wherein, the first compound is one of the compounds in Group 1: [Group 1] 8. The composition for an organic optoelectronic device according to claim 1, wherein the second compound is represented by one of Chemical Formula 2A to Chemical Formula 2J: wherein, in Chemical Formula 2A to Chemical Formula 2J, X 1 、 X 2 、 Z 1 to Z 3 、 R 4 to R 13 、 R 15 to R 17 、 L 4 to L 6 、 Ar 3 and Ar 4 are defined in claim 1.

9. The composition for an organic optoelectronic device according to claim 8, wherein, the second compound is represented by one of Chemical Formula 2A, Chemical Formula 2C, and Chemical Formula 2F.

10. The composition for an organic optoelectronic device according to claim 1, wherein, the second compound is represented by one of Chemical Formula 2A-1, Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3: wherein, in Chemical Formula 2A-1, Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3, X 1 , Z 1 to Z 3 , R 4 to R 10 , L 4 to L 6 , Ar 3 and Ar 4 are defined in claim 1.

11. The composition for an organic optoelectronic device according to claim 1, wherein, Ar 3 and Ar 4 each independently 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 phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

12. The composition for an organic optoelectronic device according to claim 1, wherein, the second compound is one of the compounds in Group 2: [Group 2] 13. The composition for an organic optoelectronic device according to claim 1, wherein, the first compound is represented by Chemical Formula 1B-I-1 or Chemical Formula 1C-I-2, the second compound is represented by one of Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3: wherein, in Chemical Formula 1B-I-1 and Chemical Formula 1C-I-2, L 1 and L 2 each independently is a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene, L 3 is a single bond Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl, and R a 、R b 、R c 、R d and R 1 to R 3 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group; wherein, in Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3, X 1 is O, S, CR b’ R c’ 、or SiR d’ R e’ , Z 1 to Z 3 each is N, R 4 to R 10 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group, L 4 to L 6 each independently is a single bond, or a substituted or unsubstituted phenylene, and Ar 3 and Ar 4 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.

14. An organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, Among them, the organic layer includes a light-emitting layer, and the light-emitting layer contains the composition for an organic optoelectronic device according to any one of claims 1 to 13.

15. The organic optoelectronic device according to claim 14, wherein, including the composition for an organic optoelectronic device as a host of the light-emitting layer.

16. A display device comprising the organic optoelectronic device according to claim 14.

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