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

Abstract

The present invention relates to a composition for an organic optoelectronic device, and an organic optoelectronic device and a display device comprising the same, the composition comprising a first compound represented by Chemical Formula 1, a second compound represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and a third compound, and the third compound is represented by a combination of Chemical Formula 5 and Chemical Formula 6. Details of Chemical Formulae 1 to 6 are the same as defined in the specification.

Description

Technical Field

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

[0002] An organic optoelectronic device (organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0003] According to the working principle, organic optoelectronic devices can be roughly divided into two categories. 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 applying a voltage or current to the electrodes.

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

[0005] 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

[0006] Technical Problem

[0007] One embodiment provides a composition for an organic optoelectronic device capable of realizing a low-drive, high-efficiency, and long-life organic optoelectronic device.

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

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

[0010] Technical Solution

[0011] According to one embodiment, the composition for an organic optoelectronic device includes a first compound, a second compound, and a third compound, wherein the first compound is represented by Chemical Formula 1, the second compound is represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and the third compound is represented by a combination of Chemical Formula 5 and Chemical Formula 6.

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] Z 1 to Z 3Each is independently N or C-L a -R a ,

[0016] Z 1 to Z 3 At least two of them are N,

[0017] L a and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof,

[0018] R 1 to R 3 Each is independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof,

[0019] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof,

[0020] m1 and m2 are each independently one of the integers from 1 to 4, and

[0021] m3 is one of the integers from 1 to 3;

[0022] [Chemical formula 2]

[0023]

[0024] In Chemical formula 2,

[0025] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted pyridyl 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,

[0026] L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted C6-C20 arylene group,

[0027] R 7 to R 11Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group,

[0028] m8 and m9 each independently is one of the integers from 1 to 3,

[0029] m7, m10 and m11 each independently is one of the integers from 1 to 4, and

[0030] n is one of the integers from 0 to 2;

[0031]

[0032] In Chemical Formula 3 and Chemical Formula 4,

[0033] Ar 5 and Ar 6 each independently is substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzosilolyl,

[0034] a in Chemical Formula 3 1 * to a 4 * each independently is a bond connecting to carbon (C) or C-L b -R b ,

[0035] a 1 * to a 4 * of the adjacent two each connects to the * of Chemical Formula 4,

[0036] In a 1 * to a 4 *, the remaining two that do not connect to the * in Chemical Formula 4 each independently is C-L b -R b ,

[0037] L b 、L 6 and L 7 each independently is a single bond or substituted or unsubstituted C6-C20 arylene, and

[0038] R b 、R 12 and R 13 each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group;

[0039]

[0040] In Chemical Formulas 5 and 6,

[0041] X 1 is O or S,

[0042] b in Chemical Formula 5 1 * to b 4 * are each independently a linking carbon (C) or C-L c -R c ,

[0043] b 1 * to b 4 * of two adjacent ones of which are each linked to the * of Chemical Formula 6,

[0044] In b 1 * to b 4 *, the remaining two not linked to the * in Chemical Formula 6 are each independently C-L c -R c ,

[0045] L c is a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof,

[0046] R c 、R 18 and R 19 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof,

[0047] m18 and m19 are each independently one of the integers from 1 to 4,

[0048] Ar 7 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof, and

[0049] R c 、R 18 、R 19 and Ar 1 at least one of which is a substituent represented by Chemical Formula A,

[0050] [Chemical Formula A]

[0051]

[0052] In Chemical Formula A,

[0053] Z 4 from Z to Z 6 each independently is N or C-L d -R d ,

[0054] Z 4 from Z to Z 6 at least two of which are N

[0055] L d and L 8 from L to L 10 each independently is a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof

[0056] R d is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof

[0057] Ar 8 and Ar 9 each independently is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof

[0058] 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 the composition for the organic optoelectronic device described above

[0059] According to another embodiment, a display device including the organic optoelectronic device is provided

[0060] Advantageous Effects

[0061] An organic optoelectronic device with low driving, high efficiency, and long lifespan can be achieved Description of the Drawings

[0062] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to one embodiment

[0063] <Description of the Reference Numerals>

[0064] 100: Organic light-emitting diode

[0065] 105: Organic layer

[0066] 110: Cathode

[0067] 120: Anode

[0068] 130: Light-emitting layer

[0069] 140: Hole transport region

[0070] 150: Electron transport region Detailed implementation mode

[0071] In the following, the implementation modes of the present invention are described in detail. However, these implementation modes are exemplary, and the present disclosure is not limited thereto.

[0072] As used herein, when no other definition is provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1-C30 amino group, nitro, substituted or unsubstituted C1-C40 silyl group, C1-C30 alkyl group, C1-C10 alkylsilyl group, C6-C30 arylsilyl group, C3-C30 cycloalkyl group, C3-C30 heterocycloalkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, C1-C20 alkoxy group, C1-C10 trifluoroalkyl group, cyano group, or a combination thereof.

[0073] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, cyano group, C1-C30 alkyl group, C1-C10 alkylsilyl group, C6-C30 arylamino group, C6-C30 arylsilyl group, C3-C30 cycloalkyl group, C3-C30 heterocycloalkyl group, C6-C30 aryl group, or C2-C30 heteroaryl 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 the following: deuterium, cyano group, C1-C20 alkyl group, C6-C30 arylamino group, C6-C30 aryl group, or C2-C30 heteroaryl 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 the following: deuterium, cyano group, C1-C5 alkyl group, C6-C20 arylamino group, C6-C18 aryl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, or pyridyl 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 the following: deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, C6-C20 arylamino group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, fluorene group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, or pyridyl group.

[0074] In this specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0075] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0076] In this specification, when no definition is provided otherwise, "hetero" means including one to three heteroatoms selected from N, O, S, P, and Si and the remaining carbons in a functional group.

[0077] In this specification, "aryl" means a group including 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.

[0078] An aryl can include a monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional group.

[0079] As used herein, "heterocyclic group" is a superordinate 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 their combination. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group can include one or more heteroatoms.

[0080] For example, "heteroaryl" can mean an aryl including 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 a 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.

[0081] 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 phenanthryl, substituted or unsubstituted fused 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 chrysenyl, substituted or unsubstituted triphenylene group, substituted or unsubstituted perylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, or a combination thereof, but not limited thereto.

[0082] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted furyl group, 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 benzofuryl 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 dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, or a combination thereof, but is not limited thereto.

[0083] As used herein, the hole property refers to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive property according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0084] In addition, the electron property refers to the ability to accept electrons when an electric field is applied, and due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0085] Hereinafter, a composition for an organic optoelectronic device according to an embodiment is described.

[0086] The organic optoelectronic device composition according to an embodiment is a mixture including three compounds. Specifically, the first compound includes at least one nitrogen-containing ring, thereby forming a structure that may accept electrons when an electric field is applied, thereby increasing the electron injection amount and making the electron (electrical) property have relatively strong bipolar properties. The second compound may have relatively strong hole properties by including a carbazole moiety.

[0087] When the first compound and the second compound are used together in the light-emitting layer, there are the following advantages: the light-emitting efficiency and lifetime characteristics can be improved by increasing the charge mobility and enhancing the stability.

[0088] On the other hand, there is a problem of increasing the driving voltage of an organic optoelectronic device due to the rapid decrease in the hole and electron transport capabilities caused by trapping phenomena resulting from the difference in the HOMO energy levels between the dopant and the host.

[0089] Therefore, by adding a third compound having excellent hole and electron characteristics, the trapping phenomena between the dopant and the host can be reduced or minimized, and the injection of holes and electrons into the light-emitting layer can be made smoother, thereby producing an organic optoelectronic device having excellent efficiency while significantly reducing the driving voltage.

[0090] By adding a third compound having excellent hole and electron characteristics, the problem of the increase in the driving voltage that may occur when only the first and second compounds are included can be solved, thereby effectively improving the power efficiency performance of the device. In addition, by using three types of hosts, the optimal position and width of the light-emitting region can be adjusted, thereby effectively improving the efficiency and lifetime.

[0091] The first compound having the above electron characteristics has a structure in which a triphenylene derivative is substituted with a nitrogen-containing 6-membered ring and is represented by Chemical Formula 1.

[0092] [Chemical Formula 1]

[0093]

[0094] In Chemical Formula 1,

[0095] Z 1 to Z 3 are each independently N or C-L a -R a ,

[0096] Z 1 to Z 3 at least two of them are N,

[0097] L a and L 1 to L 3 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,

[0098] R 1 to R 3 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0099] Ar 1 and Ar2 Each independently is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof,

[0100] m1 and m2 are each independently one of the integers from 1 to 4, and

[0101] m3 is one of the integers from 1 to 3.

[0102] In Chemical Formula 1, when there are two or more R substituents 1 each R 1 can be the same as or different from each other.

[0103] In Chemical Formula 1, when there are two or more R substituents 2 each R 2 can be the same as or different from each other.

[0104] In Chemical Formula 1, when there are two or more R substituents 3 each R 3 can be the same as or different from each other.

[0105] In Chemical Formula 1, when there are two or more R substituents a each R a can be the same as or different from each other.

[0106] Specifically, Z in Chemical Formula 1 1 to Z 3 are each independently N or CH, and at least two of Z 1 to Z 3 can be N.

[0107] For example, Z 1 to Z 3 can each be N.

[0108] For example, Z 1 and Z 3 can be N, and Z 2 can be CH.

[0109] L in Chemical Formula 1 1 can be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

[0110] L in Chemical Formula 1 2 and L 3 can each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0111] R in Chemical Formula 1 1 to R 3 may each independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C12 heterocyclic group, or a combination thereof.

[0112] Ar in Chemical Formula 1 1 and Ar 2 may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzosilolyl.

[0113] In a specific example of the present invention, L in Chemical Formula 1 1 may each independently be a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted biphenylene.

[0114] In a specific example of the present invention, L in Chemical Formula 1 2 and L 3 may each be a single bond.

[0115] In a specific example of the present invention, R in Chemical Formula 1 1 to R 3 may each independently be hydrogen, deuterium, cyano, or substituted or unsubstituted C6-C12 aryl.

[0116] In a specific example of the present invention, Ar in Chemical Formula 1 1 and Ar 2 may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, or substituted or unsubstituted fluorenyl.

[0117] For example, R in Chemical Formula 1 1 to R 3 may each independently be hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl.

[0118] The first compound may have a structure that is prone to accepting electrons when an electric field is applied by including a ring containing at least one nitrogen, and thus can reduce the driving voltage of an organic optoelectronic device to which the compound is applied.

[0119] In addition, the first compound forms a bipolar structure by including a terphenyl structure that readily accepts holes and a nitrogen-containing ring portion that readily accepts electrons, thereby appropriately balancing the flow of holes and electrons and thus improving the efficiency of the organic optoelectronic device to which the compound is applied.

[0120] L 1 may be, for example, one group selected from the substituted or unsubstituted groups listed in Group I.

[0121] [Group I]

[0122]

[0123] In Group I, * is the point of attachment.

[0124] The first compound represented by Chemical Formula 1 may desirably have at least two kinked structures, for example, may have 2 to 4 kinked structures.

[0125] The first compound represented by Chemical Formula 1 has the above-described kinked structure and thus can exhibit excellent bipolar characteristics by appropriately localizing the terphenyl structure that tends to accept holes and the nitrogen-containing ring portion that tends to accept electrons in the above bipolar structure compound and controlling the flow of the conjugated system. In addition, according to the structure, the first compound represented by Chemical Formula 1 can effectively prevent stacking of organic compounds, thereby increasing process stability and at the same time reducing the deposition temperature. When the first compound represented by Chemical Formula 1 includes a linking group (L 1 ), this anti-stacking effect can be further enhanced.

[0126] In the first compound represented by Chemical Formula 1, the structure having a linking group (L 1 ) may be represented by any one of Chemical Formulas 1-1 to 1-12, for example.

[0127]

[0128]

[0129]

[0130] In Chemical Formulas 1-1 to 1-12, Z 1 to Z 3 、R 1 to R 3 、L 2 、L 3 、Ar 1 、Ar 2 and m1 to m3 are the same as above, R 4To R 6 As for R 1 To R 3 As defined, and m4 to m6 are each independently one of the integers from 1 to 4.

[0131] In Chemical Formulas 1-1 to 1-12, two or more Rs are substituted, 4 each R 4 can be the same as or different from each other.

[0132] In Chemical Formulas 1-1 to 1-12, two or more Rs are substituted, 5 each R 5 can be the same as or different from each other.

[0133] In Chemical Formulas 1-1 to 1-12, two or more Rs are substituted, 6 each R 6 can be the same as or different from each other.

[0134] The first compound can be, for example, one selected from the compounds listed in Group 1.

[0135] [Group 1]

[0136]

[0137]

[0138]

[0139] The second compound having hole properties has a structure in which a C6 to C30 aryl group or a C2 to C30 heterocyclic group in which carbazole or a carbazole derivative is substituted or unsubstituted is substituted, and can be represented by, for example, Chemical Formula 2 or a combination of Chemical Formulas 3 and 4.

[0140] [Chemical Formula 2]

[0141]

[0142] In Chemical Formula 2,

[0143] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted pyridyl 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,

[0144] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0145] R 7 to R 11 each independently represents hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group,

[0146] m8 and m9 each independently represents one of the integers from 1 to 3,

[0147] m7, m10 and m11 each independently represents one of the integers from 1 to 4,

[0148] n represents one of the integers from 0 to 2;

[0149]

[0150] In Chemical Formula 3 and Chemical Formula 4,

[0151] Ar 5 and Ar 6 each independently represents substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzosilolyl,

[0152] a in Chemical Formula 3 1 * to a 4 * each independently represents a connecting carbon (C) or C-L b -R b ,

[0153] a 1 * to a 4 * of the adjacent two each connects to the * of Chemical Formula 4,

[0154] In a 1 * to a 4 *, the remaining two that are not connected to the * in Chemical Formula 4 each independently represents C-L b -R b ,

[0155] L b 、L 6 and L 7 each independently represents a single bond or substituted or unsubstituted C6-C20 arylene, and

[0156] R b 、R 12 and R 13Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group.

[0157] In Chemical Formula 2, when two or more Rs are substituted 7 each R 7 may be the same as or different from each other.

[0158] In Chemical Formula 2, when two or more Rs are substituted 8 each R 8 may be the same as or different from each other.

[0159] In Chemical Formula 2, when two or more Rs are substituted 9 each R 9 may be the same as or different from each other.

[0160] In Chemical Formula 2, when two or more Rs are substituted 10 each R 10 may be the same as or different from each other.

[0161] In Chemical Formula 2, when two or more Rs are substituted 11 each R 11 may be the same as or different from each other.

[0162] In Chemical Formula 3, when two or more Rs are substituted b each R b may be the same as or different from each other.

[0163] In Chemical Formula 3, when two or more Rs are substituted 12 each R 12 may be the same as or different from each other.

[0164] In Chemical Formula 4, when two or more Rs are substituted 13 each R 13 may be the same as or different from each other.

[0165] For example, in Chemical Formula 2, Ar 3 and Ar 4 may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl.

[0166] For example, in Chemical Formula 2, L 4 and L 5 can each independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted quaterphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted terphenylene or a substituted or unsubstituted phenanthrylene.

[0167] For example, in Chemical Formula 2, R 7 to R 11 can each independently be hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group or a combination thereof.

[0168] As a specific example, in Chemical Formula 2, R 7 to R 11 can each independently be hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group.

[0169] For example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 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 fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a combination thereof.

[0170] For example, in Chemical Formula 3 and Chemical Formula 4, R b , R 12 and R 13 can each independently be hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group.

[0171] As a specific example, in Chemical Formula 2, 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 fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group,

[0172] In Chemical Formula 2, L 4 and L5 Each may independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene or a substituted or unsubstituted naphthylene,

[0173] In Chemical Formula 2, R 7 to R 11 may each independently be hydrogen, deuterium, a substituted or unsubstituted C6-C12 aryl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl, and

[0174] n may be 0 or 1.

[0175] As an example, in Chemical Formulas 2 to 4, "substituted" means that at least one hydrogen is replaced by deuterium, a C1-C4 alkyl, a C6-C18 aryl or a C2-C30 heteroaryl.

[0176] In a specific embodiment of the present invention, Chemical Formula 2 may be represented by one of Chemical Formulas 2-1 to 2-15.

[0177]

[0178]

[0179] In Chemical Formulas 2-1 to 2-15, R 7 to R 11 may each independently be hydrogen, deuterium, a substituted or unsubstituted C6-C12 aryl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl, and *-L 4 -Ar 3 and *-L 5 -Ar 4 may each independently be one of the substituents listed in Group II.

[0180] [Group II]

[0181]

[0182] In Group II,

[0183] R 14 to R 17 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C4 alkyl, a substituted or unsubstituted C6-C18 aryl or a substituted or unsubstituted C2-C30 heteroaryl,

[0184] m14 is one of the integers from 1 to 5,

[0185] m15 is one of the integers from 1 to 4,

[0186] m16 is one of the integers from 1 to 3,

[0187] m17 is an integer of 1 or 2, and

[0188] * is a connecting point.

[0189] In Group II, when substituted with two or more Rs 14 each R 14 can be the same as or different from each other.

[0190] In Group II, when substituted with two or more Rs 15 each R 15 can be the same as or different from each other.

[0191] In Group II, when substituted with two or more Rs 16 each R 16 can be the same as or different from each other.

[0192] In Group II, when substituted with two or more Rs 17 each R 17 can be the same as or different from each other.

[0193] For example, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 can be represented by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0194]

[0195] In Chemical Formulas 3A to 3E, Ar 5 Ar 6 L 6 L 7 R 12 R 13 m12 and m13 are the same as those described above,

[0196] L b1 to L b4 are defined as L 6 and L 7 described above, and

[0197] R b1 to R b4 are defined as R 12 and R 13 described above.

[0198] For example, in Chemical Formulas 3 and 4, Ar 5 and Ar 6may 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 anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0199] R b1 to R b4 、R 12 and R 13 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0200] In a specific embodiment of the present invention, in Chemical Formula 3 and Chemical Formula 4, *-L 6 -Ar 5 and *-L 7 -Ar 6 may each independently be selected from the substituents listed in Group II.

[0201] In one embodiment, R b1 to R b4 、R 12 and R 13 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0202] For example, R b1 to R b4 、R 12 and R 13 may each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0203] In a specific embodiment, R b1 to R b4 、R 12 and R 13 may each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0204] In a specific embodiment of the present invention, the second compound may be represented by Chemical Formula 2-6 or Chemical Formula 2-8, wherein Ar 3 and Ar 4 may 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 terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, L 4 and L 5 may each independently be a single bond or a substituted or unsubstituted C6-C20 arylene group, and R 7 to R 11 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0205] For example, *-L 4 -Ar 3 and *-L 5 -Ar 2 may each independently be selected from the substituents listed in Group II, and in one embodiment, may be any one of C-1, C-2, C-3, C-4, C-7, C-8, and C-9.

[0206] In another specific embodiment of the present invention, the third compound may be represented by Chemical Formula 3C, wherein L b1 and L b2 may be a single bond, L 6 and L 7 may each independently be a single bond or a substituted or unsubstituted C6-C12 arylene group, R b1 、R b2 、R 12 and R 13 may each be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and Ar 5 and Ar 6 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0207] For example, the second compound may be one of the compounds listed in Group 2, but is not limited thereto.

[0208] [Group 2]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216] In addition, examples are given below in which at least one hydrogen in Compounds B-1 to B-150 listed in Group 2 is replaced by deuterium, but are not limited thereto.

[0217]

[0218]

[0219] (Dn refers to the number of deuterium substitutions and represents a structure substituted with one or more deuteriums).

[0220] According to the position and substitution rate of deuterium substitution, the most specific structures of Compounds B-151 to B-195 in Group 2 are presented below as examples, and are not intended to limit the scope of rights for compounds not listed below.

[0221] The scope of the present disclosure is determined by the claims, and when substituted with deuterium, it is not limited to the compounds illustrated below, and the deuterium substitution position, deuterium substitution rate, etc. may include all variable ranges within the scope of Compounds B-1 to B-195.

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] In addition, examples are given below in which at least one hydrogen in Compounds C-1 to C-57 listed in Group 2 is replaced by deuterium, but are not limited thereto.

[0229]

[0230]

[0231] (Dn represents the number of deuterium substitutions and represents a structure substituted with one or more deuteriums).

[0232] According to the position and substitution rate of deuterium substitution, the most specific structures of Compounds C-58 to C-72 in Group 2 are presented below as examples, and it is not intended to limit the scope of rights for compounds not listed below.

[0233] The scope of the present disclosure is determined by the claims, and when substituted with deuterium, it is not limited to the compounds illustrated below, and all variable ranges within the range of Compounds C-58 to C-72, such as the deuterium substitution position and deuterium substitution rate, can be included.

[0234]

[0235]

[0236] The second compound is a compound having relatively strong hole properties and can be used together with the first compound in the light-emitting layer to improve charge mobility and stability, thereby improving light-emitting efficiency and lifetime characteristics. In addition, the charge mobility can be controlled by controlling the ratio of the third compound having hole properties to the first compound.

[0237] In addition, the first compound and the second compound are included in a weight ratio of, for example, about 1:9 to 9:1, and specifically, the first compound and the second compound can be included in weight ratios of 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, and 5:5. By including within the above range, bipolar characteristics can be achieved, thereby improving both efficiency and lifetime.

[0238] In addition to the first compound and the second compound described above, the light-emitting layer may further include a third compound as a host.

[0239] The third compound can be represented by a combination of Chemical Formula 5 and Chemical Formula 6.

[0240]

[0241] In Chemical Formula 5 and Chemical Formula 6,

[0242] X 1 is O or S,

[0243] b in Chemical Formula 5 1 * to b 4 * are each independently a connecting carbon (C) or C-L c -Rc ,

[0244] b 1 * to b 4 Two adjacent ones among the * are each connected to the * of Chemical Formula 6,

[0245] In b 1 * to b 4 Among the *, the remaining two that are not connected to the * in Chemical Formula 6 are each independently C-L c -R c ,

[0246] L c is a single bond, a substituted or unsubstituted C6-C20 arylene, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof,

[0247] R c 、R 18 and R 19 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof,

[0248] m18 and m19 are each independently one of the integers from 1 to 4,

[0249] Ar 7 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof, and

[0250] R c 、R 18 、R 19 and Ar 1 at least one of them is a substituent represented by Chemical Formula A,

[0251] [Chemical Formula A]

[0252]

[0253] In Chemical Formula A,

[0254] Z 4 to Z 6 are each independently N or C-L d -R d ,

[0255] Z 4 to Z 6 at least two of them are N,

[0256] L d and L 8 to L 10Each is 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,

[0257] R d is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

[0258] Ar 8 and Ar 9 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0259] In Chemical Formula 5, when two or more Rs are substituted, 18 each R 18 can be the same as or different from each other.

[0260] In Chemical Formula 5, when two or more Rs are substituted, c each R c can be the same as or different from each other.

[0261] In Chemical Formula 6, when two or more Rs are substituted, 19 each R 19 can be the same as or different from each other.

[0262] In Chemical Formula A, when two or more Rs are substituted, d each R d can be the same as or different from each other.

[0263] Depending on the fusion direction of Chemical Formula 5 and Chemical Formula 6, the third compound can be represented by any one of Chemical Formulas 5A to 5F.

[0264]

[0265] In Chemical Formulas 5A to 5F,

[0266] X 1 、Ar 7 、R 18 、R 19 、m18 and m19 are the same as above,

[0267] L c1 to L c4 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, and

[0268] R c1 to Rc4 Each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof.

[0269] For example, Chemical Formula 5A can be represented by any one of Chemical Formula 5A-I, Chemical Formula 5A-II, and Chemical Formula 5A-III.

[0270]

[0271] [Chemical Formula 5A-III]

[0272]

[0273] In Chemical Formula 5A-I, Chemical Formula 5A-II, and Chemical Formula 5A-III, X 1 , Ar 7 , R 18 , R 19 , m18 and m19, Z 4 to Z 6 , L 8 to L 10 , L c1 , L c4 , R c1 , R c4 , Ar 9 and Ar 10 are the same as above, and

[0274] m18' and m19' are each independently one of the integers from 1 to 3.

[0275] For example, Chemical Formula 5B can be represented by any one of Chemical Formula 5B-I, Chemical Formula 5B-II, and Chemical Formula 5B-III.

[0276]

[0277] [Chemical Formula 5B-III]

[0278]

[0279] In Chemical Formula 5B-I, Chemical Formula 5B-II, and Chemical Formula 5B-III, X 1 , Ar 7 , R 18 , R 19 , m18 and m19, Z 4 to Z 6 , L 8 to L 10 , L c3 , L c4 , Rc3 , R c4 , Ar 8 and Ar 9 are the same as above, and

[0280] m18' and m19' are each independently one of the integers from 1 to 3.

[0281] For example, Chemical Formula 5C can be represented by any one of Chemical Formula 5C-I, Chemical Formula 5C-II, and Chemical Formula 5C-III.

[0282]

[0283]

[0284] [Chemical Formula 5C-III]

[0285]

[0286] In Chemical Formula 5C-I, Chemical Formula 5C-II, and Chemical Formula 5C-III, X 1 , Ar 7 , R 18 , R 19 , m18 and m19, Z 4 to Z 6 , L 8 to L 10 , L c1 , L c2 , R c1 , R c2 , Ar 8 and Ar 9 are the same as above, and

[0287] m13' and m14' are each independently one of the integers from 1 to 3.

[0288] For example, Chemical Formula 5D can be represented by any one of Chemical Formula 5D-I, Chemical Formula 5D-II, and Chemical Formula 5D-III.

[0289]

[0290]

[0291] [Chemical Formula 5D-III]

[0292]

[0293] In Chemical Formula 5D-I, Chemical Formula 5D-II, and Chemical Formula 5D-III, X 1 , Ar 7 , R 18 , R19 , m18 and m19, Z 4 to Z 6 , L 8 to L 10 , L c1 , L c2 , R c1 , R c2 , Ar 8 and Ar 9 Same as above, and

[0294] m18' and m19' are each independently one of the integers from 1 to 3.

[0295] For example, Chemical Formula 5E can be represented by any one of Chemical Formula 5E-I, Chemical Formula 5E-II, and Chemical Formula 5E-III.

[0296]

[0297]

[0298] [Chemical Formula 5E-III]

[0299]

[0300] In Chemical Formula 5E-I, Chemical Formula 5E-II, and Chemical Formula 5E-III, X 1 , Ar 7 , R 18 , R 19 , m18 and m19, Z 4 to Z 6 , L 8 to L 10 , L c3 , L c4 , R c3 , R c4 , Ar 8 and Ar 9 Same as above, and

[0301] m18' and m19' are each independently one of the integers from 1 to 3.

[0302] For example, Chemical Formula 5F can be represented by any one of Chemical Formula 5F-I, Chemical Formula 5F-II, and Chemical Formula 5F-III.

[0303]

[0304]

[0305] [Chemical Formula 5F-III]

[0306]

[0307] In Chemical Formula 5F-I, Chemical Formula 5F-II, and Chemical Formula 5F-III, X 1 , Ar 7 , R 18 , R 19 , m18 and m19, Z 4 to Z 6 , L 8 to L 10 , L c3 , L c4 , R c3 , R c4 , Ar 8 and Ar 9 are the same as above, and

[0308] m18' and m19' are each independently one of the integers from 1 to 3.

[0309] For example, in Chemical Formula 5A-I, Chemical Formula 5A-II, Chemical Formula 5A-III, Chemical Formula 5B-I, Chemical Formula 5B-II, Chemical Formula 5B-III, Chemical Formula 5C-I, Chemical Formula 5C-II, Chemical Formula 5C-III, Chemical Formula 5D-I, Chemical Formula 5D-II, Chemical Formula 5D-III, Chemical Formula 5E-I, Chemical Formula 5E-II, Chemical Formula 5E-III, Chemical Formula 5F-I, Chemical Formula 5F-II, and Chemical Formula 5F-III, R 18 , R 19 and Ar 7 can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0310] In one embodiment, Chemical Formula 5A-I can be represented by any one of Chemical Formula 5A-I-1 to Chemical Formula 5A-I-4.

[0311]

[0312] In Chemical Formula 5A-I-1 to Chemical Formula 5A-I-4,

[0313] X 1 is O or S,

[0314] L c1 and L c4 are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a combination thereof,

[0315] Ar 7is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenyl, or a combination thereof,

[0316] Z 4 to Z 6 each independently is N or C-L d -R d ,

[0317] Z 4 to Z 6 at least two of which are N,

[0318] L d and L 8 to L 10 each independently is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or a combination thereof,

[0319] R c1 、R c4 、R d 、R 18 and R 19 each independently is hydrogen, deuterium, substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C12 aryl, or a combination thereof,

[0320] Ar 8 and Ar 9 each independently is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzosilolyl, substituted or unsubstituted carbazolyl, or a combination thereof,

[0321] m18' is one of the integers from 1 to 3, and

[0322] m19 is one of the integers from 1 to 4.

[0323] In one embodiment, Chemical Formula 5A-II can be represented by any one of Chemical Formulas 5A-II-1 to 5A-II-4.

[0324]

[0325]

[0326] In Chemical Formulas 5A-II-1 to 5A-II-4,

[0327] X 1 、L c1 、L c4 、Ar 7 、Z 4 to Z 6 、L 2 to L 4 、R c1 、R c4 、R 18 、R 19 、Ar 2 、Ar 3 、m18 and m19' are the same as those described above.

[0328] In one embodiment, Chemical Formula 5B-I can be represented by any one of Chemical Formulas 5B-I-1 to 5B-I-4.

[0329]

[0330]

[0331] In Chemical Formulas 5B-I-1 to 5B-I-4, X 1 、Ar 7 、Z 4 to Z 6 、L 8 to L 10 、R 18 and R 19 、Ar 8 and Ar 9 、m18' and m19 are the same as those described above,

[0332] L c3 as defined by L as described above c1 and L c4 of the definition.

[0333] R c3 and R c4 as defined by R as described above 18 and R 19 of the definition.

[0334] In one embodiment, Chemical Formula 5B-II can be represented by any one of Chemical Formulas 5B-II-1 to 5B-II-4.

[0335]

[0336]

[0337] In Chemical Formulas 5B-II-1 to 5B-II-4, X 1 、Ar7 , Z 4 to Z 6 , L 8 to L 10 , R 13 and R 14 , R c3 and R c4 , Ar 8 and Ar 9 , m18 and m19' are the same as above, and

[0338] L c3 L as described above c1 and L c4 as defined.

[0339] In one embodiment, Chemical Formula 5C-I can be represented by any one of Chemical Formulas 5C-I-1 to 5C-I-4.

[0340]

[0341] In Chemical Formulas 5C-I-1 to 5C-I-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , R 18 and R 19 , R c1 and R c2 , Ar 8 and Ar 9 , m18' and m19 are the same as above, and

[0342] L c2 L as described above c1 and L c4 as defined.

[0343] In one embodiment, Chemical Formula 5C-II can be represented by any one of Chemical Formulas 5C-II-1 to 5C-II-4.

[0344]

[0345] In Chemical Formulas 5C-II-1 to 5C-II-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , R 18 and R 19 , R c1 and Rc2 , Ar 8 and Ar 9 , m18 and m19' are the same as above, and

[0346] L c2 L as described above c1 and L c4 Definition of.

[0347] In one embodiment, Chemical Formula 5D-I can be represented by any one of Chemical Formulas 5D-I-1 to 5D-I-4.

[0348]

[0349] In Chemical Formulas 5D-I-1 to 5D-I-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , L c1 and L c4 , R 18 and R 19 , R c1 and R c4 , Ar 8 and Ar 9 , m18' and m19 are the same as above.

[0350] In one embodiment, Chemical Formula 5D-II can be represented by any one of Chemical Formulas 5D-II-1 to 5D-II-4.

[0351]

[0352]

[0353] In Chemical Formulas 5D-II-1 to 5D-II-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , R 18 and R 19 , Ar 8 and Ar 9 , m18, m19', R c1 and R c4 , L c1 and L c4 are the same as above.

[0354] In one embodiment, Chemical Formula 5E-I can be represented by any one of Chemical Formulas 5E-I-1 to 5E-I-4.

[0355]

[0356]

[0357] In Chemical Formulas 5E-I-1 to 5E-I-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , R 18 and R 19 , Ar 8 and Ar 9 , R c3 and R c4 , L c3 and L c4 , m18' and m19 are the same as above.

[0358] In one embodiment, Chemical Formula 5E-II can be represented by any one of Chemical Formulas 5E-II-1 to 5E-II-4.

[0359]

[0360]

[0361] In Chemical Formulas 5E-II-1 to 5E-II-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , R 18 and R 19 , Ar 8 and Ar 9 , R c3 and R c4 , L c3 and L c4 , m18 and m19' are the same as above.

[0362] In one embodiment, Chemical Formula 5F-I can be represented by any one of Chemical Formulas 5F-I-1 to 5F-I-4.

[0363]

[0364]

[0365] In Chemical Formulas 5F-I-1 to 5F-I-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , R 18 and R 19 , Ar 8 and Ar 9 , R c1 and R c2 , L c1 and L c2 , m18' and m19 are the same as those described above.

[0366] In one embodiment, Chemical Formula 5F-II can be represented by any one of Chemical Formulas 5F-II-1 to 5F-II-4.

[0367]

[0368]

[0369] In Chemical Formulas 5F-II-1 to 5F-II-4, X 1 , Ar 7 , Z 4 to Z 6 , L 8 to L 10 , R 18 and R 19 , Ar 8 and Ar 9 , R c1 and R c2 , L c1 and L c2 , m18 and m19' are the same as those described above.

[0370] As a specific example, the third compound can be represented by any one of Chemical Formulas 5A-III, 5B-III, 5C-III, 5D-III, 5E-III, and 5F-III.

[0371] The third compound can be, for example, one selected from the compounds listed in Group 3.

[0372] [Group 3]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384] A composition for an organic optoelectronic device according to an embodiment of the present invention includes a first compound having relatively strong electron characteristics, a second compound having relatively strong hole characteristics, and a third compound having excellent hole and electron injection and transport capabilities, all of which are in a light-emitting layer, thereby enabling an organic optoelectronic device with excellent efficiency while significantly reducing the driving voltage.

[0385] In particular, by further including the third compound, the trap phenomenon between the dopant and the host can be reduced or minimized, and the injection characteristics into the light-emitting layer can be improved, thereby obtaining the effect of reducing the driving voltage. In addition, by using three hosts, the optimal position and width of the light-emitting region can be adjusted, thereby effectively improving the efficiency and lifetime.

[0386] According to an embodiment of the present invention, the light-emitting layer 130 may simultaneously include the first compound, the second compound, and the third compound as hosts, and

[0387] The first compound may be specifically represented by Chemical Formula 1-3, the second compound may be specifically represented by Chemical Formula 2-8, and the third compound may be specifically represented by Chemical Formula 5B-III.

[0388] The first compound and the second compound may be included in a weight ratio of, for example, 90:10 to 10:90, and specifically, the first compound and the second compound may be included in a weight ratio of 90:10 to 10:90, 85:15 to 15:85, 80:20 to 20:80, 70:30 to 30:70, 60:40 to 40:60, 50:50. Preferably, a mixture of the first compound and the second compound and the third compound may be included in a weight ratio of 90:10, 85:15, 80:20, or 70:30.

[0389] By including the above ranges, bipolar characteristics can be more effectively achieved, which not only improves efficiency and lifespan but also significantly reduces the driving voltage.

[0390] In addition to the first compound, the second compound, and the third compound described above, the light-emitting layer 130 may further include one or more compounds as a host.

[0391] For example, a dopant may be further included. The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a green phosphorescent dopant.

[0392] A dopant is a material that is mixed in a small amount with a composition containing the first compound, the second compound, and the third compound to cause luminescence, and may generally be a material such as a metal complex that emits light by being excited to a triplet state or more states multiple times. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0393] Examples of the dopant may be phosphorescent dopants, and examples of the phosphorescent dopants 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.

[0394] [Chemical Formula Z]

[0395] L 11 MX 2

[0396] In Chemical Formula Z, M is a metal, and L 11 and X 2 are the same or different and are ligands that form a complex with M.

[0397] 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.

[0398] Examples of the ligands represented by L 11 and X 2 may be selected from the chemical formulas listed in Group A, but are not limited thereto.

[0399] [Group A]

[0400]

[0401]

[0402] In Group A,

[0403] R 300 to R 302 are each independently hydrogen, deuterium, a halogen-substituted or unsubstituted C1-C30 alkyl group, a C6-C30 aryl group substituted or unsubstituted with a C1-C30 alkyl group, or a halogen, and

[0404] R 303 to R 324 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 heteroaryl group, a substituted or unsubstituted C1-C30 amino group, a substituted or unsubstituted C6-C30 arylamino group, SF 5 , a trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.

[0405] As an example, it may include a dopant represented by Chemical Formula IV.

[0406] [Chemical Formula IV]

[0407]

[0408] In Chemical Formula IV,

[0409] R 101 to R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 ,

[0410] R 132 to R 134 are each independently a C1-C6 alkyl group,

[0411] R 101 to R 116 at least one of which is a functional group represented by Chemical Formula IV-1,

[0412] L 100 is a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through a lone pair of electrons of a carbon or heteroatom, and

[0413] n1 and n2 are each independently any one of the integers from 0 to 3, and n1 + n2 is any one of the integers from 1 to 3.

[0414] [Chemical Formula IV-1]

[0415]

[0416] In Chemical Formula IV-1,

[0417] R 135 to 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

[0418] * represents the moiety attached to the carbon atom.

[0419] As an example, it may include a dopant represented by Chemical Formula Z-1.

[0420] [Chemical Formula Z-1]

[0421]

[0422] In Chemical Formula Z-1, rings A, B, C, and D independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0423] R A , R B , R C and R D independently represent mono-, di-, tri-, or tetra-substituted or unsubstituted;

[0424] L B , L C and L D are each independently selected from a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO 2 , CRR', SiRR', GeRR', and combinations thereof;

[0425] When nA is 1, L E is selected from a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO 2 , CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist; and

[0426] R A , R B , R C , R D, R, and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are optionally connected to each other to provide a ring; X B , X C , X D , and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 , and Q 4 each represents oxygen or a direct bond.

[0427] According to one embodiment, the dopant can be a platinum complex and can be represented, for example, by Chemical Formula V.

[0428] [Chemical Formula V]

[0429]

[0430] In Chemical Formula V,

[0431] X 100 is selected from O, S, and NR 131 ,

[0432] R 117 to R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C20 aryl, or -SiR 132 R 133 R 134 ,

[0433] R 132 to R 134 are each independently C1-C6 alkyl, and

[0434] R 117 to R 131 at least one of which is -SiR 132 R 133 R 134 or tert-butyl.

[0435] The composition for an organic optoelectronic device can be formed into a film by a dry film deposition method (such as chemical vapor deposition).

[0436] In the following, an organic optoelectronic device using the above-described composition for an organic optoelectronic device is described.

[0437] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa. For example, an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, or an organic photoreceptor drum.

[0438] In this document, with reference to the accompanying drawings, an organic light-emitting diode, which is an example of an organic optoelectronic device, is described.

[0439] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0440] Referring to 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.

[0441] The anode 120 may be made of a conductor having a large work function to assist hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc. or an alloy thereof; 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 SnO 2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylenedioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but not limited thereto.

[0442] The cathode 110 may be made of a conductor having a small work function to assist electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; a multilayer structure material such as LiF / Al, LiO 2 / Al, LiF / Ca, and BaF 2 / Ca, but not limited thereto.

[0443] The organic layer 105 may contain the above-described composition for an organic optoelectronic device.

[0444] The organic layer 105 may include a light-emitting layer 130, and the light-emitting layer 130 may contain the above-described composition for an organic optoelectronic device.

[0445] A composition for an organic optoelectronic device that also contains a dopant can be, for example, a green light emitting composition.

[0446] The light emitting layer 130 can contain, for example, the above composition for an organic optoelectronic device as a phosphorescent host.

[0447] In addition to the light emitting layer, the organic layer can also include a charge transport region.

[0448] The charge transport region can be, for example, the hole transport region 140.

[0449] The hole transport region 140 can further increase the hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0450] Specifically, the hole transport region 140 can 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 can include at least one of the compounds in Group B in at least one of the hole transport layer and the hole transport auxiliary layer.

[0451] [Group B]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457] In the hole transport region, in addition to the compounds described above, known compounds disclosed in US5061569A, JP1993 - 009471A, WO1995 - 009147A1, JP1995 - 126615A, JP1998 - 095973A, etc. and compounds with similar structures can also be used.

[0458] In addition, the charge transport region can be, for example, the electron transport region 150.

[0459] 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.

[0460] 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 may include at least one of the compounds in Group C in at least one of the electron transport layer and the electron transport auxiliary layer.

[0461] [Group C]

[0462]

[0463]

[0464]

[0465] One embodiment may be an organic light-emitting diode including a light-emitting layer as an organic layer.

[0466] Another embodiment may be an organic light-emitting diode including a light-emitting layer and a hole transport region as organic layers.

[0467] Another embodiment may be an organic light-emitting diode including a light-emitting layer and an electron transport region as organic layers.

[0468] As Figure 1 shown, another embodiment of the present invention may provide an organic light-emitting diode including a hole transport region 140 and an electron transport region 150 as organic layers 105 in addition to the light-emitting layer 130.

[0469] On the other hand, in addition to the light-emitting layer, the organic light-emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as organic layers.

[0470] The organic light-emitting diode 100 may be manufactured by: forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method (such as vacuum deposition, sputtering, plasma plating, and ion plating), and forming a cathode or an anode thereon.

[0471] The organic light-emitting diode may be applied to an organic light-emitting display device.

[0472] Mode of the Invention

[0473] Hereinafter, embodiments will be described in more detail with reference to examples. However, these examples are exemplary, and the scope of the claims is not limited thereto.

[0474] (Synthesis of the First Compound)

[0475] Synthesis Example 1: Synthesis of Compound A-3

[0476]

[0477] Compound A-3 was synthesized by referring to the method known in KR 10-1649683B1.

[0478] (Synthesis of the second compound)

[0479] Synthesis Example 2: Synthesis of Compound B-31

[0480]

[0481] Compound B-31 was synthesized by referring to the method disclosed in KR 10-1649683B1.

[0482] Synthesis Example 3: Synthesis of Compound B-99

[0483]

[0484] Compound B-99 was synthesized by referring to the method disclosed in KR 10-1649683B1.

[0485] Synthesis Example 4: Synthesis of Compound B-136

[0486]

[0487] Compound B-136 was synthesized by referring to the method disclosed in KR 10-1649683B1.

[0488] (Synthesis of the third compound)

[0489] Synthesis Example 5: Synthesis of Compound D-13

[0490]

[0491] Compound D-13 was synthesized by referring to the method disclosed in KR 10-2022-0062990A.

[0492] (Synthesis of the comparative compound)

[0493] Synthesis Example 6: Synthesis of Compound E

[0494] [Reaction Scheme 1]

[0495]

[0496] 2-Chloro-4,6-diphenyl-1,3,5-triazine (15 g, 56.2 mmol), 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (18.7 g, 56.2 mmol) and NaH (2 g, 84.3 mmol) were added to a round-bottom flask under nitrogen, dissolved in 280 ml of DMF, and then stirred and refluxed at room temperature for 12 hours. When the reaction was completed, excess distilled water was poured into it, and then stirred for 1 hour. Subsequently, the solid was filtered out, and then dissolved in MCB at high temperature. After treating the solution with MgSO 4 to remove moisture, and then filtering the organic solvent through a silica gel pad, the resulting filtrate was stirred. The solid formed therein was filtered, and then dried under vacuum to obtain 23.1 g (75%) of Compound E.

[0497] Synthesis Example 7: Synthesis of Compound F

[0498] [Reaction Scheme 2]

[0499]

[0500] Step 1: Synthesis of Intermediate Int-1

[0501] 2-(4-Biphenyl)-4,6-dichloro-1,3,5-triazine (20 g, 66.4 mmol), 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzofuran (15.6 g, 53.2 mmol), K 2 CO 3 (27.5 g, 199.3 mmol) and Pd(PPh 3 ) 4 (3.8 g, 3.3 mmol) were added to a round-bottom flask, dissolved in 250 ml of THF and 110 ml of distilled water, and then stirred and refluxed at 60 °C for 12 hours. When the reaction was completed, the aqueous layer was removed under reduced pressure and the organic solvent was removed, and the resulting solid was obtained. The obtained solid was dissolved in MCB at high temperature. After treating the solution with MgSO 4 to remove moisture, and then filtering the organic solvent through a silica gel pad, the resulting filtrate was stirred. The solid formed therein was filtered and dried under vacuum to obtain 18 g (62%) of Intermediate Int-1.

[0502] Step 2: Synthesis of Compound F

[0503] Compound F was synthesized in the same manner as in the method for synthesizing Compound E in Synthesis Example 6, except that Intermediate Int-1 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0504] Synthesis Example 8: Synthesis of Compound G

[0505]

[0506] Compound G was synthesized by referring to the method disclosed in KR 10-1805686B1.

[0507] (Manufacture of Organic Light-Emitting Diodes)

[0508] Example 1

[0509] The glass substrate coated with an ITO (indium tin oxide) film was washed with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred to a vacuum depositor. The prepared ITO transparent electrode was used as the anode, and compound A doped with 3% NDP-9 (Novaled GmbH) 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 was deposited on the hole transport layer to a thickness of to form a hole transport auxiliary layer. Compound A-3, compound B-31, and compound D-13 were simultaneously used as the host on the hole transport auxiliary layer, and 10 wt% PhGD was doped as the dopant, and a thick light-emitting layer was formed by vacuum deposition. Here, compound A-3, compound B-31, and compound D-13 were used in a weight ratio of 20:60:20, and the ratio was separately described for the following examples and comparative examples. Subsequently, on the light-emitting layer, compound C was deposited to form a thick electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited in a weight ratio of 1:1 to form a thick electron transport layer. On the electron transport layer, a cathode was formed by sequentially vacuum depositing of LiQ and of Al, thereby manufacturing an organic light-emitting diode.

[0510] An organic light-emitting diode was manufactured to have the following structure: ITO / compound A (doped with 3% NDP-9, ) / compound A / compound B / EML[{90 wt% host (A-3:B-31:D-13)}+{10 wt% dopant (PhGD)}] / compound C / compound D:LiQ / LiQ / Al

[0511] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0512] Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0513] Compound C: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0514] Compound D: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0515] [PhGD]

[0516]

[0517] Examples 2 and 3 and Comparative Examples 1 to 3

[0518] Each organic light emitting diode was fabricated in the same manner as in Example 1, except that the composition was changed to the host described in Tables 1 to 3.

[0519] Evaluation

[0520] The efficiency and lifetime of the organic light emitting diodes according to Examples 1 to 3 and Comparative Examples 1 to 3 were measured.

[0521] The specific measurement methods are described below, and the results are shown in Tables 1 to 3.

[0522] (1) Lifetime measurement

[0523] While maintaining the luminance (cd / m 2 ) at 24,000 cd / m 2 , the result was obtained by measuring the time when the current efficiency (cd / A) decreased to 90%. The relative lifetime ratio based on the lifetime value of Comparative Example 1 is shown in Table 1.

[0524] (2) Measurement of the change in current density according to voltage change

[0525] While increasing the voltage from 0 V to 10 V, the current flowing through the unit device in the fabricated organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0526] (3) Measure the luminance change based on the voltage change

[0527] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, the luminance is measured by using a luminance meter (Minolta Cs-1000A).

[0528] (4) Measure the current efficiency

[0529] Use the luminance, current density, and voltage measured according to (2) and (3) to calculate the current efficiency (cd / A) for the required luminance of 9000 nit. The relative efficiency ratios based on the current efficiency values of Comparative Examples 2 and 3 are shown in Tables 2 and 3 respectively.

[0530] [Table 1]

[0531]

[0532] [Table 2]

[0533]

[0534] [Table 3]

[0535]

[0536] Referring to Tables 1 to 3, the organic light-emitting diodes according to Embodiments 1 to 3 have significantly improved lifetime and efficiency characteristics compared to the organic light-emitting diodes according to Comparative Examples 1 to 3. By simultaneously using the first compound having a terphenyl group and hole and electron transport characteristics, the second compound having excellent hole transport characteristics, and the third compound having excellent hole and electron transport characteristics, the hole and electron characteristics of each host are complementary, thereby optimizing the position of the light-emitting region (recombination zone) and maximizing the device performance. If the position of the light-emitting region is biased towards the interface with the electron transport layer or the hole transport layer, interface degradation occurs, making the device vulnerable during its lifetime. The movement of the light-emitting region towards the center can reduce the stress on each host at the interface, thereby improving its lifetime. In addition, since the movement speeds of holes and electrons are different, optimizing the position of the light-emitting region can maximize the efficiency by balancing holes and electrons.

[0537] Although the present invention has been described in conjunction with the presently considered practical exemplary embodiments, it should be understood that the present invention is not limited to the disclosed embodiments. On the contrary, it 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 first compound; a second compound; and The third compound, in, The first compound is represented by Chemical Formula 1, and The second compound is represented by Chemical Formula 2 or by a combination of Chemical Formula 3 and Chemical Formula 4, and The third compound is represented by a combination of Chemical Formula 5 and Chemical Formula 6: [Chemical formula 1] In Chemical Formula 1, Z 1 To Z 3 Each independently is N or CL a -R a , Z 1 To Z 3 At least two of them are N, L a and L 1 To L 3 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, R 1 To R 3 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, m1 and m2 are each independently one of integers from 1 to 4, and m3 is an integer from 1 to 3; [Chemical formula 2] In chemical formula 2, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group, L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 7 To R 11 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, m8 and m9 are each independently an integer from 1 to 3, m7, m10 and m11 are each independently one of integers from 1 to 4, and n is one of integers from 0 to 2; In Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group, a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL b -R b , two adjacent ones of a1* to a4* are each connected to * of Chemical Formula 4, Among a1* to a4*, the remaining two not connected to * in Chemical Formula 4 are each independently CL b -R b , L b , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R b , R 12 and R 13 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl; In Chemical Formula 5 and Chemical Formula 6, X 1 is O or S, b1* to b4* in Chemical Formula 5 are each independently a connecting carbon (C) or CL c -R c , adjacent two of b1* to b4* are each connected to * of Chemical Formula 6, Among b1* to b4*, the remaining two not connected to * in Chemical Formula 6 are each independently CL c -R c , L c is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, R c , R 18 and R 19 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, m18 and m19 are each independently an integer from 1 to 4, Ar 7 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and R c , R 18 , R 19 and Ar 1 At least one of them is a substituent represented by Chemical Formula A, [Chemical Formula A] In chemical formula A, Z 4 To Z 6 Each independently is N or CL d -R d , Z 4 To Z 6 At least two of them are N, L d and L 8 To L 10 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, R d is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and Ar 8 and Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

2. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by any one of Chemical Formula 1-1 to Chemical Formula 1-12: In Chemical Formula 1-1 to Chemical Formula 1-12, Z 1 To Z 3 , R 1 To R 3 , L 2 , L 3 ,Ar 1 ,Ar 2 and m1 to m3 are the same as defined in claim 1, R 4 To R 6 With R 1 To R 3 The same restrictions apply, and m4 to m6 are each independently one of integers from 1 to 4.

3. The composition for an organic optoelectronic device according to claim 2, wherein The first compound is represented by Chemical Formula 1-3.

4. The composition for an organic optoelectronic device according to claim 1, wherein The second compound is represented by any one of Chemical Formula 2-6, Chemical Formula 2-8 and Chemical Formula 3C: [Chemical formula 3C] In Chemical Formula 2-6, Chemical Formula 2-8 and Chemical Formula 3C, L 4 To L 7 ,Ar 3 To Ar 6 , R 7 To R 10 , R 12 , R 13 , m7 to m10, m12 and m13 are the same as those defined in claim 1, L b1 and L b2 L in claim 1 b The same, and R b1 and R b2 R in claim 1 b same.

5. The composition for an organic optoelectronic device according to claim 1, wherein The third compound is represented by any one of Chemical Formula 5A to Chemical Formula 5F: In Chemical Formulae 5A to 5F, X 1 ,Ar 7 , R 18 , R 19 , m18 and m19 are the same as those defined in claim 1, L c1 To L c4 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, and R c1 To R c4 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

6. The composition for an organic optoelectronic device according to claim 1, wherein The third compound is represented by any one of Formula 5A-III, Formula 5B-III, Formula 5C-III, Formula 5D-III, Formula 5E-III, and Formula 5F-III: In Formula 5A-III, Formula 5B-III, Formula 5C-III, Formula 5D-III, Formula 5E-III and Formula 5F-III, X 1 , R 18 , R 19 , m18 and m19, Z 4 To Z 6 , L 8 To L 10 ,Ar 8 and Ar 9 As defined in claim 1, L c1 To L c4 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, and R c1 To R c4 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

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

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

9. The organic optoelectronic device according to claim 7, wherein The first compound, the second compound, and the third compound are each included as a host of a light-emitting layer.

10. The organic optoelectronic device according to claim 7, wherein The mixture of the first compound and the second compound and the third compound are included in a weight ratio of 90:10 to 40:

60.

11. The organic optoelectronic device according to claim 9, wherein The composition for an organic optoelectronic device further includes a phosphorescent dopant.

12. The organic optoelectronic device according to claim 11, wherein The composition for an organic optoelectronic device is a green light-emitting composition. 13 . A display device comprising the organic optoelectronic device according to claim 7 .

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