Compound for organic optoelectronic device, organic optoelectronic device, and display device

Abstract

The present invention relates to a compound for an organic optoelectronic device represented by Chemical Formula 1, and an organic optoelectronic device and a display device each comprising the same. The detailed description of the chemical formula 1 is defined in the specification.

Description

TECHNICAL FIELD

[0001] Disclosed are a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. BACKGROUND

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

[0003] Depending on the working principle, organic optoelectronic devices can be basically classified into two categories. One is a photovoltaic 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 a voltage or a current to an electrode.

[0004] Examples of the organic optoelectronic device include an organic photovoltaic device, an organic light-emitting diode, an organic solar cell, and an organic photoconductor drum.

[0005] Among them, an organic light-emitting diode (OLED) has attracted much attention due to an increase in demand for flat panel display devices in recent years. The organic light-emitting diode is a device that converts electrical energy into light, and the performance of the organic light-emitting diode is greatly influenced by an organic material between electrodes. SUMMARY

[0006] TECHNICAL PROBLEM

[0007] One embodiment provides a compound for an organic optoelectronic device that can implement an organic optoelectronic device having low driving, high efficiency, and long lifespan.

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

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

[0010] TECHNICAL SOLUTION

[0011] According to one embodiment, a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] X 1 and X 2 each independently is O or S,

[0016] R 1 to R 5each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof,

[0017] R 6 is substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl,

[0018] L 1 is a single bond, substituted or unsubstituted C6 to C20 arylene, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,

[0019] L 2 is a single bond or substituted or unsubstituted C6 to C12 arylene,

[0020] Ar 1 is substituted or unsubstituted C6 to C30 aryl,

[0021] m1 is an integer of 1 or 2,

[0022] m2 is one of an integer of 1 to 4,

[0023] m3 is one of an integer of 1 to 3, and

[0024] m4 and m5 are each independently one of an integer of 1 to 4.

[0025] According to another embodiment, an organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, and the organic layer includes a compound for the organic optoelectronic device.

[0026] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0027] Advantageous Effects

[0028] An organic optoelectronic device having high efficiency and long lifespan can be implemented. BRIEF DESCRIPTION OF DRAWINGS

[0029] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to one embodiment.

[0030] <LEGEND>

[0031] 100: organic light emitting diode

[0032] 105: organic layer

[0033] 110: cathode

[0034] 120: anode

[0035] 130: light-emitting layer

[0036] 140: hole transport zone

[0037] 150: electron transport zone DETAILED DESCRIPTION

[0038] Hereinafter, embodiments of the present application are described in detail. However, these embodiments are exemplary, the present application is not limited thereto and the present application is defined by the scope of the claims.

[0039] As used herein, when not otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 aminyl, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0040] In one example of the present application, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific example of the present application, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific example of the present application, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific example of the present application, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0041] "Unsubstituted" means that a hydrogen atom is not replaced with another substituent and the hydrogen atom is retained.

[0042] In the present specification, "deuterium-substituted (-D)" can include "tritium-substituted (-T)".

[0043] As used herein, when not otherwise provided, "hetero" means one group containing 1 to 3 heteroatoms selected from N, O, S, P, and Si in one functional group and the rest is carbon.

[0044] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals that form a conjugated pi system, such as phenyl, naphthyl, and the like, two or more hydrocarbon aromatic moieties can be connected by a sigma bond and the hydrocarbon aromatic moieties can be, for example, biphenyl, terphenyl, quaterphenyl, and the like, and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide non-aromatic fused rings, such as fluorenyl.

[0045] The aryl group can include a monocyclic, polycyclic, or fused polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional group.

[0046] As used herein, "heterocyclyl" 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, a fused ring thereof, or a combination thereof. When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl can include one or more heteroatoms.

[0047] For example, "heteroaryl" can mean an aryl group including at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings can be fused. When the heteroaryl is a fused ring, each ring can include 1 to 3 heteroatoms.

[0048] More specifically, the substituted or unsubstituted C6 to C30 aryl group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted benzophenanthryl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indenyl, or a combination thereof, but is not limited thereto.

[0049] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl 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 benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolyl group, a substituted or unsubstituted quinoxalyl group, a substituted or unsubstituted naphthylidinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenoxazinyl 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, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothienyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted benzothienofluorenyl group, or a combination thereof, but is not limited thereto.

[0050] As used herein, the hole property refers to the ability to contribute an electron to form a hole when an electric field is applied, and the hole formed in the anode can be easily injected into and transported in the light-emitting layer due to the conduction property according to the highest occupied molecular orbital (HOMO) level.

[0051] In addition, the electron property refers to the ability to accept an electron when an electric field is applied, and the electron formed in the cathode can be easily injected into and transported in the light-emitting layer due to the conduction property according to the lowest unoccupied molecular orbital (LUMO) level.

[0052] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0053] The compound for an organic optoelectronic device according to one embodiment is represented by Chemical Formula 1.

[0054] [Chemical Formula 1]

[0055]

[0056] In Chemical Formula 1,

[0057] X 1 and X2 Each is either O or S independently.

[0058] R 1 To R 5 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0059] R 6 It is a substituted or unsubstituted C1 to C20 alkyl or a substituted or unsubstituted C6 to C20 aryl.

[0060] L 1 It is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0061] L 2 It is a single bond or a substituted or unsubstituted C6 to C12 arylene.

[0062] Ar 1 It is a substituted or unsubstituted C6 to C30 aryl group.

[0063] m1 is an integer of 1 or 2.

[0064] m2 is an integer from 1 to 4.

[0065] m3 is an integer from 1 to 3, and

[0066] m4 and m5 are each an integer from 1 to 4.

[0067] The compound represented by chemical formula 1 has the following structure: the 6-5-6-5-6 ring-fused core is replaced by a 9-fluorenyl group linked to an amino group, which can improve hole mobility and thus improve charge balance, thereby reducing the driving voltage of the organic light-emitting diode to which it is applied and improving its efficiency.

[0068] Specifically, the fused form of the 6-5-6-5-6 rings forms a spherical molecular structure, which minimizes intermolecular interactions due to steric hindrance, resulting in a low deposition temperature and thus significantly improving the lifetime characteristics of organic light-emitting diodes (OLEDs) in which it is applied.

[0069] For example, Ar 1may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl.

[0070] As a specific example, Ar 1 may be selected from the substituents listed in Group I.

[0071] [Group I]

[0072]

[0073] In Group I,

[0074] R 7 to R 11 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1to C10alkyl, or substituted or unsubstituted C6to C12aryl,

[0075] R 12 and R 13 are each independently substituted or unsubstituted C1to C10alkyl, or substituted or unsubstituted C6to C12aryl,

[0076] m6is one of an integer from 1 to 5,

[0077] m7is one of an integer from 1 to 4,

[0078] m8is one of an integer from 1 to 3,

[0079] m9is an integer of 1 or 2,

[0080] m10is 1, and

[0081] * is a point of attachment.

[0082] When m6is 2 or more, each R 7 may be the same as or different from each other.

[0083] When m7is 2 or more, each R 8 may be the same as or different from each other.

[0084] When m8is 2 or more, each R 9 may be the same as or different from each other.

[0085] When m9is 2 or more, each R10 may be the same as or different from each other.

[0086] For example, L 1 may be substituted or unsubstituted phenylene.

[0087] For example, L 2 may be a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted biphenylene.

[0088] For example, R 1 to R 5 may each independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0089] For example, R 6 may be substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or a combination thereof.

[0090] For example, the compound for an organic optoelectronic device represented by Chemical Formula 1 can be one selected from the compounds listed in Group 1, but is not limited thereto.

[0091] [Group 1]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] In addition to the compounds described above for use in organic optoelectronic devices, one or more compounds can be further included.

[0128] For example, a dopant can be further included.

[0129] The dopant can be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0130] The dopant is a material mixed in a small amount with a compound or composition used for an organic optoelectronic device to cause light emission, and can be generally a material such as a metal complex that emits light by being excited to a triplet state or more. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof can be used.

[0131] Examples of the dopant can be phosphorescent dopants, and examples of the phosphorescent dopant can be organic metal compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant can be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[0132] [Chemical Formula Z]

[0133] L 3 MX 3

[0134] In Chemical Formula Z, M is a metal, and L 3 and X 3 are the same or different, and are ligands forming a complex with M.

[0135] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 3 and X 3 may be, for example, bidentate ligands.

[0136] Examples of the ligands represented by L 3 and X 3 may be selected from the chemical formulas listed in Group A, but are not limited thereto.

[0137] [Group A]

[0138]

[0139] In Group A,

[0140] R 300 to R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl substituted with or unsubstituted with halogen, C6 to C30 aryl substituted with or unsubstituted with C1 to C30 alkyl, or halogen, and

[0141] R 303 to R 324each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, dialkylaryl silyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or triaryl silyl group having a substituted or unsubstituted C6 to C30 aryl group,

[0142] n1 is one of an integer of 1 to 5,

[0143] n2 is one of an integer of 1 to 4,

[0144] n3 is one of an integer of 1 to 3,

[0145] n4 is an integer of 1 or 2, and

[0146] n5 is one of an integer of 1 to 6.

[0147] When n1 is 2 or more, each substituent can be the same as or different from each other.

[0148] When n2 is 2 or more, each substituent can be the same as or different from each other.

[0149] When n3 is 2 or more, each substituent can be the same as or different from each other.

[0150] When n4 is 2 or more, each substituent can be the same as or different from each other.

[0151] When n5 is 2 or more, each substituent can be the same as or different from each other.

[0152] The dopant according to one embodiment can be an iridium complex, and can be represented by Chemical Formula 4-1 or Chemical Formula 4-2, for example.

[0153] [Chemical Formula 4-1]

[0154]

[0155] In Chemical Formula 4-1,

[0156] R 101 to R 116 each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR132 R 133 R 134 ,

[0157] R 132 to R 134 each independently is substituted or unsubstituted C1to C6alkyl,

[0158] R 101 to R 116 at least one of which is a functional group represented by Chemical Formula V-1,

[0159] L 100 is a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through a lone electron pair of carbon or a heteroatom, and

[0160] m21and m22are each independently any one of integers from 0 to 3, and m21+m22is any one of integers from 1 to 3,

[0161] [Chemical Formula V-1]

[0162]

[0163] in Chemical Formula V-1,

[0164] R 135 to R 139 each independently is hydrogen, deuterium, substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted C6to C20aryl, or -SiR 132 R 133 R 134 , and

[0165] * indicates a moiety bonded to a carbon atom.

[0166] [Chemical Formula 4-2]

[0167]

[0168] in Chemical Formula 4-2,

[0169] R 101 to R 117 each independently is hydrogen, deuterium, substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted C6to C20aryl, or -SiR 133 R 134 R 135 ,

[0170] R 133 to R 135 each independently is substituted or unsubstituted C1to C6alkyl,

[0171] L100 is a bidentate ligand of a monovalent anion, and is a ligand that coordinates to iridium through a carbon or a heteroatom lone pair, and

[0172] n1and n2are each independently any one of an integer from 0 to 3, and n1+n2is any one of an integer from 1 to 3.

[0173] In another embodiment, the dopant can be a platinum complex, such as a platinum complex represented by Chemical Formula Z-1.

[0174] [Chemical Formula Z-1]

[0175]

[0176] In Chemical Formula Z-1, rings A, B, C, and D are each independently a five- or six-membered carbocyclic or heterocyclic ring;

[0177] R A , R B , R C , and R D are each independently mono-, di-, tri-, or tetra-substituted, or unsubstituted;

[0178] L B , L C , and L D are each independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof,

[0179] when nAis 1, L E may be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof; and when nAis 0, L E is absent;

[0180] R A , R B , R C , R D , R, and R' are each independently hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, cyano, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, or a combination thereof; any adjacent R A , R B , R C , R D , and R' are optionally linked to each other to provide a ring; X B , X C , XD and X E each independently is selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 each represents oxygen or a direct bond.

[0181] The platinum complex can be represented by Chemical Formula 5-1 or Chemical Formula 5-2, for example.

[0182] [Chemical Formula 5-1]

[0183]

[0184] [Chemical Formula 5-2]

[0185]

[0186] In Chemical Formula 5-1 and Chemical Formula 5-2,

[0187] X 100 is selected from O, S, and NR 132 ,

[0188] R 118 to R 132 each independently is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 ,

[0189] R 133 to R 135 each independently is a substituted or unsubstituted C1 to C6 alkyl,

[0190] R 118 to R 132 at least one of which is -SiR 133 R 134 R 135 or a tert-butyl group, and

[0191] R 133 to R 135 each independently is a substituted or unsubstituted C1 to C6 alkyl.

[0192] Hereinafter, an organic optoelectronic device using the above-described compound for an organic optoelectronic device will be described.

[0193] The organic optoelectronic device can be a suitable device that converts electrical energy into optical energy (or vice versa), such as an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photoconductor drum.

[0194] In this document, an organic light emitting diode is described as an example of an organic optoelectronic device, with reference to the accompanying drawings.

[0195] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0196] Reference Figure 1 The organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110.

[0197] The anode 120 can be made of a conductor having a large work function to help 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 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 SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0198] The cathode 110 can be made of a conductor having a small work function to help 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 an alloy thereof; a multi-layered structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0199] The organic layer 105 can include the above-described compound for an organic optoelectronic device.

[0200] The organic layer 105 includes an emission layer 130, and the emission layer 130 can contain the above-described compound for an organic optoelectronic device.

[0201] The composition for an organic optoelectronic device including a dopant can be, for example, a green light emitting composition.

[0202] The emission layer 130 can include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host.

[0203] The organic layer can further include a charge transport zone in addition to the emission layer.

[0204] The charge transport zone can be, for example, a hole transport zone 140.

[0205] The hole transport region 140 can further improve hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0206] Specifically, the hole transport region 140 may include a hole transport layer located between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer located between the light-emitting layer 130 and the hole transport layer, and the hole transport auxiliary layer may contain the compounds described above for organic optoelectronic devices.

[0207] At this point, the light-emitting layer includes a host and a dopant, and the host can be, for example, a phosphorescent host.

[0208] The phosphorescent host should facilitate the injection and transport of holes and electrons within the emissive layer, ultimately enabling the holes and electrons to meet and form excitons, and should be able to efficiently transfer the energy of the formed excitons to the dopant. Examples of phosphorescent hosts can include organic compounds, including carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzopyran, indolodibenzothiophene, fluorene, indobenzocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0209] The phosphorescent substrate can be used without restriction, as long as it is a known material. For example, it can be a single substrate or a composite substrate.

[0210] In addition, the compounds for organic optoelectronic devices described above may be included in the light-emitting layer, and at least one of the compounds listed in group C may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0211] [Group C]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218] (Dn refers to the number of hydrogen atoms replaced by deuterium, and indicates the structure in which one or more deuterium atoms are substituted.)

[0219] In the hole transport zone 140, in addition to the compounds described above, known compounds and compounds having similar structures disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and the like can be used.

[0220] In addition, the charge transport zone can be, for example, an electron transport zone 150.

[0221] The electron transport zone 150 can also improve electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0222] Specifically, the electron transport zone 150 can include an electron transport layer positioned between the cathode 110 and the light-emitting layer 130 and an electron transport auxiliary layer positioned between the light-emitting layer 130 and the electron transport layer, and at least one of the compounds of Group D can be contained in at least one of the electron transport layer and the electron transport auxiliary layer.

[0223] [Group D]

[0224]

[0225]

[0226]

[0227] One embodiment can be an organic light-emitting diode including a light-emitting layer as an organic layer.

[0228] Another embodiment can be an organic light-emitting diode including a light-emitting layer and a hole transport zone as organic layers.

[0229] Another embodiment can be an organic light-emitting diode including a light-emitting layer and an electron transport zone as organic layers.

[0230] In addition to the light-emitting layer 130, the organic light-emitting diode according to one embodiment includes a hole transport zone 140 and an electron transport zone 150 as organic layers 105, as Figure 1 indicated.

[0231] On the other hand, in addition to the light-emitting layer, the organic light-emitting diode can include an electron injection layer (not shown), a hole injection layer (not shown), and the like as organic layers.

[0232] The organic light-emitting diode 100 can be produced by forming an anode or a cathode on a substrate, then forming organic layers by dry film formation such as vacuum deposition, sputtering, plasma plating, and ion plating and forming a cathode or an anode thereon.

[0233] The organic light emitting diode can be applied to an organic light emitting diode display device.

[0234] Inventive modes

[0235] Hereinafter, the embodiments are described in more detail with reference to examples. However, these examples are exemplary, and the scope of the claims is not limited thereto.

[0236] Hereinafter, unless specifically mentioned, the 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 a known method.

[0237] (Preparation of compounds for organic optoelectronic devices)

[0238] Synthesis Example 1 : Synthesis of compound 1-21

[0239]

[0240] The intermediate of 8.0 g (27.33 mmol) of 1-chloro-benzo[1,2-b;3,4-b']biferan, the intermediate of 14.59 g (30.06 mmol) of N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine, 5.25 g (54.66 mmol) of sodium tert-butoxide, and 0.66 g (1.64 mmol) of tri-tert-butylphosphine were dissolved in 273 ml of toluene, and 0.75 g (0.82 mmol) of Pd2(dba)3 was added thereto, followed by stirring under reflux for 12 hours under a nitrogen atmosphere. When the reaction was completed, the organic layer thus extracted with ethyl acetate and distilled water was dried with anhydrous magnesium sulfate and filtered, and the filtrate thus obtained was concentrated under reduced pressure. The product thus obtained was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio 3:1), thereby obtaining 16.6 g (yield: 82%) of the target compound Compound 1-21 as a white solid.

[0241] Calculated: C, 89.04; H, 4.76; N, 1.89; O, 4.31

[0242] Calculated: C, 89.04; H, 4.76; N, 1.89; O, 4.31

[0243] Synthesis Example 2: Synthesis of compound 1-26

[0244]

[0245] Compound 1-26 (17.1 g, yield: 80%) was synthesized in the same manner as in Synthetic Example 1, except that 8 g of the intermediate of 1-chloro-benzo[1,2-b;3,4-b]bisbenzofuran and 15.8 g of the intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.1.

[0246] Calculated: C, 89.09; H, 5.03; N, 1.79; O, 4.09

[0247] Experimental: C, 89.09; H, 5.03; N, 1.79; O, 4.09

[0248] Synthesis Example 3: Synthesis of compound 1-53

[0249]

[0250] Compound 1-53 (19.5 g, yield: 73%) was synthesized in the same manner as in Synthetic Example 1, except that 10 g of the intermediate of 1-chloro-benzo[1,2-b;3,4-b]bisbenzofuran and 19.76 g of the intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-4-amine were used in an equivalent ratio of 1:1.1.

[0251] Calculated: C, 89.09; H, 5.03; N, 1.79; O, 4.09

[0252] Experimental: C, 89.09; H, 5.03; N, 1.78; O, 4.09

[0253] Synthesis Example 4: Synthesis of compound 1-90

[0254]

[0255] Compound 1-90 (16.0 g, yield: 86%) was synthesized in the same manner as in Synthetic Example 1, except that 7 g of the intermediate of 2-chloro-benzo[1,2-b;3,4-b]bisbenzofuran and 13.83 g of the intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.1.

[0256] Calculated: C, 89.09; H, 5.03; N, 1.79; O, 4.09

[0257] Experimental: C, 89.09; H, 5.03; N, 1.78; O, 4.09

[0258] Synthesis Example 5: Synthesis of compound 1-274

[0259]

[0260] Compound 1-274 was synthesized in the same manner as in Synthetic Example 1, except that 8 g of the intermediate of 1-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and 14.24 g of the intermediate of N-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)dibenzo[b,d]furan-2-amine were used in an equivalent ratio of 1:1.1.

[0261] Theoretical value: C, 85.58; H, 4.31; N, 1.81; O, 4.15; S, 4.15

[0262] Experimental value: C, 85.58; H, 4.31; N, 1.81; O, 4.15; S, 4.15

[0263] Synthesis Example 6: Synthesis of compound 1-330

[0264]

[0265] Compound 1-330 was synthesized in the same manner as in Synthetic Example 1, except that 8 g of the intermediate of 2-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and 14.98 g of the intermediate of 9,9-dimethyl-N-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-4-amine were used in an equivalent ratio of 1:1.1.

[0266] Theoretical value: C, 87.30; H, 4.93; N, 1.76; O, 2.00; S, 4.02

[0267] Experimental value: C, 87.30; H, 4.93; N, 1.76; O, 2.00; S, 4.03

[0268] Synthesis Example 7: Synthesis of compound 1-353

[0269]

[0270] Compound 1-353 was synthesized in the same manner as in Synthetic Example 1, except that 6 g of the intermediate of 3-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and 11.23 g of the intermediate of 9,9-dimethyl-N-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-4-amine were used in an equivalent ratio of 1:1.1.

[0271] Theoretical value: C, 87.30; H, 4.93; N, 1.76; O, 2.00; S, 4.02

[0272] Experimental value: C, 87.30; H, 4.93; N, 1.76; O, 2.00; S, 4.02

[0273] Synthesis Example 8: Synthesis of compound 1-565

[0274]

[0275] Compound 1-565 (17.4 g, yield: 84%) was synthesized in the same manner as in Synthetic Example 1, except that 8 g of the intermediate of 2-chlorobenzo[b]benzo[4,5]thieno[2,3- e]benzofuran and 16.34 g of the intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9- yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0276] Theoretical value: C, 87.30; H, 4.93; N, 1.76; O, 2.00; S, 4.02

[0277] Experimental value: C, 87.30; H, 4.93; N, 1.76; O, 2.00; S, 4.02

[0278] Synthesis Example 9: Synthesis of compound 1-571

[0279]

[0280] Compound 1-571 (15.1 g, yield: 81%) was synthesized in the same manner as in Synthetic Example 1, except that 7 g of the intermediate of 2-chlorobenzo[b]benzo[4,5]thieno[2,3- e]benzofuran and 13.7 g of the intermediate of N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)naphtho[1,2- b]benzofuran-7-amine were used in an equivalent ratio of 1:1.1.

[0281] Theoretical value: C, 86.21; H, 4.29; N, 1.70; O, 3.89; S, 3.90

[0282] Experimental value: C, 86.21; H, 4.29; N, 1.70; O, 3.89; S, 3.90

[0283] Synthesis Example 10: Synthesis of compound 1-936

[0284]

[0285] Compound 1-936 (18.2 g, yield: 82%) was synthesized in the same manner as in Synthetic Example 1, except that 9 g of the intermediate of 1-chloro-benzo[1,2-b;3,4-b']biferan-9-yl and 15.68 g of the intermediate of 9,9-dimethyl-N-(3-(9-methyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.1.

[0286] Calculated: C, 88.43; H, 5.18; N, 1.95; O, 4.44

[0287] Experimental: C, 88.43; H, 5.18; N, 1.95; O, 4.44

[0288] Synthesis Example 11 : Synthesis of compound 1-943

[0289]

[0290] Compound 1-943 (17.9 g, yield: 76%) was synthesized in the same manner as in Synthetic Example 1, except that 9 g of the intermediate of 2-chloro-benzo[1,2-b;3,4-b']biferan-9-yl and 17.32 g of the intermediate of N-(3-(9-methyl-9H-fluoren-9-yl)phenyl)-8-phenyldibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:1.1.

[0291] Calculated: C, 87.36; H, 4.58; N, 1.82; O, 6.23

[0292] Experimental: C, 87.36; H, 4.58; N, 1.82; O, 6.23

[0293] Synthesis Example 12: Synthesis of compound 1-949

[0294]

[0295] Compound 1-949 (17.5 g, yield: 75%) was synthesized in the same manner as in Synthetic Example 1, except that 10 g of the intermediate of 2-chloro-benzo[1,2-b;3,4-b']biferan-9-yl and 15.91 g of the intermediate of N-(3-(9-methyl-9H-fluoren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine were used in an equivalent ratio of 1:1.1.

[0296] Calculated: C, 88.34; H, 4.89; N, 2.06; O, 4.71

[0297] Experimental: C, 88.34; H, 4.89; N, 2.06; O, 4.71

[0298] Synthesis Example 13: Synthesis of compound 1-965

[0299]

[0300] Compound 1-965 was synthesized in the same manner as in Synthetic Example 1, except that 9 g of the intermediate of 3-chloro-benzo[1,2-b;3,4-b']bifuran and 15.68 g of the intermediate of 9,9-dimethyl-N-(3-(9-methyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-4-amine were used in an equivalent ratio of 1:1.1.

[0301] Theoretical value: C, 88.43; H, 5.18; N, 1.95; O, 4.44

[0302] Experimental value: C, 88.43; H, 5.18; N, 1.95; O, 4.44

[0303] Comparative Synthesis Example 1 : Synthesis of compound F-1

[0304]

[0305] Compound F-1 was synthesized in the same manner as in Synthetic Example 1, except that 5 g of the intermediate of 3-chlorodibenzo[b,d]furan and 13.18 g of the intermediate of N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine were used in an equivalent ratio of 1:1.1 (11.3 g, yield: 70%).

[0306] Theoretical value: C, 90.29; H, 5.10; N, 2.15; O, 2.45

[0307] Experimental value: C, 90.29; H, 5.10; N, 2.15; O, 2.45

[0308] Comparative Synthesis Example 2: Synthesis of compound F-2

[0309]

[0310] Compound F-2 was synthesized in the same manner as in Synthetic Example 1, except that 5 g of the intermediate of 1-chloro-benzo[1,2-b;3,4-b']bifuran and 9.38 g of the intermediate of N-(9,9-diphenyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine were used in an equivalent ratio of 1:1.1 (8.1 g, yield: 71%).

[0311] Theoretical value: C, 88.40; H, 4.69; N, 2.10; O, 4.81

[0312] Experimental values: C, 88.40; H, 4.69; N, 2.10; O, 4.81

[0313] Comparative Synthesis Example 3: Synthesis of compound F-3

[0314]

[0315] Compound F-3 (7.8 g, yield: 69%) was synthesized in the same manner as in Synthesis Example 1, except that 5 g of 6-chlorobenzo[b]benzo[4,5][2,3-e]bisbenzofuran intermediate and 7.69 g of N-phenyl-4-(9-phenyl-9H-fluorene-9-yl)aniline intermediate were used in an equivalent ratio of 1:1.1.

[0316] Theoretical values: C, 88.40; H, 4.69; N, 2.10; O, 4.81

[0317] Experimental values: C, 88.40; H, 4.69; N, 2.10; O, 4.81

[0318] (Production of organic light-emitting diodes)

[0319] Example 1

[0320] Glass substrates coated with ITO / Ag / ITO films were ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrates were ultrasonically cleaned with solvents such as acetone and isopropanol, dried, and then transferred to a plasma cleaner for cleaning with oxygen plasma for 10 minutes before being transferred to a vacuum deposition unit. The prepared ITO / Ag / ITO (reflective electrode) electrode was used as the anode, and compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited onto the ITO / Ag / ITO substrate to form... A thick hole injection layer, and compound A is placed in... A hole transport layer is formed by depositing compounds 1-21 obtained in Synthesis Example 1 onto the hole transport layer. The thickness is adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, 85 wt% of host H1 (40%) and host H2 (60%) are used as the host, and 15 wt% GD is doped as a dopant by vacuum deposition to form... A thick luminescent layer. Subsequently, compound C was deposited on the luminescent layer. To form an electron transport auxiliary layer, compounds D and Liq were simultaneously vacuum-deposited in a 1:1 ratio to form... A thick electron transport layer. Organic light-emitting diodes are produced by sequentially vacuum depositing Yb and AgMg on the electron transport layer to form a cathode.

[0321] ITO / Ag / ITO / Compound A (3% NDP-9 doped, ) / Compound A / Hole transport auxiliary layer: Compound 1-21 / Emission layer [Host (Host H1, Host H2): GD = 85 wt% : 15 wt%] / Compound C / Compound D: Liq / Yb / AgMg.

[0322] Compound A: N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'- spirobi[fluorene]-2-amine

[0323] Compound C: 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl]-4,6- diphenyl-1,3,5-triazine

[0324] Compound D: 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5- triazine)

[0325] Host H1: 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(triphenylene-2-yl)phenyl)-1,3,5- triazine

[0326] Host H2: 9,9 ” -diphenyl-9H,9 ” H-3,3':9',3 ” -triazole

[0327] GD:

[0328]

[0329] Examples 2 to 13 and Comparative Examples 1 to 3

[0330] The diodes of Examples 2 to 13 and Comparative Examples 1 to 3 were produced in the same manner as Example 1, except that the composition of the hole transport auxiliary layer was changed as shown in Table 1.

[0331] Evaluation

[0332] (1) Measurement of change in current density in accordance with change in voltage

[0333] The current value flowing through the unit diode in the obtained organic light emitting diode was measured using a voltammeter (Keithley 2400) while the voltage was raised from 0 V to 10 V, and the measured current value was divided by the area to provide the result.

[0334] (2) Measurement of luminance change according to voltage change

[0335] The luminance was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light emitting diode was raised from 0 V to 10 V.

[0336] (3) Measurement of luminous efficiency

[0337] The luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated using the luminance and current density measured according to the above (1) and (2).

[0338] The relative value of the luminous efficiency based on Comparative Example 1 is shown in Table 1.

[0339] (4) Measurement of lifetime

[0340] The time for each current efficiency (cd / A) to decrease to 97% while the luminance (cd / m 2 ) was maintained at 24,000 cd / m 2 was measured as the lifetime.

[0341] Table 1 shows the relative value of the lifetime measurement based on Comparative Example 1.

[0342] (Table 1)

[0343]

[0344]

[0345] Referring to Table 1, the organic light emitting diode applying the compound according to the embodiment of the present application showed significantly improved efficiency and lifetime characteristics compared to the organic light emitting diode according to the comparative example.

[0346] While the present application has been described in connection with the exemplary embodiments, as contemplated to be practical, it is understood that the present application 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 compound for use in an organic optoelectronic device, the compound represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, X 1 and X 2 each independently O or S, R 1 to R 5 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, R 6 is substituted or unsubstituted C1to C20alkyl or substituted or unsubstituted C6to C20aryl, L 1 is a single bond, substituted or unsubstituted C6to C20arylene, substituted or unsubstituted C2to C30heterocyclyl, or a combination thereof, L 2 is a single bond or substituted or unsubstituted C6to C12arylene, Ar 1 is a substituted or unsubstituted C6to C30aryl group, m1 is an integer of 1 or 2, m2 is one of integers of 1 to 4, m3 is one of integers of 1 to 3, and m4 and m5 are each independently one of integers of 1 to 4.

2. The compound for use in an organic optoelectronic device according to claim 1, wherein Ar 1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted 1 -fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl.

3. The compound for use in an organic optoelectronic device according to claim 1, wherein Ar 1 is selected from the group of substituents listed in group I: [Group I] In Group I, R 7 to R 11 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1to C10alkyl, or substituted or unsubstituted C6to C12aryl, R 12 and R 13 each independently is substituted or unsubstituted C1to C10alkyl or substituted or unsubstituted C6to C12aryl, m6 is one of integers of 1 to 5, m7 is one of integers of 1 to 4, m8 is one of integers of 1 to 3, m9 is an integer of 1 or 2, m10 is 1, and * is a connecting point. 4.The compound for use in an organic optoelectronic device according to claim 1, wherein L 1 is substituted or unsubstituted phenylene, and L 2 is a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted biphenylene. 5.The compound for use in an organic optoelectronic device according to claim 1, wherein R 1 to R 5 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1to C10alkyl, or substituted or unsubstituted C6to C12aryl, and R 6 is substituted or unsubstituted C1to C5alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or a combination thereof. 6.A compound for use in an organic optoelectronic device, selected from the compounds listed in Group 1: [Group 1] 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, wherein the organic layer comprises the compound for use in 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 comprises an emission layer, and the emission layer comprises the compound for use in an organic optoelectronic device. 9.The organic optoelectronic device according to claim 7, wherein the organic layer comprises an emission layer, a hole transport layer between the anode and the emission layer, and a hole transport auxiliary layer between the emission layer and the hole transport layer, wherein the hole transport auxiliary layer comprises the compound for use in an organic optoelectronic device. 10.A display device comprising the organic optoelectronic device according to claim 7.

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